(E)-N-[4-(1-{diaminomethylene}hydrazono)ethyl]-3-nitrobenzene hydrochloride | 1020087-28-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-N-[4-(1-{diaminomethylene}hydrazono)ethyl]-3-nitrobenzene hydrochloride
• CAS: 1020087-28-8
• 化学式: C₉H₁₁N₅O₂*ClH
• 分子量: 257.68
• InChiKey: VNMHTOMTDBURFR-WXIWBVQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.01
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  119.9
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-N-[4-(1-{diaminomethylene}hydrazono)ethyl]-3-nitrobenzene hydrochloride 在 吡啶 、 盐酸 、 铁粉 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 65.0h， 生成 (E)-N-[3-(1-{(diaminomethylene)hydrazono}ethyl)phenyl]-4-[6-(dimethylamino)quinolin-4-ylamino]benzamide dihydrochloride
  参考文献：
  名称：

  Structure–activity relationships for 4-anilinoquinoline derivatives as inhibitors of the DNA methyltransferase enzyme DNMT1

  摘要：

  A series of 4-anilinoquinoline derivatives related to the known inhibitor SGI-1027, containing side chains of varying pK(a), were prepared by acid-catalysed coupling of the pre-formed side chains with 4-chloroquinolines. The compounds were evaluated for their ability to reduce the level of DNMT1 protein in HCT116 human colon carcinoma cells by Western blotting. With a very strongly basic N-methylpyridinium side chain, only NHCO-linked compounds were effective, whereas less strongly basic ((diaminomethylene) hydrazono)ethyl or 3-methylpyrimidine-2,4-diamine side chains allowed both NHCO- and CONH-linked compounds to show activity. In contrast, the pK(a) of the quinoline unit had little apparent influence on activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.033
• 作为产物：
  描述：

  间硝基苯乙酮 、 氨基胍半硫酸盐 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 14.0h， 生成 (E)-N-[4-(1-{diaminomethylene}hydrazono)ethyl]-3-nitrobenzene hydrochloride
  参考文献：
  名称：

  Structure–activity relationships for 4-anilinoquinoline derivatives as inhibitors of the DNA methyltransferase enzyme DNMT1

  摘要：

  A series of 4-anilinoquinoline derivatives related to the known inhibitor SGI-1027, containing side chains of varying pK(a), were prepared by acid-catalysed coupling of the pre-formed side chains with 4-chloroquinolines. The compounds were evaluated for their ability to reduce the level of DNMT1 protein in HCT116 human colon carcinoma cells by Western blotting. With a very strongly basic N-methylpyridinium side chain, only NHCO-linked compounds were effective, whereas less strongly basic ((diaminomethylene) hydrazono)ethyl or 3-methylpyrimidine-2,4-diamine side chains allowed both NHCO- and CONH-linked compounds to show activity. In contrast, the pK(a) of the quinoline unit had little apparent influence on activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.033

文献信息

• WO2008/46085
  申请人：——

  公开号：——

  公开（公告）日：——