8-bromo-2-chloro-5,11-dihydro-11-ethyl-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one | 380379-06-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 8-bromo-2-chloro-5,11-dihydro-11-ethyl-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one
• 英文别名: 13-bromo-5-chloro-2-ethyl-7-methyl-2,4,9,15-tetrazatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-10-one
• CAS: 380379-06-6
• 化学式: C₁₄H₁₂BrClN₄O
• 分子量: 367.632
• InChiKey: VJEPIDBBYRHPKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  58.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-bromo-2-chloro-5,11-dihydro-11-ethyl-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one 在 四(三苯基膦)钯 、 四溴化碳 、 臭氧 、 三苯基膦 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-Bromomethyl-7-chloro-5-ethyl-9-methyl-5,10-dihydro-4,5,6,10-tetraaza-dibenzo[a,d]cyclohepten-11-one
  参考文献：
  名称：

  Novel nevirapine-like inhibitors with improved activity against NNRTI-resistant HIV: 8-heteroarylthiomethyldipyridodiazepinone derivatives

  摘要：

  A series of 8-heteroarylthiomethyidipyridodiazepinone derivatives were prepared and evaluated for their antiviral profile against wild type virus and the important K103N/Y181C mutant as an indicator for broad activity. 2,6-Dimethylpyridine derivative 16 was found to have a good pharmacokinetic profile in spite of poor metabolic stability in rat liver microsomes. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2003.11.049
• 作为产物：
  描述：

  N-(2,6-dichloro-4-methyl-3-pyridinyl)-5-bromo-2-ethylamino-3-pyridinecarboxamide 在 吡啶 、 sodium hexamethyldisilazane 作用下， 以 甲苯 为溶剂， 反应 0.25h， 以85%的产率得到8-bromo-2-chloro-5,11-dihydro-11-ethyl-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one
  参考文献：
  名称：

  Dipyridodiazepinone derivatives; synthesis and anti HIV-1 activity

  摘要：

  合成了十种二吡啶基二氮杂环己酮衍生物，并针对野生型和突变型酶K103N和Y181C评估它们对HIV-1逆转录酶的抑制活性。其中有两种被发现是有希望的HIV-1 RT抑制剂。

  DOI：

  10.3762/bjoc.5.36

文献信息

• Non-nucleoside reverse transcriptase inhibitors
  申请人：——

  公开号：US20020028807A1

  公开（公告）日：2002-03-07

  Provided are compounds of the general formula I: 1 wherein R 2 is selected from the group consisting of H, F, Cl, (C 1-4 ) alkyl, (C 3-4 ) cycloalkyl and CF 3 ; R 4 is H or Me; R 5 is H, Me or Et, with the proviso that R 4 and R 5 are not both Me, and if R 4 is Me then R 5 cannot be Et; R 11 is Et, cyclopropyl, propyl, isopropyl, or isobutyl; and is selected from the group consisting of: 2 and pharmaceutically acceptable salts thereof, as inhibitors of HIV reverse transcriptase, wild-type and several mutant strains.

  提供的是一般式I的化合物：其中R2从H、F、Cl、(C1-4)烷基、(C3-4)环烷基和CF3组成的群体中选择；R4为H或Me；R5为H、Me或Et，但R4和R5不能同时为Me，如果R4为Me，则R5不能为Et；R11为Et、环丙基、丙基、异丙基或异丁基；并选择自以下组合物：2和其药学上可接受的盐，作为HIV逆转录酶、野生型和几种突变株的抑制剂。
• NON-NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS
  申请人：BOEHRINGER INGELHEIM (CANADA) LTD.

  公开号：EP1294720B1

  公开（公告）日：2006-04-05
• US6420359B1
  申请人：——

  公开号：US6420359B1

  公开（公告）日：2002-07-16
• Novel nevirapine-like inhibitors with improved activity against NNRTI-resistant HIV: 8-heteroarylthiomethyldipyridodiazepinone derivatives
  作者：C. Yoakim、P.R. Bonneau、R. Déziel、L. Doyon、J. Duan、I. Guse、S. Landry、E. Malenfant、J. Naud、W.W. Ogilvie、J.A. O'Meara、R. Plante、B. Simoneau、B. Thavonekham、M. Bös、M.G. Cordingley

  DOI：10.1016/j.bmcl.2003.11.049

  日期：2004.2

  A series of 8-heteroarylthiomethyidipyridodiazepinone derivatives were prepared and evaluated for their antiviral profile against wild type virus and the important K103N/Y181C mutant as an indicator for broad activity. 2,6-Dimethylpyridine derivative 16 was found to have a good pharmacokinetic profile in spite of poor metabolic stability in rat liver microsomes. (C) 2003 Published by Elsevier Ltd.
• Dipyridodiazepinone derivatives; synthesis and anti HIV-1 activity
  作者：Nisachon Khunnawutmanotham、Nitirat Chimnoi、Arunee Thitithanyanont、Patchreenart Saparpakorn、Kiattawee Choowongkomon、Pornpan Pungpo、Supa Hannongbua、Supanna Techasakul

  DOI：10.3762/bjoc.5.36

  日期：——

  Ten dipyridodiazepinone derivatives were synthesized and evaluated for their anti HIV-1 reverse transcriptase activity against wild-type and mutant type enzymes, K103N and Y181C. Two of them were found to be promising inhibitors for HIV-1 RT.

  合成了十种二吡啶基二氮杂环己酮衍生物，并针对野生型和突变型酶K103N和Y181C评估它们对HIV-1逆转录酶的抑制活性。其中有两种被发现是有希望的HIV-1 RT抑制剂。