2-(4-aminophenyl)-6-amidinobenzothiazole hydrochloride | 1221689-03-7

• 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: 2-(4-aminophenyl)-6-amidinobenzothiazole hydrochloride
• 英文别名: 2-(4-Aminophenyl)-1,3-benzothiazole-6-carboximidamide;hydrochloride
• CAS: 1221689-03-7
• 化学式: C₁₄H₁₂N₄S*ClH
• 分子量: 304.803
• InChiKey: RONGYLUPYLBTRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  20
• 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：
  117
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲烷磺酸 、 2-(4-aminophenyl)-6-amidinobenzothiazole hydrochloride 在 sodium hydroxide 作用下， 以 水 、 乙醇 为溶剂， 以73.1%的产率得到2-(4-aminophenyl)-6-amidinium benzothiazole methanesulfonate hydrate
  参考文献：
  名称：

  Interactions with polynucleotides and antitumor activity of amidino and imidazolinyl substituted 2-phenylbenzothiazole mesylates

  摘要：

  Based on previously reported antiproliferative activity screening, four most promising disubstituted 2-phenylbenzothiazole hydrochlorides were chosen for detailed study. Water solubility, as well as liphophilicity/hydrophilicity balance of organic core were modified by conversion to mesylate salts. For purpose of structure/activity studies their structures were determined by X-ray structure analysis. Detailed analysis of interactions of new compounds with double stranded (ds-) DNA/RNA by UV/Vis and CD titrations, thermal melting and viscometry experiments revealed that most of studied compounds intercalate into ds-RNA but bind into minor groove of AT-DNA, and agglomerate along GC-DNA. Furthermore, compounds also interact with ss-RNA, but only amino-imidazolinyl 2-phenylbenzothiazole, 4b displayed well defined orientation and dominant binding mode (by induced CD signals) with poly A and poly G. Besides, in vitro investigations revealed moderate to high antiproliferative activity of benzothiazoles against seven human cancer cell lines, while in some cases (HTC 116, SW620, MIA PaCa-2) high correlation between the type of the amidino group and cytotoxic activity was observed. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.072
• 作为产物：
  描述：

  2-(4-nitrophenyl)-6-amidinobenzothiazole hydrochloride 在 盐酸 、 tin(II) chloride dihydrate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以75.4%的产率得到2-(4-aminophenyl)-6-amidinobenzothiazole 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.
• Interactions with polynucleotides and antitumor activity of amidino and imidazolinyl substituted 2-phenylbenzothiazole mesylates
  作者：Livio Racané、Ranko Stojković、Vesna Tralić-Kulenović、Helena Cerić、Marijana Đaković、Katja Ester、Ana Mišir Krpan、Marijana Radić Stojković

  DOI：10.1016/j.ejmech.2014.08.072

  日期：2014.10

  Based on previously reported antiproliferative activity screening, four most promising disubstituted 2-phenylbenzothiazole hydrochlorides were chosen for detailed study. Water solubility, as well as liphophilicity/hydrophilicity balance of organic core were modified by conversion to mesylate salts. For purpose of structure/activity studies their structures were determined by X-ray structure analysis. Detailed analysis of interactions of new compounds with double stranded (ds-) DNA/RNA by UV/Vis and CD titrations, thermal melting and viscometry experiments revealed that most of studied compounds intercalate into ds-RNA but bind into minor groove of AT-DNA, and agglomerate along GC-DNA. Furthermore, compounds also interact with ss-RNA, but only amino-imidazolinyl 2-phenylbenzothiazole, 4b displayed well defined orientation and dominant binding mode (by induced CD signals) with poly A and poly G. Besides, in vitro investigations revealed moderate to high antiproliferative activity of benzothiazoles against seven human cancer cell lines, while in some cases (HTC 116, SW620, MIA PaCa-2) high correlation between the type of the amidino group and cytotoxic activity was observed. (C) 2014 Elsevier Masson SAS. All rights reserved.