硝基卡拉米芬盐酸盐 | 98636-73-8

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 硝基卡拉米芬盐酸盐
• 英文名称: Nitrocaramiphen hydrochloride
• 英文别名: 2-(diethylaino)ethyl 1-(p-nitrophenyl)cyclopentanecarboxylate hydrochloride；2-(diethylamino)ethyl 1-(4-nitrophenyl)cyclopentane-1-carboxylate;hydrochloride
• CAS: 98636-73-8
• 化学式: C₁₈H₂₆N₂O₄*ClH
• 分子量: 370.876
• InChiKey: XWQWACGTGFICFO-UHFFFAOYSA-N

物化性质

• 溶解度：
  可微溶于水

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  75.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  硝基卡拉米芬盐酸盐 在 platinum on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以80%的产率得到2-(diethylaino)ethyl 1-(p-aminophenyl)cyclopentanecarboxylate hydrochloride
  参考文献：
  名称：

  Muscarinic receptor binding profile of para-substituted caramiphen analogs

  摘要：

  Para-substituted analogues of the antimuscarinic agent caramiphen were synthesized and evaluated for their ability to bind to the M1 and M2 subtypes of the muscarinic receptor. The purpose of the set was to look for a possible relationship in binding affinity or receptor subtype selectivity with aromatic substituent parameters such as Hammett's-sigma or Hansch's pi-values. It is felt this could be determined initially with only four properly chosen substituents. In this approach, substituents were chosen which have an extreme value for sigma and for pi, in a positive and negative direction, in all combinations. The substituents chosen for examination were amino (-sigma, -pi); 1-pyrrolidinyl (-sigma, +pi); 1-tetrazolyl (+sigma, -pi), and iodo (+sigma, +pi). It was determined in this research that caramiphen binds with high affinity (K(i) = 1.2 nM) and is selective for the M1 over M2 muscarinic receptor subtype (26-fold). An examination of para-substitution reveals that compounds with electron-withdrawing (+sigma) substituents showed M1 selectivity, while the derivatives with electron-donating groups (-sigma) were nonselective in the binding assays. On the basis of this finding, the nitro and cyano derivatives were prepared and found to be M1 selective. The +sigma derivatives showed a decrease in M2 affinity while the p-nitro and p-iodo derivatives retained approximately equal affinity as caramiphen for the M1 site. The nitro- and iodocaramiphen derivatives were as potent (M1, K(i) = 5.52 and 2.11 nM, respectively) and showed a greater selectivity of M1 over M2 binding than the M1 prototypical agent pirenzepine (M1, K(i) = 5.21 nM).

  DOI：

  10.1021/jm00114a005

文献信息

• [EN] METHODS FOR TREATING AND/OR PREVENTING PERVASIVE DEVELOPMENTAL DISORDERS IN A SUBJECT<br/>[FR] PROCEDES PERMETTANT DE TRAITER ET/OU DE PREVENIR LES TROUBLES PERVASIFS DU DEVELOPPEMENT CHEZ UN SUJET
  申请人：ECOLE POLYTECH

  公开号：WO2007029063A2

  公开（公告）日：2007-03-15

  [EN] The present invention concerns a method for treating and/or preventing a Pervasive Developmental Disorder in a subject in need thereof comprising the step of modulating the synaptic connectivity in the neocortex by administering a therapeutically effective amount of a composition capable of reducing memory, perception and/or attention.
  [FR] Procédé permettant de traiter et/ou de prévenir les troubles pervasifs du développement chez un sujet : modulation de la connectivité synaptique dans le néocortex par administration de quantité thérapeutiquement efficace de composition capable de réduire la mémoire, la perception et/ou l'attention.