6-Bromoindole-3-acetamide

• 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: 6-Bromoindole-3-acetamide
• 英文别名: 2-(6-bromo-1H-indol-3-yl)acetamide
• 化学式: C₁₀H₉BrN₂O
• 分子量: 253.098
• InChiKey: VNGQPZHGKOMZAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  吲哚-3-乙醛酸甲酯 、 6-Bromoindole-3-acetamide 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 2-(6-bromo-1H-indol-3-yl)-3-(1H-indol-3-yl)-maleinimide
  参考文献：
  名称：

  Synthesis, Structure−Activity Relationship, and Biological Studies of Indolocarbazoles as Potent Cyclin D1-CDK4 Inhibitors

  摘要：

  Novel substituted indolocarbazoles were synthesized, and their kinase inhibitory capability was evaluated in vitro. 6-Substituted indolocarbazoles 4 were found to be potent and selective D1/CDK4 inhibitors. 4d and 4h exhibited potent and ATP-competitive D1/CDK4 activities with IC50 values of 76 and 42 nM, respectively. Both compounds had high selectivity against the other kinases. These D1/CDK4 inhibitors inhibited tumor cell growth, arrested tumor cells at the G1 phase, and inhibited pRb phosphorylation.

  DOI：

  10.1021/jm0256169
• 作为产物：
  描述：

  potassium carbonate 、 6-溴吲哚-3-乙腈 、 水 、 双氧水 在 盐酸 、 乙酸乙酯 、 disodium;dioxido-oxo-sulfanylidene-λ6-sulfane 、 magnesium sulfate 、 二氯甲烷 作用下， 以 二甲基亚砜 为溶剂， 反应 3.33h， 以to give 273 mg (55%) of the title compound的产率得到6-Bromoindole-3-acetamide
  参考文献：
  名称：

  Methods and compounds for treating proliferative diseases

  摘要：

  本文所披露的化合物是公式（I）的吲哚咔唑，它们是有效的CDK4抑制剂，可用于治疗细胞增殖性疾病，包括癌症。公式（I）。

  公开号：

  US07109229B2

文献信息

• Agents and methods for the treatment of proliferative diseases
  申请人：——

  公开号：US20030229026A1

  公开（公告）日：2003-12-11

  The present invention provides selective kinase inhibitors of formula (I). 1

  这项发明提供了式（I）的选择性激酶抑制剂。
• Novel, potent and selective cyclin D1/CDK4 inhibitors: indolo[6,7-a]pyrrolo[3,4-c]carbazoles
  作者：Thomas A. Engler、Kelly Furness、Sushant Malhotra、Concha Sanchez-Martinez、Chuan Shih、Walter Xie、Guoxin Zhu、Xun Zhou、Scott Conner、Margaret M. Faul、Kevin A. Sullivan、Stanley P. Kolis、Harold B. Brooks、Bharvin Patel、Richard M. Schultz、Tammy B. DeHahn、Kashif Kirmani、Charles D. Spencer、Scott A. Watkins、Eileen L. Considine、Jack A. Dempsey、Catherine A. Ogg、Nancy B. Stamm、Bryan D. Anderson、Robert M. Campbell、Vasu Vasudevan、Michelle L. Lytle

  DOI：10.1016/s0960-894x(03)00461-x

  日期：2003.7

  The synthesis and CDK inhibitory properties of a series of indolo[6,7-a]pyrrolo[3,4-c]carbazoles is reported. In addition to their potent CDK activity, the compounds display antiproliferative activity against two human cancer cell lines. These inhibitors also effect strong G1 arrest in these cell lines and inhibit Rb phosphorylation at Ser780 consistent with inhibition of cyclin D1/CDK4.

  报道了一系列吲哚[6，7-a]吡咯并[3，4-c]咔唑的合成和CDK抑制性能。这些化合物除了具有强大的CDK活性外，还具有针对两种人类癌细胞系的抗增殖活性。这些抑制剂还影响这些细胞系中的强G1阻滞，并抑制Ser780处的Rb磷酸化，这与抑制细胞周期蛋白D1 / CDK4一致。
• Synthesis of 1,7-annulated indoles and their applications in the studies of cyclin dependent kinase inhibitors
  作者：Guoxin Zhu、Scott E. Conner、Xun Zhou、Ho-Kit Chan、Chuan Shih、Thomas A. Engler、Rima S. Al-awar、Harold B. Brooks、Scott A. Watkins、Charles D. Spencer、Richard M. Schultz、Jack A. Dempsey、Eileen L. Considine、Bharvin R. Patel、Catherine A. Ogg、Vasu Vasudevan、Michelle L. Lytle

  DOI：10.1016/j.bmcl.2004.04.033

  日期：2004.6

  The synthesis of a novel series of 1,7-annulated indolocarbazoles 2 and 16 is described. These compounds were found to be potent cyclin dependent kinase inhibitors with good antiproliferative activity against two human carcinoma cell lines. These inhibitors also arrested tumor cells at the G1 phase and inhibited pRb phosphorylation. (C) 2004 Elsevier Ltd. All rights reserved.
• 1,7-Annulated indolocarbazoles as cyclin-dependent kinase inhibitors
  作者：Rima S. Al-awar、James E. Ray、Kyle A. Hecker、Jianping Huang、Philip P. Waid、Chuan Shih、Harold B. Brooks、Charles D. Spencer、Scott A. Watkins、Bharvin R. Patel、Nancy B. Stamm、Catherine A. Ogg、Richard M. Schultz、Eileen L. Considine、Margaret M. Faul、Kevin A. Sullivan、Stanley P. Kolis、John L. Grutsch、Sajan Joseph

  DOI：10.1016/j.bmcl.2004.03.105

  日期：2004.6

  The synthesis and kinase inhibitory activity of a series of novel 1,7-annulated indolocarbazoles 6 and 16 is described. These compounds exhibited potent inhibitory activity against cyclin-dependent kinase 4 and good antiproliferative activity in a human colon carcinoma cell line. (C) 2004 Elsevier Ltd. All rights reserved.
• AGENTS AND METHODS FOR THE TREATMENT OF PROLIFERATIVE DISEASES
  申请人：ELI LILLY AND COMPANY

  公开号：EP1242420A2

  公开（公告）日：2002-09-25