endo-9-methyl-9-azabicyclo<3.3.1>nonan-3-ol hydrochloride | 60205-58-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: endo-9-methyl-9-azabicyclo<3.3.1>nonan-3-ol hydrochloride
• 英文别名: endo-9-methyl-9-azabicyclo[3.3.1]nonan-3-ol hydrochloride；9-Methyl-9-azabicyclo[3.3.1]nonan-3-ol hydrochloride；9-methyl-9-azabicyclo[3.3.1]nonan-3-ol;hydrochloride
• CAS: 60205-58-5
• 化学式: C₉H₁₇NO*ClH
• 分子量: 191.701
• InChiKey: HIXYALRNLOELPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.42
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.47
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  endo-9-methyl-9-azabicyclo<3.3.1>nonan-3-ol hydrochloride 、 3-acetyloxy-2-(4-chlorophenyl)propanoic acid 在 盐酸 、 氯化亚砜 作用下， 生成
  参考文献：
  名称：

  Differential analgesic activity of the enantiomers of atropine derivatives does not correlate with their muscarinic subtype selectivity

  摘要：

  The enantiomers of several tropic and p-substituted tropic acid esters related to atropine obtained by esterification under non-racemizing conditions after resolution of the corresponding racemic acids [(+)- and (-)-18, (+)- and (-)-19] are reported. They were tested in vitro on muscarinic subtype receptors and in vivo for their analgesic activity on mice. As in the case of the lead compound, R-(+)-hyoscyamine, these substances show enantioselectivity in analgesic tests, the eutomers being the R-(+) or R-(+)-p-substituted tropic acid derivatives. However, this property, which is a consequence of increased central release of ACh, seems unrelated to muscarinic subtype selectivity insofar as the compounds are unable to discriminate muscarinic subtype receptors. A possible explanation of these results which does not involve subtype selectivity is proposed, based on the recently developed concept of inverse agonism.

  DOI：

  10.1016/s0223-5234(97)83285-0

文献信息

• Synthesis of a new class of 2,3-dihydro-2-oxo-1H-benzimidazole-1-carboxylic acid derivatives as highly potent 5-HT3 receptor antagonists
  作者：Marco Turconi、Massimo Nicola、Myrna Gil Quintero、Luciano Maiocchi、Rosella Micheletti、Ettore Giraldo、Arturo Donetti

  DOI：10.1021/jm00170a009

  日期：1990.8

  synthesized and evaluated for 5-HT3 antagonistic activity in a radioligand binding assay ([3H]ICS 205930) and in the 5-HT-induced von Bezold-Jarisch reflex in the rat. It was found that endo-substituted azabicycloalkyl derivatives (e.g. 7a, 12a, 12b) were much more active than the corresponding exo analogues (e.g. 7b, 12h, 12i) or azacycloalkyl compounds. Amidic derivatives 12a, 12b, 12c, 12e, 13b, and

  合成了一系列含有碱性氮杂环或氮杂双环烷基部分的2,3-二氢-2-氧代-1H-苯并咪唑-1-羧酸酯和酰胺，并在放射性配体结合测定中评估了其对5-HT3的拮抗活性（[ 3H] ICS 205930）和5-HT诱导的大鼠von Bezold-Jarisch反射。发现内取代的氮杂双环烷基衍生物（例如7a，12a，12b）比相应的exo类似物（例如7b，12h，12i）或氮杂环烷基化合物具有更高的活性。事实证明，酰胺衍生物12a，12b，12c，12e，13b和13c的活性比相应的酯衍生物7a，11a，7c，7d，8a和8b高约10倍。特别是化合物12a（DA 6215）在结合试验中的Ki = 3.8 nM，在von Bezold-Jarisch反射试验中的ED50 = 1 nM / kg iv，活性与参考化合物2（ICS 205930，Ki = 2 nM，ED50 = 2.1 nM / kg）相当