| 1421053-51-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• CAS: 1421053-51-1
• 化学式: C₁₃H₁₃N₅O
• 分子量: 255.279
• InChiKey: YJDJKIIBWLSEEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.03
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  107.22
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 硫酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 18.0h， 生成 8-Ethyl-5,11-bis[(4-methoxyphenyl)methyl]-3,5,7,9,11,13-hexazatricyclo[8.3.0.02,6]trideca-1(10),2,6,8,12-pentaen-4-one
  参考文献：
  名称：

  Structure-based drug design and potent anti-cancer activity of tricyclic 5:7:5-fused diimidazo[4,5-d:4′,5′-f][1,3]diazepines

  摘要：

  Judicial structural modifications of 5: 7-fused ring-expanded nucleosides (RENs), based on molecular modeling studies with one of its known targets, human RNA helicase (hDDX3), led to the lead, novel, 5:7-5-fused tricyclic heterocycle (1). The latter exhibited promising broad-spectrum in vitro anti-cancer activity against a number of cancer cell lines screened. This paper describes our systematic, albeit limited, structure-activity relationship (SAR) studies on this lead compound, which produced a number of analogs with broad-spectrum in vitro anti-cancer activities against lung, breast, prostate, and ovarian cancer cell lines, in particular compounds 15i, 15j, 15m and 15n which showed IC50 values in submicromolar to micromolar range, and are worthy of further explorations. The SAR data also enabled us to propose a tentative SAR model for future SAR efforts for ultimate realization of optimally active and minimally toxic anti-cancer compounds based on the diimidazo[4,5-d:4',5'-f][1,3]diazepine structural skeleton of the lead compound 1. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.050
• 作为产物：
  描述：

  N-(2-amino-1,2-dicyano-vinyl)-formimydic acid ethyl ester 、 4-甲氧基苄胺 在 aniline hydrochloride 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以65%的产率得到
  参考文献：
  名称：

  Structure-based drug design and potent anti-cancer activity of tricyclic 5:7:5-fused diimidazo[4,5-d:4′,5′-f][1,3]diazepines

  摘要：

  Judicial structural modifications of 5: 7-fused ring-expanded nucleosides (RENs), based on molecular modeling studies with one of its known targets, human RNA helicase (hDDX3), led to the lead, novel, 5:7-5-fused tricyclic heterocycle (1). The latter exhibited promising broad-spectrum in vitro anti-cancer activity against a number of cancer cell lines screened. This paper describes our systematic, albeit limited, structure-activity relationship (SAR) studies on this lead compound, which produced a number of analogs with broad-spectrum in vitro anti-cancer activities against lung, breast, prostate, and ovarian cancer cell lines, in particular compounds 15i, 15j, 15m and 15n which showed IC50 values in submicromolar to micromolar range, and are worthy of further explorations. The SAR data also enabled us to propose a tentative SAR model for future SAR efforts for ultimate realization of optimally active and minimally toxic anti-cancer compounds based on the diimidazo[4,5-d:4',5'-f][1,3]diazepine structural skeleton of the lead compound 1. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.050

文献信息

• A Simple Precursor for Highly Functionalized Fused Imidazo[4,5-b]pyridines and Imidazo[4,5-b]-1,8-naphthyridine
  作者：Omar Al-duaij、Magdi Zaki、Abdel-Rhman El Gazzar

  DOI：10.3390/molecules21121646

  日期：——

  5-amino-3-(substituted benzyl)-6,7-dicyano-3H-imidazo[4,5-b]pyridines 5 and 6,8-diamino-3-(4-substituted benzyl)-3H-imidazo[4,5-b]-1,8-naphthyridine-7,9-dicarbonitrile 6, respectively, when the reaction was carried out in the absence of a base, or to 5,7-diamino-3-(4-alkyl aryl)-3H-imidazo[4,5-b]pyridine-6-carbonitrile 8, and 6,8,9-triamino-3-(4-substitutedbenzyl)-3H-imidazo[4,5-b]-1,8-naphthyridine-7-carbonitrile 10

  在温和的实验条件下，使1-烷基芳基-5-氨基-4-（氰基甲酰亚胺基）咪唑4与丙二腈和2-氨基-1,1,3-丙烯三腈反应，生成5-氨基-3-（取代的苄基） -6,7-二氰基-3H-咪唑并[4,5-b]吡啶5和6,8-二氨基-3-（4-取代的苄基）-3H-咪唑并[4,5-b] -1,8-萘啶-7,9-二腈6，当反应在没有碱的情况下进行时，或与5,7-二氨基-3-（4-烷基芳基）-3H-咪唑并[4,5-b在存在下，]吡啶-6-腈8和6,8,9-三氨基-3-（4-取代的苄基）-3H-咪唑并[4,5-b] -1,8-萘啶-7-腈10 1,8-二氮杂双环（5.4.0）十一碳-7-烯（DBU）。这两个反应都是由丙二腈或2-氨基-1,1,3-丙烯三腈的亲核攻击形成的加合物演化为氰基甲亚胺基取代基的碳。在丙二腈阴离子的情况下，当该反应在DBU存在下进行时，分离出5-氨基-1-烷基芳基-4-（1-氨基-2,2