3-[(氯乙酰基)氨基]-2-噻吩羧酸甲酯 | 146381-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 3-[(氯乙酰基)氨基]-2-噻吩羧酸甲酯
• 中文别名: 3-[(2-氯乙酰)氨基]噻吩-2-甲酸甲酯
• 英文名称: PCM-0102367
• 英文别名: Methyl 3-[(chloroacetyl)amino]thiophene-2-carboxylate；methyl 3-[(2-chloroacetyl)amino]thiophene-2-carboxylate
• CAS: 146381-88-6
• 化学式: C₈H₈ClNO₃S
• mdl: MFCD00120696
• 分子量: 233.675
• InChiKey: UQIQUQQCIXVKLY-UHFFFAOYSA-N

物化性质

• 沸点：
  430.6±40.0 °C(Predicted)
• 密度：
  1.448±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2934999090
• 危险类别：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  3-[(氯乙酰基)氨基]-2-噻吩羧酸甲酯 、 吲哚美辛 在 4-二甲氨基吡啶 、 三乙胺 作用下， 反应 24.0h， 以82%的产率得到3-(2-{2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetoxy}acetylamino)thiophene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Evaluation of glycolamide esters of indomethacin as potential cyclooxygenase-2 (COX-2) inhibitors☆

  摘要：

  A number of novel indomethacin glycolamide esters were synthesized and tested for their cyclooxygenase (COX-1 and COX-2) inhibition properties in vitro. Many of these compounds proved to be selective COX-2 inhibitors, and subtle structural changes in the substituents on the glycolamide ester moiety altered the inhibitory properties as well as potencies significantly. Their in vitro data were rationalized through molecular modeling studies. Few of them displayed anti-inflammatory activity in vivo. Compound 32, [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid 2-morpholin-4-yl-2-oxo ethyl ester, was identified as a promising compound in this class and its good anti-inflammatory activity was demonstrated in the in vivo model. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.023
• 作为产物：
  描述：

  3-氨基-2-噻吩甲酸甲酯 、 氯乙酰氯 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 3-[(氯乙酰基)氨基]-2-噻吩羧酸甲酯
  参考文献：
  名称：

  Evaluation of glycolamide esters of indomethacin as potential cyclooxygenase-2 (COX-2) inhibitors☆

  摘要：

  A number of novel indomethacin glycolamide esters were synthesized and tested for their cyclooxygenase (COX-1 and COX-2) inhibition properties in vitro. Many of these compounds proved to be selective COX-2 inhibitors, and subtle structural changes in the substituents on the glycolamide ester moiety altered the inhibitory properties as well as potencies significantly. Their in vitro data were rationalized through molecular modeling studies. Few of them displayed anti-inflammatory activity in vivo. Compound 32, [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid 2-morpholin-4-yl-2-oxo ethyl ester, was identified as a promising compound in this class and its good anti-inflammatory activity was demonstrated in the in vivo model. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.023

文献信息

• Discovery of novel 2-(3-(2-chlorophenyl)pyrazin-2-ylthio)-N-arylacetamides as potent HIV-1 inhibitors using a structure-based bioisosterism approach
  作者：Peng Zhan、Wenmin Chen、Zhenyu Li、Xiao Li、Xuwang Chen、Ye Tian、Christophe Pannecouque、Erik De Clercq、Xinyong Liu

  DOI：10.1016/j.bmc.2012.09.058

  日期：2012.12

  The present work is an extension of our ongoing efforts towards the development and identification of new molecules with anti-HIV activity which have previously led to the discovery of arylazolylthioacetanilides as highly active NNRTIs. In this article, a series of 2-2-(3-(2-chlorophenyl)pyrazin-2-ylthio)-N-arylacetamide derivatives were synthesized and evaluated for in vitro anti-HIV activity. Most of the tested compounds exhibited moderate activities against wild-type HIV-1. Among them, compound 6k showed significant activity against wild-type HIV-1 with an EC50 value of 1.7 mu M, along with moderate activity against wild-type reverse transcriptase (RT). The preliminary structure-activity relationship (SAR) and docking calculations of this new series of compounds were also investigated, which may help designing more potent molecules. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.