5-(1,2-benzisotiazol-3-ilmetil)tetrazolo | 66713-70-0

• 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-(1,2-benzisotiazol-3-ilmetil)tetrazolo
• 英文别名: 3-(2H-tetrazol-5-ylmethyl)-1,2-benzothiazole
• CAS: 66713-70-0
• 化学式: C₉H₇N₅S
• 分子量: 217.254
• InChiKey: LZCGYVWCXDIIRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  95.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(1,2-苯并异噻唑-3-基)乙腈 在 sodium azide 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-(1,2-benzisotiazol-3-ilmetil)tetrazolo
  参考文献：
  名称：

  Synthesis and pharmacological properties of benzisothiazole/benzimidazole derivatives with acidic groups

  摘要：

  The synthesis and the pharmacological evaluation of benzisothiazole and benzimidazole tetrazolyl- and carboxyl-derivatives 1-6 are described. Structural modification was aimed at investigating the influence of two isosteric substituents (tetrazolyl- and carboxyl-) on the title benzofused heterocycles. The antiphlogistic, antipyretic and analgesic activities have been investigated in in vivo experimental models. Additional investigations have been performed in vitro to study the antiplatelet and spasmolytic activity of the compounds synthetized. All the compounds produced peripheral analgesic effects, but were less effective in hot plate test. The tetrazole and the carboxylic benzisothiazole derivatives 2 and 3 proved to be the most effective drugs within the series, exhibiting maximal inhibition of writhes with a potency 3-fold higher than that of acetaminophen. Only compound 5 provided indication for a central analgesic activity since it was active in hot plate test although with a low potency. The findings obtained in these in vivo and in vitro studies indicate that these compounds do not share the same mechanism of action of acetaminophen. All of the compounds under study present lower acute toxicity than acetaminophen when orally administered in mice. (C) 2002 Published by Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0014-827x(02)01219-3

文献信息

• Vicini; Amoretti; Barocelli, Farmaco, Edizione Scientifica, 1986, vol. 41, # 2, p. 111 - 118
  作者：Vicini、Amoretti、Barocelli、et al.

  DOI：——

  日期：——
• VICINI, P.;AMORETTI, L.;BAROCELLI, E.;CHIAVARINI, M.;IMPICCIATORE, M., FARMACO. ED. SCI., 1986, 41, N 2, 111-118
  作者：VICINI, P.、AMORETTI, L.、BAROCELLI, E.、CHIAVARINI, M.、IMPICCIATORE, M.

  DOI：——

  日期：——
• Synthesis and pharmacological properties of benzisothiazole/benzimidazole derivatives with acidic groups
  作者：Paola Vicini、Matteo Incerti、Loredana Amoretti、Vigilio Ballabeni、Massimiliano Tognolini、Elisabetta Barocelli

  DOI：10.1016/s0014-827x(02)01219-3

  日期：2002.4

  The synthesis and the pharmacological evaluation of benzisothiazole and benzimidazole tetrazolyl- and carboxyl-derivatives 1-6 are described. Structural modification was aimed at investigating the influence of two isosteric substituents (tetrazolyl- and carboxyl-) on the title benzofused heterocycles. The antiphlogistic, antipyretic and analgesic activities have been investigated in in vivo experimental models. Additional investigations have been performed in vitro to study the antiplatelet and spasmolytic activity of the compounds synthetized. All the compounds produced peripheral analgesic effects, but were less effective in hot plate test. The tetrazole and the carboxylic benzisothiazole derivatives 2 and 3 proved to be the most effective drugs within the series, exhibiting maximal inhibition of writhes with a potency 3-fold higher than that of acetaminophen. Only compound 5 provided indication for a central analgesic activity since it was active in hot plate test although with a low potency. The findings obtained in these in vivo and in vitro studies indicate that these compounds do not share the same mechanism of action of acetaminophen. All of the compounds under study present lower acute toxicity than acetaminophen when orally administered in mice. (C) 2002 Published by Editions scientifiques et medicales Elsevier SAS.