2-bromo-1-(p-methoxyphenyl)ethylidenemalononitrile | 75562-68-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-bromo-1-(p-methoxyphenyl)ethylidenemalononitrile
• 英文别名: 2-[2-Bromo-1-(4-methoxyphenyl)ethylidene]propanedinitrile
• CAS: 75562-68-4
• 化学式: C₁₂H₉BrN₂O
• 分子量: 277.12
• InChiKey: GTCMSCWSZZREAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  56.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromo-1-(p-methoxyphenyl)ethylidenemalononitrile 在 一水合肼 、 三氯氧磷 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 1.0h， 生成 [7-(3-Chloro-4-fluorophenyl)-5-(4-methoxyphenyl)pyrrolo[2,3-d]pyrimidin-4-yl]hydrazine
  参考文献：
  名称：

  氟芳基取代的2-氨基-3-氰基吡咯和吡咯并[2,3- d ]嘧啶的合成及反应

  摘要：

  在Gewald反应条件下，由（2-溴-1-芳基亚烷基）丙二腈1与氟芳基取代的芳族胺反应合成了一些氟芳基取代的2-氨基-3-氰基吡咯2，与甲酰胺和甲酸反应生成4-氨基吡咯并[2，3- d ]嘧啶3和吡咯并[2，3 - d ]-嘧啶-4（3H）-一4。4-氯代吡咯并[2,3- d ]嘧啶5是通过四氯氧磷氯化制备的，在肼解作用下提供了4-肼基吡咯并[ 2-3 - d ]嘧啶6。

  DOI：

  10.1002/jhet.5570360325
• 作为产物：
  描述：

  对甲氧基苯乙酮 、 丙二腈 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 生成 2-bromo-1-(p-methoxyphenyl)ethylidenemalononitrile
  参考文献：
  名称：

  Berg, Arne; Kolsaker, Per, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1980, vol. 34, # 4, p. 289 - 294

  摘要：

  DOI：

文献信息

• 2-Haloalkylidenepropanedinitriles in the Synthesis of Fused Pyrimidines
  作者：Chaitanya G. Dave、Rina D. Shah

  DOI：10.3987/com-97-8011

  日期：——
• Dave; Shah; Upadhyaya, Journal of the Indian Chemical Society, 1987, vol. 64, # 11, p. 713 - 716
  作者：Dave、Shah、Upadhyaya

  DOI：——

  日期：——
• Optimization of Ligand and Lipophilic Efficiency To Identify an in Vivo Active Furano-Pyrimidine Aurora Kinase Inhibitor
  作者：Hui-Yi Shiao、Mohane Selvaraj Coumar、Chun-Wei Chang、Yi-Yu Ke、Ya-Hui Chi、Chang-Ying Chu、Hsu-Yi Sun、Chun-Hwa Chen、Wen-Hsing Lin、Ka-Shu Fung、Po-Chu Kuo、Chin-Ting Huang、Kai-Yen Chang、Cheng-Tai Lu、John T. A. Hsu、Chiung-Tong Chen、Weir-Torn Jiaang、Yu-Sheng Chao、Hsing-Pang Hsieh

  DOI：10.1021/jm4006059

  日期：2013.7.11

  Ligand efficiency (LE) and lipophilic efficiency (LipE) are two important indicators of "drug-likeness", which are dependent on the molecules activity and physicochemical properties. We recently reported a furano-pyrimidine Aurora kinase inhibitor 4 (LE = 0.25; LipE = 1.75), with potent activity in vitro; however, 4 was inactive in vivo. On the basis of insights obtained from the X-ray co-crystal structure of the lead 4, various solubilizing functional groups were introduced to optimize both the activity and physicochemical properties. Emphasis was placed on identifying potential leads with improved activity as well as better LE and LipE by exercising tight control over the molecular weight and lipophilicity of the molecules. Rational optimization has led to the identification of Aurora kinase inhibitor 27 (IBPR001; LE = 0.26; LipE = 4.78), with improved in vitro potency and physicochemical properties, resulting in an in vivo active (HCT-116 colon cancer xenograft mouse model) anticancer agent.
• Dave, Chaitanya G; Upadhyaya, S P, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 6, p. 672 - 674
  作者：Dave, Chaitanya G、Upadhyaya, S P

  DOI：——

  日期：——
• Application of NAD(P)H Model Hantzsch 1,4-Dihydropyridine as a Mild Reducing Agent in Preparation of Cyclo Compounds
  作者：Xiao-Qing Zhu、Hong-Yi Wang、Jian-Shuang Wang、You-Cheng Liu

  DOI：10.1021/jo001434f

  日期：2001.1.1