7-chloro-4,5-dihydro-2,3-dimethyl-4-phenyl-3H-1,3-benzodiazepine | 81170-81-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 7-chloro-4,5-dihydro-2,3-dimethyl-4-phenyl-3H-1,3-benzodiazepine
• 英文别名: 7-Chloro-2,3-dimethyl-4-phenyl-4,5-dihydro-1,3-benzodiazepine
• CAS: 81170-81-2
• 化学式: C₁₇H₁₇ClN₂
• 分子量: 284.788
• InChiKey: JMISQCVGJXTELH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-phenyl-2-(5-chloro-2-nitrophenyl)ethan-1-one 在 盐酸 、 硼烷四氢呋喃络合物 、 盐酸羟胺 、 sodium acetate 、 铁粉 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 生成 7-chloro-4,5-dihydro-2,3-dimethyl-4-phenyl-3H-1,3-benzodiazepine
  参考文献：
  名称：

  (.+-.)-4-Aryl-4,5-dihydro-3H-1,3-benzodiazepines. 2. Nuclear substituted analogs of (.+-.)-4,5-dihydro-2,3-dimethyl-4-phenyl-3H-1,3-benzodiazepine and (.+-.)-4,5-dihydro-2-ethyl-3-methyl-4-phenyl-3H-1,3-benzodiazepine as potential antidepressant agents

  摘要：

  Antidepressant-like activity, as evidenced by marked inhibition of tetrabenazine-induced ptosis, was previously reported for (+/-)-4,5-dihydro-4-phenyl-3H-1,3-benzodiazepine derivatives. Since optimal antitetrabenazine activity was associated with (+/-)-4,5-dihydro-2,3-dimethyl-4-phenyl-3H-1,3-benzodiazepine (9k, HRP 543) and the 2-ethyl-3-methyl analogue (10k), the synthesis and evaluation of nuclear-substituted derivatives of these two compounds was also investigated. The initial synthesis involved Friedel-Crafts acylation of substituted benzenes with 2-nitrophenylacetyl chloride to afford 1-aryl-2-(2-nitrophenyl)ethanones 2, which were converted in five steps to (+/-)-alpha-aryl-N-methyl-2-nitrobenzeneethanamines 7. Greater flexibility with respect to the introduction of nuclear substituents was achieved by conversion of 2-nitrotoluene derivatives to 2 via acylation of intermediate beta-(dimethylamino)-2-nitrostyrenes with various aroyl chlorides and hydrolysis. Reductive amination of 2 with methylamine and sodium cyanoborohydride afforded 7 directly and significantly reduced the number of synthetic steps. Reduction of 7a-j to diamines 8a-j and cyclization with appropriate ortho esters gave nuclear-substituted analogues of 9k and 10k. Marked antitetrabenazine activity was associated with many of these compounds. Significant enhancement of activity with respect to the unsubstituted analogues 9k and 10k was not observed, with the exception of 9c which appeared to be slightly more potent than 9k.

  DOI：

  10.1021/jm00346a004

文献信息

• 4-Phenyl-1,3-benzodiazepines, method for their preparation, pharmaceutical compositions containing them, and the compounds for use as medicaments
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0009800A2

  公开（公告）日：1980-04-16

  Compounds of the formula in which R and R, are the same or different and each can be hydrogen, alkyl of from 1 to 3 carbon atoms, cycloalkyl- C-C3-alkyl, wherein the cycloalkyl radical has 3 - carbon atoms, or aralkyl having up to 8 carbon atoms, X and Y are the same or different and each can be chlorine, bromine, fluorine, alkoxy or alkyl, each of from 1 to 3 carbon atoms, hydroxy, or trifluoromethyl, m is the integer 0,1 or 2, n is the integer 0,1,2 or 3, the optical antipodes thereof, physiologically acceptable salts thereof, and pharmaceutical compositions containing them. They are prepared by the cyclisation of compounds of the formula with a compound of the formula

  式中的化合物 其中 R 和 R, 相同或不同，各自可以是氢、1 至 3 个碳原子的烷基、环烷基-C-C3-烷基（其中环烷基有 3 - 个碳原子）或具有最多 8 个碳原子的芳烷基；X 和 Y 相同或不同，各自可以是氯、溴、氟、烷氧基或烷基（各自具有 1 至 3 个碳原子）、羟基或三氟甲基；m 是 0、1 或 2 的整数；n 是 0、1 或 2 的整数、溴、氟、烷氧基或烷基，每个烷基有 1 至 3 个碳原子、羟基或三氟甲基，m 为 0、1 或 2 的整数，n 为 0、1、2 或 3 的整数。其制备方法是将式化合物 与式
• US4309424A
  申请人：——

  公开号：US4309424A

  公开（公告）日：1982-01-05
• US4409145A
  申请人：——

  公开号：US4409145A

  公开（公告）日：1983-10-11
• US4459230A
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  公开号：US4459230A

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• US4462933A
  申请人：——

  公开号：US4462933A

  公开（公告）日：1984-07-31