7-acetyl-3-chloro-1H-indole-2-carboxylic acid | 1026775-61-0

• 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: 7-acetyl-3-chloro-1H-indole-2-carboxylic acid
• CAS: 1026775-61-0
• 化学式: C₁₁H₈ClNO₃
• 分子量: 237.642
• InChiKey: JNECCNZOBHCMKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  70.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-acetyl-3-chloro-1H-indole-2-carboxylic acid 、 1-(4-氟苄基)哌嗪 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以63%的产率得到1-(3-chloro-2-(4-(4-fluorobenzyl)piperazin-1-carbonyl)-1H-indol-7-yl)ethanone
  参考文献：
  名称：

  Investigations of SCIO-469-like compounds for the inhibition of p38 MAP kinase

  摘要：

  The p38 MAP kinase is implicated in the release of the pro-inflammatory cytokines TNF alpha and IL-1b. Inhibition of cytokine release may be a useful treatment for inflammatory conditions such as rheumatoid arthritis and Crohn's disease. A new lead structure for p38 MAP kinase inhibition was identified. Herein, we report the SAR of this new class of p38 inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.023
• 作为产物：
  描述：

  ethyl 7-acetyl-3-chloro-1H-indole-2-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 以52%的产率得到7-acetyl-3-chloro-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Design and synthesis of dual inhibitors of HIV reverse transcriptase and integrase: Introducing a diketoacid functionality into delavirdine

  摘要：

  Cost and toxicity problems associated with highly active antiretroviral therapy (HAART) in HIV/AIDS treatment could be alleviated by using designed multiple ligands (DMLs). Dual inhibitors of HIV reverse transcriptase (RT) and integrase (IN) were rationally designed by introducing a diketoacid (DKA) functionality into the tolerant C-5 site of RT inhibitor delavirdine. The resulting compounds all demonstrate good activity against both RT and IN in enzymatic assays and HIV in cell-based assay, whereas their C-7 regioisomers are all inactive in these assays. Balanced activities were observed with C-3 halogenated inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.02.007

文献信息

• Design and synthesis of dual inhibitors of HIV reverse transcriptase and integrase: Introducing a diketoacid functionality into delavirdine
  作者：Zhengqiang Wang、Robert Vince

  DOI：10.1016/j.bmc.2008.02.007

  日期：2008.4.1

  Cost and toxicity problems associated with highly active antiretroviral therapy (HAART) in HIV/AIDS treatment could be alleviated by using designed multiple ligands (DMLs). Dual inhibitors of HIV reverse transcriptase (RT) and integrase (IN) were rationally designed by introducing a diketoacid (DKA) functionality into the tolerant C-5 site of RT inhibitor delavirdine. The resulting compounds all demonstrate good activity against both RT and IN in enzymatic assays and HIV in cell-based assay, whereas their C-7 regioisomers are all inactive in these assays. Balanced activities were observed with C-3 halogenated inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.
• Investigations of SCIO-469-like compounds for the inhibition of p38 MAP kinase
  作者：Stefan Laufer、Frank Lehmann

  DOI：10.1016/j.bmcl.2009.01.023

  日期：2009.3

  The p38 MAP kinase is implicated in the release of the pro-inflammatory cytokines TNF alpha and IL-1b. Inhibition of cytokine release may be a useful treatment for inflammatory conditions such as rheumatoid arthritis and Crohn's disease. A new lead structure for p38 MAP kinase inhibition was identified. Herein, we report the SAR of this new class of p38 inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.