3-amino-5-(2-phenylethyl)-1-propyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one | 478055-41-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 3-amino-5-(2-phenylethyl)-1-propyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one
• 英文别名: 3-amino-5-phenethyl-1-propyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one；3-Amino-1,3-dihydro-5-(2-phenylethyl)-1-propyl-2H-1,4-benzodiazepin-2-one；3-amino-5-(2-phenylethyl)-1-propyl-3H-1,4-benzodiazepin-2-one
• CAS: 478055-41-3
• 化学式: C₂₀H₂₃N₃O
• 分子量: 321.422
• InChiKey: PWPONGZFEHLPFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-amino-5-(2-phenylethyl)-1-propyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one 在 TEA 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-N-[2-oxo-5-(2-phenylethyl)-1-propyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]-N'-[4-(4-pyridin-4-ylpiperazin-1-yl)phenyl]urea
  参考文献：
  名称：

  Benzodiazepines as Potent and Selective Bradykinin B₁ Antagonists

  摘要：

  Antagonism of the bradykinin B-1 receptor was demonstrated to be a potential treatment for chronic pain and inflammation. Novel benzodiazepines were designed that display subnanomolar affinity for the bradykinin B, receptor (K-i = 0.59 nM) and high selectivity against the bradykinin B-2 receptor (K-i > 10 muM). In vivo efficacy, comparable to morphine, was demonstrated for lead compounds in a rodent hyperalgesia model.

  DOI：

  10.1021/jm034020y
• 作为产物：
  描述：

  5-phenethyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one 在 双(三甲基硅烷基)氨基钾 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-amino-5-(2-phenylethyl)-1-propyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one
  参考文献：
  名称：

  Benzodiazepines as Potent and Selective Bradykinin B₁ Antagonists

  摘要：

  Antagonism of the bradykinin B-1 receptor was demonstrated to be a potential treatment for chronic pain and inflammation. Novel benzodiazepines were designed that display subnanomolar affinity for the bradykinin B, receptor (K-i = 0.59 nM) and high selectivity against the bradykinin B-2 receptor (K-i > 10 muM). In vivo efficacy, comparable to morphine, was demonstrated for lead compounds in a rodent hyperalgesia model.

  DOI：

  10.1021/jm034020y

文献信息

• Novel compounds useful for bradykinin B1 receptor antagonism
  申请人：Tung S. Jay

  公开号：US20060217362A1

  公开（公告）日：2006-09-28

  Disclosed are compounds that are bradykinin B 1 receptor antagonists and are useful for treating diseases, or relieving adverse symptoms associated with disease conditions, in mammals mediated by bradykinin B 1 receptor. Certain of the compounds exhibit increased potency and are also expected to exhibit increased duration of action.

  揭示了一些化合物，它们是激肽酶B1受体拮抗剂，可用于治疗哺乳动物中由激肽酶B1受体介导的疾病，或缓解与疾病状况相关的不良症状。其中某些化合物表现出增强的效力，并且预计还将表现出延长的作用持续时间。
• [EN] 4- BROMO - 5 - (2- CHLORO - BENZOYLAMINO) - 1H - PYRAZOLE - 3 - CARBOXYLIC ACID AMIDE DERIVATIVES AND RELATED COMPOUNDS AS BRADYKININ B1 RECEPTOR ANTAGONISTS FOR THE TREATMENT OF INFLAMMATORY DISEASES<br/>[FR] DERIVES AMIDES DE L'ACIDE CARBOXYLIQUE DE 4- BROMO - 5 - (2- CHLORO - BENZOYLAMINO) - 1H - PYRAZOLE 3 ET COMPOSES ASSOCIES EN TANT QU'ANTAGONISTES DE RECEPTEUR DE B1 DE LA BRADYKININE POUR LE TRAITEMENT DE MALADIES INFLAMMATOIRES
  申请人：ELAN PHARM INC

  公开号：WO2004098589A1

  公开（公告）日：2004-11-18

  Disclosed are compounds of formula I and II that are bradykinin B1 receptor antagonists and are useful for treating diseases, or relieving adverse symptoms associated with disease conditions, in mammals mediated by bradykinin B1 receptor. Certain of the compounds exhibit increased potency and are also expected to exhibit increased duration of action.

  公开的是化合物I和II的结构式，它们是激肽酶B1受体拮抗剂，适用于治疗哺乳动物中由激肽酶B1受体介导的疾病，或缓解与疾病状况相关的不良症状。其中某些化合物表现出增强的效力，并且预计还将表现出延长作用的特性。
• Substituted pyrazole derivatives and related compounds as bradykinin B1 receptor antagonists
  申请人：Tung S. Jay

  公开号：US20050020659A1

  公开（公告）日：2005-01-27

  Disclosed are compounds that are bradykinin B 1 receptor antagonists and are useful for treating diseases, or relieving adverse symptoms associated with disease conditions, in mammals mediated by bradykinin B 1 receptor. Certain of the compounds exhibit increased potency and are also expected to exhibit increased duration of action.

  本发明公开了一种布雷肯肽B1受体拮抗剂化合物，可用于治疗哺乳动物中由布雷肯肽B1受体介导的疾病或缓解与疾病状况相关的不良症状。其中某些化合物表现出增强的效力，并且预计也会表现出增强的作用持续时间。
• 4-Bromo-5-(2-chloro-benzoylamino)-1h-pyrazole-3-carvoxylic acid amide derivatives and related compounds as bradykinin b1 receptor antagonists for the treatment of inflammatory diseases
  申请人：Tung S. Jay

  公开号：US20060281733A1

  公开（公告）日：2006-12-14

  Disclosed are compounds of formula I and II that are bradykinin B 1 receptor antagonists and are useful for treating diseases, or relieving adverse symptoms associated with disease conditions, in mammals mediated by bradykinin B 1 receptor. Certain of the compounds exhibit increased potency and are also expected to exhibit increased duration of action.

  本发明公开了式I和式II的化合物，它们是缓激肽B1受体拮抗剂，可用于治疗哺乳动物中由缓激肽B1受体介导的疾病，或缓解与疾病条件相关的不良症状。其中某些化合物表现出增强的效力，预计也会表现出增强的持续时间。
• 4- BROMO - 5 - (2- CHLORO - BENZOYLAMINO) - 1H - PYRAZOLE - 3 - CARBOXYLIC ACID AMIDE DERIVATIVES AND RELATED COMPOUNDS AS BRADYKININ B sb 1 /sb RECEPTOR ANTAGONISTS FOR THE TREATMENT OF INFLAMMATORY DISEASES
  申请人：ELAN PHARMACEUTICALS, INC.

  公开号：EP1633348A1

  公开（公告）日：2006-03-15