[5-(3,4-dichlorophenyl)-7-(hydroxymethyl)-2,3-dihydropyrrolo[2,1-b][1,3]thiazol-6-yl]methanol | 114199-35-8

• 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-(3,4-dichlorophenyl)-7-(hydroxymethyl)-2,3-dihydropyrrolo[2,1-b][1,3]thiazol-6-yl]methanol
• CAS: 114199-35-8
• 化学式: C₁₄H₁₃Cl₂NO₂S
• 分子量: 330.235
• InChiKey: XSXXJVFDUONJRK-UHFFFAOYSA-N

物化性质

• 熔点：
  142-143 °C
• 沸点：
  549.2±50.0 °C(predicted)
• 密度：
  1.56±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  45.39
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [5-(3,4-dichlorophenyl)-7-(hydroxymethyl)-2,3-dihydropyrrolo[2,1-b][1,3]thiazol-6-yl]methanol 、 异氰酸异丙酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以90%的产率得到5-(3,4-dichlorophenyl)-2,3-dihydropyrrolo[2,1-b]thiazole-6,7-methanol 6,7-bis(isopropylcarbamate)
  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：

  5-(4-Chloro-phenyl)-2,3-dihydro-pyrrolo[2,1-b]thiazole-6,7-dicarboxylic acid dimethyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以87%的产率得到[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

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：——