2-<(1,4-benzodioxan-2-yl)methyl>benzimidazole | 80637-52-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 2-<(1,4-benzodioxan-2-yl)methyl>benzimidazole
• 英文别名: 2-(1,4-benzodioxan-2-ylmethyl)benzimidazole；2-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)-1H-benzimidazole
• CAS: 80637-52-1
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: HIZQQOPJQGUZJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  47.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  盐酸 、 2-<(1,4-benzodioxan-2-yl)methyl>benzimidazole 、 乙醚 在 乙醚 、 methanol+acetone 作用下， 以 甲醇 为溶剂， 以to yield 2-(1,4-benzodioxan-2-ylmethyl)benzimidazole hydrochloride, m.p. 221°-224° C.(d)的产率得到2-<(1,4-benzodioxan-2-yl)methyl>benzimidazole hydrochloride
  参考文献：
  名称：

  2-(1,4-Benzodioxan-2-ylalkyl)benzimidazoles useful as anti-depressants

  摘要：

  式子为##STR1##的化合物和其药学上可接受的无毒盐，其中：R是氢、低烷基或苄基；X是苯环中任意位置的氢的替代物，选自低烷基、低烷氧基、苄基和卤素；m是从0到4的整数；n是从0到2的整数；这些化合物是新颖的。这些化合物已被证明是α2受体阻滞剂，因此是抗抑郁剂。

  公开号：

  US04301171A1
• 作为产物：
  描述：

  (2,3-二氢苯并[1,4]二恶烷-2-基)乙腈 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 114.0h， 生成 2-<(1,4-benzodioxan-2-yl)methyl>benzimidazole
  参考文献：
  名称：

  Structure-activity relationships for 2-substituted imidazoles as .alpha.2-adrenoceptor antagonists

  摘要：

  Several 2-[(1,4-benzodioxan-2-yl)alkyl]imidazoles were prepared and evaluated for their blocking activity and relative selectivity on presynaptic (alpha 2) and postsynaptic (alpha 1) receptors in the isolated rat vas deferens. 1-Ethyl-2-[(1,4-benzodioxan 2-yl)methyl]imidazole (13) was the most selective alpha 2-adrenoceptor antagonist of the series and was, for practical purposes, devoid of alpha 1-adrenoceptor antagonist activity. The lipophilicity of 13 (log D = 2.31) indicated that it would have an excellent chance to enter the central nervous system. Compound 13 was selected for clinical evaluation as an antidepressant agent.

  DOI：

  10.1021/jm00348a012

文献信息

• US4301171A
  申请人：——

  公开号：US4301171A

  公开（公告）日：1981-11-17
• Structure-activity relationships for 2-substituted imidazoles as .alpha.2-adrenoceptor antagonists
  作者：Joan M. Caroon、Robin D. Clark、Arthur F. Kluge、Ronald Olah、David B. Repke、Stefan H. Unger、Anton D. Michel、Roger L. Whiting

  DOI：10.1021/jm00348a012

  日期：1982.6

  Several 2-[(1,4-benzodioxan-2-yl)alkyl]imidazoles were prepared and evaluated for their blocking activity and relative selectivity on presynaptic (alpha 2) and postsynaptic (alpha 1) receptors in the isolated rat vas deferens. 1-Ethyl-2-[(1,4-benzodioxan 2-yl)methyl]imidazole (13) was the most selective alpha 2-adrenoceptor antagonist of the series and was, for practical purposes, devoid of alpha 1-adrenoceptor antagonist activity. The lipophilicity of 13 (log D = 2.31) indicated that it would have an excellent chance to enter the central nervous system. Compound 13 was selected for clinical evaluation as an antidepressant agent.
• 2-(1,4-Benzodioxan-2-ylalkyl)benzimidazoles useful as anti-depressants
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04301171A1

  公开（公告）日：1981-11-17

  Compounds of the formula ##STR1## and the pharmaceutically acceptable, non-toxic salts thereof, wherein: R is hydrogen, lower alkyl, or benzyl; X is a substitution for hydrogen at any position in the benzene ring and is selected from the group consisting of lower alkyl, lower alkoxyl, benzyl and halo; m is an integer from 0 to 4; and n is an integer from 0 to 2; are novel. These compounds have been shown to be .alpha..sub.2 blockers, and are, therefore, anti-depressants.

  式子为##STR1##的化合物和其药学上可接受的无毒盐，其中：R是氢、低烷基或苄基；X是苯环中任意位置的氢的替代物，选自低烷基、低烷氧基、苄基和卤素；m是从0到4的整数；n是从0到2的整数；这些化合物是新颖的。这些化合物已被证明是α2受体阻滞剂，因此是抗抑郁剂。