(Z)-5-(2-hydroxybenzylidene)-3-(3-(diethylamino)propyl)-2-thioxo-4-thiazolidinone | 1314887-83-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (Z)-5-(2-hydroxybenzylidene)-3-(3-(diethylamino)propyl)-2-thioxo-4-thiazolidinone
• 英文别名: (5Z)-3-[3-(diethylamino)propyl]-5-[(2-hydroxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 1314887-83-6
• 化学式: C₁₇H₂₂N₂O₂S₂
• 分子量: 350.506
• InChiKey: FLQACZFMJAUOLS-QINSGFPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-5-(2-hydroxybenzylidene)-3-(3-(diethylamino)propyl)-2-thioxo-4-thiazolidinone 在 三氟化硼乙醚 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 8.0h， 生成 (2Z,5Z)-3-(3-(3-(diethylamino)propyl)-5-(2-hydroxybenzylidene)-4-oxo-2-thiazolidinylidene)-5-bromoindolin-2-one 、 (2E,5Z)-3-(3-(3-(diethylamino)propyl)-5-(2-hydroxybenzylidene)-4-oxo-2-thiazolidinylidene)-5-bromoindolin-2-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel 4-thiazolidinones containing indolin-2-one moiety as potential antitumor agent

  摘要：

  A series of novel 4-thiazolidinone and indolin-2-one hybrid derivatives 5a-5s and 10a-10s have been designed and synthesized and their cytotoxic activities were evaluated in vitro against three human cancer cell lines including HT-29 (human colon cancer), H460 (human lung cancer), MDA-MB-231 (human breast cancer) by MTT assay. Several potent target compounds (5m, 5p, 5s, 10a, 10c-10g, 10m, 10p) were further evaluated against one cancer cell line SMMC-7721 (human liver cancer) and one normal cell line WI-38 (human fetal lung fibroblasts). Most of the prepared compounds exhibited significant antitumor activities against different human cancer cell lines. Compound 10c (IC50 = 0.025 mu M. 0.075 mu M, 0.77 mu M, 1.95 mu M) was 52, 36, 4.8 and 3.3 times more active than Sunitinib (IC50 = 1.3 mu M, 2.7 mu M, 3.7 mu M, 6.47 mu M) against HT-29, H460, MDA-MB-231 and SMMC-7721 cancer cell line, respectively. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.017
• 作为产物：
  描述：

  3-二乙胺基丙胺 在 哌啶 、 potassium carbonate 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 12.0h， 生成 (Z)-5-(2-hydroxybenzylidene)-3-(3-(diethylamino)propyl)-2-thioxo-4-thiazolidinone
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel 4-thiazolidinones containing indolin-2-one moiety as potential antitumor agent

  摘要：

  A series of novel 4-thiazolidinone and indolin-2-one hybrid derivatives 5a-5s and 10a-10s have been designed and synthesized and their cytotoxic activities were evaluated in vitro against three human cancer cell lines including HT-29 (human colon cancer), H460 (human lung cancer), MDA-MB-231 (human breast cancer) by MTT assay. Several potent target compounds (5m, 5p, 5s, 10a, 10c-10g, 10m, 10p) were further evaluated against one cancer cell line SMMC-7721 (human liver cancer) and one normal cell line WI-38 (human fetal lung fibroblasts). Most of the prepared compounds exhibited significant antitumor activities against different human cancer cell lines. Compound 10c (IC50 = 0.025 mu M. 0.075 mu M, 0.77 mu M, 1.95 mu M) was 52, 36, 4.8 and 3.3 times more active than Sunitinib (IC50 = 1.3 mu M, 2.7 mu M, 3.7 mu M, 6.47 mu M) against HT-29, H460, MDA-MB-231 and SMMC-7721 cancer cell line, respectively. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.017

文献信息

• Design, synthesis and biological evaluation of novel 4-thiazolidinones containing indolin-2-one moiety as potential antitumor agent
  作者：Shuobing Wang、Yanfang Zhao、Guogang Zhang、Yingxiang Lv、Ning Zhang、Ping Gong

  DOI：10.1016/j.ejmech.2011.05.017

  日期：2011.8

  A series of novel 4-thiazolidinone and indolin-2-one hybrid derivatives 5a-5s and 10a-10s have been designed and synthesized and their cytotoxic activities were evaluated in vitro against three human cancer cell lines including HT-29 (human colon cancer), H460 (human lung cancer), MDA-MB-231 (human breast cancer) by MTT assay. Several potent target compounds (5m, 5p, 5s, 10a, 10c-10g, 10m, 10p) were further evaluated against one cancer cell line SMMC-7721 (human liver cancer) and one normal cell line WI-38 (human fetal lung fibroblasts). Most of the prepared compounds exhibited significant antitumor activities against different human cancer cell lines. Compound 10c (IC50 = 0.025 mu M. 0.075 mu M, 0.77 mu M, 1.95 mu M) was 52, 36, 4.8 and 3.3 times more active than Sunitinib (IC50 = 1.3 mu M, 2.7 mu M, 3.7 mu M, 6.47 mu M) against HT-29, H460, MDA-MB-231 and SMMC-7721 cancer cell line, respectively. (C) 2011 Elsevier Masson SAS. All rights reserved.