(E,E)-2-(benzylaminocarbonyl)-3-styrylacrylonitrile | 368836-79-7

• 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,E)-2-(benzylaminocarbonyl)-3-styrylacrylonitrile
• 英文别名: (2E,4E)-N-benzyl-2-cyano-5-phenylpenta-2,4-dienamide
• CAS: 368836-79-7
• 化学式: C₁₉H₁₆N₂O
• 分子量: 288.349
• InChiKey: RUZVBNIIMZBGQA-NTIJCTKGSA-N

物化性质

• 沸点：
  555.9±50.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二溴丙二酸二乙酯 、 (E,E)-2-(benzylaminocarbonyl)-3-styrylacrylonitrile 在 锌 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以61%的产率得到ethyl 5-cyano-3-benzyl-2,4-dioxo-6-(2-phenylvinyl)-3-azabicyclo[3.1.0]hexane-1-carboxylate
  参考文献：
  名称：

  Reaction of organozinc reagents formed from α,α-dibromocarbonyl compounds and zinc with (3-phenylprop-2-enylidene)malonodinitriles and primary amides of 2-Cyano-5-phenylpenta-2,4-dienoic acid

  摘要：

  Organozinc compounds formed from I-aryi-2,2-dibromoalkanes, a,a-dibromopinacoline, and dialkyl dibromomalonates and zinc react with (3-phenylprop-2-enylidene)inalonodinitriles and primary amides of 2-cyano-5-phenylpenta-2.4-dienoic acid to form 2-alkyl-2-aroyl-3-(phenylvinyl)cyclopropan-1,1dicarboxylic acid dinitriles, N-substituted amides of 3-(phenylvinyl)-2-(2,2-dimethylpropanoyl)-lcyanocyclopropan-l-carboxylic acids, and alkyl 3-R-6-(phenylvinyl)-2.4-dioxo-5-cyano-3-azabicyclo[3.1.01hexan- I -carboxylates as a single stereoisomer.

  DOI：

  10.1134/s1070363208060145
• 作为产物：
  描述：

  苄胺 在 N-甲基哌嗪 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 (E,E)-2-(benzylaminocarbonyl)-3-styrylacrylonitrile
  参考文献：
  名称：

  Novel soluble myeloid cell leukemia sequence 1 (Mcl-1) inhibitor (E,E)-2-(benzylaminocarbonyl)-3-styrylacrylonitrile (4g) developed using a fragment-based approach

  摘要：

  Based on a known nanomolar Bcl-2 homology domain 3 (BH3) mimetic 3-thiomorpholin-8-oxo-8H-acenaphtho[1,2-b] pyrrole-9-carbonitrile (SI, MW: 331), we applied a fragment-based approach to obtain BH3 mimetics with improved affinity and improved solubility in a water ethanol (9:1) cosolvent. After the deconstruction of 1 (S1), we obtained fragment cyanoacetamide (4), which was determined to be a ligand efficiency (LE) hot part. After a rational optimization through fragment evolution beginning with fragment 4, a smaller Mcl-1 inhibitor (E,E)-2-(benzylaminocarbonyl)-3-styrylacrylonitrile (4g, MW: 288) with a 6-fold increase in affinity compared to I was obtained, as predicted by our optimization curve and identified by Mcl-1 protein nuclear magnetic resonance (NMR). (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.050

文献信息

• Tyrenes: synthesis of new antiproliferative compounds with an extended conjugation
  作者：Peter Demin、Olga Rounova、Thomas Grunberger、Lorand Cimpean、Nigel Sharfe、Chaim M Roifman

  DOI：10.1016/j.bmc.2004.03.043

  日期：2004.6

  3,4-dihydroxystyryl-acrylonitriles, in particular CR-4, revealed great potency as antitumor agents, and also exhibited low toxicity to normal cells. The effectiveness of these compounds with extended conjugation may be due to their possible functioning as reactive Michael acceptors.

  设计并合成了一系列取代的苯乙烯基-丙烯腈。测试了称为轮胎的新化合物抑制急性淋巴细胞白血病（ALL）癌细胞生长的能力，以及它们对正常骨髓（NBM）细胞的毒性。结果显示3，4-二羟基苯乙烯基-丙烯腈，特别是CR-4，显示出作为抗肿瘤剂的强大功效，并且对正常细胞显示出低毒性。这些化合物具有延长的共轭作用的有效性可能是由于它们可能起反应性迈克尔受体的作用。
• [EN] NOVEL COMPOUNDS FOR MODULATING CELL PROLIFERATION<br/>[FR] NOUVEAUX COMPOSES POUR LA MODULATION DE LA PROLIFERATION CELLULAIRE
  申请人：HSC RES DEV LP

  公开号：WO2005092904A1

  公开（公告）日：2005-10-06

  Novel styrylacrylonitrile compounds which are useful in treating a variety of cell proliferative disorders such as cancer are disclosed.

  新型的苯乙烯丙烯腈化合物被揭示，这些化合物在治疗各种细胞增殖性疾病，如癌症方面具有用处。
• [EN] SELECTIVE α-CYANOACRYLAMIDE AND α-CYANOACRYLATE INHIBTORS OF THE MCL-1 ONCOPROTEIN AND METHODS OF USING THE SAME<br/>[FR] INHIBITEURS α-CYANOACRYLAMIDE ET α-CYANOACRYLATE SÉLECTIFS DE L'ONCOPROTÉINE MCL-1 ET LEURS MÉTHODES D'UTILISATION
  申请人：UNIV MARYLAND

  公开号：WO2019040467A1

  公开（公告）日：2019-02-28

  α-Cyanoacrylamide and α-cyanoacrylate compounds that allosterically inhibit Myeloid Cell Leukemia-1 (Mcl-1) oncoprotein, and methods of using the same, are provided for treating disease.

  提供了α-氰基丙烯酰胺和α-氰基丙烯酸酯化合物，它们以变构方式抑制髓细胞白血病-1（Mcl-1）致癌蛋白，并提供了使用这些化合物治疗疾病的方法。
• Novel Compounds for Modulating Cell Proliferation
  申请人：Roifman M. Chaim

  公开号：US20070243612A1

  公开（公告）日：2007-10-18

  Novel styrylacrylonitrile compounds which are useful in treating a variety of cell proliferative disorders such as cancer are disclosed.

  本发明揭示了一种新型的苯乙烯腈化合物，可用于治疗多种细胞增殖性疾病，如癌症。
• Compounds for modulating cell proliferation
  申请人：HSC Research and Development Limited Partnership

  公开号：US06800659B2

  公开（公告）日：2004-10-05

  Novel styrylacrylonitrile compounds which are useful in treating a variety of cell proliferative disorders such as cancer are disclosed. The compounds are of the Formula I:

  本发明揭示了一种新型的苯乙烯腈化合物，可用于治疗多种细胞增殖性疾病，如癌症。该化合物的化学式为I：