N1,n1-双(3,4-二氯苯基)丙二酰胺 | 1677-30-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N1,n1-双(3,4-二氯苯基)丙二酰胺
• 英文名称: N1,N3-bis(3,4-dichlorophenyl)malonamide
• 英文别名: malonic acid bis-(3,4-dichloro-anilide)；Malonsaeure-bis-(3,4-dichlor-anilid)；N,N'-Bis-(3,4-dichlor-phenyl)-malonsaeurediamid；N,N'-bis(3,4-dichlorophenyl)propanediamide
• CAS: 1677-30-1
• 化学式: C₁₅H₁₀Cl₄N₂O₂
• mdl: MFCD00394415
• 分子量: 392.069
• InChiKey: USNJUUHHKPWGHO-UHFFFAOYSA-N

物化性质

• 熔点：
  227.8-228.6 °C
• 沸点：
  632.1±55.0 °C(Predicted)
• 密度：
  1.582±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N1,n1-双(3,4-二氯苯基)丙二酰胺 在 甲烷磺酸 、 phosphorus pentoxide 作用下， 反应 1.33h， 生成 5,6-dichloro-2,4-quinolinediol 、 6,7-dichloro-4-hydroxyquinolin-2(1H)-one
  参考文献：
  名称：

  Kappe, Thomas; Karem, Abdel S.; Stadlbauer, Wolfgang, Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 857 - 862

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二氯苯胺 、 丙二酰氯 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以61%的产率得到N1,n1-双(3,4-二氯苯基)丙二酰胺
  参考文献：
  名称：

  Ligand-based modelling followed by synthetic exploration unveil novel glycogen phosphorylase inhibitory leads

  摘要：

  Glycogen phosphorylase (GP) is a valid anti-diabetic target. Accordingly, we applied a drug discovery workflow to unveil novel inhibitory GP leads via combining pharmacophore modeling, QSAR analysis and in silico screening, followed by synthetic exploration of active hits. Virtual screening identified six low micromolar inhibitory leads from the National Cancer Institute (NCI) list of compounds. The most potent hits exhibited anti-GP IC50 values of 3.2 and 4.1 mu M. Synthetic exploration of hit 59 (IC50 = 4.1 mu M) yielded 25 lead inhibitors with the best illustrating IC50 of 3.0 mu M. Interestingly, we prepared several novel mixed oxalyl amide anti-GP leads employing new chemical reaction involving succinic acid-based adducts. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.086

文献信息

• Isopropyl N-Arylmalonamates. Synthesis, Structure, Conformation and Reactions with Carbon Disulfide
  作者：Wolf-Dieter Rudorf、Dušan Loos、Joanna Wybraniec、Naďa Prónayová、Ryszard Gawinecki、Zora Šusteková

  DOI：10.1135/cccc20060059

  日期：——

  Acylation of aromatic amines 1 with diisopropyl malonate (2) leads to a mixture of isopropyl N-arylmalonamates 3 and malonanilides 4. The reaction of 3 with carbon disulfide in the presence of sodium hydride gives disodium salts 5. Treatment of 5 with an alkylating agent yields the open-chain or cyclic ketene dithioacetals 6, 7 or 8. The molecular structure, hydrogen bonding and preferential conformation of the isopropyl N-arylmalonamates 3, 6 and 7 were investigated using correlation analyses of IR, ¹³C NMR and AM1 semiempirical data.

  芳香胺与二异丙基丙二酸酯（2）发生酰基化反应，得到异丙基N-芳基丙二酰胺（3）和马隆酰苯胺（4）的混合物。将3与二硫化碳在氢化钠存在下反应，得到二钠盐（5）。用烷基化剂处理5，得到开链或环状酮二硫乙醇（6、7或8）。通过对异丙基N-芳基丙二酰胺（3、6和7）的分子结构、氢键和偏好构象的相关分析，研究了其红外、13C核磁共振和AM1半经验数据。
• 10.1007/s10593-024-03311-5
  作者：Khachatryan, Anush Kh.、Avagyan, Katya A.、Sargsyan, Anush A.、Simonyan, Anait G.、Panosyan, Henrik A.、Ayvazyan, Armen G.、Badasyan, Alik E.

  DOI：10.1007/s10593-024-03311-5

  日期：——

  A new method for the synthesis of previously unknown ethyl 2-amino-1-(aryl)-5-(arylcarbamoyl)-6-oxo-1,6-dihydropyridine-3-carboxylates by a reaction of ethyl 2-cyano-3-ethoxyacrylate with N1,N3-diarylmalonamides was developed. The antibacterial activity of some of the synthesized compounds was assayed.

  一种通过 2-氰基-3-乙酯反应合成以前未知的 2-氨基-1-(芳基)-5-(芳基氨基甲酰基)-6-氧代-1,6-二氢吡啶-3-甲酸乙酯的新方法开发了N 1 ,N 3 -二芳基丙二酰胺的乙氧基丙烯酸酯。测定了一些合成化合物的抗菌活性。
• KAPPE, THOMAS;KAREM, ABDEL S.;STADLBAUER, WOLFGANG, J. HETEROCYCL. CHEM., 25,(1988) N 3, C. 857-862
  作者：KAPPE, THOMAS、KAREM, ABDEL S.、STADLBAUER, WOLFGANG

  DOI：——

  日期：——
• Ligand-based modelling followed by synthetic exploration unveil novel glycogen phosphorylase inhibitory leads
  作者：Maha Habash、Mutasem O. Taha

  DOI：10.1016/j.bmc.2011.06.086

  日期：2011.8

  Glycogen phosphorylase (GP) is a valid anti-diabetic target. Accordingly, we applied a drug discovery workflow to unveil novel inhibitory GP leads via combining pharmacophore modeling, QSAR analysis and in silico screening, followed by synthetic exploration of active hits. Virtual screening identified six low micromolar inhibitory leads from the National Cancer Institute (NCI) list of compounds. The most potent hits exhibited anti-GP IC50 values of 3.2 and 4.1 mu M. Synthetic exploration of hit 59 (IC50 = 4.1 mu M) yielded 25 lead inhibitors with the best illustrating IC50 of 3.0 mu M. Interestingly, we prepared several novel mixed oxalyl amide anti-GP leads employing new chemical reaction involving succinic acid-based adducts. (C) 2011 Elsevier Ltd. All rights reserved.
• Kappe, Thomas; Karem, Abdel S.; Stadlbauer, Wolfgang, Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 857 - 862
  作者：Kappe, Thomas、Karem, Abdel S.、Stadlbauer, Wolfgang

  DOI：——

  日期：——