Bioisosterism: A Rational Approach in Drug Design

Chemical Reviews - Tập 96 Số 8 - Trang 3147-3176 - 1996
George Patani1, Edmond J. LaVoie1
1Department of Pharmaceutical Chemistry, College of Pharmacy, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08855-0789

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Tài liệu tham khảo

Martin Y. C, 1981, J. Med. Chem., 24, 237

Friedman H. L, 1951, NASNRS, 206, 358

Thornber C. W, 1979, Chem. Soc. Rev., 8, 580, 10.1039/cs9790800563

Lipinski C. A, 1986, Annu. Rep. Med. Chem., 21, 291

Burger A, 1991, Prog. Drug Res., 37, 371

Hansch C, 1981, Drug Dev. Res., 1, 267, 10.1002/ddr.430010403

Langmuir I., 1919, J. Am. Chem. Soc., 41, 1559, 10.1021/ja02231a010

Seifriz W, 1948, Science, 107, 16, 10.1126/science.107.2766.15

Grimm H. G, 1925, Electrochem., 31, 480

Grimm H. G, 1929, Naturwissenschaften, 17, 564, 10.1007/BF01505901

Erlenmeyer H., 1932, Helv. Chim. Acta, 15, 1186

Burger, 1970, Medicinal Chemistry, 3, 80

Pauling, 1940, The Nature of the Chemical Bond, 2, 189

Zhang, 1994, J. Med. Chem., 34, 757

Phillipps G. H., 1994, J. Med. Chem., 37, 3729, 10.1021/jm00048a008

Tonelli G., 1965, Endocrinology, 77, 634, 10.1210/endo-77-4-625

Skagerberg B., 1989, Quant. Struct.-Act. Relat., 8, 38, 10.1002/qsar.19890080105

Elguero J., 1976, Advances in Heterocyclic Chemistry

Fusco T., 1948, Gazz. Chim. Ital., 78, 951

Kelley J. L., 1989, J. Med. Chem., 32, 1024, 10.1021/jm00125a016

Bennett L. L., 1963, Cancer Res., 23, 1580

LePage G. A., 1964, Cancer Res., 24, 840

Atwal K. S., 1990, J. Med. Chem., 33, 2635, 10.1021/jm00171a045

Hine, 1962, Physical Organic Chemistry, 28

Kimmey M. B., 1992, J. Rheumatol., 19, 73

Peskar B. M, 1977, Biochem. Biophys. Acta, 487, 314, 10.1016/0005-2760(77)90007-8

Unangst P. C., 1994, J. Med. Chem., 37, 328, 10.1021/jm00028a017

Vane J. R, 1971, Nature (New Biol.), 231, 235, 10.1038/newbio231235a0

Huheey J. E, 1965, J. Phys. Chem., 69, 3291, 10.1021/j100894a011

Fournie-Zaluski M. C., 1994, J. Med. Chem., 37, 1083, 10.1021/jm00034a005

Bott G., 1980, J. Am. Chem. Soc., 102, 5626, 10.1021/ja00537a036

Chae M., 1995, J. Med. Chem., 38, 365, 10.1021/jm00002a018

Takemoto T., 1994, J. Med. Chem., 37, 25, 10.1021/jm00027a003

Pendergast W., 1993, J. Med. Chem., 36, 2291

Roberts D, 1966, Biochemistry, 5, 3548

Dev I. K., 1989, J. Biol. Chem., 264, 19137

Saunders J., 1989, Trends Pharmacol. Sci., 75

Rogers E. F., 1953, J. Am. Chem. Soc., 75, 2999

Büchi V. J., 1971, Arzneim. Forsch., 7, 1017

Ahmad A., 1985, Cell. Immunol., 94, 280, 10.1016/0008-8749(85)90104-2

Li, 1995, J. Med. Chem., 38, 1461

Wrobel J., 1989, J. Med. Chem., 32, 2500, 10.1021/jm00131a012

Bonnet P. A., 1993, J. Med. Chem., 36, 653, 10.1021/jm00058a001

Walsh D. A., 1989, J. Med. Chem., 32, 118, 10.1021/jm00121a022

Wheland G., 1955, Resonance in Organic Chemistry, 784

Michne W. F., 1995, J. Med. Chem., 38, 2569

Counsell R. E., 1965, J. Med. Chem., 8, 48, 10.1021/jm00325a011

Lide D., 1990, Handbook of Chemistry and Physics, 71, 5

Saeed A., 1994, J. Med. Chem., 37, 3251, 10.1021/jm00046a008

Yamakawa T., 1990, J. Med. Chem., 33, 1437, 10.1021/jm00167a024

Hunt R., 1925, J. Pharmacol. Exp. Ther., 25, 355

Grisar J. M., 1995, J. Med. Chem., 38, 2886

Eydoux F., 1995, Bioorg. Med. Chem. Lett., 5, 944, 10.1016/0960-894X(95)00147-L

Alousi A. A., 1982, Pharmacological and Biochemical Properties of Drug Substances, 3, 147

Alousi A. A., 1983, J. Cardiovasc. Pharmacol., 5, 811

Singh B., 1991, J. Heterocycl. Chem., 28, 937

Singh B., 1994, J. Med. Chem., 37, 254, 10.1021/jm00028a007

Brewer M. D., 1989, J. Med. Chem., 32, 2062, 10.1021/jm00129a007

Forest M., 1992, J. Med. Chem., 35, 172, 10.1021/jm00079a022

Ahluwalia G. S., 1987, Concepts, Clinical Developments, and Therapeutic Advances in Cancer Chemotherapy

Franchetti P., 1990, J. Med. Chem., 33, 2852, 10.1021/jm00172a027

Lakhan, R.; Ternai, B InAdvances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Ed.; Academic Press:  New York, 1974; Vol. 17, p 173.

Uno T., 1990, J. Med. Chem., 33, 2932

Yoshino K., 1989, J. Med. Chem., 32, 1532, 10.1021/jm00127a021

Dunn D. L., 1981, J. Pharm. Sci., 70, 446, 10.1002/jps.2600700427

Sauerberg P., 1989, J. Med. Chem., 32, 1326, 10.1021/jm00126a030

Sun Q., 1995, J. Med. Chem., 38, 3644

Wang J. C., 1985, Annu. Rev. Biochem., 54, 697

Dodds E. C., 1938, Nature (London), 141, 248, 10.1038/141247b0

Walton E., 1943, Nature, 151, 306, 10.1038/151305a0

Blanchard E. W., 1943, Endocrinology, 32, 307, 10.1210/endo-32-4-307

Baker B. R, 1943, J. Am. Chem. Soc., 65, 1572, 10.1021/ja01248a036

Macchia B., 1985, J. Med. Chem., 28, 160, 10.1021/jm00380a001

Balsamo A., 1992, Eur. J. Med. Chem., 27, 764, 10.1016/0223-5234(92)90110-M

Balsamo A., 1992, XVIIth National Meeting of the Italian Chemical Society

Triggle D., 1981, Burger's Medicinal Chemistry

Weiner, 1980, The Pharmacological Basis of Therapeutics

Petrongolo C., 1977, J. Med. Chem., 20, 1653, 10.1021/jm00222a021

Macchia B., 1980, Eur. J. Med. Chem., 15, 520

Macchia B., 1990, J. Med. Chem., 33, 1430, 10.1021/jm00167a023

Balsamo A., 1989, J. Med. Chem., 32, 1401

Balsamo A., 1994, Farmaco, 49, 82

Macchia B., 1994, J. Med. Chem., 37, 1525, 10.1021/jm00036a018

MacLeod A. M., 1994, J. Med Chem., 37, 1274, 10.1021/jm00035a006

MacLeod A. M., 1995, J. Med. Chem., 38, 941

Lewis R. T., 1995, J. Med. Chem., 38, 933, 10.1021/jm00006a011

Freedman S. B., 1990, Br. J. Pharmacol., 101, 580, 10.1111/j.1476-5381.1990.tb14123.x

Eglen R. M., 1992, Naunyn-Schmiedeberg's Arch. Pharmacol., 345, 381, 10.1007/BF00176613

Sauerberg P., 1991, J. Med. Chem., 34, 692, 10.1021/jm00106a033

Saunders J., 1990, J. Med. Chem., 33, 1138, 10.1021/jm00166a008

Street L. J., 1990, J. Med. Chem., 33, 2697, 10.1021/jm00172a003

Freedman S. B., 1990, Eur. J. Pharm., 187, 199, 10.1016/0014-2999(90)90006-R

Sauerberg P., 1986, J. Med. Chem., 29, 1009, 10.1021/jm00156a018

Krogsgaard-Larsen, P.; Pedersen, H.; Falch, E. Eur. Pat. Appl. 336 555, 11 Oct 1989.

Sauerberg P., 1992, J. Med. Chem., 35, 2283, 10.1021/jm00090a019

Moltzen E. K., 1994, J. Med. Chem., 37, 4099, 10.1021/jm00050a006

MacDonald R. L., 1994, Annu. Rev. Neurosci., 17, 602, 10.1146/annurev.ne.17.030194.003033

Bonanno G., 1993, Trends Pharmacol. Sci., 14, 261, 10.1016/0165-6147(93)90124-3

Krogsgaard-Larsen P., 1994, Design and Therapeutic Prospects. J. Med. Chem., 37, 2505

Krogsgaard-Larsen P., 1975, J. Neurochem., 25, 809

Krogsgaard-Larsen P., 1979, J. Neurochem., 32, 1724, 10.1111/j.1471-4159.1979.tb02284.x

Krogsgaard-Larsen P., 1985, Prog. Med. Chem., 22, 120

Krogsgaard-Larsen P., 1988, Adv. Drug. Res., 17, 456

Krogsgaard-Larsen P., 1977, Nature (London), 268, 55, 10.1038/268053a0

Krogsgaard-Larsen P., 1983, J. Med. Chem., 26, 900, 10.1021/jm00360a020

Arnt J., 1979, Brain Res., 177, 400, 10.1016/0006-8993(79)90793-5

Byberg J. R., 1987, Drug Des. Delivery, 1, 274

Kristiansen U., 1991, Br. J. Pharmacol., 104, 90, 10.1111/j.1476-5381.1991.tb12389.x

Buur J. R. B., 1993, Drug Des. Discovery, 10, 229

Frølund B., 1995, J. Med. Chem., 38, 3296, 10.1021/jm00017a014

Johnson R. L., 1986, J. Med. Chem., 29, 2104, 10.1021/jm00160a052

Chiu S., 1981, Peptides, 2, 111, 10.1016/S0196-9781(81)80019-8

Srivastava L. K., 1988, J. Neurochem., 50, 968, 10.1111/j.1471-4159.1988.tb03005.x

Yu K. L., 1988, J. Med. Chem., 31, 1436

Sreenivasan U., 1993, J. Med. Chem., 36, 263, 10.1021/jm00054a010

Subasinghe N. L., 1993, Med. Chem., 36, 2361, 10.1021/jm00068a013

Hansch C., 1995, Exploring QSAR. Fundamentals and Applications in Chemistry and Biology

Larsen, A. A.; Lish, P. M. A New Bioisostere:  AlkylsulphonamidophenethanolaminesNature1964,203, 1283.

Larsen A. A., 1967, J. Med. Chem., 10, 472, 10.1021/jm00315a037

Kaiser C., 1974, J. Med. Chem., 17, 57, 10.1021/jm00247a012

Ross S. B, 1963, Acta Pharmacol. Toxicol., 20, 267, 10.1111/j.1600-0773.1963.tb01744.x

Clark R. D., 1987, J. Pharm. Sci., 76, 415

Seiler M. P., 1982, Vivo Regulation of Muscarinic Cholinergic Receptors in Embryonic Chick Brain. Mol. Pharmacol., 22, 289

McDermed J. D., 1976, J. Med. Chem., 19, 549, 10.1021/jm00226a021

Tedesco J. T., 1979, Mol. Pharmacol., 16, 381

Asselin A., 1986, J. Med. Chem., 29, 654

Rosei E. A., 1977, Am. Heart J., 93, 125, 10.1016/S0002-8703(77)80182-8

Brogden R. N., 1978, Drugs, 15, 270

Asselin A. A., 1986, J. Med. Chem., 29, 1015, 10.1021/jm00156a020

Hashiguchi H., 1977, Mol. Pharmacol., 13, 367

Inoue S., 1975, Chem. Pharm. Bull., 23, 2677

Norton S. J., 1967, J. Med. Chem., 10, 963, 10.1021/jm00317a053

Harris R. N. L., 1977, Austr. J. Chem., 30, 655

Hansch C., 1979, Substituent Constants For Correlation Analysis in Chemistry and Biology

Gapinski D. M., 1990, J. Med. Chem., 33, 2807, 10.1021/jm00172a020

Brain S. D., 1984, Br. J. Pharmacol., 83, 317, 10.1111/j.1476-5381.1984.tb10148.x

Brain S. D., 1984, J. Invest. Dermatol., 83, 73, 10.1111/1523-1747.ep12261712

Sharon P., 1984, Gastroenterology, 86, 460, 10.1016/S0016-5085(84)80015-3

Peskar B. M., 1985, Gut, 26, A542

Calhoun W., 1995, J. Med. Chem., 38, 1481, 10.1021/jm00009a008

Chihiro M., 1995, J. Med. Chem., 38, 358, 10.1021/jm00002a017

Hanna N. B., 1994, Alkyl Purines and Purine Ribonucleosides. J. Med. Chem., 37, 183

Shah S. K., 1990, J. Med. Chem., 33, 2535, 10.1021/jm00171a031

Rizzi J. P., 1989, J. Med. Chem., 32, 1213, 10.1021/jm00126a011

Muchowski J. M., 1989, J. Med. Chem., 32, 1207, 10.1021/jm00126a010

Sarges R., 1986, Metabolism, 35, 104, 10.1016/0026-0495(86)90196-4

Sarges R., 1988, J. Med. Chem., 31, 243, 10.1021/jm00396a037

DeFronzo R. A, 1988, Diabetes, 37, 687, 10.2337/diab.37.6.667

Turner R. C., 1988, Baillieres Clin. Endocrinol. Metab., 2, 342, 10.1016/S0950-351X(88)80035-1

Goldman J. M, 1989, Drugs Today, 25, 695

Kolterman O. G., 1983, Am. J. Med., 74, 101, 10.1016/0002-9343(83)90655-1

Dow R. L., 1991, Potent Hypoglycemic Agents. J. Med. Chem., 34, 1544

Hulin B., 1992, J. Med. Chem., 35, 1864, 10.1021/jm00088a022

Yee Y. K., 1990, J. Med. Chem., 33, 2451

Domagk G, 1935, Deut. Med. Wochschr., 61, 3

Tréfouel J., 1935, Compt. Rend. Soc. Bio., 120, 758

Anand, 1979, Burger's Medicinal Chemistry, 4

Bock M. G., 1994, J. Med. Chem., 37, 724

Hammarstrom S., 1979, Biochem. Biophys. Res. Commun., 91, 1266, 10.1016/0006-291X(79)91203-8

Schaaf T. K., 1979, J. Med. Chem., 22, 1340, 10.1021/jm00197a012

Guida W. C., 1994, J. Med. Chem., 37, 1114, 10.1021/jm00034a008

Spatola A., 1983, Chemistry and Biochemistry of Amino Acids, Peptides and Proteins, 357

Giannis A., 1993, Angew. Chem., Int. Ed. Engl., 32, 1267, 10.1002/anie.199312441

Boyd S. A., 1994, J. Med. Chem., 37, 3007

Andersen K. E., 1994, Eur. J. Med. Chem., 29, 399, 10.1016/0223-5234(94)90065-5

Carroll F. I., 1993, J. Med. Chem., 36, 2890, 10.1021/jm00072a007

Street L. J., 1993, J. Med. Chem., 36, 1538, 10.1021/jm00063a003

Dunbar P. G., 1993, J. Med. Chem., 36, 847, 10.1021/jm00059a008

Adelstein G. W., 1976, A Novel Series of Antidiarrheal Agents J. Med. Chem., 19, 1225

Tully W. R., 1991, J. Med. Chem., 34, 2067, 10.1021/jm00111a021

Orlek B. S., 1991, J. Med. Chem., 34, 2735, 10.1021/jm00113a009

Thompson S. K., 1994, Bioorg. Med. Chem. Lett., 4, 2446, 10.1016/S0960-894X(01)80406-6

Kim B. H., 1992, Tetrahedron Lett., 33, 6814

Jones C. F. R., 1988, Tetrahedron Lett., 29, 3856

Clercq E. D, 1995, Med. Chem., 38, 2517, 10.1021/jm00014a001

Suckling K. E., 1985, J. Lipid Res., 26, 671, 10.1016/S0022-2275(20)34322-4

Sliskovic D. R., 1991, Trends Pharmacol. Sci., 11, 199

Roark W. H., 1993, J. Med. Chem., 36, 1668, 10.1021/jm00063a016

Kagechika H., 1989, J. Med. Chem., 32, 2296

Kagechika H., 1984, Chem. Pharm. Bull., 32, 4212, 10.1248/cpb.32.4209

Kagechika H., 1988, J. Med. Chem., 31, 2192, 10.1021/jm00119a021

Kagechika H., 1986, Chem. Pharm. Bull., 34, 2278, 10.1248/cpb.34.2275

Shudo K., 1985, Chem. Pharm. Bull., 33, 407, 10.1248/cpb.33.404

Kagechika H., 1989, J. Med. Chem., 32, 840

Kagechika H., 1985, Chem. Pharm. Bull., 33, 5600, 10.1248/cpb.33.5597

Katsura Y., 1994, J. Med. Chem., 37, 66, 10.1021/jm00027a007

Orr F. G., 1995, J. Med. Chem., 38, 3856

el Kouni M. H., 1993, Cancer Res., 53, 3693

Chu M. Y. W., 1984, Cancer Res., 44, 1856

Tokarski J. S., 1994, J. Med. Chem., 37, 3654, 10.1021/jm00047a021

Gertz B. J., 1988, Neurol. Neurobiol., 47, 342