2-[3-(4-methoxy-phenyl)-thioureido]-4-phenyl-thiophene-3-carboxylic acid ethyl ester | 65233-80-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[3-(4-methoxy-phenyl)-thioureido]-4-phenyl-thiophene-3-carboxylic acid ethyl ester
• 英文别名: ethyl 2-[(4-methoxyphenyl)carbamothioylamino]-4-phenylthiophene-3-carboxylate
• CAS: 65233-80-9
• 化学式: C₂₁H₂₀N₂O₃S₂
• 分子量: 412.533
• InChiKey: LHRCGEQPBOHZEU-UHFFFAOYSA-N

物化性质

• 熔点：
  164-168 °C(Solv: chloroform (67-66-3); ethanol (64-17-5))
• 沸点：
  550.5±60.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  59.59
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-[3-(4-methoxy-phenyl)-thioureido]-4-phenyl-thiophene-3-carboxylic acid ethyl ester 在 sodium methylate 、 potassium carbonate 、 肼 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 [3-(4-methoxyphenyl)-4-oxo-5-phenyl-3,4-dihydrothieno[2,3-d]pyrimidin-2-ylsulfanyl]acetic acid hydrazide
  参考文献：
  名称：

  Structure–activity relationship study of novel tissue transglutaminase inhibitors

  摘要：

  Thieno[2,3-d]pyrimidin-4-one acylhydrazide derivatives were discovered as moderately potent inhibitors of TGase 2 (tissue transglutaminase) utilizing a fluorescence-based assay that measured TGase 2 catalyzed incorporation of the dansylated Lys derivative alpha-N-Boc-Lys-CH2-CH2-dansyl into the protein substrate N,N-dimethylated-casein. A SAR study revealed that the acylhydrazide thioether side-chain and the thiophene ring were critical to inhibitory activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.005
• 作为产物：
  描述：

  苯乙酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 、 sulfur 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 0.33h， 生成 2-[3-(4-methoxy-phenyl)-thioureido]-4-phenyl-thiophene-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Structure–activity relationship study of novel tissue transglutaminase inhibitors

  摘要：

  Thieno[2,3-d]pyrimidin-4-one acylhydrazide derivatives were discovered as moderately potent inhibitors of TGase 2 (tissue transglutaminase) utilizing a fluorescence-based assay that measured TGase 2 catalyzed incorporation of the dansylated Lys derivative alpha-N-Boc-Lys-CH2-CH2-dansyl into the protein substrate N,N-dimethylated-casein. A SAR study revealed that the acylhydrazide thioether side-chain and the thiophene ring were critical to inhibitory activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.005

文献信息

• Devani,M.B. et al., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1977, vol. 15B, p. 575 - 577
  作者：Devani,M.B. et al.

  DOI：——

  日期：——
• DEVANI M. B.; SHISHOO C. J.; PATHAK U. S.; SHARMA B. G.; GOKHALE S. V.; P+, INDIAN J. CHEM. <IJOC-AP>, 1977, B 15, NO 6, 575-577
  作者：DEVANI M. B.、 SHISHOO C. J.、 PATHAK U. S.、 SHARMA B. G.、 GOKHALE S. V.、 P+

  DOI：——

  日期：——