1-benzyl-2-(1,4-benzodioxan-2-ylmethyl)imidazole | 81403-81-8

• 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: 1-benzyl-2-(1,4-benzodioxan-2-ylmethyl)imidazole
• 英文别名: 1-benzyl-2-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)imidazole
• CAS: 81403-81-8
• 化学式: C₁₉H₁₈N₂O₂
• 分子量: 306.364
• InChiKey: CBOZFUUOUBOVHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  盐酸 、 1-benzyl-2-(1,4-benzodioxan-2-ylmethyl)imidazole 、 乙醚 在 乙醚 、 methanol+acetone 作用下， 以 甲醇 为溶剂， 以to yield 1-benzyl-2-(1,4-benzodioxan-2-ylmethyl)imidazole hydrochloride, m.p. 105°-107° C.(d)的产率得到1-benzyl-2-(1,4-benzodioxan-2-ylmethyl)imidazole hydrochloride
  参考文献：
  名称：

  2-(1,4-Benzodioxan-2-ylalkyl)imidazoles

  摘要：

  具有一般式##STR1##的2-(1,4-苯并二氧杂环戊烷-2-基烷基)咪唑化合物，其中R.sup.1和R.sup.2各自独立地选自氢、烷基、可选取代的苯基和可选取代的苯基低烷基；R.sup.3为氢、烷基或可选取代的苯基低烷基；n为0、1或2的整数；但R.sup.1、R.sup.2和R.sup.3不能全都是氢和/或烷基；以及其药学上可接受的酸盐，可用作抗抑郁剂。

  公开号：

  US04315021A1
• 作为产物：
  描述：

  (2,3-二氢苯并[1,4]二恶烷-2-基)乙腈 在 盐酸 、 sodium hydride 作用下， 反应 139.0h， 生成 1-benzyl-2-(1,4-benzodioxan-2-ylmethyl)imidazole
  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

• [EN] 2-(1,4-BENZODOIOXAN-2-YLALKYL)IMIDAZOLES USEFUL AS ANTIDEPRESSANTS
  申请人：SYNTEX (U.S.A.) INC.

  公开号：WO1982001874A1

  公开（公告）日：1982-06-10

  (EN) 2-(1,4-Benzodioxan-2-ylalkyl)imidazoles having the general formula (FORMULA) wherein R1 and R2 are each independently selected from the group consisting of hydrogen, alkyl, optionally substituted phenyl, and optionally substituted phenyl lower alkyl; R3 is hydrogen, alkyl, or optionally substituted phenyl lower alkyl; n is an integer equal to 0,1 or 2; with the proviso that R1, R2 and R3 cannot all be hydrogen and/or alkyl; and the pharmaceutically acceptable acid addition salts thereof, are useful as antidepressants. (FR) 2-(1,4-benzodioxan-2-ylalkyl)imidazole ayant la formule generale (FORMULE) ou R1 et R2 sont selectionnes independamment parmi le groupe comprenant un hydrogene, un alkyl, un phenyl eventuellement substitue, et un alkyl inferieur a phenyl eventuellement substitue; R3 represente l'hydrogene, un alkyl, ou un alkyl inferieur a phenyl eventuellement substitue; n est un nombre entier egal a 0,1 ou 2 avec la condition que R1, R2 et R3 ne puissent etre tous l'hydrogene et/ou un alkyl; et leurs sels d'addition acide pharmaceutiquement acceptables, sont utiles comme antidepressifs.

  具有一般式（FORMULA）的二氨基（2-（1,4-苯并呋喃-2-yl）基团）imidazole化合物，其中R1和R2各自独立地从氢、烷基、可能被取代的苯基和可能被取代的苯基低取代基中选择；R3为氢、烷基或可能被取代的苯基低取代基；n为整数，等于0、1或2；但R1、R2和R3不能全部为氢和/或烷基；以及该化合物的有效成药的酸性加成盐，可用于作抗抑郁药。
• KLUGE, A. F.;STROSBERG, A. M.;WHITING, R.;CHRISTIE, G. A.
  作者：KLUGE, A. F.、STROSBERG, A. M.、WHITING, R.、CHRISTIE, G. A.

  DOI：——

  日期：——
• US4315021A
  申请人：——

  公开号：US4315021A

  公开（公告）日：1982-02-09
• US4402967A
  申请人：——

  公开号：US4402967A

  公开（公告）日：1983-09-06
• 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.