4-[5-(1H-indol-3-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-[5-(1H-indol-3-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acid
• 英文别名: 4-[(5Z)-5-(1H-indol-3-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acid
• 化学式: C₁₆H₁₄N₂O₃S₂
• 分子量: 346.431
• InChiKey: NCILNNGPOXLNPV-JYRVWZFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  73.4
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-[5-(1H-indol-3-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acid 在 氯化亚砜 作用下， 以 甲苯 为溶剂， 反应 0.17h， 以63%的产率得到4-[5-(1H-indol-3-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoyl chloride
  参考文献：
  名称：

  Synthesis and Primary Antitumor Screening of 4-[5-(1H-Indol-3-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanamides

  摘要：

  A preparative procedure was developed for the synthesis of 4-[5-(1-R-1H-indol-3-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acids which were converted to acid chlorides, and the latter reacted with aromatic and heterocyclic amines to afford a series of previously unknown 4-[5-(1H-indol-3-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanamides. The synthesized compounds showed a moderate antitumor activity against most malignant tumor cells. UO31 renal cancer cell line turned out to be most sensitive to most of the tested compounds.

  DOI：

  10.1134/s1070428020070040
• 作为产物：
  描述：

  4-(4-氧代-2-硫代氧基-3-噻唑基)丁酸 、 3-吲哚甲醛 在 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 以67%的产率得到4-[5-(1H-indol-3-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acid
  参考文献：
  名称：

  Synthesis and Primary Antitumor Screening of 4-[5-(1H-Indol-3-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanamides

  摘要：

  A preparative procedure was developed for the synthesis of 4-[5-(1-R-1H-indol-3-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acids which were converted to acid chlorides, and the latter reacted with aromatic and heterocyclic amines to afford a series of previously unknown 4-[5-(1H-indol-3-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanamides. The synthesized compounds showed a moderate antitumor activity against most malignant tumor cells. UO31 renal cancer cell line turned out to be most sensitive to most of the tested compounds.

  DOI：

  10.1134/s1070428020070040

文献信息

• Synthesis and Primary Antitumor Screening of 4-[5-(1H-Indol-3-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanamides
  作者：V. Ya. Horishny、V. S. Matiychuk

  DOI：10.1134/s1070428020070040

  日期：2020.7

  A preparative procedure was developed for the synthesis of 4-[5-(1-R-1H-indol-3-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanoic acids which were converted to acid chlorides, and the latter reacted with aromatic and heterocyclic amines to afford a series of previously unknown 4-[5-(1H-indol-3-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]butanamides. The synthesized compounds showed a moderate antitumor activity against most malignant tumor cells. UO31 renal cancer cell line turned out to be most sensitive to most of the tested compounds.