(Z)-2'-(2-naphthylsulfonyloxy)-5-benzylidene-thiazolidine-2,4-dione | 1402084-21-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-2'-(2-naphthylsulfonyloxy)-5-benzylidene-thiazolidine-2,4-dione
• 英文别名: [2-[(Z)-(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenyl] naphthalene-2-sulfonate
• CAS: 1402084-21-2
• 化学式: C₂₀H₁₃NO₅S₂
• 分子量: 411.459
• InChiKey: NZQVSEVCGRXQHZ-PDGQHHTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  水杨醛 在 sodium acetate 、 三乙胺 作用下， 以 丙酮 为溶剂， 反应 0.17h， 生成 (Z)-2'-(2-naphthylsulfonyloxy)-5-benzylidene-thiazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis and Antiproliferative Evaluation of 2′-Arenesulfonyloxy-5-benzylidene-thiazolidine-2,4-diones

  摘要：

  A series of 2′‐arenesulfonyloxy‐5‐benzylidene‐thiazolidine‐2,4‐diones (TZDs) were synthesized and examined for their antiproliferative effects on a panel of carcinoma cell lines. Our results indicated that initial synthesis of 5‐[2′‐hydroxybenzylidene]‐2,4‐thiazolidinone (9) by Knoevenagel condensation followed by nucleophilic substitution with arylsulfonyl chlorides exhibited superior efficiency to the alternative synthetic route. Among tested compounds, only 8c and 8e showed significant antiproliferative activity against PC‐3 and BT474 cells with GI50 values of 8.4 and 20.6 μM, respectively. SKHep cells displayed interesting structure‐activity relationships in response to TZD derivatives treatment. Alkyl group‐substituted TZD analogs such as 8a (4‐Me, GI50, 9.4 μM) and 8k (4‐iso‐propyl, GI50, 9.8 μM) revealed better antiproliferative activity than those with bulkier alkyl groups. On the other hand, halogen‐substituted TZD analogs 8c, 8h, and 8i showed better antiproliferative activity against H460 cell line. Together, the new synthesized TZD derivatives 8a, 8b, 8c, 8d, 8e, 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p exhibited appreciable antiproliferative activity worth for further study.

  DOI：

  10.1002/jhet.859

文献信息

• Synthesis and Antiproliferative Evaluation of 2′-Arenesulfonyloxy-5-benzylidene-thiazolidine-2,4-diones
  作者：Emily M. Chen、Pei-Jung Lu、Arthur Y. Shaw

  DOI：10.1002/jhet.859

  日期：2012.7

  A series of 2′‐arenesulfonyloxy‐5‐benzylidene‐thiazolidine‐2,4‐diones (TZDs) were synthesized and examined for their antiproliferative effects on a panel of carcinoma cell lines. Our results indicated that initial synthesis of 5‐[2′‐hydroxybenzylidene]‐2,4‐thiazolidinone (9) by Knoevenagel condensation followed by nucleophilic substitution with arylsulfonyl chlorides exhibited superior efficiency to the alternative synthetic route. Among tested compounds, only 8c and 8e showed significant antiproliferative activity against PC‐3 and BT474 cells with GI50 values of 8.4 and 20.6 μM, respectively. SKHep cells displayed interesting structure‐activity relationships in response to TZD derivatives treatment. Alkyl group‐substituted TZD analogs such as 8a (4‐Me, GI50, 9.4 μM) and 8k (4‐iso‐propyl, GI50, 9.8 μM) revealed better antiproliferative activity than those with bulkier alkyl groups. On the other hand, halogen‐substituted TZD analogs 8c, 8h, and 8i showed better antiproliferative activity against H460 cell line. Together, the new synthesized TZD derivatives 8a, 8b, 8c, 8d, 8e, 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p exhibited appreciable antiproliferative activity worth for further study.