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Synthesis and Antibacterial Activity of Some Novel

Synthesis and Antibacterial Activity of Some Novel

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Published by IJRRR
A series of novel β-diketones/β-ketoesters
have been synthesized from 4-acetylaminobenzene
sulphonyl chloride. Desired compounds were prepared
by the reaction of [N4-(4-acetylamino) benzene
sulphonyl piperazinyl-N1-1-bromopropane] (III) with
β-diketone/β-ketoester to synthesize novel β-diketone/β-
ketoester derivatives of [N4-(4-acetylamino) benzene
sulphonyl piperazinyl-N1-1-bromopropane] (5a-d). All
the newly synthesized compounds were characterized
with IR and 1HNMR studies.
A series of novel β-diketones/β-ketoesters
have been synthesized from 4-acetylaminobenzene
sulphonyl chloride. Desired compounds were prepared
by the reaction of [N4-(4-acetylamino) benzene
sulphonyl piperazinyl-N1-1-bromopropane] (III) with
β-diketone/β-ketoester to synthesize novel β-diketone/β-
ketoester derivatives of [N4-(4-acetylamino) benzene
sulphonyl piperazinyl-N1-1-bromopropane] (5a-d). All
the newly synthesized compounds were characterized
with IR and 1HNMR studies.

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Published by: IJRRR on Dec 16, 2013
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12/16/2013

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1
 International Journal of Recent Research and Review, Vol. VI,Issue 3,December2013
ISSN 2277 –8322
Synthesis andAntibacterial ActivityofSomeNovel
-Diketones/
-Ketoesters, from 4-AcetylaminobenzeneSulphonylChloride
Pradeep Yadav*, Shalini Saingar,Ashutosh Sharma,Yogesh C. Joshi
 Department ofChemistry, UniversityofRajasthan, Jaipur,India
Email: pradeepyadav78@gmail.com
 Abstract:
A series of nove
l β
-diketone
s/β
-ketoesters have been synthesized from 4-acetylaminobenzene sulphonyl chloride. Desired compounds were prepared by the reaction of [N
4
-(4-acetylamino) benzene sulphonyl piperazinyl-N
1
-1-bromopropane] (III) with
β
-diket
one/β
-ketoester to synthesize nove
l β
-diket
one/β
-ketoesterderivativesof[N
4
-(4-acetylamino) benzene sulphonyl piperazinyl-N
1
-1-bromopropane] (5a-d). All the newly synthesized compounds were characterized with IR and
1
HNMR studies.
 Keywords
:
β
-diketone,
β
-ketoester,4-acetylaminobenzene sulphonyl chloride
.
Graphical Abstract:
NHCOCH
3
SOON N BNHCOCH
3
SOON NR
1
 R
2
O O
Sodium Methoxide
 R
1
R
2
OO
I. INTRODUCTIONThe quest for a more reliable and suitable drug is alwaysa fascinating and challenging task. A number ofmedicinescontainingsimpleheterocyclesocombination of different heterocyclic moieties have  beenusedthesedays.4-acetyleaminobenzenesulphonylchloride nucleus is well known for its antibacterial[1], antifungal[2], antitumer[3],neuroprotectiveand antiproliferativeproperties [4].Variousderivativesofpiperazinehavebeenfoundusefulasbrainprotecting[5],inthe diagnosisoschizophrenia[6],neurokinine[7-8],serotoninantagonistreceptor[9-11],heartmusclereceptor[12],andcholesterolreducingagents[13],HIV-Iinhibitors[14-15],dopaminetransporter[16-18],andsorbitoldehydrogenaseinhibitor[19-21].Bythecondensationof4-acetylaminobenzenesulphonylchloridewith piperazinealargenumberofmoleculeswereobtained,whichpossessvariousbiologicalpropertieslikeanti-inflammatory[22],antibiotic[23],anticancer[24],andinthetreatmentofErectileDysfunction[25].
β
-diketonesand
 
-ketoesterspossesmanybiological propertiessuchasanticarcinogenicproperties[26],antioxidant[27-29],antihistaminic[30],anticoagulant[31].Themedicinalpropertiesoftheabovementionedcompoundsencourageustosynthesizevariousnovelsubstituted
β
-diketoneand
β
-ketoestersasprecursorswitharylsulphonylchlorideofpiperazinederivative.II. EXPERMENTALAlltherecordedmeltingpointsareuncorrected.Purityofthecompoundswascheckedby thinlayer chromatographyusingsilicagelGasstationary phaseandbenzene:ethanol: ammonia(7:2:1)upper layerasmobilephase.IRspectrawererecordedonPerkin-Elmer infraredspectrometerbyusingKB pellets.
1
HNMRspectrawererecordedonmodel DRX-300 at300.13 MHzspectrometer, usingTMSas an internal standard. Thechemical shifts werereported i
n δ
 ppm.
General Method of Preparation of 4- Acetyleaminobenzene Sulphonyl Piperazine (II):
Piperazine(2g.0.023M)wastakeninpyridine(4
 
3
TableISubstitutionPatternandPhysicalPropertiesforNovel
β
-Diketone
-Ketoester,(5a-d)
Compno.
1
2
M.P.Yield5aCH3CH3175555bCH3C6H5180655cC6H5C6H5185705dCH3OC2H517050
TableII
Molecular Formula and Elemental analysis
for  Nove
l β
-Diketone
-Ketoester, (5a-d)
Com pno.Molecular FormulaElemental analysisCalculated (Found) %CHN5aC20H29N3O5S56.737(56.532)6.856(6.432)9.929 (9.725)5bC25H31N3O561.983(61.632)6.198(6.024)8.677(8.432)5cC30H33N3O5S65.813(65.432)6.032(6.011)7.678(7.532)5dC21H31N3O6S55.629(55.417)6.843(6.425)9.271(9.019)
TableIIISpectralDetailsofSynthesizedNovel
β
-Diketone
-Ketoester,(5a-d)
Comp. No.IRSpectra(KBr)cm
 –11
HNMRSpectra(CDCl3/DMSO-d6) (
δ
ppm)
5a3310(N-H),3020(Ar-H),2850(C-H),1700(C=O),1320(-SO
2
),1150 (-SO
2
)1.10(2H,q,CH
2
-CH
2
-CH
2
),1.40(2H,t,CH
2
-CH
2
-CH
2
),1.90(6H,s,COCH
3
),2.10(3H,sCH
3
CO),2.30(2H,t,CH
2
-CH
2
-CH
2
),2.80-2.36(8H,m,-CH
2
Piperazin),7.12(1H,s,-CH=),7.60-7.80(4H,dd,Ar-H),10.38(1H,s,NH)5b3320(N-H),3050(Ar-H),2940(C-H),1735(C=O),1325(-SO
2
),1175 (-SO
2
)1.12(2H,q,CH
2
-CH
2
-CH
2
),1.39(2H,t,CH
2
-CH
2
-CH
2
),1.91(6H,s,COCH
3
),2.11(3H,sCH
3
CO),2.32(2H,t,CH
2
-CH
2
-CH
2
),2.79-2.36(8H,m,-CH
2
Piperazin),7.18(1H,s,-CH=),7.40-7.79(9H,m,Ar-H),10.34(1H,s,NH)5c3330(N-H),3040(Ar-H)2900(C-H),1750(C=O),1351(-SO
2
),1176 (-SO
2
)1.09(2H,q,CH
2
-CH
2
-CH
2
),1.38(2H,t,CH
2
-CH
2
-CH
2
),2.12(3H,s,COCH
3
),2.30(2H,t,CH
2
-CH
2
-CH
2
),2.81-2.40(8H,m,-CH
2
Piperazin),7.15(1H,s,-CH=),7.31-7.80(14H,m,Ar-H),10.35(1H,s,NH)5d3350(N-H),3010(Ar-H),2860(C-H),1760(C=O),1350(-SO
2
),1130(-SO
2
),1.10(2H,q,CH
2
-CH
2
-CH
2
),1.41(2H,t,CH
2
-CH
2
-CH
2
),1.63(3H,t,-OCH
2
-

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