苯酰胺,N-[(1-氮杂二环[2.2.2]辛-3-基氨基)羰基]-2-甲氧基-,(S)- | 124808-66-8

• 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: 苯酰胺,N-[(1-氮杂二环[2.2.2]辛-3-基氨基)羰基]-2-甲氧基-,(S)-
• 英文名称: (S)-N-[[[1-Azabicyclo[2.2.2]octan-3-yl] amino]carbonyl]-2-methoxybenzamide
• 英文别名: (S)-N-[[[1-Azabicyclo[2.2.2]octan-3-yl]amino]carbonyl]-2-methoxybenzamide；N-[[(3S)-1-azabicyclo[2.2.2]octan-3-yl]carbamoyl]-2-methoxybenzamide
• CAS: 124808-66-8
• 化学式: C₁₆H₂₁N₃O₃
• 分子量: 303.361
• InChiKey: HMKDNNXFHIJZJQ-CYBMUJFWSA-N

物化性质

• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-甲氧基苯甲酰胺 以 四氢呋喃 、 正己烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 19.0h， 生成 苯酰胺,N-[(1-氮杂二环[2.2.2]辛-3-基氨基)羰基]-2-甲氧基-,(S)-
  参考文献：
  名称：

  Novel antagonists of the 5-HT3 receptor. Synthesis and structure-activity relationships of (2-alkoxybenzoyl)ureas

  摘要：

  A series of benzoylureas derived from bicycle amines were prepared and evaluated for 5-HT3 antagonist activity on the rat isolated vagus nerve. From among these compounds, those analogues which were ortho substituted by an alkoxy group on the benzoyl function were shown to be potent 5-HT3 antagonists with similar or greater potency than the standard agent ondansetron. NMR and X-ray crystallography studies showed these o-alkoxy compounds to exist as a planar, hydrogen-bonded, tricyclic ring system. In molecular modeling studies on endo-N-[[(8-methyl-8-azabicyclo [3.2.1]octan-3-yl)amino]carbonyl]-2-(cyclopropylmethoxy)benzamide (30) the central hydrogen-bonded ring was able to mimic an aromatic ring present in previously reported 5-HT3 antagonists.

  DOI：

  10.1021/jm00087a003

文献信息

• Heterocyclic compounds useful as 5-HT.sub.3 antagonists
  申请人：John Wyeth & Brother Limited

  公开号：US04983600A1

  公开（公告）日：1991-01-08

  Aroyl ureas and carbamic acid derivatives of formula A--CO--NHCW--Y--B and pharmaceutically acceptable salts thereof wherein A is a specified aromatic radical including optionally substituted phenyl W is O or S Y is NH or S and B is a specified saturated azacyclic ring, eg tropan-3-yl or quinuclidin-3-yl, possess 5-HT.sub.3 -antagonistic activity and are, for example, useful in treatment of migraine, emesis, anxiety, gastro-intestinal disorders and as anti-psychotics.

  Aroyl尿素和公式A--CO--NHCW--Y--B的氨基甲酸衍生物及其药学上可接受的盐，其中A是指定的芳香基团，包括可选择地取代的苯基；W是O或S；Y是NH或S；B是指定的饱和氮杂环环，例如tropan-3-基或quinuclidin-3-基，具有5-HT.sub.3-拮抗活性，并且例如，在治疗偏头痛、呕吐、焦虑、胃肠道疾病和作为抗精神病药物方面是有用的。
• Heterocyclic compounds
  申请人：JOHN WYETH & BROTHER LIMITED

  公开号：EP0323077B1

  公开（公告）日：1991-09-11
• US4983600A
  申请人：——

  公开号：US4983600A

  公开（公告）日：1991-01-08
• US5106843A
  申请人：——

  公开号：US5106843A

  公开（公告）日：1992-04-21