DESAIN MOLEKUL, SINTESIS DAN UJI IN SILICO ANALOG PARASETAMOL

DRS. HARI PURNOMO, M.S.,APT

Universitas Gadjah Mada, 2016 | Diunduh dari http://etd.repository.ugm.ac.id/

DAFTAR PUSTAKA

Adnan AZ, Manjang Y, Rozani F, 1993, “Sintesis Senyawa Analgetika Baru : 2,6
dimetil 4 hidroksi acetanilida”, dalam “Prosiding Seminar nasional Hasil
Penelitian Perguruan Tinggi”, Buku IV, hal. 15-27.

Anthony L. et all,2007, Synthesis and in vivo evaluation of non-hepatotoxic

acetaminophen analogs. Journal Bioorganic and Medicinal Chemistry 15
(2007) 2206–2215

Block,J.H., and Beale Jr, J.M., 2004, Wilson and Gisvold’s Textbook of Organic
Medicinal and Pharmaceutical Chemistry, eleventh ed, Lippincotts
Williams and Wilkins, Philadelphia

Caterina M J, Schumacher M A, Tominaga MRosen T A,Levine J D,Julius

D(1997) Nature (London) 389:816–824.

Caterina M J, Rosen T A,Tominaga M, Brake A J,Julius D(1999) Nature

(London) 398:441–446.

Caterina M J, Leffler A,Malmberg A B, Martin W J,Trafton J,Petersen-Zeitz K R,

Koltzenburg M, Basbaum A I, Julius D,(2000) Science 288:306–313.

Chandrasekharan NV, Dai H, Roos KL, et al (2002). "COX-3, a cyclooxygenase-

1 variant inhibited by acetaminophen and other analgesic/antipyretic
drugs: cloning, structure, and expression". Proc. Natl. Acad. Sci. U.S.A. 99
(21): 13926–31. doi:10.1073/pnas.162468699. PMID 12242329

Chen ,YC., 2015, Beware of Docking, Trends in Pharmacological Sciences

(Opinion), Vol 34, No.2

Clark, AJ., The reaction between acetyl choline and muscle cells.J Physiol. 1926
Aug 6; 61(4):530-46.

Conforth, JW, 1994, The Trouble With Synthesis, Aldrchimica Acta, Vol.27,
No.3, 71-77.

Corey, EJ and Cheng, XM, 1989, The Logic of Chemical Synthesis, John Wiley
and Sons, NY-Singapore, 1-3.

Davis, T.L., and Blanchard, K.C., 1923, The Urea Dearrangement II, Organic
Syntheses, 3, 95.

Davis J B, Gray J, Gunthorpe M J,Hatcher J P, Davey P T,Overend P, Harries M

H, Latcham J,Clapham C, Atkinson K,et al.,2000, Nature (London)
405:183–187

142
 DESAIN MOLEKUL, SINTESIS DAN UJI IN SILICO ANALOG PARASETAMOL
DRS. HARI PURNOMO, M.S.,APT
Universitas Gadjah Mada, 2016 | Diunduh dari http://etd.repository.ugm.ac.id/

.
DepKes RI, 2014, Farmakope Indonesia, Ed.V, Jakata

Doerge, R.F., 1982, ’Wilson and Gisvold’s Textbooki of Organic Medicinal and
Pharmaceutical Chemistry‘, 8th ed., p.85, J.P. Lippincott, Philadelphia.

Dudley H. Williams and Ian Fleming, 1995, Spectroscopic Methods in Organic

Chemistry (5th Ed), The McGraw-Hill Companies, London – Toronto.

Ebel, S., 1979, Obat Sintetik. Buku Ajar dan Buku Pegangan, diterjemahkan oleh:
Mathilda B Widiianto, Gadjah Mada University Press, Yogyakarta.

Febriyanto, E., 2009, Sintesis Senyawa 4-t-butil-N-(4’-hidroksifenil)benzamida

dan Uji Aktivitas Analgesiknya Pada Mencit (Mus musculus), Skripsi,
Fakultas Farmasi Universitas Airlangga.

Gaddum JH.1937, J. Physiol. 1937;89:144.

Gilman, A G, 1992,’ Goodman and Gilman’s The Pharmacological Basis of

Therapeutics’, 8 ed, vol 2, MacMillan Publishing Co, New York.

Hesti P D.,2014,Uji Hepatotoksis senyawa MH2011 pada Mencit Jantan Galur

BALB/C Dengan Pembanding Parasetamol, Skripsi Fakultas Farmasi
UGM,Yogyakarta

Hinz,B., Cheremina,O.,Brune,K.,2008,Acetaminophen (paracetamol) is a

selective cyclooxygenase-2 inhibitor in man,The FASEB Journal,vol 22.

Hinz,B., Brune,K.,2011,Paracetamol and cyclooxygenase inhibition: is there

a cause for concern?, Ann Rheum Dis 2012;71:20–25

http://www.chemaxon.com/marvin/download-user.html

http://www.yasara.org/viewdl.htm

http://www.tcd.uni-konstanz.de/research/plants.php

http://www.pendrivelinux.com/run-pendrivelinux-2009-in-windows/
Huang, N., Shoichet,BK., and Irwin, J J.,2006, Benchmarking Sets For Molecular
Docking, J. Med. Chem, 49, 6789-6801

Istyastono, E. P. , Pelatihan Pemodelan Molekul, USD – MOLMOD.ORG,

Yogyakarta,13-15 Januari 2010.

143
 DESAIN MOLEKUL, SINTESIS DAN UJI IN SILICO ANALOG PARASETAMOL
DRS. HARI PURNOMO, M.S.,APT
Universitas Gadjah Mada, 2016 | Diunduh dari http://etd.repository.ugm.ac.id/

Jenie, U.A., Kardono. L.B.S, Hanafi, M., Rumampuk, R.J. dan Darmawan, A.,
2014, Teknik Modern Spektroskopi NMR, Teori dan Aplikasi dalam
Elusidasi Struktur Molekul Organik (Edisi Pertama), LIPI Press.

Jerman, C., 2009, Acetaminophen modification in an attempt to lessen the liver

damage while retaining drug function, cluster8, Cosmos, UC Davis

Kis, B., Snipes, J.A., Busija, D.W. (2005). "Acetaminophen and the
cyclooxygenase- 3puzzle: sorting out facts, fictions, and uncertainties". J.
Pharmacol. Exp. Ther. 315 (1): 1–7. doi:10.1124/jpet.105.085431.
PMID 15879007.
Klaassen, C.D., 2001, Casarett And Doull’s : Toxicology The Basic Science Of
Poisons, Sixth Ed., McGraw-Hill Inc., New York.

Korb, O., Stützle, T , Exner, T. E.,2006, "PLANTS: Application of Ant Colony

Optimization to Structure-Based Drug Design" Lecture Notes in Computer
Science 4150, 247-258 (2006).

Korb, O., Stützle, T , Exner, T. E., 2007, "An ant colony optimization approach to
flexible protein-ligand docking" Swarm Intell. 1, 115-134 (2007).

Korb, O., Stützle, T , Exner, T. E.,2009, "Empirical Scoring Functions for

Advanced Protein-Ligand Docking with PLANTS" J.Chem.Inf.Model. 49,
84-96 (2009).

Korb, O., Stützle, T , Exner, T. E., 2010, "NMR-guided Molecular Docking of a

Protein-Peptide Complex Based on Ant Colony Optimization"
ChemMedChem 5, 1001-1006 (2010).
Lawson, J.A., Farhoo, A., Hopper, R.D., Bajt, M.L.,andJaeschke, H., 2000, The
Hepatic Inflammatory Response After Acetaminophen Overdose : Role Of
Neutrophils, Toxicol Sci., 54, 509-516.

McLafferty, M.F, 1980, Interpretation of Mass Spectra (3rd Ed), University

Science Books.

Molecular Operating Environment (MOE).2010.10; Chemical Computing Group

Inc, 1010 Sherbooke St. West, Suite #910, Montreal,QC, Canada, H3A
2R7,2010.

Molecular Operating Environment (MOE).2008.10; Chemical Computing Group

Inc, 1010 Sherbooke St. West, Suite #910, Montreal,QC, Canada, H3A
2R7,2008

Nogrady, T., 2005, Medicinal Chemistry : A Biochemical Approach, Oxford

University Press, Oxford

144
 DESAIN MOLEKUL, SINTESIS DAN UJI IN SILICO ANALOG PARASETAMOL
DRS. HARI PURNOMO, M.S.,APT
Universitas Gadjah Mada, 2016 | Diunduh dari http://etd.repository.ugm.ac.id/

Pavia,D.L., Lampman, G.M., andKrizJr, G.S.., 2001, Introduction to

Spectroscopy, W. B. Saunders Company, Philadelphia.

Pudjono, Susilowati,S.S.,dan Rehana, 2011,Pemodelan senyawa turunan p-

aminofenolsebagai analgetik anti-inflamasi berdasarkanhubungan struktur
dan aktivitas biologisnya, Majalah Farmasi Indonesia, 22(2), 144 – 150,
2011

Purnomo, H, Masitoh S. P, Supardjan A.M., 2009,”Disain Molekul 1,3 bis(4-

hidroksifenil)urea Sebagai Analgetika Kompetitor Parasetamol” Kongres
Nasional ISFI XVIII- Kongres Ilmiah ISFI XVII, ISFI, Jakarta, 7-9 Des
2009.

Purnomo, H., 2011, Kimia Komputasi: Penambatan Molekul PLANTS,Penerbit

Pustaka Pelajar, Yogyakarta.

Purnomo, H,2012, Mendesain Molekul Obat sebagai Analgetika, Penerbit

Pustaka Pelajar, Yogyakarta.

Purnomo,H, 2011 “Analisis Mekanisme Kerja in Siliko Senyawa HP2009 [1,3

bis(para-hidroksifenil)urea]:Docking HP2009 Terhadap COX-1 dan COX-
2 dengan PLANTS”, dalam Prosiding Seminar Nasional Eight Star
Performance Pharmacist, Program Pascasarjana Fakultas Farmasi UGM,
Yogyakarta, hal.190-203,2011

Qureshi, M.A., Khan, T.J., Qureshi, M.S., 2011,Molecular Docking helps

inunderstanding the action of Paracetamol (acetaminophen): an approach
towards finding a better COX2 inhibitor. RMJ. 2011; 36(3): 238-241.

Silverman, R.B., 1992, The Organic Chemistry ofDrug Design and Drug Action,
Academic Press., San Diego.

Silverstein, R.M., Bassler,G.C. and Morrill,T.C., 1991., Spectrometric

Identification of Organic Compounds (5th Ed), John Wiley and Sons,
Inc., New York – Singapore.

Silverstein, R.M. and Francis, X., Webster, F.X., 1996. Spectrometric

Identification of Organic Compounds (6th Ed), Printed in USA.

Siswandono dan Soekardjo, B., 1995, Kimia Medisinal, jilid 1, Airlangga

University Press, Surabaya.

Siswandono dan Soekardjo, B., 2000, Kimia Medisinal, jilid 2, Airlangga

University Press, Surabaya.

145
 DESAIN MOLEKUL, SINTESIS DAN UJI IN SILICO ANALOG PARASETAMOL
DRS. HARI PURNOMO, M.S.,APT
Universitas Gadjah Mada, 2016 | Diunduh dari http://etd.repository.ugm.ac.id/

Sofiana,2013, Uji Aktivitas Analgetik Senyawa MH2011 Pada mencit Jantan

Galur BALB/C Dengan Metode Geliat ( Writhing Test), Skripsi Fakultas
Farmasi UGM, Yogyakarta

Streitwieser, A. And Heatcook,C.H., 1976,’Introduction to Organic Chemistry,

MacMillan Publishing Co. Inc.,United States.

Sudewi M K, 2010, Aktivitas Analgetik Dan Tinjauan Efek Samping

Hepatotoksik Senyawa Baru 1,3-Bis(4-Hidroksi-Fenil)-Urea Sebagai
Kompetitor Parasetamol, Skripsi Fakultas Farmasi UGM, Yogyakarta.

Thoolen, B., Maronpot, R.R., Harada, T., Nyska, A., Rousseaux, C., Nolte, T.,
Malarkey, D.E., Kaufmann, W., Kuttler, K., Deschl, U., Nakae, D.,
Gregson, R., Vinlove, M.P., Brix, A.E., Singh, B., Belpoggi, F.,and Ward,
J.M., 2010, Proliferative And NonproliferativeLessions Of The RatAnd
Mouse Hepatobiliary System, ToxicolPathol, 38, 5S-81S.

Vaccarino, A.L., Paul, D.. Mukherjee,P.K., Rodrı´guez de Turco,E.B.,

Marcheselli,V.L., Xu, L., Trudell,M.L., Minguez,J.M., Matı´a,M.P.,
Sunkel,C., Builla,J.A., . Bazan, N.G., 2006, Synthesis And In Vivo
Evaluation Of Non-HepatotoxicAcetaminophen Analogs, Bioorganic and
Medicinal Chemistry 15 (2007) 2206–2215

Van de Straat R, De Vries J, Kulkens T et al, 1986, “Paracetamol, 3- monoalkyl

and 3,5 dialkyl derivates”, Biochem. Pharmacol,35; p. 3693-3699.

Van de Straat, R, 1987,’Paracetamol-Induced Hepatotoxicity and Prevention

byStructural Modification- A Molecular Toxicological Study’,
Dissertation, Free University Press, Amsterdam.p.37-38.

Warren, S.,1992, Workbook for Organic Synthesis The Disconnection Approach,

John Wiley and Sons, Chichester, Singapore.

Warren, S. and Wyatt, P.,2008, Organic Synthesis The Disconnection

Approach,(2nd Ed), John Wiley and Sons, Chichester, Singapore.

Warrent,G.L., Andrews,C.W.,Capelli, A.M., Clarke ,B. et al., 2006, J. Med.

Chem 49,5912-5931

Williams, D.H. and Fleming, I., 1995, Spectroscopic Methods in Organic

Chemistry (5th Ed),The McGraw-Hill Companies.

Woolf, C. J., and Salter, M. W., 2000,Science 288:1765–1768.

146