2-[((3-氰基苯基)氨基)亚甲基]丙二酸二乙酯 | 59551-10-9

• 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: 2-[((3-氰基苯基)氨基)亚甲基]丙二酸二乙酯
• 英文名称: diethyl {[(3-cyanophenyl)amino]methylene}malonate
• 英文别名: diethyl 2-((3-cyanophenylamino)methylene)malonate；ethyl-α-carbethoxy-β-(m-cyanoanilino)acrylate；Diethyl 2-[(3-cyanoanilino)methylidene]propanedioate
• CAS: 59551-10-9
• 化学式: C₁₅H₁₆N₂O₄
• 分子量: 288.303
• InChiKey: VTCVHSVVBDHVIN-UHFFFAOYSA-N

物化性质

• 熔点：
  119 °C
• 沸点：
  379.8±42.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  88.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[((3-氰基苯基)氨基)亚甲基]丙二酸二乙酯 在 sodium hydroxide 、 三氯氧磷 作用下， 以 甲醇 、 二苯醚 、 水 为溶剂， 反应 9.5h， 生成 4-(methylamino)quinolin-7-carbonitrile
  参考文献：
  名称：

  Structure–activity relationships for ferriprotoporphyrin IX association and β-hematin inhibition by 4-aminoquinolines using experimental and ab initio methods

  摘要：

  In order to probe structure-activity relationships of association with ferriprotoporphyrin IX (logK) and inhibition of beta-hematin formation, a series of 4-aminoquinolines with varying substituents at the 7-position (X) have been synthesized. These have been further elaborated by introduction of two different R groups on the 4-amino nitrogen atom in the form of methyl (R = Me) and ethylamine (R = EtNH2) side chains. Data for a previously investigated series containing an N,N-diethyl-ethylamine side chain were also compared with the findings of this study. Experimentally, logK values for the simple 4-aminoquinoline series (R = H) were found to correlate with the hydrophobicity constant (pi) of the group X. The logK values for the series with R = Me and EtNH2 were found to correlate with those of the series with R = H. The log of the 50% beta-hematin inhibitory activity (log BHIA(50)) was found to correlate with logK and either meta (sigma(m)) or para (sigma(p)) Hammett constants for the series with R = Me and EtNH2, but not the simple series with R = H. To further improve predictability, correlations with ab initio electrostatic parameters, namely Mulliken and CHelpG charges were investigated. The best correlations were found with CHelpG charges which indicated that logK values can be predicted from the charges on atom H-8 and the group X in the quinolinium species computed in vacuum, while log BHIA50 values can be predicted from the CHelpG charges on C-7, C-8 and N-1 for the neutral species in vacuum. These correlations indicate that association and inhibition of beta-hematin formation are separately determined. They also suggest that electron withdrawing groups at the 7-position, but not necessarily hydrophobic groups are required for hemozoin inhibition. The upshot is that the correlations imply that considerably more hydrophilic hemozoin inhibitors are feasible. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.040
• 作为产物：
  描述：

  乙氧基甲叉丙二酸二乙酯 、 间氨基苯甲腈 反应 1.0h， 生成 2-[((3-氰基苯基)氨基)亚甲基]丙二酸二乙酯
  参考文献：
  名称：

  The inhibition of factor inhibiting hypoxia-inducible factor (FIH) by β-oxocarboxylic acids

  摘要：

  环状β-氧羰基酸通过结合到活性位点铁而抑制缺氧诱导因子抑制因子。

  DOI：

  10.1039/b510707e

文献信息

• The inhibition of factor inhibiting hypoxia-inducible factor (FIH) by β-oxocarboxylic acids
  作者：Biswadip Banerji、Ana Conejo-Garcia、Luke A. McNeill、Michael A. McDonough、Matthew R. G. Buck、Kirsty S. Hewitson、Neil J. Oldham、Christopher J. Schofield

  DOI：10.1039/b510707e

  日期：——

  Cyclic β-oxocarboxylic acids inhibit factor inhibiting hypoxia-inducible factor via ligation to the active site iron.

  环状β-氧羰基酸通过结合到活性位点铁而抑制缺氧诱导因子抑制因子。
• Carboxamine compounds, methods and compositions for inhibiting PARP activity
  申请人：Guilford Pharmaceuticals Inc.

  公开号：US20020156050A1

  公开（公告）日：2002-10-24

  A compound of formula I: 1 or a pharmaceutically acceptable salt, hydrate, ester, solvate, prodrug, metabolite, stereoisomer, or mixtures thereof; wherein: Y represents the atoms necessary to form a fused 5- to 6-membered, aromatic or non-aromatic, carbocyclic or N-containing heterocyclic ring, wherein Y and any heteroatom(s) therein are unsubstituted or independently substituted by at least one non-interfering alkyl, alkenyl, cycloalkyl, cycloalkenyl, aralkyl, aryl, carboxy or halo substituent; X is at the 1-position of ring Y and is —COOR 5 or a substituted or unsubstituted moiety selected from the group consisting of 2 wherein R 7 is hydrogen, alkyl, alkenyl, cycloalkyl or cycloalkenyl, and is itself either unsubstituted or substituted with an alkyl, alkenyl, cycloalkyl or cycloalkenyl group; R 1 is hydrogen, alkyl, alkenyl, cycloalkyl or cycloalkenyl, and is itself either unsubstituted or substituted with an alkyl, alkenyl, cycloalkyl or cycloalkenyl group; R 2 , R 3 , R 4 and R 5 are independently hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aralkyl, or aryl, and are either unsubstituted or substituted with a moiety selected from the group consisting of alkyl, alkenyl, alkoxy, phenoxy, benzyloxy, cycloalkyl, cycloalkenyl, hydroxy, carboxy, carbonyl, amino, amido, cyano, isocyano, nitro, nitroso, nitrilo, isonitrilo, imino, azo, diazo, sulfonyl, sulfoxy, thio, thiocarbonyl, sulfhydryl, halo, haloalkyl, trifluoromethyl and aryl.

  式 I 的化合物： 1 或其药学上可接受的盐、水合物、酯、溶液剂、原药、代谢物、立体异构体或混合物；其中 Y 代表形成融合的 5 至 6 元、芳香族或非芳香族、碳环或含 N 的杂环所需的原子，其中 Y 及其中的任何杂原子未被取代或独立地被至少一个无干扰的烷基、烯基、环烷基、环烯基、芳基、芳基、羧基或卤代取代基取代； X 位于环 Y 的 1 位，并且是 -COOR 5 或选自以下组别的取代或未取代分子 2 其中 R 7 是氢、烷基、烯基、环烷基或环烯基，且本身未被取代或被烷基、烯基、环烷基或环烯基取代； R 1 是氢、烷基、烯基、环烷基或环烯基，且本身未被取代或被烷基、烯基、环烷基或环烯基取代； R 2 , R 3 , R 4 和 R 5 环烷基、环烯基、羟基、羧基、羰基、氨基、酰胺基、氰基、异氰基、硝基、亚硝基、 尼基、异尼基、亚氨基、偶氮、重氮、磺酰基、磺氧、硫代、硫代羰基、巯基、卤代、 卤代烷基、三氟甲基和芳基。
• A Small-Molecule Inhibitor of Nipah Virus Envelope Protein-Mediated Membrane Fusion
  作者：Sabine Niedermeier、Katrin Singethan、Sebastian G. Rohrer、Magnus Matz、Markus Kossner、Sandra Diederich、Andrea Maisner、Jens Schmitz、Georg Hiltensperger、Knut Baumann、Ulrike Holzgrabe、Jürgen Schneider-Schaulies

  DOI：10.1021/jm900411s

  日期：2009.7.23

  Nipah virus (NiV), a highly pathogenic paramyxovirus. causes respiratory disease in pigs and severe febrile encephalitis in humans with high mortality rates. On the basis of the structural similarity of viral fusion (F) proteins within the family Paramyxoviridae, we designed and tested 18 quinolone derivatives in a NiV and measles virus (MV) envelope protein-based fusion assay beside evaluation of cytotoxicity. We found five compounds successfully inhibiting NiV envelope protein-induced cell fusion. The most active molecules (19 and 20), which also inhibit the syncytium formation induced by infectious NiV and show a low cytotoxicity in Vero cells, represent a promising lead quinolone-type compound structure. Molecular modeling indicated that compound 19 fits well into a particular protein cavity present on the NiV F protein that is important for the fusion process.
• WAGNER G.; VIEWEG H., PHARMAZIE <PHAR-AT>, 1976, 31, NO 3, 145-148
  作者：WAGNER G.、 VIEWEG H.

  DOI：——

  日期：——
• US6395749B1
  申请人：——

  公开号：US6395749B1

  公开（公告）日：2002-05-28