2-(6-methyl-2,3-dihydrobenzofuran-2-yl)-4,5-dihydro-1H-imidazole | 89210-21-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 2-(6-methyl-2,3-dihydrobenzofuran-2-yl)-4,5-dihydro-1H-imidazole
• 英文别名: RX 811046；2-(6-methyl-2,3-dihydro-1-benzofuran-2-yl)-4,5-dihydro-1H-imidazole
• CAS: 89210-21-9
• 化学式: C₁₂H₁₄N₂O
• 分子量: 202.256
• InChiKey: MNBOAOHNXHZJLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  33.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-甲基-苯并呋喃-2-羧酸 在 sodium amalgam 、 氯化亚砜 、 氨 、 sodium methylate 、 phosphorus pentoxide 作用下， 以 1,4-二氧六环 、 sodium hydroxide 、 甲苯 、 苯 为溶剂， 反应 11.25h， 生成 2-(6-methyl-2,3-dihydrobenzofuran-2-yl)-4,5-dihydro-1H-imidazole
  参考文献：
  名称：

  .alpha.-Adrenoceptor reagents. 2. Effects of modification of the 1,4-benzodioxan ring system on .alpha.-adrenoreceptor activity

  摘要：

  Modification of the 1,4-benzodioxan ring present in RX 781094 has not previously been considered. This paper describes a number of analogues of this ring system, including compounds in which one of the oxygen atoms has been replaced by a methylene group and also those in which the ring size has been changed to give, for example, furan and thiophene derivatives. The dihydrobenzofuranylimidazoline compound 7 is the only analogue possessing presynaptic antagonist potency potency and selectivity comparable to that of 1. In view of this result, a number of derivatives was prepared to determine the structure-activity relationships within this series. Many derivatives, as well as the parent compound 7, were found to possess presynaptic alpha 2-adrenoreceptor antagonist and postsynaptic alpha 1-adrenoreceptor partial agonist properties. Two of the selective presynaptic antagonists, 13 and 14 possess greater potency and selectivity than that possessed by 1. The 5-chloro derivative 25 is twice as potent as after oral administration but only about half as potent when given intravenously.

  DOI：

  10.1021/jm00371a003

文献信息

• Imidazoline derivatives
  申请人：RECKITT AND COLMAN PRODUCTS LIMITED

  公开号：EP0071368A1

  公开（公告）日：1983-02-09

  Imidazoline derivatives of the formula wherein R' is hydrogen or alkyl C1-6; R2 is hydrogen, methyl, chloro, bromo or fluoro; R3 is hydrogen, methyl, hydroxy, methoxy, fluoro, chloro or bromo; and their non-toxic salts. Processes for their preparation and pharmaceutical compositions thereof. The compounds exhibit presynaptic α2-adrenoreceptor antagonist activity.

  式中R'为氢或C1-6烷基；R2为氢、甲基、氯、溴或氟；R3为氢、甲基、羟基、甲氧基、氟、氯或溴的咪唑啉衍生物及其无毒盐。 其制备方法及其药物组合物。 这些化合物具有突触前α2-肾上腺素受体拮抗剂活性。
• US4411908A
  申请人：——

  公开号：US4411908A

  公开（公告）日：1983-10-25
• .alpha.-Adrenoceptor reagents. 2. Effects of modification of the 1,4-benzodioxan ring system on .alpha.-adrenoreceptor activity
  作者：Christopher B. Chapleo、Peter L. Myers、Richard C. M. Butler、John A. Davis、John C. Doxey、Stanley D. Higgins、Malcolm Myers、Alan G. Roach、Colin F. C. Smith

  DOI：10.1021/jm00371a003

  日期：1984.5

  Modification of the 1,4-benzodioxan ring present in RX 781094 has not previously been considered. This paper describes a number of analogues of this ring system, including compounds in which one of the oxygen atoms has been replaced by a methylene group and also those in which the ring size has been changed to give, for example, furan and thiophene derivatives. The dihydrobenzofuranylimidazoline compound 7 is the only analogue possessing presynaptic antagonist potency potency and selectivity comparable to that of 1. In view of this result, a number of derivatives was prepared to determine the structure-activity relationships within this series. Many derivatives, as well as the parent compound 7, were found to possess presynaptic alpha 2-adrenoreceptor antagonist and postsynaptic alpha 1-adrenoreceptor partial agonist properties. Two of the selective presynaptic antagonists, 13 and 14 possess greater potency and selectivity than that possessed by 1. The 5-chloro derivative 25 is twice as potent as after oral administration but only about half as potent when given intravenously.