(R,Z)-2-(5-(3-methoxybenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)propanoic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R,Z)-2-(5-(3-methoxybenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)propanoic acid
• 英文别名: (2R)-2-[(5Z)-5-[(3-methoxyphenyl)methylene]-4-oxo-2-thioxo-thiazolidin-3-yl]propanoic acid；(2R)-2-[(5Z)-5-[(3-methoxyphenyl)methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]propanoic acid
• 化学式: C₁₄H₁₃NO₄S₂
• 分子量: 323.394
• InChiKey: FJIUKWTXHQDLEI-XNYAHFKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (R)-2-(4-oxo-2-thioxothiazolidin-3-yl)propanoic acid 、 3-甲氧基苯甲醛 在 溶剂黄146 、 β-丙氨酸 作用下， 反应 6.0h， 以87%的产率得到(R,Z)-2-(5-(3-methoxybenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)propanoic acid
  参考文献：
  名称：

  Design, synthesis, SAR and biological investigation of 3-(carboxymethyl)rhodanine and aminothiazole inhibitors of Mycobacterium tuberculosis Zmp1

  摘要：

  Sixteen 3-(carboxymethyl)rhodanines, and twelve aminothiazoles as rhodanine-mimetics were designed, synthesized and tested as inhibitors of the Zmp1 enzyme from Mycobacterium tuberculosis (Mtb). Almost all rhodanines (5a-d, 5f-n, and 7a-b) exhibited Zmp1 inhibition with IC50 values in the range 1.3-43.9 mu M, whereas only aminothiazoles 12b and 12d proved active with IC50 values of 41.3 and 35.7 mu M, respectively. Structure-activity relationships (SAR) were coupled with molecular modeling studies to highlight structural determinants for Zmp1 inhibition. Moreover, rhodanines 5a and 5c induced 23.4 and 53.8% of Mtb growth inhibition in THP-1 infected cells, respectively, at the non-toxic concentration of 10 mu g/ml. This work represents a step forward in targeting Zmp1 by small molecules. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2018.01.031

文献信息

• Solid-phase combinatorial synthesis of 5-arylalkylidene rhodanine
  作者：Cheng Leng Lee、Mui Mui Sim

  DOI：10.1016/s0040-4039(00)00866-2

  日期：2000.7

  Rhodanine-3-acetic acid was loaded on Wang resin or Rink amide resin. Alternatively, the thiocarbonyl-diimidazole-activated Wang amino acid resin or 2-chlorotrityl resin was reacted with methyl thioglycolate to yield the rhodanine moieties. It was then condensed at the C-5 active methylene with either aromatic aldehydes or aromatic ketones. 5-Arylalkylidene rhodanine was obtained upon resin cleavage. (C) 2000 Elsevier Science Ltd. All rights reserved.