3-[N'-(3,5-Bis-trifluoromethyl-benzoyl)-N'-methyl-N-naphthalen-2-ylmethyl-hydrazino]-propionic acid ethyl ester | 398148-07-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-[N'-(3,5-Bis-trifluoromethyl-benzoyl)-N'-methyl-N-naphthalen-2-ylmethyl-hydrazino]-propionic acid ethyl ester
• CAS: 398148-07-7
• 化学式: C₂₆H₂₄F₆N₂O₃
• 分子量: 526.479
• InChiKey: ARJJYEHGMRGUQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.32
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  49.85
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-[N'-(3,5-Bis-trifluoromethyl-benzoyl)-N'-methyl-N-naphthalen-2-ylmethyl-hydrazino]-propionic acid ethyl ester 在 4-二甲氨基吡啶 、 sodium hydroxide 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成
  参考文献：
  名称：

  Dual neurokinin NK1/NK2 antagonists: N-[(R,R)-(E)-1-arylmethyl-3-(2-oxo-azepan-3-yl)carbamoyl]allyl-N-methyl-3,5-bis(trifluoromethyl)benzamides and 3-[N′-3,5-bis(trifluoromethyl)benzoyl-N-arylmethyl-N′-methylhydrazino]-N-[(R)-2-oxo-azepan-3-yl]propionamides

  摘要：

  Based on the structure of N-[(R,R)-(E)-1-(4-chlorobenzyl)- 3-(2-oxoazepan-3-yl)carbamoyl]allyl-N-methyl-3,5-bis(trifluoromethyl)benzamide (1), attempts to improve the NK2 affinity have resulted in the discovery of N-[(R,R)-(E)-1-(3,4-dichlorobenzyl)-3-(2-oxoazepan-3- yl)carbamoyl]allyl-N-methyl-3,5-bis(trifluoromethyl)benzamide (9, DNK333) exhibiting a 5-fold improved affinity to the NK2 receptor in comparison to 1. Simplification of the structure via elimination of a chiral centre led to 3-[N'-3,5-bis(trifluoromethyl)benzoyl-N-(3,4-dichlorobenzyl)-N'-methylhydrazino]-N-[(R)-2-oxo-azepan-3-yl]propionamide (22), a potent and fairly balanced NK1/NK2 antagonist. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00631-x
• 作为产物：
  描述：

  3,5-二(三氟甲基)苯-1-碳酰肼 在 氢气 、 sodium cyanoborohydride 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 3-[N'-(3,5-Bis-trifluoromethyl-benzoyl)-N'-methyl-N-naphthalen-2-ylmethyl-hydrazino]-propionic acid ethyl ester
  参考文献：
  名称：

  Dual neurokinin NK1/NK2 antagonists: N-[(R,R)-(E)-1-arylmethyl-3-(2-oxo-azepan-3-yl)carbamoyl]allyl-N-methyl-3,5-bis(trifluoromethyl)benzamides and 3-[N′-3,5-bis(trifluoromethyl)benzoyl-N-arylmethyl-N′-methylhydrazino]-N-[(R)-2-oxo-azepan-3-yl]propionamides

  摘要：

  Based on the structure of N-[(R,R)-(E)-1-(4-chlorobenzyl)- 3-(2-oxoazepan-3-yl)carbamoyl]allyl-N-methyl-3,5-bis(trifluoromethyl)benzamide (1), attempts to improve the NK2 affinity have resulted in the discovery of N-[(R,R)-(E)-1-(3,4-dichlorobenzyl)-3-(2-oxoazepan-3- yl)carbamoyl]allyl-N-methyl-3,5-bis(trifluoromethyl)benzamide (9, DNK333) exhibiting a 5-fold improved affinity to the NK2 receptor in comparison to 1. Simplification of the structure via elimination of a chiral centre led to 3-[N'-3,5-bis(trifluoromethyl)benzoyl-N-(3,4-dichlorobenzyl)-N'-methylhydrazino]-N-[(R)-2-oxo-azepan-3-yl]propionamide (22), a potent and fairly balanced NK1/NK2 antagonist. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00631-x