2-(2-chloroacetamino)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-(2-chloroacetamino)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylic acid
• 英文别名: 2-[(2-chloroacetyl)amino]-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylic acid
• 化学式: C₁₀H₁₀ClNO₃S
• 分子量: 259.713
• InChiKey: GYIABFVGVZEILQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  94.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-chloroacetamino)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylic acid 在 甲醇 、 sodium carbonate 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.17h， 生成 N-benzyl-2-(2-hydroxyacetamino)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxamide
  参考文献：
  名称：

  Design, Synthesis, in vitro Antiproliferative Activity Evaluation of 2-Acylaminothiopene-3-carboxamide Derivatives

  摘要：

  A series of 2-alkanoylamidothiophene-3-carboxamide derivatives were synthesized based on the hit compound 1. The anti-proliferative activity of all the compounds in vitro against MGC-803 (stomach) and HCT-116 (colon) cancer cell lines using SRB assays were tested. Several compounds showed improved anti-proliferative activity against MGC-803 and HCT-116. SAR study revealed that chlorine substituent in the 2-acetylamino part was important for anti-proliferative activity. 5a, 11b, 11c and lid were the most potent compounds against MGC-803 (IC(50)s = 2.32-2.95 mu M), and 5a and 11c also showed good anti-proliferative activity against HCT-116 cells (IC(50)s = 3.41-3.75 mu M). In addition, the anti-proliferative activity of llb and lid could be attributed to the apoptosis in HCT116 cells via caspase 3 activation, confirmed by flow cytometry assay and western blot analysis. Meanwhile, lib and lid decreased the mitochondrial membrane potential (MMP) in HCT116 cells.

  DOI：

  10.3987/com-16-13558
• 作为产物：
  描述：

  tert-butyl 2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 2-(2-chloroacetamino)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylic acid
  参考文献：
  名称：

  Design, Synthesis, in vitro Antiproliferative Activity Evaluation of 2-Acylaminothiopene-3-carboxamide Derivatives

  摘要：

  A series of 2-alkanoylamidothiophene-3-carboxamide derivatives were synthesized based on the hit compound 1. The anti-proliferative activity of all the compounds in vitro against MGC-803 (stomach) and HCT-116 (colon) cancer cell lines using SRB assays were tested. Several compounds showed improved anti-proliferative activity against MGC-803 and HCT-116. SAR study revealed that chlorine substituent in the 2-acetylamino part was important for anti-proliferative activity. 5a, 11b, 11c and lid were the most potent compounds against MGC-803 (IC(50)s = 2.32-2.95 mu M), and 5a and 11c also showed good anti-proliferative activity against HCT-116 cells (IC(50)s = 3.41-3.75 mu M). In addition, the anti-proliferative activity of llb and lid could be attributed to the apoptosis in HCT116 cells via caspase 3 activation, confirmed by flow cytometry assay and western blot analysis. Meanwhile, lib and lid decreased the mitochondrial membrane potential (MMP) in HCT116 cells.

  DOI：

  10.3987/com-16-13558

文献信息

• Design, Synthesis, in vitro Antiproliferative Activity Evaluation of 2-Acylaminothiopene-3-carboxamide Derivatives
  作者：Jie Tang、Jiefeng Zhang、Fengjie Guan、Jiakun Qiu、Yanfen Fang、Lifang Yu、Jingya Li、Fan Yang、Xiongwen Zhang、Jia Li

  DOI：10.3987/com-16-13558

  日期：——

  A series of 2-alkanoylamidothiophene-3-carboxamide derivatives were synthesized based on the hit compound 1. The anti-proliferative activity of all the compounds in vitro against MGC-803 (stomach) and HCT-116 (colon) cancer cell lines using SRB assays were tested. Several compounds showed improved anti-proliferative activity against MGC-803 and HCT-116. SAR study revealed that chlorine substituent in the 2-acetylamino part was important for anti-proliferative activity. 5a, 11b, 11c and lid were the most potent compounds against MGC-803 (IC(50)s = 2.32-2.95 mu M), and 5a and 11c also showed good anti-proliferative activity against HCT-116 cells (IC(50)s = 3.41-3.75 mu M). In addition, the anti-proliferative activity of llb and lid could be attributed to the apoptosis in HCT116 cells via caspase 3 activation, confirmed by flow cytometry assay and western blot analysis. Meanwhile, lib and lid decreased the mitochondrial membrane potential (MMP) in HCT116 cells.