cis-bicyclo[3.3.0]oct-endo-2-ylcarbonyl chloride | 72028-18-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: cis-bicyclo[3.3.0]oct-endo-2-ylcarbonyl chloride
• CAS: 72028-18-3
• 化学式: C₉H₁₃ClO
• 分子量: 172.655
• InChiKey: OQILNGGRRHAVQS-GCJDJSOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  cis-bicyclo[3.3.0]oct-endo-2-ylcarbonyl chloride 在 吡啶 、 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 11.0h， 生成 (1'R^*,2'R^*,5'R^*)-8-bicyclo<3.3.0>octan-2-yl-1,3-dipropylxanthine
  参考文献：
  名称：

  8-Polycycloalkyl-1,3-dipropylxanthines as potent and selective antagonists for A1-adenosine receptors

  摘要：

  With the aim of characterizing the hydrophobic interactions between xanthines and the A1 receptor site, 1,3-dipropyl-8-substituted xanthines were synthesized. Introduction of a quaternary carbon and the conformationally restricted cyclopentyl moiety into the 8-position of xanthines enhanced the adenosine A1 antagonism. 1,3-Dipropyl-8-(3-noradamantyl)xanthine (42) was identified to be a selective and the most potent A1 receptor antagonist reported to date. Under our structure-activity relationship, the 8-substituent of xanthine antagonists and the N6-substituent of adenosine agonists appears to bind to the same region of the A1 receptor.

  DOI：

  10.1021/jm00083a018
• 作为产物：
  描述：

  cis-bicyclo<3.3.0>octane-2-carboxylic acid 在 氯化亚砜 作用下， 以 吡啶 为溶剂， 反应 0.17h， 生成 cis-bicyclo[3.3.0]oct-endo-2-ylcarbonyl chloride
  参考文献：
  名称：

  8-Polycycloalkyl-1,3-dipropylxanthines as potent and selective antagonists for A1-adenosine receptors

  摘要：

  With the aim of characterizing the hydrophobic interactions between xanthines and the A1 receptor site, 1,3-dipropyl-8-substituted xanthines were synthesized. Introduction of a quaternary carbon and the conformationally restricted cyclopentyl moiety into the 8-position of xanthines enhanced the adenosine A1 antagonism. 1,3-Dipropyl-8-(3-noradamantyl)xanthine (42) was identified to be a selective and the most potent A1 receptor antagonist reported to date. Under our structure-activity relationship, the 8-substituent of xanthine antagonists and the N6-substituent of adenosine agonists appears to bind to the same region of the A1 receptor.

  DOI：

  10.1021/jm00083a018

文献信息

• New (2-Methoxyphenyl)piperazine Derivatives as 5-HT1A Receptor Ligands with Reduced .alpha.1-Adrenergic Activity. Synthesis and Structure-Affinity Relationships
  作者：Aurelio Orjales、Luisa Alonso-Cires、Luis Labeaga、Reyes Corcostegui

  DOI：10.1021/jm00008a005

  日期：1995.4

  New 2-(methoxyphenyl)piperazine derivatives 1 and 2 containing a terminal heteroaryl or cycloalkyl amide fragment were prepared and their 5-HT1A affinities evaluated by radioligand binding assays. The influence of the alkyl chain length or the amide group on affinity was evaluated. A four-carbon chain appears to be optimal when the amide fragment is a heteroaryl group. Derivatives with a cycloalkyl

  制备含有末端杂芳基或环烷基酰胺片段的新的2-（甲氧基苯基）哌嗪衍生物1和2，并通过放射性配体结合测定法评估它们的5-HT1A亲和力。评价了烷基链长度或酰胺基对亲和力的影响。当酰胺片段是杂芳基时，四碳链似乎是最佳的。具有环烷基部分的衍生物在两个亚甲基链系列中显示出最大的亲和力。酰胺区内的电子分布似乎对杂芳基衍生物中的亲和力有影响。杂芳基部分被环烷基取代导致化合物具有增强的亲和力。通过环化和/或饱和增加环烷基衍生物的亲脂性，增加了它们对5-HT1A位点的亲和力。具有顺式双环的化合物[3.3。0]辛烷（2a，2c），降冰片烷（2f，2g）和降冰片烯（2h，2i）基团在5-HT1A位点结合的亲和力比NAN-190高2-10倍。对于在5-HT1A位点具有高亲和力的化合物，评估了其对α1-肾上腺素能受体的拮抗活性。化合物2a，2c，2f，2g和2h与5-HT1A受体牢固结合（Ki = 0.12-0.63