trans-9-bromo-2,5-dimethyl-1-oxo-5,6,11,11a-tetrahydro-1H-imidazo[1',5':1,6]pyrido[3,4-b]indole-3(2H)-thione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: trans-9-bromo-2,5-dimethyl-1-oxo-5,6,11,11a-tetrahydro-1H-imidazo[1',5':1,6]pyrido[3,4-b]indole-3(2H)-thione
• 英文别名: (10S,15R)-4-bromo-10,13-dimethyl-12-sulfanylidene-8,11,13-triazatetracyclo[7.7.0.02,7.011,15]hexadeca-1(9),2(7),3,5-tetraen-14-one
• 化学式: C₁₅H₁₄BrN₃OS
• 分子量: 364.266
• InChiKey: VRISHWQRRVQFGV-JVXZTZIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-9-bromo-2,5-dimethyl-1-oxo-5,6,11,11a-tetrahydro-1H-imidazo[1',5':1,6]pyrido[3,4-b]indole-3(2H)-thione 、 苯硼酸 在 potassium phosphate 、 双(三环己基膦)二氯化钯 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 4.0h， 以92%的产率得到trans-9-phenyl-2,5-dimethyl-1-oxo-5,6,11,11a-tetrahydro-1H-imidazo[1',5':1,6]pyrido[3,4-b]indole-3(2H)-thione
  参考文献：
  名称：

  Synthesis and biological evaluation of novel tryptoline derivatives as indoleamine 2,3-dioxygenase (IDO) inhibitors

  摘要：

  Indoleamine 2,3-dioxygenase (IDO) plays a significant role in several disorders such as Alzheimer's disease, age-related cataracts and tumors. A series of novel tryptoline derivatives were synthesized and evaluated for their inhibitory activity against IDO. Substituted tryptoline derivatives (11a, 11c, 11e, 12b and 12c) were demonstrated to be more potent than known inhibitor MTH-Trp. Suzuki-Miyaura cross-coupling reaction of 11a-d with phenylboronic acid proceeded in high yields. In most cases, C5 and C6 substitutions on the corresponding indole ring were well tolerated. The tryptoline derivative 11c is a promising chemical lead for the discovery of novel IDO inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.028
• 作为产物：
  描述：

  、 异硫氰酸甲酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 trans-9-bromo-2,5-dimethyl-1-oxo-5,6,11,11a-tetrahydro-1H-imidazo[1',5':1,6]pyrido[3,4-b]indole-3(2H)-thione
  参考文献：
  名称：

  Synthesis and biological evaluation of novel tryptoline derivatives as indoleamine 2,3-dioxygenase (IDO) inhibitors

  摘要：

  Indoleamine 2,3-dioxygenase (IDO) plays a significant role in several disorders such as Alzheimer's disease, age-related cataracts and tumors. A series of novel tryptoline derivatives were synthesized and evaluated for their inhibitory activity against IDO. Substituted tryptoline derivatives (11a, 11c, 11e, 12b and 12c) were demonstrated to be more potent than known inhibitor MTH-Trp. Suzuki-Miyaura cross-coupling reaction of 11a-d with phenylboronic acid proceeded in high yields. In most cases, C5 and C6 substitutions on the corresponding indole ring were well tolerated. The tryptoline derivative 11c is a promising chemical lead for the discovery of novel IDO inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.028

文献信息

• Synthesis and biological evaluation of novel tryptoline derivatives as indoleamine 2,3-dioxygenase (IDO) inhibitors
  作者：Minoru Tanaka、Xin Li、Hidemasa Hikawa、Takafumi Suzuki、Katsuhiko Tsutsumi、Masashi Sato、Osamu Takikawa、Hideharu Suzuki、Yuusaku Yokoyama

  DOI：10.1016/j.bmc.2012.12.028

  日期：2013.3

  Indoleamine 2,3-dioxygenase (IDO) plays a significant role in several disorders such as Alzheimer's disease, age-related cataracts and tumors. A series of novel tryptoline derivatives were synthesized and evaluated for their inhibitory activity against IDO. Substituted tryptoline derivatives (11a, 11c, 11e, 12b and 12c) were demonstrated to be more potent than known inhibitor MTH-Trp. Suzuki-Miyaura cross-coupling reaction of 11a-d with phenylboronic acid proceeded in high yields. In most cases, C5 and C6 substitutions on the corresponding indole ring were well tolerated. The tryptoline derivative 11c is a promising chemical lead for the discovery of novel IDO inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.