Structure-activity relationship for a series of 2-substituted 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indoles:: Potent subtype-selective inhibitors of N-methyl-D-aspartate (NMDA) receptors

被引：6
|
作者：
Tamiz, AP
Whittemore, ER
Woodward, RM
Upasani, RB
Keana, JFW
机构：
[1] CoCensys Inc, Irvine, CA 92618 USA
[2] Univ Oregon, Dept Chem, Eugene, OR 97403 USA
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1999年 / 9卷 / 11期
关键词：
D O I：
10.1016/S0960-894X(99)00248-6
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
series of 2-substituted 1,2,3,4-tetrahydro-9H-pyrido[3,4-b] indoles was synthesized as potential antagonists for the NR1A/2B subtype of N-methyl-D-aspartate (NMDA) receptors. Assayed by electrical recording under steady-state conditions, 7-hydroxy-2-(4-phenylbutyl)-1,2,3,4-tetrahydropyrido-[3,4-b]indole (30) was the most potent compound in the series having an IC50 value of 50 nM at the MR1A/2B receptors. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：1619 / 1624
页数：6
相关论文
共 50 条
  • [1] Structure-activity relationships for a series of bis(phenylalkyl)amines: Potent subtype-selective inhibitors of N-methyl-D-aspartate receptors
    Tamiz, AP
    Whittemore, ER
    Zhou, ZL
    Huang, JC
    Drewe, JA
    Chen, JC
    Cai, SX
    Weber, E
    Woodward, RM
    Keana, JFW
    JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (18) : 3499 - 3506
  • [2] Synthesis of 1-aryl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indoles (1,2,3,4-tetrahydro-β-carbolines) under high pressures
    Agafonov, NE
    Dudin, AV
    Preobrazhenskii, AA
    Zhulin, VM
    RUSSIAN CHEMICAL BULLETIN, 2001, 50 (03) : 560 - 562
  • [3] Synthesis of 1-aryl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indoles (1,2,3,4-tetrahydro-β-carbolines) under high pressures
    N. E. Agafonov
    A. V. Dudin
    A. A. Preobrazhenskii
    V. M. Zhulin
    Russian Chemical Bulletin, 2001, 50 : 560 - 562
  • [4] STEREOCHEMICAL ASSIGNMENT OF 3-(METHOXYCARBONYL)-1-SUBSTITUTED-1,2,3,4-TETRAHYDRO-9H-PYRIDO[3,4-B]INDOLES BY MASS-SPECTROMETRY
    KUMAR, S
    SETH, M
    BHADURI, AP
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1981, 20 (12): : 1078 - 1079
  • [5] STEREOCHEMISTRY OF METHYL 2-BENZYL-3-METHOXYCARBONYL-9-METHYL-1,2,3,4-TETRAHYDRO-9H-PYRIDO[3,4-B]INDOLE-1-PROPIONATE
    SHIMIZU, M
    ISHIKAWA, M
    KOMODA, Y
    NAKAJIMA, T
    YAMAGUCHI, K
    YONEDA, N
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1984, 32 (02) : 463 - 474
  • [6] POSSIBLE ANTHELMINTIC AGENTS - SYNTHESES OF 1,3-DISUBSTITUTED 1,2,3,4-TETRAHYDRO-9H-PYRIDO[3,4-B]INDOLES AND 6,8-DISUBSTITUTED 7,8,9,14B-TETRAHYDRO-14H-QUINAZOLINO[3'4'-1,2]PYRIDO[3,4-B]INDOLES
    KUMAR, S
    ROY, J
    SETH, M
    BHADURI, AP
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1983, 22 (01): : 54 - 59
  • [7] PSILOCIN ANALOGS .3. SYNTHESIS OF 5-METHOXY AND 5-HYDROXY-1,2,3,4-TETRAHYDRO-9H-PYRIDO[3,4-B]INDOLES
    REPKE, DB
    FERGUSON, WJ
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (04) : 845 - 848
  • [8] SYNTHESIS AND SAR STUDIES IN 2-SUBSTITUTED 1,2,3,4-TETRAHYDRO-9H-PYRIDO-[3,4-B]INDOLE-3-CARBOXYLIC ACIDS - A NEW CLASS OF POTENT ANTIULCER AGENTS
    TRIPATHI, RC
    PATNAIK, GK
    SAXENA, AK
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1989, 28 (04): : 333 - 337
  • [9] SYNTHESIS AND ANALYSIS OF 1,2,3,4-TETRAHYDRO-(9H)-PYRIDO[3,4-B]INDOLE
    RODRIGUEZ, JG
    GILLOPETEGUI, P
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1993, 30 (02) : 373 - 378
  • [10] Synthesis, molecular modeling and QSAR studies in chiral 2,3-disubstituted-1,2,3,4-tetrahydro-9H-pyrido(3,4-b)indoles as potential modulators of opioid antinociception
    Saxena, AK
    Pandey, SK
    Tripathi, RC
    Raghubir, R
    BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (06) : 1559 - 1570
12345