<8aS*-(8aα,12aα,13aα)>-11β-hydroxy-12β-(hydroxymethyl)-5,6,8a,9,10,11,12,12a,13,13a-decahydro-8H-benzo-1,3-benzodioxolo<5,6-a>quinolizine | 108647-27-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: <8aS*-(8aα,12aα,13aα)>-11β-hydroxy-12β-(hydroxymethyl)-5,6,8a,9,10,11,12,12a,13,13a-decahydro-8H-benzo-1,3-benzodioxolo<5,6-a>quinolizine
• 英文别名: (1S,15S,18R,19R,20S)-19-(hydroxymethyl)-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9-trien-18-ol
• CAS: 108647-27-4
• 化学式: C₁₉H₂₅NO₄
• 分子量: 331.412
• InChiKey: BTDBEHJEPKRBOL-NOYHWAJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (+/-)-methyl 7,8-(methylenedioxy)-14-oxo-13-alloberbanecarboxylate 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 以47%的产率得到<8aS*-(8aα,12aα,13aα)>-11β-hydroxy-12β-(hydroxymethyl)-5,6,8a,9,10,11,12,12a,13,13a-decahydro-8H-benzo-1,3-benzodioxolo<5,6-a>quinolizine
  参考文献：
  名称：

  Berbanes: a new class of selective .alpha.2-adrenoceptor antagonists

  摘要：

  The alpha-adrenoceptor blocking properties of some berbanes have been studied and compared with those of idazoxan, yohimbine, phentolamine, and prazosin. Their effects on presynaptic alpha 2-adrenoceptors were studied on chemical neurotransmission of isolated rat vas deferens and longitudinal muscle strip of guinea pig ileum; xylazine or norepinephrine was employed as agonist. The alpha 1-adrenoceptor blocking activities of the berbanes were tested on isolated rat vas deferens and rabbit pulmonary artery by using phenylephrine or norepinephrine as agonist. The antagonistic activity of the berbanes and the reference compounds on alpha 2- and alpha 1-adrenoceptors was characterized by the apparent pA2 values. Of the compounds studied, [8aS*-(8a alpha,12a alpha,13a alpha)]-11 alpha-hydroxy-5,6,8a,9,10,11,12a,13,13,a-decahydro-8H-benzo[g]-1,3 -benzodioxolo[5,6-a]quinoli zine, 6d, proved to be the most selective antagonist at the presynaptic alpha 2-adrenoceptors (alpha 1:alpha 2 ratio = 1659). Since blockade of alpha 2-adrenoceptors located on noradrenergic axon terminals leads to an increase of norepinephrine release, this compound could have potential as an antidepressant agent.

  DOI：

  10.1021/jm00391a015

文献信息

• Berbanes: a new class of selective .alpha.2-adrenoceptor antagonists
  作者：E. Sylvester Vizi、Istvan Toth、George T. Somogyi、Lajos Szabo、Laszlo G. Harsing、Csaba Szantay

  DOI：10.1021/jm00391a015

  日期：1987.8

  The alpha-adrenoceptor blocking properties of some berbanes have been studied and compared with those of idazoxan, yohimbine, phentolamine, and prazosin. Their effects on presynaptic alpha 2-adrenoceptors were studied on chemical neurotransmission of isolated rat vas deferens and longitudinal muscle strip of guinea pig ileum; xylazine or norepinephrine was employed as agonist. The alpha 1-adrenoceptor blocking activities of the berbanes were tested on isolated rat vas deferens and rabbit pulmonary artery by using phenylephrine or norepinephrine as agonist. The antagonistic activity of the berbanes and the reference compounds on alpha 2- and alpha 1-adrenoceptors was characterized by the apparent pA2 values. Of the compounds studied, [8aS*-(8a alpha,12a alpha,13a alpha)]-11 alpha-hydroxy-5,6,8a,9,10,11,12a,13,13,a-decahydro-8H-benzo[g]-1,3 -benzodioxolo[5,6-a]quinoli zine, 6d, proved to be the most selective antagonist at the presynaptic alpha 2-adrenoceptors (alpha 1:alpha 2 ratio = 1659). Since blockade of alpha 2-adrenoceptors located on noradrenergic axon terminals leads to an increase of norepinephrine release, this compound could have potential as an antidepressant agent.