The TosMIC approach to 3-(oxazol-5-yl) indoles: Application to the synthesis of indole-based IMPDH inhibitors

被引：25

作者：

Dhar, TGM ^{[1
]}

Shen, ZQ ^{[1
]}

Fleener, CA ^{[1
]}

Rouleau, KA ^{[1
]}

Barrish, JC ^{[1
]}

Hollenbaugh, DL ^{[1
]}

Iwanowicz, EJ ^{[1
]}

机构：

[1] Bristol Myers Squibb Co, Pharmaceut Res Inst, Princeton, NJ 08543 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2002年 / 12卷 / 22期

关键词：

D O I：

10.1016/S0960-894X(02)00748-5

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A modified approach to the synthesis of 3-(oxazolyl-5-yl) indoles is reported. This method was applied to the synthesis of series of novel indole based inhibitors of inosine monophosphate dehydrogenase (IMPDH). The synthesis and the structure-activity relationships (SARs), derived from in vitro studies, for this new series of inhibitors is given. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：3305 / 3308

页数：4

共 19 条

[1] COLLART FR, 1988, J BIOL CHEM, V263, P15769
[2] COLLART FR, 1990, Patent No. 5665583
[3] Discovery of N-[2-[2-[[3-methoxy-4-(5-oxazolyl)phenyl]-amino]-5-oxazolyl]phenyl]-N-methyl-4-morpholineacetamide as a novel and potent inhibitor of inosine monophosphate dehydrogenase with excellent in vivo activity
Dhar, TGM
Shen, ZQ
Guo, JQ
Liu, CJ
Watterson, SH
Gu, HH
Pitts, WJ
Fleener, CA
Rouleau, KA
Sherbina, NZ
McIntyre, KW
Witmer, MR
Tredup, JA
Chen, BC
Zhao, RL
Bednarz, MS
Cheney, DL
MacMaster, JF
Miller, LM
Berry, KK
Harper, TW
Barrish, JC
Hollenbaugh, DL
Iwanowicz, EJ
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (11) : 2127 - 2130
[4] Novel diamide-based inhibitors of IMPDH
Gu, HH
Iwanowicz, EJ
Guo, JQ
Watterson, SH
Shen, ZQ
Pitts, WJ
Dhar, TGM
Fleener, CA
Rouleau, K
Sherbina, NZ
Witmer, M
Tredup, J
Hollenbaugh, D
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (09) : 1323 - 1326
[5] SYNTHESIS OF 2,5-DISUBSTITUTED OXAZOLES FROM ALDEHYDES AND N-(TOSYLMETHYL)IMINO SYNTHONS - APPLICATION TO THE SYNTHESIS OF PIMPRININE ANALOGS
HOUWING, HA
WILDEMAN, J
VANLEUSEN, AM
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1981, 18 (06) : 1133 - 1139
[6] IMP DEHYDROGENASE, AN ENZYME LINKED WITH PROLIFERATION AND MALIGNANCY
JACKSON, RC
WEBER, G
MORRIS, HP
[J]. NATURE, 1975, 256 (5515) : 331 - 333
[7] Jain J, 2001, J PHARM SCI-US, V90, P625, DOI 10.1002/1520-6017(200105)90:5<625::AID-JPS1019>3.0.CO
[8] 2-1
[9] Jayaram HN, 1999, CURR MED CHEM, V6, P561
[10] ISOLATION, CHARACTERIZATION AND SYNTHESIS OF PIMPRININE, PIMPRINETHINE AND PIMPRINAPHINE, METABOLITES OF STREPTOVERTICILLIUM-OLIVORETICULI
KOYAMA, Y
YOKOSE, K
DOLBY, LJ
[J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1981, 45 (05): : 1285 - 1287

← 1 2 →