5-甲基-2,3-二氢吡咯并[2,1-b]噻唑-6,7-二羧酸二甲酯 | 114199-26-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 5-甲基-2,3-二氢吡咯并[2,1-b]噻唑-6,7-二羧酸二甲酯
• 英文名称: dimethyl 2,3-dihydro-5-methylpyrrolo<2,1-b>thiazole-6,7-dicarboxylate
• 英文别名: Dimethyl 5-methyl-2,3-dihydropyrrolo[2,1-b][1,3]thiazole-6,7-dicarboxylate
• CAS: 114199-26-7
• 化学式: C₁₁H₁₃NO₄S
• 分子量: 255.295
• InChiKey: ZPNHXRCUMKUHTP-UHFFFAOYSA-N

物化性质

• 溶解度：
  >38.3 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  82.8
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  5-甲基-2,3-二氢吡咯并[2,1-b]噻唑-6,7-二羧酸二甲酯 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以78%的产率得到(6-Hydroxymethyl-5-methyl-2,3-dihydro-pyrrolo[2,1-b]thiazol-7-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：

  3-acetylthiazolidine-2-carboxylic acid 、 丁炔二酸二甲酯 在 乙酸酐 作用下， 反应 1.0h， 以62%的产率得到5-甲基-2,3-二氢吡咯并[2,1-b]噻唑-6,7-二羧酸二甲酯
  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.