2-<(1,4-benzodioxan-2-yl)methyl>imidazole hydrochloride | 81167-19-3

• 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>imidazole hydrochloride
• 英文别名: 2-(1,4-benzodioxan-2-ylmethyl)imidazole hydrochloride；2-(1,4-benzodioxan-2-ylmethyl)imidazole.HCl；2-[(1,4-benzodioxan-2-yl)methyl]imidazole hydrochloride；2-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)-1H-imidazole;hydrochloride
• CAS: 81167-19-3
• 化学式: C₁₂H₁₂N₂O₂*ClH
• 分子量: 252.7
• InChiKey: BPHGCPDJBLTTQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  47.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<(1,4-benzodioxan-2-yl)methyl>imidazole hydrochloride 、 potassium carbonate 在 水 、 magnesium sulfate 作用下， 以 乙醚 为溶剂， 以to yield 2-(1,4-benzodioxan-2-ylmethyl)imidazole的产率得到2-(1,4-benzodioxan-2-ylmethyl)-imidazole
  参考文献：
  名称：

  2-(1,4-Benzodioxan-2-ylalkyl)imidazoles useful as antidepressants

  摘要：

  具有一般式的2-(1,4-苯并二氧杂环戊烷-2-基烷基)咪唑类化合物：##STR1## 其中R1，R2和R3分别独立地选自氢和烷基的群，n是等于0，1或2的整数，以及其药学上可接受的酸盐，可用作抗抑郁剂。

  公开号：

  US04302469A1
• 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， 反应 138.0h， 生成 2-<(1,4-benzodioxan-2-yl)methyl>imidazole hydrochloride
  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

• .alpha.-Adrenoreceptor reagents. 1. Synthesis of some 1,4-benzodioxans as selective presynaptic .alpha.2-adrenoreceptor antagonists and potential antidepressants
  作者：Christopher B. Chapleo、Peter L. Myers、Richard C. M. Butler、John C. Doxey、Alan G. Roach、Colin F. C. Smith

  DOI：10.1021/jm00360a008

  日期：1983.6

  None of these derivatives are as potent or selective as 5, although some do display a degree of selectivity as antagonists. Some derivatives were found to possess agonist properties that, with the exception of 23, favored the postsynaptic site. Compounds 9, 12, 16, 21, 30, and 51 possessing presynaptic alpha 2-adrenoreceptor antagonist and postsynaptic alpha 1-adrenoreceptor partial agonist properties

  讨论了RX 781094，2-（1,4-苯并二恶烷-2-基）-2-咪唑啉盐酸盐（5）的合理设计，该化合物是新型的α2-肾上腺素受体有效和选择性拮抗剂。在突触前α2肾上腺素受体上起拮抗剂作用的化合物可能是有效的新型抑郁症治疗方法，因为它具有增加中央受体部位去甲肾上腺素浓度的能力。已经研究了芳族和咪唑啉环中取代基的作用，以及用examined官能团或其他杂环系统取代咪唑啉环的作用。尽管有些衍生物确实表现出一定程度的拮抗剂，但这些衍生物都不像5那样有效或具有选择性。发现一些衍生物具有激动剂特性，除23种外，它们更有利于突触后位点。化合物9
• 2-(1,4-Benzodioxan-2-ylalkyl)imidazoles useful as antihypertensives and
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04497818A1

  公开（公告）日：1985-02-05

  2-(1,4-Benzodioxan-2-ylalkyl)imidazoles having the general formula: ##STR1## wherein R.sup.1, and R.sup.2 and R.sup.3 are independently selected from the group consisting of hydrogen, and alkyl (1-6C), and wherein n is an integer equal to 0, 1 or 2, and the pharmaceutically acceptable acid addition salts thereof, are .alpha..sub.2 blockers and thus are useful as affectors of the CNS, specifically as platelet aggregation inhibitors and as antihypertensives.

  具有通式：##STR1##其中R.sup.1、R.sup.2和R.sup.3独立地选自氢、烷基（1-6C）的群，n是等于0、1或2的整数，以及其药学上可接受的酸盐，是.alpha..sub.2阻滞剂，因此可用作影响中枢神经系统的药物，具体用途为血小板聚集抑制剂和降压剂。
• 2-(1,4-Benzodioxan-2-ylalkyl) imidazoles, their preparation and pharmaceutical compositions containing them
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0047531A1

  公开（公告）日：1982-03-17

  2-(1,4-Benzodioxan-2-ylalkyl)imidazoles having the general formula: wherein R', and R2 and R' are independently selected from the group consisting of hydrogen, and alkyl (1-6C), and wherein n is an integer equal to 0, 1 or 2, and the pharmaceutically acceptable acid addition salts thereof, are useful as affectors of the CNS, specifically as antidepressants, and are also useful as agents for the control of intraoccular pressure.

  具有通式的 2-(1,4-苯并二恶烷-2-基烷基)咪唑： 其中 R'、R2 和 R'独立地选自氢和烷基（1-6C）组成的组，n 是等于 0、1 或 2 的整数，其药学上可接受的酸加成盐可用作中枢神经系统的影响剂，特别是抗抑郁剂，还可用作控制肌内压的药物。
• [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.
  作者：KLUGE, A. F.、STROSBERG, A. M.、WHITING, R.、CHRISTIE, G.

  DOI：——

  日期：——