2-(4-amidinophenyl)-6-nitrobenzothiazole hydrochloride | 1221688-97-6

• 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: 2-(4-amidinophenyl)-6-nitrobenzothiazole hydrochloride
• 英文别名: 4-(6-Nitro-1,3-benzothiazol-2-yl)benzenecarboximidamide;hydrochloride
• CAS: 1221688-97-6
• 化学式: C₁₄H₁₀N₄O₂S*ClH
• 分子量: 334.786
• InChiKey: FKKOLCBIHUUNSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  137
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-amidinophenyl)-6-nitrobenzothiazole hydrochloride 在 盐酸 、 tin(II) chloride dihydrate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以68.7%的产率得到2-(4-amidinophenyl)-6-aminobenzothiazole hydrochloride
  参考文献：
  名称：

  Novel amidino substituted 2-phenylbenzothiazoles: Synthesis, antitumor evaluation in vitro and acute toxicity testing in vivo

  摘要：

  The efficient synthesis of new bis-substituted nitro-amidino, amino-amidino (10a, 10b-13a, 13b) and previously prepared diamidino 2-phenyl-benzothiazoles (9a, 9b) is described. The compounds 11a and 11b were prepared by recently developed methodology of the key precursors in zwitterionic form 8a and 8b with 4-nitrobenzoylchloride in a very good yield (70%). All compounds except diamidino-substituted 2-phenylbenzothiazole 9a show exceptionally prominent tumor cell-growth inhibitory activity and cytotoxicity, whereby the special selectivity of amino-amidine 2-phenylbenzothiazole 12a towards MCF-7 and H 460 cells makes this compound a prospective lead compound that should be further evaluated in animal models. All in vivo tested compounds (12a, 12b, 13a and 13b) are absorbed from mice gastrointestinal system. LD50 are between 67.33 and 696.2 mg/kg body weight (OECD/EPA toxicity categories 2-3). (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2009.12.054
• 作为产物：
  描述：

  在 氨 作用下， 以 乙醇 为溶剂， 以0.956 g的产率得到2-(4-amidinophenyl)-6-nitrobenzothiazole hydrochloride
  参考文献：
  名称：

  Novel amidino substituted 2-phenylbenzothiazoles: Synthesis, antitumor evaluation in vitro and acute toxicity testing in vivo

  摘要：

  The efficient synthesis of new bis-substituted nitro-amidino, amino-amidino (10a, 10b-13a, 13b) and previously prepared diamidino 2-phenyl-benzothiazoles (9a, 9b) is described. The compounds 11a and 11b were prepared by recently developed methodology of the key precursors in zwitterionic form 8a and 8b with 4-nitrobenzoylchloride in a very good yield (70%). All compounds except diamidino-substituted 2-phenylbenzothiazole 9a show exceptionally prominent tumor cell-growth inhibitory activity and cytotoxicity, whereby the special selectivity of amino-amidine 2-phenylbenzothiazole 12a towards MCF-7 and H 460 cells makes this compound a prospective lead compound that should be further evaluated in animal models. All in vivo tested compounds (12a, 12b, 13a and 13b) are absorbed from mice gastrointestinal system. LD50 are between 67.33 and 696.2 mg/kg body weight (OECD/EPA toxicity categories 2-3). (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2009.12.054

文献信息

• Novel amidino substituted 2-phenylbenzothiazoles: Synthesis, antitumor evaluation in vitro and acute toxicity testing in vivo
  作者：Livio Racané、Marijeta Kralj、Lidija Šuman、Ranko Stojković、Vesna Tralić-Kulenović、Grace Karminski-Zamola

  DOI：10.1016/j.bmc.2009.12.054

  日期：2010.2

  The efficient synthesis of new bis-substituted nitro-amidino, amino-amidino (10a, 10b-13a, 13b) and previously prepared diamidino 2-phenyl-benzothiazoles (9a, 9b) is described. The compounds 11a and 11b were prepared by recently developed methodology of the key precursors in zwitterionic form 8a and 8b with 4-nitrobenzoylchloride in a very good yield (70%). All compounds except diamidino-substituted 2-phenylbenzothiazole 9a show exceptionally prominent tumor cell-growth inhibitory activity and cytotoxicity, whereby the special selectivity of amino-amidine 2-phenylbenzothiazole 12a towards MCF-7 and H 460 cells makes this compound a prospective lead compound that should be further evaluated in animal models. All in vivo tested compounds (12a, 12b, 13a and 13b) are absorbed from mice gastrointestinal system. LD50 are between 67.33 and 696.2 mg/kg body weight (OECD/EPA toxicity categories 2-3). (C) 2010 Published by Elsevier Ltd.