[5-phenyl-7-(propan-2-ylcarbamoyloxymethyl)-2,3-dihydropyrrolo[2,1-b][1,3]thiazol-6-yl]methyl N-propan-2-ylcarbamate | 114199-36-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: [5-phenyl-7-(propan-2-ylcarbamoyloxymethyl)-2,3-dihydropyrrolo[2,1-b][1,3]thiazol-6-yl]methyl N-propan-2-ylcarbamate
• CAS: 114199-36-9
• 化学式: C₂₂H₂₉N₃O₄S
• 分子量: 431.556
• InChiKey: SXYWDXWTTQJBLF-UHFFFAOYSA-N

物化性质

• 熔点：
  76-78 °C
• 沸点：
  624.9±55.0 °C(predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-Phenyl-2,3-dihydro-pyrrolo[2,1-b]thiazole-6,7-dicarboxylic acid dimethyl ester 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 [5-phenyl-7-(propan-2-ylcarbamoyloxymethyl)-2,3-dihydropyrrolo[2,1-b][1,3]thiazol-6-yl]methyl N-propan-2-ylcarbamate
  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.