2-(4-benzoamidinium)-6-aminobenzothiazole methanesulfonate | 1628117-80-5

• 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-benzoamidinium)-6-aminobenzothiazole methanesulfonate
• 英文别名: 4-(6-Amino-1,3-benzothiazol-2-yl)benzenecarboximidamide;methanesulfonic acid；4-(6-amino-1,3-benzothiazol-2-yl)benzenecarboximidamide;methanesulfonic acid
• CAS: 1628117-80-5
• 化学式: CH₄O₃S*C₁₄H₁₂N₄S
• 分子量: 364.449
• InChiKey: JEOFLLOUTKXMAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  180
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  甲烷磺酸 、 2-(4-amidinophenyl)-6-aminobenzothiazole hydrochloride 在 sodium hydroxide 作用下， 以 水 、 乙醇 为溶剂， 以64.3%的产率得到2-(4-benzoamidinium)-6-aminobenzothiazole methanesulfonate
  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

文献信息

• 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.