3-(Furan-2-ylmethyl)-2-[(2-oxo-1,3-thiazolidin-4-ylidene)hydrazinylidene]-5-phenacyl-1,3-thiazolidin-4-one | 873572-03-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(Furan-2-ylmethyl)-2-[(2-oxo-1,3-thiazolidin-4-ylidene)hydrazinylidene]-5-phenacyl-1,3-thiazolidin-4-one
• 英文别名: 3-(furan-2-ylmethyl)-2-[(2-oxo-1,3-thiazolidin-4-ylidene)hydrazinylidene]-5-phenacyl-1,3-thiazolidin-4-one
• CAS: 873572-03-3
• 化学式: C₁₉H₁₆N₄O₄S₂
• 分子量: 428.492
• InChiKey: DYIIUZNCITVYSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  155
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-苯甲酰丙烯酸 、 N-(furan-2-ylmethyl)-2-(2-oxothiazolidin-4-ylidene)hydrazine-1-carbothioamide 在 溶剂黄146 作用下， 反应 1.0h， 以63%的产率得到3-(Furan-2-ylmethyl)-2-[(2-oxo-1,3-thiazolidin-4-ylidene)hydrazinylidene]-5-phenacyl-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Synthesis and Anticancer Activity of Novel Nonfused Bicyclic Thiazolidinone Derivatives

  摘要：

  A series of new 2-{4-oxo-2-[(4-oxothiazolidin-2-ylidene)-hydrazono]-thiazolidin-5-yl}-N-arylacetamides (4a-e), 5-(2-oxo-2-aryl-ethyl)-2-[(4-oxothiazolidin-2-ylidene)-hydrazono]-thiazolidine-4-ones (5a-d), 2-(4-oxo-2-[(2-oxothiazolidin-4-ylidene)-hydrazono]-thiazolidin-5-yl)-N-arylacetamides (7a-e), and 5-(2-oxo-2-aryl-ethyl)-2-[(2-oxothiazolidin-4-ylidene)-hydrazono]-thiazolidine-4-ones (8a-d) have been synthesized starting from 2-thioxothiazolidin-4-one and 4-thioxothiazolidin-2-one through a multistep reaction sequence. 2-Thioxothiazolidin-4-one was alkylated via the intermediate formation of the triethylammonium salt 1 by ethyl chloroacetate. Compound 2 and 4-thioxothiazolidin-2-one reacted with thiosemicarbazides to give the 1-(4-thiazolidinone-2-ylidene)-4-R-thiosemicarbazones (3a,b) and 1-(2-thiazolidinone-4-ylidene)thiosemicarbazones (6a,b), respectively. Following [2+3]-cyclization of thiazolidinone-substituted thiosemicarbazones (3a,b and 6a,b) with N-arylmaleimides and aroylacrylic acids as equivalents of dielectrophilic synthon [C2]2 +, novel non-fused bicyclic thiazolidinones (4a-e, 5a-d, 7a-e, 8a-d) were synthesized. The structures of the new compounds (4a-e, 5a-d, 7a-e, 8a-d) were established on the basis of their elemental analysis and 1H NMR and mass spectral data. Eight of the synthesized compounds were tested, and three of them displayed different levels of antitumor activity. The most efficient antitumor agent2-{4-oxo-3-furylmethyl-2-[(4-oxothiazolidin-2-ylidene)-hydrazono]-thiazolidin-5-yl}-N-4-chlorophenylacetamide (4d) was found to be active against leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancer cell lines with mean lgGI50 and lgTGI values of -5.35 and -4.78, respectively.

  DOI：

  10.1080/10426500802247563

文献信息

• Synthesis and Anticancer Activity of Novel Nonfused Bicyclic Thiazolidinone Derivatives
  作者：Dmytro Havrylyuk、Borys Zimenkovsky、Roman Lesyk

  DOI：10.1080/10426500802247563

  日期：2009.3.10

  A series of new 2-4-oxo-2-[(4-oxothiazolidin-2-ylidene)-hydrazono]-thiazolidin-5-yl}-N-arylacetamides (4a-e), 5-(2-oxo-2-aryl-ethyl)-2-[(4-oxothiazolidin-2-ylidene)-hydrazono]-thiazolidine-4-ones (5a-d), 2-(4-oxo-2-[(2-oxothiazolidin-4-ylidene)-hydrazono]-thiazolidin-5-yl)-N-arylacetamides (7a-e), and 5-(2-oxo-2-aryl-ethyl)-2-[(2-oxothiazolidin-4-ylidene)-hydrazono]-thiazolidine-4-ones (8a-d) have been synthesized starting from 2-thioxothiazolidin-4-one and 4-thioxothiazolidin-2-one through a multistep reaction sequence. 2-Thioxothiazolidin-4-one was alkylated via the intermediate formation of the triethylammonium salt 1 by ethyl chloroacetate. Compound 2 and 4-thioxothiazolidin-2-one reacted with thiosemicarbazides to give the 1-(4-thiazolidinone-2-ylidene)-4-R-thiosemicarbazones (3a,b) and 1-(2-thiazolidinone-4-ylidene)thiosemicarbazones (6a,b), respectively. Following [2+3]-cyclization of thiazolidinone-substituted thiosemicarbazones (3a,b and 6a,b) with N-arylmaleimides and aroylacrylic acids as equivalents of dielectrophilic synthon [C2]2 +, novel non-fused bicyclic thiazolidinones (4a-e, 5a-d, 7a-e, 8a-d) were synthesized. The structures of the new compounds (4a-e, 5a-d, 7a-e, 8a-d) were established on the basis of their elemental analysis and 1H NMR and mass spectral data. Eight of the synthesized compounds were tested, and three of them displayed different levels of antitumor activity. The most efficient antitumor agent2-4-oxo-3-furylmethyl-2-[(4-oxothiazolidin-2-ylidene)-hydrazono]-thiazolidin-5-yl}-N-4-chlorophenylacetamide (4d) was found to be active against leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancer cell lines with mean lgGI50 and lgTGI values of -5.35 and -4.78, respectively.