6-phenyl-11H-benzo[e]pyrido[3,2-b][1,4]diazepine | 83166-07-8

• 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: 6-phenyl-11H-benzo[e]pyrido[3,2-b][1,4]diazepine
• 英文别名: 6-phenyl-11H-pyrido[2,3-b][1,4]benzodiazepine；6-Phenyl-11H-pyrido[2,3-b][1,4]benzodiazepine
• CAS: 83166-07-8
• 化学式: C₁₈H₁₃N₃
• 分子量: 271.321
• InChiKey: WUFWBVLAMURTLR-UHFFFAOYSA-N

物化性质

• 沸点：
  444.8±37.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-phenyl-11H-benzo[e]pyrido[3,2-b][1,4]diazepine 生成 11-[3-(4-Morpholinyl)propyl]-6-phenyl-11H-pyrido[2,3-b][1,4]benzodiazepine fumarate
  参考文献：
  名称：

  TAYLOR, CHANDLER R. JR.

  摘要：

  DOI：
• 作为产物：
  描述：

  [2-[(3-硝基吡啶-2-基)氨基]苯基]-苯基甲酮 在 palladium 10% on activated carbon 、 氢气 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 0.58h， 生成 6-phenyl-11H-benzo[e]pyrido[3,2-b][1,4]diazepine
  参考文献：
  名称：

  An efficient synthesis of substituted 1,4-diazepines by a Pd catalyzed amination and sequential hydrogenation condensation

  摘要：

  An efficient synthesis of substituted 1,4-diazepines is developed. The accessible intermediates have been obtained via Pd-catalyzed amination. The subsequent hydrogenation and intramolecular condensation sequences could be conducted successively in one pot without special operation. The mild and general strategy enables the synthesis of various substituted 1,4-diazepines in high yields. (C) 2013 Da-Li Yin. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.04.028

文献信息

• Aryl substituted pyrido[1,4]benzodiazepines and their use as
  申请人：A. H. Robins Company, Incorporated

  公开号：US04556667A1

  公开（公告）日：1985-12-03

  Novel [2-[(aminopyridinyl)amino]phenyl]arylmethanones and their thioxomethyl, ketal or thioketal analogs of the formula: ##STR1## wherein; R is selected from the group consisting of hydrogen, loweralkyl, --alk.sup.1 --halo, --alk.sup.1 --NR.sup.1 --NR.sup.1 R.sup.2 or --alk.sup.1 --N.dbd.CH--OC.sub.2 H.sub.5 ; R.sup.1 and R.sup.2 are selected from the group consisting of hydrogen, loweralkyl, --C(O)O-loweralkyl or R.sup.1 and R.sup.2 taken together with the adjacent nitrogen atom may form a heterocyclic residue selected from the group consisting of 1-piperidinyl, 1-phthalimido, 1-pyrrolidinyl, 4-morpholinyl, 1-piperazinyl and 4-substituted-1-piperazinyl; B is selected from carbonyl, thioxomethyl, ketal or thioketal; Ar is selected from the group consisting of 2, 3 and 4-pyridinyl, 2 or 3-thienyl, phenyl or phenyl substituted by 1 to 3 radicals selected from halo, loweralkyl, loweralkoxy, trifluoromethyl or nitro and may be the same of different; alk.sup.1 is a straight or branched hydrocarbon chain containing 1-8 carbon atoms; Z is selected from the group consisting of hydrogen, halogen, loweralkyl, loweralkoxy, hydroxy or nitro; Y is selected from the group consisting of hydrogen or 1-2 radicals selected from loweralkyl, loweralkoxy or hydroxy and may be the same of different, and the acid addition salts thereof. These compounds are intermediates in the preparation of novel aryl substituted pyrido[1,4]benzodiazepines having antidepression activity. Some of these intermediates are useful in treating depression.

  新型[2-[(氨基吡啶基)氨基]苯基]芳基甲酮及其硫羰甲基、缩酮或硫代缩酮类似物，其通式为：##STR1## 其中：R选自氢、低级烷基、--alk^1--卤素、--alk^1--NR^1--NR^1R^2或--alk^1--N=CH--OC2H5；R^1和R^2选自氢、低级烷基、--C(O)O-低级烷基，或者R^1和R^2与相邻的氮原子一起可以形成选自1-哌啶基、1-邻苯二甲酰亚胺、1-吡咯烷基、4-吗啉基、1-哌嗪基和4-取代的1-哌嗪基的杂环残基；B选自羰基、硫羰甲基、缩酮或硫代缩酮；Ar选自2、3和4-吡啶基、2或3-噻吩基、苯基或被1至3个选自卤素、低级烷基、低级烷氧基、三氟甲基或硝基的取代基取代的苯基，这些取代基可以相同或不同；alk^1是含有1-8个碳原子的直链或支链烃链；Z选自氢、卤素、低级烷基、低级烷氧基、羟基或硝基；Y选自氢或1-2个选自低级烷基、低级烷氧基或羟基的取代基，这些取代基可以相同或不同，以及它们的酸加成盐。这些化合物是制备具有抗抑郁活性的新型芳基取代的吡啶并[1,4]苯并二氮杂卓的中间体。其中一些中间体可用于治疗抑郁症。
• Aryl substituted pyrido[1,4]benzodiazepines
  申请人：A. H. Robins Company, Inc.

  公开号：US04447361A1

  公开（公告）日：1984-05-08

  Pyrido[1,4]benzodiazepines having antidepressant activity of the formula ##STR1## wherein Ar is 2, 3 and 4-pyridinyl, 2 or 3-thienyl, phenyl or a substituted phenyl; R is hydrogen, loweralkyl or an amine on the end of a hydrocarbon chain; Z is hydrogen, halogen, trifluoromethyl, loweralkyl, loweralkoxy, hydroxy or nitro; and Y is hydrogen, loweralkyl, loweralkoxy or hydroxy; and the pharmaceutical salts are prepared from [2-[(aminopyridinyl)amino]phenyl]arylmethanones which also have antidepressant activity.

  具有抗抑郁活性的吡啶并[1,4]苯二氮卓类化合物，其结构式如##STR1##所示，其中Ar为2、3和4-吡啶基，2或3-噻吩基，苯基或取代苯基；R为氢、低级烷基或位于碳氢链末端的胺；Z为氢、卤素、三氟甲基、低级烷基、低级烷氧基、羟基或硝基；Y为氢、低级烷基、低级烷氧基或羟基；以及由[2-[(氨基吡啶基)氨基]苯基]芳基甲酮制备的药用盐，这些化合物也具有抗抑郁活性。
• Aryl substituted pyrido[1,4]benzodiazepines for treatment of depression
  申请人：A. H. Robins Company, Incorporated

  公开号：US04495183A1

  公开（公告）日：1985-01-22

  Pyrido[1,4]benzodiazepines having antidepressant activity of the formula ##STR1## wherein Ar is 2, 3 and 4-pyridinyl, 2 or 3-thienyl, phenyl or a substituted phenyl; R is hydrogen, loweralkyl or an amine on the end of a hydrocarbon chain; Z is hydrogen, halogen, trifluoromethyl, loweralkyl, lower-alkoxy, hydroxy or nitro; and Y is hydrogen, loweralkyl, loweralkoxy or hydroxy; and the pharmaceutical salts are prepared from [2-[(aminopyridinyl)amino]phenyl]arylmethanones which also have antidepressant activity.

  具有抗抑郁活性的吡啶并[1,4]苯二氮卓类化合物，其结构式如上所示，其中Ar为2,3和4-吡啶基、2或3-噻吩基、苯基或取代苯基；R为氢、低级烷基或位于烃链末端的胺；Z为氢、卤素、三氟甲基、低级烷基、低级烷氧基、羟基或硝基；Y为氢、低级烷基、低级烷氧基或羟基；以及由[2-[(氨基吡啶基)氨基]苯基]芳基甲酮制备的药用盐，这些化合物也具有抗抑郁活性。
• Process and intermediates for the preparation of aryl substituted
  申请人：A. H. Robins Company, Incorporated

  公开号：US04560510A1

  公开（公告）日：1985-12-24

  A process for preparing pyrido[1,4]benzodiazepines having antidepressant activity illustrated by the formula: ##STR1## wherein Ar is pyridinyl, thienyl or phenyl; R is alkali-metal ion, hydrogen, loweralkyl or an amine or an amine precursor on the end of a hydrocarbon chain and wherein in the process condensation of an amino-chloropyridine with an aryl(aminophenyl)methanone is accomplished with a strong non-nucleophilic base in stirrable admixture with an inert liquid carrier. Alternatively, condensation is accomplished sequentially using titanium tetrachloride first followed by non-nucleophilic base.

  一种制备具有抗抑郁活性的吡啶并[1,4]苯二氮杂环己烯的方法，其示例如下：##STR1##其中Ar为吡啶基、噻吩基或苯基；R为碱金属离子、氢、较低的烷基或碳氢链末端的胺或胺前体，其中在该过程中，通过在可搅拌的惰性液体载体中与强非亲核碱一起使氨基氯吡啶与芳基(氨基苯基)甲酮发生缩合来实现。或者，可以先使用四氯化钛，然后使用非亲核碱顺序完成缩合。
• 2-[(amino-pyridinyl)amine]phenyl]aryl methanones, their thioxomethyl,
  申请人：A. H. Robins Company, Incorporated

  公开号：US04668675A1

  公开（公告）日：1987-05-26

  Pyrido[1,4]benzodiazepines having antidepressant activity of the formula ##STR1## wherein Ar is 2, 3 and 4-pyridinyl, 2 or 3-thienyl, phenyl or a substituted phenyl; R is hydrogen, loweralkyl or an amine on the end of a hydrocarbon chain; Z is hydrogen, halogen, trifluoromethyl, loweralkyl, lower-alkoxy, hydroxy or nitro; and Y is hydrogen, loweralkyl, loweralkoxy or hydroxy; and the pharmaceutical salts are prepared from [2-[(aminopyridinyl)amino]phenyl]arylmethanones which also have antidepressant activity.

  具有抗抑郁活性的吡啶并[1,4]苯二氮平化合物的化学式为##STR1## 其中Ar为2,3和4-吡啶基，2或3-噻吩基，苯基或取代苯基; R为氢，低碳基或碳链末端的胺基; Z为氢，卤素，三氟甲基，低碳基，低-烷氧基，羟基或硝基; Y为氢，低碳基，低-烷氧基或羟基; 药物盐由也具有抗抑郁活性的[2-[(氨基吡啶基)氨基]苯基]芳基甲酮制备而成。