N,N-dibutyl-4-(4-chlorophenyl)-4-oxobutanamide | 247085-65-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N,N-dibutyl-4-(4-chlorophenyl)-4-oxobutanamide
• CAS: 247085-65-0
• 化学式: C₁₈H₂₆ClNO₂
• 分子量: 323.863
• InChiKey: PWWIPSBWXKGIDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-dibutyl-4-(4-chlorophenyl)-4-oxobutanamide 在 溴 作用下， 以 四氯化碳 为溶剂， 生成 3-bromo-N,N-dibutyl-4-(4-chlorophenyl)-4-oxobutanamide
  参考文献：
  名称：

  Structure−Activity Relationships and Effects on Neuroactive Steroid Synthesis in a Series of 2-Phenylimidazo[1,2-a]pyridineacetamide Peripheral Benzodiazepine Receptors Ligands

  摘要：

  A series of 36 imidazopyridineacetamides (2-37) were designed and synthesized to evaluate the effects of structural changes on the amide nitrogen at both central (CBRs) and peripheral benzodiazepine receptors (PBRs). These changes include variations in the length and number of the alkyl groups as well as introduction of different aromatic, heteroaromatic, and conformationally constrained groups. The affinities of these compounds for CBRs and PBRs were determined, and the results indicate that bulkiness of the substituents, their branching, and length beyond an optimal value may cause hindrance to the ligand in its interaction with the receptor. The presence of aromatic or conformationally constrained substituents on the carboxamide nitrogen can be conducive to high affinity and selectivity. Furthermore, the ability of a subset of the most active ligands to stimulate synthesis of neuroactive steroids in plasma and brain was evaluated in vivo and in vitro. Compound 3 exhibited very marked effects on the peripheral and central synthesis of neuroactive steroids, while 36 (potent at subnanomolar level) showed a slight ability to affect neuroactive steroid content in the cerebral cortex.

  DOI：

  10.1021/jm049610q
• 作为产物：
  描述：

  3-(4-氯苯甲酰)丙酸 、 二正丁胺 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 四氢呋喃 为溶剂， 生成 N,N-dibutyl-4-(4-chlorophenyl)-4-oxobutanamide
  参考文献：
  名称：

  Structure−Activity Relationships and Effects on Neuroactive Steroid Synthesis in a Series of 2-Phenylimidazo[1,2-a]pyridineacetamide Peripheral Benzodiazepine Receptors Ligands

  摘要：

  A series of 36 imidazopyridineacetamides (2-37) were designed and synthesized to evaluate the effects of structural changes on the amide nitrogen at both central (CBRs) and peripheral benzodiazepine receptors (PBRs). These changes include variations in the length and number of the alkyl groups as well as introduction of different aromatic, heteroaromatic, and conformationally constrained groups. The affinities of these compounds for CBRs and PBRs were determined, and the results indicate that bulkiness of the substituents, their branching, and length beyond an optimal value may cause hindrance to the ligand in its interaction with the receptor. The presence of aromatic or conformationally constrained substituents on the carboxamide nitrogen can be conducive to high affinity and selectivity. Furthermore, the ability of a subset of the most active ligands to stimulate synthesis of neuroactive steroids in plasma and brain was evaluated in vivo and in vitro. Compound 3 exhibited very marked effects on the peripheral and central synthesis of neuroactive steroids, while 36 (potent at subnanomolar level) showed a slight ability to affect neuroactive steroid content in the cerebral cortex.

  DOI：

  10.1021/jm049610q

文献信息

• Structure−Activity Relationships and Effects on Neuroactive Steroid Synthesis in a Series of 2-Phenylimidazo[1,2-<i>a</i>]pyridineacetamide Peripheral Benzodiazepine Receptors Ligands
  作者：Giuseppe Trapani、Valentino Laquintana、Nunzio Denora、Adriana Trapani、Angela Lopedota、Andrea Latrofa、Massimo Franco、Mariangela Serra、Maria Giuseppina Pisu、Ivan Floris、Enrico Sanna、Giovanni Biggio、Gaetano Liso

  DOI：10.1021/jm049610q

  日期：2005.1.1

  A series of 36 imidazopyridineacetamides (2-37) were designed and synthesized to evaluate the effects of structural changes on the amide nitrogen at both central (CBRs) and peripheral benzodiazepine receptors (PBRs). These changes include variations in the length and number of the alkyl groups as well as introduction of different aromatic, heteroaromatic, and conformationally constrained groups. The affinities of these compounds for CBRs and PBRs were determined, and the results indicate that bulkiness of the substituents, their branching, and length beyond an optimal value may cause hindrance to the ligand in its interaction with the receptor. The presence of aromatic or conformationally constrained substituents on the carboxamide nitrogen can be conducive to high affinity and selectivity. Furthermore, the ability of a subset of the most active ligands to stimulate synthesis of neuroactive steroids in plasma and brain was evaluated in vivo and in vitro. Compound 3 exhibited very marked effects on the peripheral and central synthesis of neuroactive steroids, while 36 (potent at subnanomolar level) showed a slight ability to affect neuroactive steroid content in the cerebral cortex.