5-chloro-6-fluoro-N-((R)-1-phenylpropyl)benzo[d]thiazol-2-amine | 1166399-12-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 5-chloro-6-fluoro-N-((R)-1-phenylpropyl)benzo[d]thiazol-2-amine
• 英文别名: 5-chloro-6-fluoro-N-[(1R)-1-phenylpropyl]-1,3-benzothiazol-2-amine
• CAS: 1166399-12-7
• 化学式: C₁₆H₁₄ClFN₂S
• 分子量: 320.818
• InChiKey: MEXWPJOFTOHMFP-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(3-chloro-4-fluorophenyl)-3-((R)-1-phenylpropyl)thiourea 在 溴 作用下， 以 氯仿 为溶剂， 以40%的产率得到5-chloro-6-fluoro-N-((R)-1-phenylpropyl)benzo[d]thiazol-2-amine
  参考文献：
  名称：

  Synthesis and antitumor activity of optically active thiourea and their 2-aminobenzothiazole derivatives: A novel class of anticancer agents

  摘要：

  A novel series of optically active 2-aminobenzothiazole derivatives were synthesized by reaction of optically active amine (1) with thiophosgene to obtain optically active isothiocyanates (IIa-h) which on condensation with 4-fluoro-3-chloro aniline (III) yielded various optically active thioureas (IVa-h). Further oxidative cyclisation in the presence of bromine and chloroform yielded title compounds (Va-h). The structures of these compounds were established by IR, H-1 NMR, C-13 NMR, Mass and HRMS. The compounds (IVA-h and Va-h) were evaluated for in vitro cytotoxicity against mouse Ehrlich Ascites Carcinoma (EAC) and two human cancer cell lines (MCF-7 and HeLa). In preliminary MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] cytotoxicity studies the optically active thiourea derivatives (IVe, IVf and IVh) were found most effective. In EAC cells the IC50 values for IVe, IVf, IVh and Vg were found in the range of 10-24 mu M, whereas in MCF-7 and HeLa cells the IC50 values were observed in the range of 15-30 mu M and 33-48 mu M, respectively. In alkaline comet assay the compounds (We and IVf) showed dose-dependent DNA damaging activity. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.12.002

文献信息

• Synthesis and antitumor activity of optically active thiourea and their 2-aminobenzothiazole derivatives: A novel class of anticancer agents
  作者：S.N. Manjula、N. Malleshappa Noolvi、K. Vipan Parihar、S.A. Manohara Reddy、Vijay Ramani、Andanappa K. Gadad、Gurdial Singh、N. Gopalan Kutty、C. Mallikarjuna Rao

  DOI：10.1016/j.ejmech.2008.12.002

  日期：2009.7

  A novel series of optically active 2-aminobenzothiazole derivatives were synthesized by reaction of optically active amine (1) with thiophosgene to obtain optically active isothiocyanates (IIa-h) which on condensation with 4-fluoro-3-chloro aniline (III) yielded various optically active thioureas (IVa-h). Further oxidative cyclisation in the presence of bromine and chloroform yielded title compounds (Va-h). The structures of these compounds were established by IR, H-1 NMR, C-13 NMR, Mass and HRMS. The compounds (IVA-h and Va-h) were evaluated for in vitro cytotoxicity against mouse Ehrlich Ascites Carcinoma (EAC) and two human cancer cell lines (MCF-7 and HeLa). In preliminary MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] cytotoxicity studies the optically active thiourea derivatives (IVe, IVf and IVh) were found most effective. In EAC cells the IC50 values for IVe, IVf, IVh and Vg were found in the range of 10-24 mu M, whereas in MCF-7 and HeLa cells the IC50 values were observed in the range of 15-30 mu M and 33-48 mu M, respectively. In alkaline comet assay the compounds (We and IVf) showed dose-dependent DNA damaging activity. (C) 2008 Elsevier Masson SAS. All rights reserved.