(R)-7-phenyl-8,9-dihydro-8-methyl-5-(4-nitrophenyl)-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine | 178751-12-7

• 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: (R)-7-phenyl-8,9-dihydro-8-methyl-5-(4-nitrophenyl)-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine
• 英文别名: (8R)-8-methyl-5-(4-nitrophenyl)-7-phenyl-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepine
• CAS: 178751-12-7
• 化学式: C₂₃H₁₉N₃O₄
• 分子量: 401.422
• InChiKey: VJIFZVIZLXWDCR-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  79.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-7-phenyl-8,9-dihydro-8-methyl-5-(4-nitrophenyl)-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine 在 palladium-carbon potassium formate 作用下， 以 乙醇 、 水 、 乙酸乙酯 、 异丙醇 为溶剂， 以61%的产率得到(R)-7-phenyl-8,9-dihydro-8-methyl-5-(4-aminophenyl)-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine
  参考文献：
  名称：

  Dihydro-2,3-benzodiazepine derivatives

  摘要：

  通式（I）的化合物，其中R为氢或C.sub.1-C.sub.10烷基；X为芳香基，选择自苯基，噻吩基，呋喃基，吡啶基，咪唑基，苯并咪唑基，苯并噻唑基和邻苯二氮杂茂基，它们未被取代或被一个或多个取代基所取代，所述取代基选自卤素，羟基，氰基，硝基，C.sub.1-C.sub.6烷基，C.sub.3-C.sub.6环烷基，C.sub.1-C.sub.4烷氧基，羧基，C.sub.1-C.sub.6烷氧羰基，乙酰基，甲酰基，羧甲基，羟甲基，氨基，氨甲基，亚甲二氧基和三氟甲基；“芳基”表示对硝基苯基，对氨基苯基或对（保护氨基）苯基；或其药学上可接受的盐，用作抗癫痫药物。

  公开号：

  US05795886A1
• 作为产物：
  描述：

  (5RS,7S)-7,8-dihydro-7-methyl-5-(4-nitrophenyl)-5H-1,3-dioxolo[4,5-G][2]benzopyran-5-ol 在 盐酸 、 sodium hydroxide 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 (R)-7-phenyl-8,9-dihydro-8-methyl-5-(4-nitrophenyl)-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine
  参考文献：
  名称：

  Synthesis and anticonvulsant activity of 3-aryl-5H-2,3-benzodiazepine ampa antagonists

  摘要：

  A novel series of 3-aryl-5H-2,3-benzodiazepines. with N-3 aromatic substituents has been synthesized. Good in vivo anticonvulsant activity of the new compounds has been demonstrated employing the maximal electroshock seizure test in mice. Evaluation of a subset of the compounds in the cortical wedge assay confirmed the new structures to be AMPA antagonists. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00315-7

文献信息

• Dihydro-2,3-benzodiazepine derivatives
  申请人：Eli Lilly and Company

  公开号：US05795886A1

  公开（公告）日：1998-08-18

  Compounds having general formula (I) wherein R is hydrogen or C.sub.1 -C.sub.10 alkyl; X is an aromatic moiety selected from phenyl, thienyl, furyl, pyridyl, imidazolyl, benzimidazolyl, benzothiazolyl and phthalazinyl which is unsubstituted or substituted with one or more moieties chosen from the group consisting of halogen, hydroxy, cyano, nitro, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkoxy, carboxy, C.sub.1 -C.sub.6 alkoxycarbonyl, acetyl, formyl, carboxymethyl, hydroxymethyl, amino, aminomethyl, methylenedioxy and trifluoromethyl; and "Aryl" represents p-nitrophenyl, p-aminophenyl or p-(protected amino) phenyl; or a pharmaceutically acceptable salt thereof, are useful as anticonvulsants.

  通式（I）的化合物，其中R为氢或C.sub.1-C.sub.10烷基；X为芳香基，选择自苯基，噻吩基，呋喃基，吡啶基，咪唑基，苯并咪唑基，苯并噻唑基和邻苯二氮杂茂基，它们未被取代或被一个或多个取代基所取代，所述取代基选自卤素，羟基，氰基，硝基，C.sub.1-C.sub.6烷基，C.sub.3-C.sub.6环烷基，C.sub.1-C.sub.4烷氧基，羧基，C.sub.1-C.sub.6烷氧羰基，乙酰基，甲酰基，羧甲基，羟甲基，氨基，氨甲基，亚甲二氧基和三氟甲基；“芳基”表示对硝基苯基，对氨基苯基或对（保护氨基）苯基；或其药学上可接受的盐，用作抗癫痫药物。
• DIHYDRO-2,3-BENZODIAZEPINE DERIVATIVES
  申请人：ELI LILLY AND COMPANY

  公开号：EP0771198B1

  公开（公告）日：2002-02-06
• Dihydro-2,3-Benzodiazepine derivatives
  申请人：ELI LILLY AND COMPANY

  公开号：EP1157992B1

  公开（公告）日：2005-08-24
• Synthesis and anticonvulsant activity of 3-aryl-5H-2,3-benzodiazepine ampa antagonists
  作者：Benjamin A. Anderson、Nancy K. Harn、Marvin M. Hansen、Allen R. Harkness、David Lodge、J.David Leander

  DOI：10.1016/s0960-894x(99)00315-7

  日期：1999.7

  A novel series of 3-aryl-5H-2,3-benzodiazepines. with N-3 aromatic substituents has been synthesized. Good in vivo anticonvulsant activity of the new compounds has been demonstrated employing the maximal electroshock seizure test in mice. Evaluation of a subset of the compounds in the cortical wedge assay confirmed the new structures to be AMPA antagonists. (C) 1999 Elsevier Science Ltd. All rights reserved.