1,5-benzodioxepin-2-carboxamide | 89197-56-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-benzodioxepin-2-carboxamide
• 英文别名: (3,4-dihydro-2H-1,5-benzodioxepin-2-yl)methylamide；3,4-dihydro-2H-1,5-benzodioxepine-4-carboxamide
• CAS: 89197-56-8
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: XLEKCMBFYXZLLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,5-benzodioxepin-2-carboxamide 在 吡啶 、 三氯氧磷 作用下， 反应 2.5h， 以96%的产率得到1,5-benzodioxepin-2-nitrile
  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paper describes a number of analogues of this ring system, including compounds in which one of the oxygen atoms has been replaced by a methylene group and also those in which the ring size has been changed to give, for example, furan and thiophene derivatives.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
• 作为产物：
  描述：

  ethyl 1,5-benzodioxepin-2-carboxylate 在 氨 作用下， 以 乙醇 为溶剂， 以15%的产率得到1,5-benzodioxepin-2-carboxamide
  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paper describes a number of analogues of this ring system, including compounds in which one of the oxygen atoms has been replaced by a methylene group and also those in which the ring size has been changed to give, for example, furan and thiophene derivatives.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

• [DE] SUBSTITUIERTE BENZDIOXEPINE<br/>[EN] SUBSTITUTED BENZODIOXEPINS<br/>[FR] BENZODIOXEPINES SUBSTITUEES
  申请人：MERCK PATENT GMBH

  公开号：WO2004058746A1

  公开（公告）日：2004-07-15

  Benzdioxepine der Formel (I) sowie deren physiologisch verträgliche Salze and Solvate, worin Rl, R2, R3, R4, A, B, a and b die in Anspruch 1 angegebenen Bedeutungen besitzen, sind Liganden der 5HT1A Rezeptoren und/oder der 5HT4 Rezeptoren mit gleichzeitig starker Serotonin-Wiederaufnahmehemmung. Sie können zur Behandlung and Prophylaxe verschiedener Erkrankungen eingesetzt werden.

  公式为（I）的苯并二氧杂环己烷和其生理相容性盐和溶剂，其中R1、R2、R3、R4、A、B、a和b具有权利要求1所述的含义，是5HT1A受体和/或5HT4受体的配体，并具有强烈的血清素再摄取抑制作用。它们可用于治疗和预防各种疾病。