(3R)-6-hydroxymethyl-5-methyl-3-phenyl-1H,3H-pyrrolo[1,2-c]thiazole benzylcarbamate | 1252613-15-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (3R)-6-hydroxymethyl-5-methyl-3-phenyl-1H,3H-pyrrolo[1,2-c]thiazole benzylcarbamate
• 英文别名: [(3R)-5-methyl-3-phenyl-1,3-dihydropyrrolo[1,2-c][1,3]thiazol-6-yl]methyl N-benzylcarbamate
• CAS: 1252613-15-2
• 化学式: C₂₂H₂₂N₂O₂S
• 分子量: 378.495
• InChiKey: VSYQPHBKBCVFGJ-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  68.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3R)-7-hydroxymethyl-5-methyl-3-phenyl-1H,3H-pyrrolo[1,2-c]thiazole 、 异氰酸苄酯 生成 (3R)-6-hydroxymethyl-5-methyl-3-phenyl-1H,3H-pyrrolo[1,2-c]thiazole benzylcarbamate
  参考文献：
  名称：

  Chiral 6-hydroxymethyl-1H,3H-pyrrolo[1,2-c]thiazoles: Novel antitumor DNA monoalkylating agents

  摘要：

  New chiral 1H,3H-pyrrolo[1,2-c]thiazoles were synthesized and screened for their in vitro activity as anti-cancer agents in three human tumor cell lines, colorectal adenocarcinoma, melanoma and breast adenocarcinoma. (R)-6-Hydroxymethyl-5-methyl-3-phenyl-1H,3H-pyrrolo[1,2-c]thiazole and the corresponding benzylcarbamate showed selectivity for breast cancer cell lines with IC(50) values of 24 mu M and 2.2 mu M, respectively. The latter also showed significant activity against colorectal adenocarcinoma cancer cell lines (IC(50) = 8.7 mu M) In contrast, the 7-hydroxymethyl-5-methyl-3-phenyl-1H,3H-pyrrolo[1,2-c] thiazole gave moderate anti-cancer activity. The performance against breast cancer cell lines (IC(50) = 10 mu M) of a potential bisalkylating agent, a (3R)-6,7-bis(hydroxymethyl)-1H,3H-pyrrolo[1,2-c] thiazole, wasn't significantly different from the one observed for the monoalkylating derivatives indicating that the main mechanism of action may in fact be the monoalkylation process. (C) 2010 Elsevier Masson SAS. All rights reserved

  DOI：

  10.1016/j.ejmech.2010.07.029

文献信息

• Chiral 6-hydroxymethyl-1H,3H-pyrrolo[1,2-c]thiazoles: Novel antitumor DNA monoalkylating agents
  作者：Maria I.L. Soares、Ana Filipa Brito、Mafalda Laranjo、Ana Margarida Abrantes、M. Filomena Botelho、José A. Paixão、Ana Matos Beja、Manuela Ramos Silva、Teresa M.V.D. Pinho e Melo

  DOI：10.1016/j.ejmech.2010.07.029

  日期：2010.10

  New chiral 1H,3H-pyrrolo[1,2-c]thiazoles were synthesized and screened for their in vitro activity as anti-cancer agents in three human tumor cell lines, colorectal adenocarcinoma, melanoma and breast adenocarcinoma. (R)-6-Hydroxymethyl-5-methyl-3-phenyl-1H,3H-pyrrolo[1,2-c]thiazole and the corresponding benzylcarbamate showed selectivity for breast cancer cell lines with IC(50) values of 24 mu M and 2.2 mu M, respectively. The latter also showed significant activity against colorectal adenocarcinoma cancer cell lines (IC(50) = 8.7 mu M) In contrast, the 7-hydroxymethyl-5-methyl-3-phenyl-1H,3H-pyrrolo[1,2-c] thiazole gave moderate anti-cancer activity. The performance against breast cancer cell lines (IC(50) = 10 mu M) of a potential bisalkylating agent, a (3R)-6,7-bis(hydroxymethyl)-1H,3H-pyrrolo[1,2-c] thiazole, wasn't significantly different from the one observed for the monoalkylating derivatives indicating that the main mechanism of action may in fact be the monoalkylation process. (C) 2010 Elsevier Masson SAS. All rights reserved