2-cyano-N'-(1-(thiophen-2-yl)ethylidene)acetohydrazide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-cyano-N'-(1-(thiophen-2-yl)ethylidene)acetohydrazide
• 英文别名: 2-cyano-N-[(E)-1-thiophen-2-ylethylideneamino]acetamide
• 化学式: C₉H₉N₃OS
• 分子量: 207.256
• InChiKey: HJAWKOATZXCLHI-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  93.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-cyano-N'-(1-(thiophen-2-yl)ethylidene)acetohydrazide 在 potassium hydroxide 作用下， 反应 48.0h， 生成 ethyl 4-(1-(thiophen-2-yl)ethylideneaminocarbamoyl)-3-amino-5-(phenylamino)thiophene-2-carboxylate
  参考文献：
  名称：

  Syntheses, crystal structures, in vitro antitumor and free radical scavenging activity evaluation of a series of 2-substituted thiophenes

  摘要：

  A series of thiazole, pyridine and benzylidene derivatives derived from thiophene scaffold have been synthesized. The antitumor evaluation of the newly synthesized products against four cancer cell lines, namely breast carcinoma (MCF-7), liver carcinoma (HepG2), colon carcinoma (HCT-116) and prostate carcinoma (PC3), indicated that the thiazole derivative 11b showed remarkable activity against all cell lines with LC50 values of 18.3, 2.5, 7.5 and 7.6 A mu M, respectively. Cytotoxicity toward normal cell lines was also investigated and indicated that compound 21c displayed remarkable potency against PC3 with LC50 values of 7.1 A mu M and showed weak inhibition of normal cell lines at (GI %) of 41.2 % and thus could be considered as an important lead compound for potential application in anticancer chemotherapy. Brine shrimp lethality assay of the most active compounds was carried out to detect possible cytotoxicity effects and indicated that highly active compound, 21c, is not harmful. The X-ray crystallographic analysis of compounds 3 and 11b was obtained thus establishing with certainty the proposed structures in this work. The synthesized compounds were also screened for their free radical scavenging activity. Hydrazino-thiazole derivatives 15 and 16 showed remarkable antioxidant activity with IC50 values of 60.9 and 61.9 mu g ml(-1), respectively.

  DOI：

  10.1007/s00044-015-1353-5
• 作为产物：
  描述：

  2-乙酰基噻吩 、 氰乙酰肼 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以72%的产率得到2-cyano-N'-(1-(thiophen-2-yl)ethylidene)acetohydrazide
  参考文献：
  名称：

  Syntheses, crystal structures, in vitro antitumor and free radical scavenging activity evaluation of a series of 2-substituted thiophenes

  摘要：

  A series of thiazole, pyridine and benzylidene derivatives derived from thiophene scaffold have been synthesized. The antitumor evaluation of the newly synthesized products against four cancer cell lines, namely breast carcinoma (MCF-7), liver carcinoma (HepG2), colon carcinoma (HCT-116) and prostate carcinoma (PC3), indicated that the thiazole derivative 11b showed remarkable activity against all cell lines with LC50 values of 18.3, 2.5, 7.5 and 7.6 A mu M, respectively. Cytotoxicity toward normal cell lines was also investigated and indicated that compound 21c displayed remarkable potency against PC3 with LC50 values of 7.1 A mu M and showed weak inhibition of normal cell lines at (GI %) of 41.2 % and thus could be considered as an important lead compound for potential application in anticancer chemotherapy. Brine shrimp lethality assay of the most active compounds was carried out to detect possible cytotoxicity effects and indicated that highly active compound, 21c, is not harmful. The X-ray crystallographic analysis of compounds 3 and 11b was obtained thus establishing with certainty the proposed structures in this work. The synthesized compounds were also screened for their free radical scavenging activity. Hydrazino-thiazole derivatives 15 and 16 showed remarkable antioxidant activity with IC50 values of 60.9 and 61.9 mu g ml(-1), respectively.

  DOI：

  10.1007/s00044-015-1353-5