2-(1-(4-nitrophenyl)-3-oxo-3-phenylpropyl)malononitrile | 88783-75-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 2-(1-(4-nitrophenyl)-3-oxo-3-phenylpropyl)malononitrile
• 英文别名: 1-Phenyl-3-(4-nitro-phenyl)-4,4-dicyan-butanon-(1)；Propanedinitrile, [1-(4-nitrophenyl)-3-oxo-3-phenylpropyl]-；2-[1-(4-nitrophenyl)-3-oxo-3-phenylpropyl]propanedinitrile
• CAS: 88783-75-9
• 化学式: C₁₈H₁₃N₃O₃
• 分子量: 319.32
• InChiKey: VQBZNGYQYYXIDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(1-(4-nitrophenyl)-3-oxo-3-phenylpropyl)malononitrile 在 硫化氢 、 氧气 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 0.5h， 生成 4-(4-Chlor-phenyl)-6-phenyl-2-thioxo-1,2-dihydro-pyridin-3-carbonitril
  参考文献：
  名称：

  Synthesis of 3-cyano-4, 6-diaryl-3, 4-dihydropyridine-2-thionks

  摘要：

  DOI：

  10.1007/bf00515357
• 作为产物：
  描述：

  对硝基苯甲醛 在 三丁基膦 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 2-(1-(4-nitrophenyl)-3-oxo-3-phenylpropyl)malononitrile
  参考文献：
  名称：

  Linifanib 的支架跳跃设计 6-苯基异恶唑并[3,4-b]吡啶-3-胺衍生物作为 FLT3 抑制剂治疗急性髓系白血病

  摘要：

  背景：急性髓系白血病（AML）是最常见的血癌类型。 Fmslike 酪氨酸激酶 3 (FLT3) 是 III 类受体酪氨酸激酶家族的成员。 70-100% 的急性髓系白血病患者中发现 FLT3 过度表达。 FLT3内部串联重复改变（ITD）和酪氨酸激酶结构域（TKD）是AML中最常见的分子改变，FLT3已成为AML有前途的药物靶点。目的：设计并合成一系列具有酰胺键的6-苯基异恶唑并[3,4-b]吡啶-3-胺衍生物F1-F15作为FLT3抑制剂，以寻找治疗AML的新先导化合物。方法：我们通过将 RECAP 工具与基于 Gilde 的 Core-Hopping 工具相结合，设计了原始的支架跳跃方案，以设计基于 Linifanib 的新型 FLT3 抑制剂。组装的抑制剂根据 Glide 生成的对接分数进行排名。选择前10名中未公开的化合物来设计一系列6-苯基异恶唑并[3,4-b]吡啶-3-胺衍生

  DOI：

  10.2174/1570180820666230519140242

文献信息

• One-Pot Cascade Heterocyclization of γ- and β-Ketomalononitriles to 2,4-Dichloro-Substituted Pyrano[2,3-<i>d</i>]pyrimidines and Furo[2,3-<i>d</i>]pyrimidines Mediated by Triphosgene and Triphenylphosphine Oxide
  作者：Zhen-Hua Li、Zhi-Jiang Jiang、Qiao-Ling Shao、Jin-Jing Qin、Qiang-Feng Shu、Wen-Hao Lu、Wei-Ke Su

  DOI：10.1021/acs.joc.8b00669

  日期：2018.6.15

  A one-pot cascade heterocyclization strategy has been developed for the synthesis of 2,4-dichloro-substituted pyrano[2,3-d]pyrimidines and furo[2,3-d]pyrimidines from linear γ- and β-ketomalononitriles using triphosgene and triphenylphosphine oxide. The reaction afforded synthetic useful products with moderate to good yields, bypassing the conventional harsh conditions of chlorination. The mechanistic

  已开发出一锅级联杂环化策略，使用三光气从线性γ-和β-酮基乙腈合成2,4-二氯取代的吡喃并[2,3- d ]嘧啶和呋喃并[2,3- d ]嘧啶和三苯基氧化膦。该反应绕开了常规的苛刻氯化条件，提供了具有中等至良好收率的合成有用产物。机理研究表明反应是通过非异氰酸酯途径进行的，第二步可能以三苯膦氧化物催化的方式进行。
• An active and selective heterogeneous catalytic system for Michael addition
  作者：Hoda Keipour、Mohammad A. Khalilzadeh、Abolfazl Hosseini、Afsaneh Pilevar、Daryoush Zareyee

  DOI：10.1016/j.cclet.2012.02.006

  日期：2012.5

  Potassium fluoride doped natural zeolite was found to be an efficient and selective solid base catalyst for 1,4-Michael addition. The catalyst is easily prepared and the workup procedure simplified by simple filtration. All products were obtained in high yields as well as short reaction times. (C) 2012 Mohammad A. Khalilzadeh. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Conjugate addition of malononitrile on chalcone: Biocatalytic C C bond formation
  作者：Nitesh D. Punyapreddiwar、Sangesh P. Zodape、Atul V. Wankhade、Umesh R. Pratap

  DOI：10.1016/j.molcatb.2016.08.004

  日期：2016.11

  An efficient, cost effective and environmentally friendly protocol has been developed for the Michael addition of malononitrile on 1,3-diaryl-2-propen-1-ones (Chalcones) using very cheaper, easily available natural catalyst, baker's yeast. The whole cells of yeast excellently worked in nonaqueous medium, ethanol without decrease in catalytic activity. (C) 2016 Elsevier B.V. All rights reserved.
• A MILD AND CONVENIENT ONE-POT SYNTHESIS OF 4,6-DIARYL-3-AMINOISOXAZOLO[3,4-B]PYRIDINES
  作者：Chun-Bao Miao、Yan-Hong Wang、Chun-Ping Dong、Hai-Tao Yang、Qi Meng、Xiao-Qiang Sun

  DOI：10.3987/com-13-12802

  日期：——

  We have developed a convenient method for the synthesis of a series of new 4,6-diaryl-3-aminoisoxazolo[3,4-b]pyridines through one-pot reaction starting from the easily available chalcones, malononitrile, and hydroxylamine. This class of compounds might have potential pharmacological activities in medicinal chemistry.
• Design, synthesis and structure-activity relationship of diaryl-ureas with novel isoxazol[3,4-b]pyridine-3-amino-structure as multi-target inhibitors against receptor tyrosine kinase
  作者：Zhi-Hao Shi、Feng-Tao Liu、Hao-Zhong Tian、Yan-Min Zhang、Nian-Guang Li、Tao Lu

  DOI：10.1016/j.bmc.2018.08.013

  日期：2018.9

  Inspired by that the multi-target inhibitors against receptor tyrosine kinases (RTKs) have significantly improved the effect of clinical treatment for cancer, and based on the chemical structure of Linifanib (ABT-869, Abbott), two series of diaryl-ureas with novel isoxazol[3,4-b]pyridine-3-amino-structure were designed and synthesized as multi-target inhibitors against RTKs. The preliminary biological evaluation showed that several compounds exhibited comparable potency with Linifanib. Compound S21 was identified as the most potent inhibitor against Fms-like tyrosine kinase 3 (FLT-3), kinase insert domain containing receptor (KDR) and platelet-derived growth factor receptor beta (PDGFR-beta) with its IC50 values were 4 nM, 3 nM and 8 nM respectively, it also showed potent inhibitory activities against several cancer cells.