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Culture Documents
Task History
Source: ACS Medicinal Chemistry Letters, Volume: 6, Issue: 2, Pages: 146-150, Journal; Online Computer File, 2015, CODEN: AMCLCT,
ISSN: 1948-5875, DOI: 10.1021/ml500380f
Company/Organization: Department of Bioorganic Chemistry, Faculty of Chemistry, Wroclaw University of Technology, Wroclaw, Pol., 50-370
Abstract
Inhibitors of bacterial ureases are considered to be promising compds. in the treatment of infections caused by
Helicobacter pylori in the gastric tract and/or by urealytic bacteria (e.g., Proteus species) in the urinary tract. A new,
extended transition state scaffold, bis(aminomethyl)phosphinic acid, was successfully explored for the construction of
effective enzyme inhibitors. A reliable methodol. for the synthesis of phosphinate analogs in a three-component
Mannich-type reaction was elaborated. The obtained mols. were assayed against ureases purified from Sporosarcina
pasteurii and Proteus mirabilis, and aminomethyl(N-n-hexylaminomethyl)phosphinic acid was found to be the most potent
inhibitor, with a Ki = 108 nM against the S. pasteurii enzyme.
Indexing
Enzymes (Section 7-3)
Concepts
Enzyme functional sites
active; bis(aminomethyl)phosphinic acid provides synthetically useful extended transition state scaffold for development
of bacterial urease inhibitors
Enzyme inhibition kinetics
Molecular association
Molecular recognition
bis(aminomethyl)phosphinic acid provides synthetically useful extended transition state scaffold for development of
bacterial urease inhibitors
Structure-activity relationship
enzyme-inhibiting; bis(aminomethyl)phosphinic acid provides synthetically useful extended transition state scaffold for
development of bacterial urease inhibitors
C-P bond
stability; bis(aminomethyl)phosphinic acid provides synthetically useful extended transition state scaffold for development
of bacterial urease inhibitors
Substances
9002-13-5 Urease
bis(aminomethyl)phosphinic acid provides synthetically useful extended transition state scaffold for development of
bacterial urease inhibitors
SciFinder Page 3
Biological study, unclassified; Properties; Biological study
1643319-10-1P
bis(aminomethyl)phosphinic acid provides synthetically useful extended transition state scaffold for development of
bacterial urease inhibitors
Biological study, unclassified; Properties; Reactant; Synthetic preparation; Biological study; Preparation; Reactant or
reagent
127590-10-7P
1643318-96-0P
1643318-97-1P
1643318-98-2P
1643318-99-3P
1643319-00-9P
1643319-01-0P
1643319-02-1P
1643319-03-2P
1643319-04-3P
1643319-05-4P
1643319-06-5P
1643319-07-6P
1643319-08-7P
1643319-09-8P
1643319-11-2P
bis(aminomethyl)phosphinic acid provides synthetically useful extended transition state scaffold for development of
bacterial urease inhibitors
bis(aminomethyl)phosphinic acid provides synthetically useful extended transition state scaffold for development of
bacterial urease inhibitors
Byproduct; Preparation
1643319-14-5P
1643319-15-6P
SciFinder Page 4
1643319-16-7P
1643319-17-8P
1643319-18-9P
1643319-19-0P
1643319-20-3P
1643319-21-4P
1643319-22-5P
1643319-23-6P
1643319-24-7P
1643319-25-8P
bis(aminomethyl)phosphinic acid provides synthetically useful extended transition state scaffold for development of
bacterial urease inhibitors
bis(aminomethyl)phosphinic acid provides synthetically useful extended transition state scaffold for development of
bacterial urease inhibitors
bis(aminomethyl)phosphinic acid provides synthetically useful extended transition state scaffold for development of
bacterial urease inhibitors
2. Metal complexes of a new class of polydentate Mannich bases: Synthesis and spectroscopic characterisation
By: Al-Jeboori, Mohamad J.; Al-Jebouri, Fahad A.; Al-Azzawi, Muayed A. R.
Source: Inorganica Chimica Acta, Volume: 379, Issue: 1, Pages: 163-170, Journal; Online Computer File, 2011, CODEN: ICHAA3, ISSN:
0020-1693, DOI: 10.1016/j.ica.2011.10.013
SciFinder Page 6
Company/Organization: Department of Chemistry, College of Education, Ibn Al-Haitham, University of Baghdad, Baghdad, Iraq
Abstract
A new class of polydentate Mannich bases featuring an N2S2 donor system, bis((2-mercapto-N-
phenylacetamido)methyl)phosphinic acid H3L1 and bis((2-mercapto-N-propylacetamido)methyl)phosphinic acid H3L2,
was synthesized from condensation of phosphinic acid and paraformaldehyde with 2-mercaptophenylacetamide W1 and
2-mercaptopropylacetamide W2, resp. Monomeric complexes of these ligands, K2[CrIII(Ln)Cl2], K3[M'II(Ln)Cl2] and
K[M(Ln)] (M' = Mn(II) or Fe(II); M = Co(II), Ni(II), Cu(II), Zn(II), Cd(II) or Hg(II); n = 1, 2) are reported. The structures of
new ligands, mode of bonding and overall geometry of the complexes were detd. through IR, UV-visible, NMR, and mass
spectral studies, magnetic moment measurements, elemental anal., metal content, and conductance. These studies
revealed octahedral geometries for the Cr(III), Mn(II) and Fe(II) complexes, square planar for Ni(II) and Cu(II) complexes
and tetrahedral for the Co(II), Zn(II), Cd(II) and Hg(II) complexes. Complex formation studies via molar ratio in DMF soln.
were consistent to those found in the solid complexes with a ratio of (M:L) as (1:1).
Indexing
Inorganic Chemicals and Reactions (Section 78-7)
Concepts
Transition metal complexes
prepn. of transition metal complexes of bis(mercaptoacetamide)phosphinic acid polydentate Mannich bases
Synthetic preparation; Preparation
Mannich bases
transition metal complexes; prepn. of transition metal complexes of bis(mercaptoacetamide)phosphinic acid polydentate
Mannich bases
Synthetic preparation; Preparation
Substances
62-53-3 Benzenamine, reactions
68-11-1 reactions
107-10-8 1-Propanamine, reactions
6303-21-5 Phosphinic acid
30525-89-4 Paraformaldehyde
1350517-95-1P
1350517-97-3P
SciFinder Page 8
1350517-98-4P
1350517-99-5P
SciFinder Page 9
1350518-00-1P
1350518-01-2P
SciFinder Page 10
1350518-02-3P
1350518-03-4P
SciFinder Page 11
1350518-04-5P
1350518-05-6P
1350518-06-7P
1350518-07-8P
1350518-08-9P
1350518-09-0P
1350518-10-3P
1350518-11-4P
1350518-12-5P
3. Synthesis and spectral studies of new N2S2 and N2O2 Mannich base ligands and their metal complexes
By: Abdul-Ghani, Ahlam Jamil; Al-Jeboori, Mohamad Jaber; Al-Karawi, Ahmed Jasim M.
Source: Journal of Coordination Chemistry, Volume: 62, Issue: 16, Pages: 2736-2744, Journal, 2009, CODEN: JCCMBQ, ISSN: 0095-
8972, DOI: 10.1080/00958970902878327
Company/Organization: Department of Chemistry, College of Sciences, University of Baghdad, Baghdad, Jaderiya, Iraq
Abstract
The new Mannich bases dimethylphosphinic acid bis(thiosemicarbazide) (H3L1) and dimethylphosphinic acid bis(1-
phenylsemicarbazide) (H3L2) were synthesized from condensation of phosphinic acid and formaldehyde with
thiosemicarbazide and 1-phenylsemicarbazide, resp. Monomeric complexes of these ligands, K2[CrIII(Ln)Cl2],
K3[FeII(L1)Cl2], K3[MnII(L2)Cl2], and K[M(Ln)] (M = Co(II), Ni(II), Cu(II), Zn(II) or Cd(II); n = 1, 2) are reported. The mode
of bonding and overall geometry of the complexes were detd. through IR, UV-visible, NMR, and mass spectral studies,
magnetic moment measurements, elemental anal., metal content, and conductance. These studies revealed octahedral
geometries for the Cr(III), Mn(II), and Fe(II) complexes, square planar for Co(II), Ni(II), and Cu(II) complexes and
tetrahedral for the Zn(II) and Cd(II) complexes. Complex formation via molar ratio in DMF soln. was studied and results
were consistent to those found in the solid complexes with a ratio of (M:L) as (1:1).
Indexing
Inorganic Chemicals and Reactions (Section 78-7)
Concepts
IR spectra
UV and visible spectra
prepn. and IR and UV-visible spectra of transition metal dimethylphosphinic acid
bis(thiosemicarbazide/phenylsemicarbazide) Mannich base complexes
Transition metal complexes
prepn. and IR and UV-visible spectra of transition metal dimethylphosphinic acid
bis(thiosemicarbazide/phenylsemicarbazide) Mannich base complexes
Properties; Synthetic preparation; Preparation
Mannich bases
transition metal complexes; prepn. and IR and UV-visible spectra of transition metal dimethylphosphinic acid
bis(thiosemicarbazide/phenylsemicarbazide) Mannich base complexes
Properties; Synthetic preparation; Preparation
Substances
1187655-64-6P
1187655-65-7P
1187655-66-8P
1187655-67-9P
1187655-68-0P
1187655-69-1P
1187655-70-4P
1187655-71-5P
SciFinder Page 14
1187655-72-6P
SciFinder Page 15
1187655-73-7P
1187655-74-8P
SciFinder Page 16
1187655-75-9P
SciFinder Page 17
1187655-76-0P
4. Synthesis of the new adducts of imines and enamines with PH acids and their derivatives
By: Prishchenko, Andrey A.; Livantsov, Mikhail V.; Novikova, Olga P.; Livantsova, Ludmila I.; Milaeva, Elena R.
Source: Heteroatom Chemistry, Volume: 20, Issue: 2, Pages: 70-80, Journal, 2009, CODEN: HETCE8, ISSN: 1042-7163, DOI:
10.1002/hc.20513
Company/Organization: Department of Chemistry, M. V. Lomonosov Moscow State University, Moscow, Russia, 119991
Abstract
SciFinder Page 19
A nucleophilic or radical addn. of esters of trivalent organophosphorus acids with PH fragments to various imines and
enamines is proposed as convenient methods for the synthesis of substituted aminomethyl organophosphorus compds.
with three-coordinate, four-coordinate and five-coordinate phosphorus derivs. Example compds. thus prepd. included 4-
[1-(1,4,6,9-tetraoxa-55-phosphaspiro[4.4]non-5-yl)propyl]morpholine and 5,5'-[1,2-ethanediylbis(oxy)]bis[2,2,3,3-
tetramethyl-1,4,6,9-tetraoxa-55-phosphaspiro[4.4]nonane], [1-(4-morpholinyl)cyclohexyl]phosphonous acid
bis(trimethylsilyl) ester, etc. Also, functionalized derivs. of these compds. with acyl and methanesulfonyl moieties were
synthesized and some properties of the obtained compds. were described.
Indexing
Organometallic and Organometalloidal Compounds (Section 29-7)
Section cross-reference(s):27, 28
Concepts
Imines
aldimines; prepn. of aminomethyl organophosphorus compds. by radical addn. or nucleophilic addn. reaction of imines or
enamines with organophosphorus acids
Reactant; Reactant or reagent
Group 15 element compounds
hypophosphites; prepn. of aminomethyl organophosphorus compds. by radical addn. or nucleophilic addn. reaction of
imines or enamines with organophosphorus acids
Reactant; Reactant or reagent
Elimination reaction
Homolytic addition reaction
Nucleophilic addition reaction
prepn. of aminomethyl organophosphorus compds. by radical addn. or nucleophilic addn. reaction of imines or enamines
with organophosphorus acids
Acid chlorides
Enamines
Imines
prepn. of aminomethyl organophosphorus compds. by radical addn. or nucleophilic addn. reaction of imines or enamines
with organophosphorus acids
Reactant; Reactant or reagent
Phosphonates
prepn. of aminomethyl organophosphorus compds. by radical addn. or nucleophilic addn. reaction of imines or enamines
with organophosphorus acids
Reactant; Synthetic preparation; Preparation; Reactant or reagent
Addition reaction
regioselective; prepn. of aminomethyl organophosphorus compds. by radical addn. or nucleophilic addn. reaction of
imines or enamines with organophosphorus acids
Sulfonyl halides
sulfonyl chlorides; prepn. of aminomethyl organophosphorus compds. by radical addn. or nucleophilic addn. reaction of
imines or enamines with organophosphorus acids
Reactant; Reactant or reagent
Substances
75-77-4 Chlorotrimethylsilane, reactions
124-63-0 Methanesulfonyl chloride
622-29-7 N-(Phenylmethylene)methanamine
670-80-4 4-(1-Cyclohexen-1-yl)morpholine
762-04-9 Diethyl phosphite
3646-10-4 1,4,6,9-Tetraoxa-55-phosphaspiro[4.4]nonane
4023-34-1 Cyclopropanecarbonyl chloride
6852-58-0 2-Methyl-N-(phenylmethylene)-2-propanamine
7182-09-4 1-(1-Propenyl)piperidine
7313-26-0 2,6-Bis(1,1-dimethylethyl)-4-[(phenylimino)methyl]phenol
7803-65-8 Ammonium hypophosphite
13114-23-3 N-[(4-Methoxyphenyl)methylene]methanamine
SciFinder Page 20
15430-99-6 1-(Diethylamino)-1-butene
15431-03-5 4-(1-Butenyl)morpholine
16273-54-4 N-(3-Pyridinylmethylene)methanamine
17599-61-0 1,1,1-Trimethyl-N-(phenylmethylene)silanamine
18389-64-5
20521-59-9 4-(1-Propen-1-yl)morpholine
21064-27-7 N-(Phenylmethylene)-2-propen-1-amine
30148-50-6 Phosphonous acid bis(trimethylsilyl ester)
30653-71-5 Dibutoxyphosphine
39558-97-9 N-(2-Furanylmethylene)methanamine
104971-42-8 Phosphonous acid ethyl trimethylsilyl ester
104971-44-0 Phosphonous acid butyl trimethylsilyl ester
prepn. of aminomethyl organophosphorus compds. by radical addn. or nucleophilic addn. reaction of imines or enamines
with organophosphorus acids
prepn. of aminomethyl organophosphorus compds. by radical addn. or nucleophilic addn. reaction of imines or enamines
with organophosphorus acids
SciFinder Page 21
78-67-1 AIBN
prepn. of aminomethyl organophosphorus compds. by radical addn. or nucleophilic addn. reaction of imines or enamines
with organophosphorus acids
5. Synthesis and structural studies of new Mannich base ligands and their metal complexes
By: Al-Jeboori, Mohamad Jaber; Abdul-Ghani, Ahlam Jamil; Al-Karawi, Ahmed Jasim
Source: Transition Metal Chemistry (Dordrecht, Netherlands), Volume: 33, Issue: 7, Pages: 925-930, Journal, 2008, CODEN:
TMCHDN, ISSN: 0340-4285, DOI: 10.1007/s11243-008-9134-3
Company/Organization: Department of Chemistry, College of Education Ibn Al-Haitham, University of Baghdad, Baghdad, Iraq
Abstract
SciFinder Page 23
L1
The new Mannich bases bis(1,4-diphenylthiosemicarbazide methyl) phosphinic acid H3 and bis(1,4-
diphenylsemicarbazide methyl) phosphinic acid H3L2 were synthesized from the condensation of phosphinic acid,
formaldehyde with 1,4-diphenylthiosemicarbazide and 1,4-diphenylsemicarbazide, resp. Monomeric complexes of these
ligands, of general formulas K2[CrIII(Ln)Cl2], K3[MnII(Ln)Cl2] and K[M(Ln)] (M = Co(II), Ni(II), Cu(II), Zn(II) or Hg(II); n = 1,
2), are reported. The mode of bonding and overall geometry of the complexes were detd. through physicochem. and
spectroscopic methods. These studies revealed octahedral geometries for the Cr(III), Mn(II) complexes, square planar
for Co(II), Ni(II) and Cu(II) complexes and tetrahedral for the Zn(II) and Hg(II) complexes.
Indexing
Inorganic Chemicals and Reactions (Section 78-7)
Concepts
Mannich bases
metal complexes; prepn. of Mannich base ligands by condensation of phosphinic acid, formaldehyde, and
diphenyl(thio)semicarbazide and their metal complexes
Synthetic preparation; Preparation
Transition metal complexes
prepn. of Mannich base ligands by condensation of phosphinic acid, formaldehyde, and diphenyl(thio)semicarbazide and
their metal complexes
Synthetic preparation; Preparation
Substances
621-12-5 1,4-Diphenylsemicarbazide
1768-59-8 1,4-Diphenylthiosemicarbazide
6303-21-5 Phosphinic acid
prepn. of Mannich base ligands by condensation of phosphinic acid, formaldehyde, and diphenyl(thio)semicarbazide and
their metal complexes
prepn. of Mannich base ligands by condensation of phosphinic acid, formaldehyde, and diphenyl(thio)semicarbazide and
their metal complexes
1177451-07-8P
SciFinder Page 25
1177451-10-3P
SciFinder Page 26
1177451-11-4P
SciFinder Page 27
1177451-12-5P
SciFinder Page 28
1177451-14-7P
SciFinder Page 29
1177451-15-8P
SciFinder Page 30
1177451-16-9P
SciFinder Page 31
1177451-17-0P
SciFinder Page 32
1177451-18-1P
SciFinder Page 33
1177451-19-2P
SciFinder Page 34
1177451-20-5P
SciFinder Page 35
1177451-21-6P
SciFinder Page 36
1177451-22-7P
SciFinder Page 37
prepn. of Mannich base ligands by condensation of phosphinic acid, formaldehyde, and diphenyl(thio)semicarbazide and
their metal complexes
Source: Russian Journal of General Chemistry, Volume: 78, Issue: 2, Pages: 324-326, Journal, 2008, CODEN: RJGCEK, ISSN: 1070-
3632, DOI: 10.1134/S1070363208020278
Abstract
The title reaction is described. Thus, acylation of HOP(O)P[CH(NHMe)Ph]2 with Ac2O or oleoyl chloride gave isomers of
HOP(O)[CH(NMeAc)Ph]2 and HOP(O)[CH(NMeCOR)Ph]2 (R = oleyl) resp.
Indexing
Organometallic and Organometalloidal Compounds (Section 29-7)
Concepts
Acylation
acylation of aryl-substituted bis(aminomethyl)phosphinic acids
Substances
112-77-6 Oleoyl chloride
345254-23-1
1135948-75-2
7. Complexation properties of the di-, tri-, and tetraacetate derivatives of bis(aminomethyl)phosphinic acid
By: Tircso, Gyula; Benyei, Attila; Kiraly, Robert; Lazar, Istvan; Pal, Robert; Brucher, Erno
SciFinder Page 40
Source: European Journal of Inorganic Chemistry, Issue: 5, Pages: 701-713, Journal, 2007, CODEN: EJICFO, ISSN: 1434-1948, DOI:
10.1002/ejic.200600891
Company/Organization: Department of Inorganic and Analytical Chemistry, University of Debrecen, Debrecen, Hung., 4010
Abstract
N-Carboxymethyl-substituted bis(aminomethyl)phosphinic acids R1R2NCH2P(O)(OH)CH2NR3R4 (HL0, R1-R4 = H; H3L1,
R1 = R3 = H, R2 = R4 = CH2CO2H; H3L2, R1 = R2 = H, R3 = R4 = CH2CO2H; H4L3, R1 = H, R2 = R3 = R4 = CH2CO2H;
H5L4, R1-R4 = CH2CO2H) were prepd. by condensation of amines, (dibenzylamine, iminodiacetic acid, N-benzylglycine)
with formaldehyde and H3PO2 with subsequent benzylic deprotection and carboxyalkylation by Br2CH2CO2H. The
ligands L0-L4 can be considered as di- (L1, L2), tri- (L3) and tetraacetate (L4) derivs. of bis(aminomethyl)phosphinic acid
(L0); their complexation equil. involving Mg2+, Ca2+, Ni2+, Cu2+, Zn2+, Cd2+, and Pb2+ were studied by pH potentiometry.
The first two protonation consts. of the ligands are lower than those of the analogous diaminopolycarboxylates due to the
electron-withdrawing effect of the phosphinate group. The asym. ligands L2 and L3 and their complexes are protonated
first at the primary (NH2) and secondary (NH) amine groups, resp. The ligands L0, L1, L2, and L3 form the species ML,
MLH, ML2, and ML2H whereas heptadentate L4 forms very stable ML complexes, protonated (MLH and MLH2) species
and, unlike the other ligands, it also forms dinuclear M2L complexes. The stability consts. of the complexes of L0, L1, L2,
and L3 are generally lower, while those of the L4 are similar or higher, than those of the analogous diaminocarboxylate
derivs. The phosphinate group is not directly coordinated to the metal ions but may contribute to the stability by
increasing the electrostatic interaction, which is significant for the complexes of L4. The 1H NMR spectra of complexes
ZnL2, ZnL3, and ZnL4 show an AB multiplet pattern for the protons of the iminodiacetate moiety of the ligands, which
indicates the long half-life of the Zn2+-N bond and the rigid structure of this segment of the complexes. The solid-state
structure of the ligand [H5L3]Cl and complex K[CuL1]H2O have been detd. by x-ray diffraction techniques. The
arrangement of the ligand L1 is square planar around Cu2+ with two nitrogen and carboxylate oxygen donor atoms,
although the axial proximity of a carboxylate and a phosphinate oxygen atom in two neighboring mols. results in a
distorted octahedral coordination.
Indexing
Organometallic and Organometalloidal Compounds (Section 29-7)
Section cross-reference(s):75, 78, 79
Concepts
Amines
aminophosphinates, acetate derivs.; prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs. and formation
consts. of metal complexes with acetate-phosphinate diamine chelate complexons
Physical, engineering or chemical process; Properties; Reactant; Synthetic preparation; Preparation; Process; Reactant
or reagent
Diamines
Phosphinates
aminophosphinates, acetate derivs.; prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and
formation consts. of metal complexes with acetate-phosphinate diamine chelate complexons
Physical, engineering or chemical process; Properties; Reactant; Synthetic preparation; Preparation; Process; Reactant
or reagent
Carboxylic acids
complexes, aminophosphinates, acetate derivs.; prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs.,
acidity and formation consts. of metal complexes with acetate-phosphinate diamine chelate complexons
Physical, engineering or chemical process; Properties; Reactant; Synthetic preparation; Preparation; Process; Reactant
or reagent
Protonation
const.; prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and formation consts. of metal
complexes with acetate-phosphinate diamine chelate complexons
Crystal structure
Molecular structure
of copper complex with phosphinate-diacetate diamine chelate ligand
Acidity
Carboxyalkylation
Complexation
Condensation reaction
prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs. and formation consts. of metal complexes with
acetate-phosphinate diamine chelate complexons
SciFinder Page 41
Chelating agents
Formation constant
Mannich reaction
prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and formation consts. of metal complexes with
acetate-phosphinate diamine chelate complexons
Chelates
prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and formation consts. of metal complexes with
acetate-phosphinate diamine chelate complexons
Physical, engineering or chemical process; Properties; Reactant; Synthetic preparation; Preparation; Process; Reactant
or reagent
Complexing agents
transition metal complexes; prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and formation
consts. of metal complexes with acetate-phosphinate diamine chelate complexons
Substances
949573-13-1P
949573-14-2P
crystal structure; prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and formation consts. of
metal complexes with acetate-phosphinate diamine chelate complexons
mol. structure; prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and formation consts. of metal
complexes with acetate-phosphinate diamine chelate complexons
Physical, engineering or chemical process; Properties; Reactant; Synthetic preparation; Preparation; Process; Reactant
or reagent
69219-70-1
prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and formation consts. of metal complexes with
acetate-phosphinate diamine chelate complexons
prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and formation consts. of metal complexes with
acetate-phosphinate diamine chelate complexons
Physical, engineering or chemical process; Properties; Reactant; Synthetic preparation; Preparation; Process; Reactant
or reagent
prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and formation consts. of metal complexes with
acetate-phosphinate diamine chelate complexons
prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and formation consts. of metal complexes with
acetate-phosphinate diamine chelate complexons
Physical, engineering or chemical process; Reactant; Synthetic preparation; Preparation; Process; Reactant or reagent
prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and formation consts. of metal complexes with
acetate-phosphinate diamine chelate complexons
68733-66-4P
69219-71-2P
949573-07-3P
949573-09-5P
949573-11-9P
prepn. of bis(aminomethyl)phosphinic acid, its oligoacetate derivs., acidity and formation consts. of metal complexes with
acetate-phosphinate diamine chelate complexons
Abstract
The prepn. of new title compds., R4NHCHR2P(O)(OR5)CHR3NHR4 [R2, R3 = H, (un)substituted C1-18 alkyl, C2-18 alkenyl,
C2-18 alkynyl, etc.; R4 = protecting group for amino group; R5 = C1-18 alkyl, C2-18 alkenyl, C2-18 alkynyl, C6-12 aryl, C7-20
arylalkyl, etc.], useful in pharmaceutical as well as in agriculture chem., is described. Thus, reaction of Et bis(N-
benzoylamino(bromo)methyl)phosphonate (prepn. given) with 1-morpholino-1-cyclohexene in the presence of N-
ethyldiisopropylamine in THF gave 35% diastereoisomeric mixt. of title compd. Et bis(N-benzoylamino(2-
cyclohexanone)methyl)phosphonate.
Patent Information
Patent No. Kind Date Application No. Date
DE 4310815 A1 Oct 06, 1994 DE 1993-4310815 Apr 02, 1993
WO 9422879 A1 Oct 13, 1994 WO 1994-EP950 Mar 24, 1994
EP 691975 A1 Jan 17, 1996 EP 1994-912541 Mar 24, 1994
EP 691975 B1 Jun 04, 1997
JP 08508276 T Sep 03, 1996 JP 1994-521647 Mar 24, 1994
JP 3994171 B2 Oct 17, 2007
AT 154024 T Jun 15, 1997 AT 1994-912541 Mar 24, 1994
ES 2102852 T3 Aug 01, 1997 ES 1994-912541 Mar 24, 1994
US 5608098 A Mar 04, 1997 US 1995-525787 Sep 28, 1995
Priority Application
DE 1993-4310815 A Apr 02, 1993
WO 1994-EP950 W Mar 24, 1994
Indexing
Organometallic and Organometalloidal Compounds (Section 29-7)
Substances
159532-09-9P
159532-10-2P
SciFinder Page 45
159532-11-3P
159532-12-4P
159532-13-5P
159532-14-6P
159532-15-7P
prepn. of
152862-45-8P
152862-46-9P
155387-28-3P
159532-03-3P
159532-04-4P
159532-05-5P
159532-06-6P
159532-07-7P
159532-08-8P
9. Preparation of amino acid and peptidylphosphinates and related compounds as retroviral protease inhibitors
By: Budt, Karl Heinz; Peyman, Anuschirwan
Assignee: Hoechst A.-G., Germany
Priority: Dec 16, 1989, DE 1989-3941607, Jun 13, 1990, DE 1990-4018942, Dec 14, 1990, US 1990-627818, Dec 16, 1993, US 1993-167613,
Aug 19, 1994, US 1994-293112
Classifications: Main IPC: C07F009-30, Secondary IPC: C07K005-06; C07F009-32; C07F009-36; C07K005-04; A61K031-66; A61K037-02;
Abstract
AR4NCR2R3QCRR1NR6A1 [Q = S, SO, SO2, R9(R5Y)P, R9(R7R8N)P; A,A1 = DEnFoGp; E, F, G = (un)natural amino acid,
azaaminoacid-, or imino acid residue, n, o, p = 0, 1; D = H, carboxy, SH, OH, alkoxy, amino, amidino, carbamoyl,
alkanoyloxy, F, Cl, Br, iodo, (substituted) aminomethylcarbonyl, propionyl, etc.; Y = O, S; R,R2 = H, CO2H, SH, OH,
alkoxy, carbamoyl, alkanoyloxy, carboxy, alkoxycarbonyl, F, Cl, Br, iodo, amino, amidino, alkylsulfonyl, alkylsufinyl,
alkylthio, hydroxamino, sulfamoyl, CHO, etc.; R1,R3R4,R6 = H, alkyl; R2R4,RR6 = atoms to complete (unsatd.) (bicyclic) 5-
12 membered rings; R5 = H, alkyl, alkenyl, alkynyl, aralkyl, aryl, (substituted) cycloalkyl, cation, phosphate prodrug
moiety; R7,R8 = H, alkyl, alkenyl, alkynyl, aryl, (substituted) aralkyl; R7R8 = atoms to complete a ring contg. 2-6 C atoms;
R9 = O, S], were prepd. as retroviral protease inhibitors (no data). Thus, (H2NCH2)2P(O).HCl (prepn. starting H3PO2 and
H2CO given) and BOC-Val-OH (BOC = Me3CO2C) were coupled in DMF at 0 using N-ethylmorpholine,
hydroxybenzotriazole, and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride to give 81% (BOC-Val-
NHCH2)2P(O)(OH).
Patent Information
Patent No. Kind Date Application No. Date
DE 4039569 A1 Jun 20, 1991 DE 1990-4039569 Dec 11, 1990
EP 435059 A1 Jul 03, 1991 EP 1990-123779 Dec 11, 1990
EP 435059 B1 Nov 05, 1997
AT 159946 T Nov 15, 1997 AT 1990-123779 Dec 11, 1990
ES 2110404 T3 Feb 16, 1998 ES 1990-123779 Dec 11, 1990
FI 9006140 A Jun 17, 1991 FI 1990-6140 Dec 13, 1990
SciFinder Page 47
CA 2032303 A1 Jun 17, 1991 CA 1990-2032303 Dec 14, 1990
CA 2032303 C Mar 19, 2002
NO 9005410 A Jun 17, 1991 NO 1990-5410 Dec 14, 1990
AU 9068025 A Jun 20, 1991 AU 1990-68025 Dec 14, 1990
AU 641197 B2 Sep 16, 1993
ZA 9010068 A Sep 25, 1991 ZA 1990-10068 Dec 14, 1990
HU 59147 A2 Apr 28, 1992 HU 1990-8276 Dec 14, 1990
JP 05331067 A Dec 14, 1993 JP 1990-419203 Dec 14, 1990
JP 2816253 B2 Oct 27, 1998
KR 203231 B1 Jun 15, 1999 KR 1990-20696 Dec 15, 1990
US 5629431 A May 13, 1997 US 1995-479562 Jun 07, 1995
Priority Application
DE 1989-3941607 A1 Dec 16, 1989
DE 1990-4018942 A1 Jun 13, 1990
US 1990-627818 B1 Dec 14, 1990
US 1993-167613 B1 Dec 16, 1993
US 1994-293112 B1 Aug 19, 1994
Indexing
Amino Acids, Peptides, and Proteins (Section 34-3)
Section cross-reference(s):1
Concepts
Peptides, preparation
phosphinate derivs., prepn. of, as retroviral protease inhibitors
Synthetic preparation; Preparation
Amino acids, preparation
phosphinates, prepn. of, as retroviral protease inhibitors
Synthetic preparation; Preparation
Immunodeficiency
acquired immune deficiency syndrome, deriv. of, amino acid- and peptidylphosphinates for
Substances
13734-41-3
condensation and coupling of, with aminomethylphosphinate, in prepn. of retroviral protease inhibitor
5824-40-8 Triphenylmethylamine
122-78-1 Phenylacetaldehyde
127590-10-7P
137283-91-1P
137283-92-2P
SciFinder Page 50
137283-93-3P
137283-94-4P
137283-95-5P
137283-96-6P
137306-09-3P
137331-82-9P
137331-83-0P
Biological activity or effector, except adverse; Biological study, unclassified; Synthetic preparation; Biological study;
Preparation
9001-92-7 Protease
10. Preparation of bis(aminomethyl)phosphinic acid from acylaminomethanols and trivalent phosphorus halides
By: Kober, Reiner; Seele, Rainer; Steglich, Wolfgang; Schrader, Thomas
Assignee: BASF A.-G., Germany
Abstract
(H2NCH2)2P(O)(OH) (I), a known plant growth inhibitor (West German OS 2,805,074) was prepd. by condensation of
RCONHCH2OH [R = (substituted) alkyl, cycloalkyl, aralkyl, aryl] with a trivalent P halide optionally in the presence of an
alkali, alk. earth, or ammonium bromide or iodide to give (RCONHCH2)2P(O)(OH) (II), followed by hydrolysis. Thus, a
mixt. of PhCONHCH2OH (prepn. given) and PCl3 was heated to 150 over 30 min. H2O was added to the cooled mixt.
and the residue was refluxed 5 min in EtOAc to give 61% II (R = Ph). The latter was heated at 120 in concd. HCl for 16
h to give 94% I.
SciFinder Page 51
Patent Information
Patent No. Kind Date Application No. Date
DE 3824961 A1 Jan 25, 1990 DE 1988-3824961 Jul 22, 1988
Priority Application
DE 1988-3824961 Jul 22, 1988
Indexing
Organometallic and Organometalloidal Compounds (Section 29-7)
Section cross-reference(s):5
Concepts
Plant hormones and regulators
bis(aminomethyl)phosphinic acid
Reactant; Reactant or reagent
Substances
7789-60-8 Phosphorus tribromide
55-21-0 Benzamide
hydroxymethylation of
6282-02-6P N-Hydroxymethylbenzamide
Source: Inorganic Chemistry, Volume: 23, Issue: 15, Pages: 2315-18, Journal, 1984, CODEN: INOCAJ, ISSN: 0020-1669, DOI:
10.1021/ic00183a021
Company/Organization: Dep. Chem., Univ. Alberta, Edmonton, AB, Can., T6G 2G2
Abstract
The reaction of an EtOH soln. of bis(4,5-diisopropylimidazol-2-yl)(imidazol-2-yl)phosphine with aq. ZnCl2 results in the
formation of ZnCl2(OPR2OH)2.H2O (R = 4,5-diisopropylimidazol-2-yl), which was characterized by x-ray crystallog. The
complex crystallizes in the space group P21/c with a 9.805(3), b 26.202(7), c 10.924(3) , 111.79(2), and Z = 4. The
structure refined routinely to a final R of 6.6%. The structural results indicate that the original phosphine has undergone
oxidn. and replacement of an imidazole by OH-, the latter process apparently being promoted by the presence of ZnCl2.
Thus tris(imidazol-2-yl)phosphine-Zn2+ complexes, which are catalytically active models for the active site of carbonic
anhydrase, suffer an apparent Zn2+-promoted decompn., which accounts for the obsd. loss of activity when they are
allowed to stand in soln.
Indexing
Inorganic Chemicals and Reactions (Section 78-7)
Section cross-reference(s):7, 25, 29
Concepts
Crystal structure
Molecular structure
of [bis(diisopropylimidazolyl)phosphinic acid]dichlorozinc hydrate
Substances
7646-85-7 uses and miscellaneous
Uses
89210-50-4
oxidn. and substitution of hydroxide for imidazole in, in presence of zinc chloride in aq. ethanol
SciFinder Page 53
Reactant; Reactant or reagent
90481-58-6P
Source: Journal of Organometallic Chemistry, Volume: 178, Issue: 1, Pages: 157-69, Journal, 1979, CODEN: JORCAI, ISSN: 0022-
328X, DOI: 10.1016/S0022-328X(00)87867-5
72190-60-4P
72190-61-5P
72190-62-6P
prepn. of
Abstract
H3PO2 and paraformaldehyde gave 86.2% (HOCH2)2P(O)OH, which, with SOCl2 gave 94.5% (ClCH2)2P(O)OH (I).
Amination of I with PhCH2NH2 gave 84.8% (PhCH2NHCH2)P(O)OH, debenzylation of which gave 87.4%
(H2NCH2)2P(O)OH, useful as a plant growth regulator.
Patent Information
Patent No. Kind Date Application No. Date
DE 2805074 A1 Aug 17, 1978 DE 1978-2805074 Feb 07, 1978
CH 627477 A5 Jan 15, 1982 CH 1977-1614 Feb 10, 1977
US 4171969 A Oct 23, 1979 US 1978-875842 Feb 07, 1978
FR 2380289 A1 Sep 08, 1978 FR 1978-3565 Feb 08, 1978
FR 2380289 B1 Dec 17, 1982
JP 53098929 A Aug 29, 1978 JP 1978-14018 Feb 09, 1978
GB 1594436 A Jul 30, 1981 GB 1978-5265 Feb 09, 1978
Priority Application
CH 1977-1614 A Feb 10, 1977
Indexing
Organometallic and Organometalloidal Compounds (Section 29-7)
Section cross-reference(s):5
Concepts
Plant hormones and regulators
bis(aminomethyl)phosphinic acid
Reactant; Reactant or reagent
Substances
2074-67-1P
68358-05-4P
68358-06-5P
68358-07-6P
68358-08-7P
68358-09-8P
prepn. of
75-64-9 reactions
100-46-9 reactions
14. Inorganic coordination polymers. XXII. Manganese(II), cobalt(II), nickel(II), copper(II), and zinc(II) bis[bis(N-
phenylaminomethyl)phosphinates]. Effects of coordinating side groups
By: Gillman, H. D.; Eichelberger, J. L.
Source: Inorganica Chimica Acta, Volume: 24, Issue: 1, Pages: 31-4, Journal, 1977, CODEN: ICHAA3, ISSN: 0020-1693, DOI:
10.1016/S0020-1693(00)93846-5
Abstract
The metal(II) bis[bis(N-phenylaminomethyl)phosphinates], M[OP(CH2NHPh)2O]2 (M = Mn, Co, Ni, Cu, and Zn), were
investigated. The Mn, Co, and Ni derivs. all have similar structures with octahedrally coordinated metal centers, the Cu
deriv. is probably tetragonally distorted octahedral and the Zn deriv. is tetrahedral. All of these compds. contain some
coordinating amine groups except the Zn complex in which no amine groups coordinate. Most likely, all of these
compds. contain sym. bridging O,O'-phosphinate groups. The thermal stabilities of these complexes are markedly
different from one another and appear to be dependent on the ligand-field stabilization energies but not on the chelation
of the amine groups.
Indexing
Inorganic Chemicals and Reactions (Section 78-7)
Concepts
Transition metals, compounds
with bis(phenylaminomethyl)phosphinate ligands
Reactant; Reactant or reagent
Substances
68010-31-1P
68026-30-2P
68026-29-9
C28 H32 Cu N4 O4 P2
68026-32-4P
SciFinder Page 59
68026-31-3
C28 H32 N4 Ni O4 P2
68026-34-6P
68026-33-5
C28 H32 Co N4 O4 P2
68026-36-8P
68026-35-7
C28 H32 Mn N4 O4 P2
prepn. of
15. Inorganic coordination polymers. XXI. Manganese(II), cobalt(II), nickel(II), copper(II), and zinc(II) bis(N-
phenylaminomethyl) phosphinates. Effects of coordinating side groups
By: Eichelberger, J. L.; Gillman, H. D.
Source: U. S. NTIS, AD Rep., Issue: AD-A035099, 18 pp., Report, 1977, CODEN: XADRCH
SciFinder Page 60
Company/Organization: Res. Dev. Dep., Pennwalt Corp., King of Prussia, PA, USA
Publisher: From Gov. Rep. Announce. Index (U. S.) 1977, 77(8), 119, Avail. NTIS
Language: English
Abstract
The metal(II) bis[bis(phenylaminomethyl)phosphinates], M[O2P(CH2NHPh)2]2 (M = Mn, Co, Ni, Cu, and Zn) were
investigated. The Mn, Co, and Ni derivs. all have similar structures with octahedrally coordinated metal centers, the Cu
deriv. is probably tetragonally distorted octahedral, and the Zn deriv. is tetrahedral. All of these compds. contain some
coordinating amine groups except the Zn complex in which no amine groups coordinate. Most likely, all of these
compds. contain sym. bridging O,O'-phosphinate groups. The thermal stabilities of these complexes are markedly
different from one another and appear to be dependent on the ligand-field stabilization energies but not on the chelation
of the amine groups.
Indexing
Inorganic Chemicals and Reactions (Section 78-7)
Concepts
Energy level splitting
crystal-field, of transition metal bis(phenylaminomethyl)phosphinate-bridged complexes, thermal stability in relation to
Substances
7439-96-5DP bis(phenylaminomethyl)phosphinate polymeric complexes
7440-02-0DP bis(phenylaminomethyl)phosphinate polymeric complexes
7440-48-4DP bis(phenylaminomethyl)phosphinate polymeric complexes
7440-50-8DP bis(phenylaminomethyl)phosphinate polymeric complexes
7440-66-6DP bis(phenylaminomethyl)phosphinate polymeric complexes
20384-96-7DP transition metal polymeric complexes
prepn. of
Abstract
Heating 284 g. PhNH2 and 50 g. (ClCH2)2PO2H 10 hrs. at 110-20 gave 63% (PhNHCH2)2PO2H (I) m. 180-1;
benzylamine similarly gave 72% (PhCH2NHCH2)2PO2HHCl, m. 220-2, while allylamine gave 33%
(CH2:CHCH2NHCH2)2PO2HHCl m. 200-2, and BuNH2 gave (BuNHCH2)2PO2HHCl, m. 240-2; propylamine gave
47% (PhNHCH2)2PO2HHCl, m. 238-9. I and CH2:CMeCOCl in CHCl3 in the presence of aq. NaOH gave in 1 hr. at 0,
followed by acidification with concd. HCl, and evapn. of org. layer and treatment with Et2O a ppt. of
[[PhN(COCMe:CH2)CH2]2PO2H]2CH2:CMeCO2Na, m. 239-41. Acidification with HCl gave [PhN(COCMe:CH2)CH2]2-
PO2HHCl m. 70-1;similarly obtained was [PhCH2N(COCMe:-CH2)CH2]2PO2H, m. 146-7, via
[PhCH2N(COCMe:CH2)CH2]2PO2Na, m. 272.5-3.5.
Indexing
Organometallic and Organometalloidal Compounds (Section 29)
Substances
1071708-06-9P
1087409-20-8P
21852-07-3P
SciFinder Page 62
21852-08-4P
21852-09-5P
21852-10-8P
21852-11-9P
21852-12-0P
21852-13-1P
23273-72-5P
prepn. of
Indexing
Organometallic and Organometalloidal Compounds (Section 29)
Substances
20384-96-7P
20384-97-8P
prepn. of
18. Sydonones. III. Reactions of lithium phenylsydone with acid nonmetallic chlorides
By: Suciu, Nausicaa; Mihai, Gheorghe
Source: Tetrahedron, Volume: 24, Issue: 1, Pages: 37-42, Journal, 1968, CODEN: TETRAB, ISSN: 0040-4020, DOI: 10.1016/0040-
4020(68)89005-2
Abstract
The reactions of lithium phenylsydnone (I) with the acid chloride of 3-phenylsydnonyl-4-carboxylic acid gave Q2CO (Q =
phenylsydnonyl) and Q2C(OH)H. I with acetyl, valerianyl, and benzoyl gave Q2C(OH)R (R = Me, Bu, and Ph). I with
oxalyl chloride gave QCOCOQ and QCH2COQ. I with PCl3 gave Q3P. I with POCl3 gave Q2P(O)OH. I with S2Cl2 and
SOCl2 gave Q2S and Q2SO, resp.
Indexing
Heterocyclic Compounds (More Than One Hetero Atom) (Section 28)
Concepts
Acid chlorides
reaction of, by 4-lithio-3-phenylsydnone
Reactant; Reactant or reagent
SciFinder Page 64
Substances
13973-33-6P
16796-16-0P
16796-20-6P
16796-22-8P
16796-23-9P
16796-25-1P
16796-26-2P
16796-27-3P
16796-28-4P
16796-29-5P
prepn. of