3-(4-Chlorobenzoyl)-1,3-thiazolidine-2-carboxylic acid | 114199-24-5

• 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: 3-(4-Chlorobenzoyl)-1,3-thiazolidine-2-carboxylic acid
• CAS: 114199-24-5
• 化学式: C₁₁H₁₀ClNO₃S
• 分子量: 271.724
• InChiKey: FQGHSDUCZGIUPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-Chlorobenzoyl)-1,3-thiazolidine-2-carboxylic acid 在 lithium aluminium tetrahydride 、 乙酸酐 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 [5-(3,4-dichlorophenyl)-7-(hydroxymethyl)-2,3-dihydropyrrolo[2,1-b][1,3]thiazol-6-yl]methanol
  参考文献：
  名称：

  Synthesis and antineoplastic activity of 5-aryl-2,3-dihydropyrrolo[2,1-b]thiazole-6,7-dimethanol 6,7-bis(isopropylcarbamates)

  摘要：

  A series of 1-thia analogues of the pyrrolizine bis(carbamate) 9 (NSC-278214), namely 5-aryl-2,3-dihydropyrrolo-[2,1-b]thiazole-6,7-dimethanol 6,7-bis(isopropylcarbamates) (7a-d), were prepared by multistep syntheses from the proline analogue thiazolidine-2-carboxylic acid. The compounds were tested for growth inhibitory activity with the HL-60 human promyelocytic leukemia cell line. Three of the compounds had antileukemic activity equal to that of 9, while a 4-chlorophenyl analogue was approximately 75% more potent. A simple aromatic derivative, 1,2-benzenedimethanol 1,2-bis(isopropylcarbamate) (8), had no activity in this system. Antitumor activity was also tested in a colony formation assay with HT-29 human colon carcinoma cells. Compounds 7a-d reduced relative cell survival by over 3 logs at a concentration of 300 microM (2-h exposure), while a comparable inhibition was observed with 150 microM 9. Hence compounds 7a-d retain significant antineoplastic activity.

  DOI：

  10.1021/jm00402a030
• 作为产物：
  描述：

  噻唑烷-2-甲酸 、 4-氯苯甲酰氯 在 sodium hydroxide 作用下， 以96%的产率得到3-(4-Chlorobenzoyl)-1,3-thiazolidine-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and antineoplastic activity of 5-aryl-2,3-dihydropyrrolo[2,1-b]thiazole-6,7-dimethanol 6,7-bis(isopropylcarbamates)

  摘要：

  A series of 1-thia analogues of the pyrrolizine bis(carbamate) 9 (NSC-278214), namely 5-aryl-2,3-dihydropyrrolo-[2,1-b]thiazole-6,7-dimethanol 6,7-bis(isopropylcarbamates) (7a-d), were prepared by multistep syntheses from the proline analogue thiazolidine-2-carboxylic acid. The compounds were tested for growth inhibitory activity with the HL-60 human promyelocytic leukemia cell line. Three of the compounds had antileukemic activity equal to that of 9, while a 4-chlorophenyl analogue was approximately 75% more potent. A simple aromatic derivative, 1,2-benzenedimethanol 1,2-bis(isopropylcarbamate) (8), had no activity in this system. Antitumor activity was also tested in a colony formation assay with HT-29 human colon carcinoma cells. Compounds 7a-d reduced relative cell survival by over 3 logs at a concentration of 300 microM (2-h exposure), while a comparable inhibition was observed with 150 microM 9. Hence compounds 7a-d retain significant antineoplastic activity.

  DOI：

  10.1021/jm00402a030

文献信息

• LALEZARI, IRAJ;SCHWARTZ, EDWARD L., J. MED. CHEM., 31,(1988) N 7, 1427-1429
  作者：LALEZARI, IRAJ、SCHWARTZ, EDWARD L.

  DOI：——

  日期：——
• Synthesis and antineoplastic activity of 5-aryl-2,3-dihydropyrrolo[2,1-b]thiazole-6,7-dimethanol 6,7-bis(isopropylcarbamates)
  作者：Iraj Lalezari、Edward L. Schwartz

  DOI：10.1021/jm00402a030

  日期：1988.7

  A series of 1-thia analogues of the pyrrolizine bis(carbamate) 9 (NSC-278214), namely 5-aryl-2,3-dihydropyrrolo-[2,1-b]thiazole-6,7-dimethanol 6,7-bis(isopropylcarbamates) (7a-d), were prepared by multistep syntheses from the proline analogue thiazolidine-2-carboxylic acid. The compounds were tested for growth inhibitory activity with the HL-60 human promyelocytic leukemia cell line. Three of the compounds had antileukemic activity equal to that of 9, while a 4-chlorophenyl analogue was approximately 75% more potent. A simple aromatic derivative, 1,2-benzenedimethanol 1,2-bis(isopropylcarbamate) (8), had no activity in this system. Antitumor activity was also tested in a colony formation assay with HT-29 human colon carcinoma cells. Compounds 7a-d reduced relative cell survival by over 3 logs at a concentration of 300 microM (2-h exposure), while a comparable inhibition was observed with 150 microM 9. Hence compounds 7a-d retain significant antineoplastic activity.