2-((4-硝基苯基)氨基)-2-丁烯二酸二甲酯 | 16133-44-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-((4-硝基苯基)氨基)-2-丁烯二酸二甲酯
• 英文名称: dimethyl 2-<(4-nitrophenyl)amino>-2-butenedioate
• 英文别名: dimethyl p-nitroanilinofumarate；dimethyl 2-[(4-nitrophenyl)amino]-2-butenedioate；Dimethyl (2Z)-2-(4-nitroanilino)-2-butenedioate；dimethyl (Z)-2-(4-nitroanilino)but-2-enedioate
• CAS: 16133-44-1
• 化学式: C₁₂H₁₂N₂O₆
• 分子量: 280.237
• InChiKey: CGQGMMOPLVKRTB-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-((4-硝基苯基)氨基)-2-丁烯二酸二甲酯 在 镍 sodium hydroxide 、 氢气 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 25.0~240.0 ℃ 、344.73 kPa 条件下， 反应 80.17h， 生成 1-Methyl-6-(4-methyl-benzoylamino)-4-oxo-1,4-dihydro-quinoline-2-carboxylic acid
  参考文献：
  名称：

  Kynurenic Acid Derivatives Inhibit the Binding of Nerve Growth Factor (NGF) to the Low-Affinity p75 NGF Receptor

  摘要：

  The ability of a series of substituted kynurenic acids, thienopyridinonecarboxylic acids, and related compounds to inhibit the binding of nerve growth factor (NGF) to the p75 NGF receptor (NGFR) was evaluated in a radioligand binding assay that utilized a biotinylated derivative of the extracellular domain of p75 NGFR (p75(ext)) fixed to streptavidin-coated plastic wells. Two compounds, 6-aminokynurenic acid (5h) and the 3-methyl ester of 4,7-dihydro-2-methyl-7-oxo-thieno[3,2-b]pyridine-3,5-dicarboxylic acid (16), were found to inhibit the binding of [I-125]NGF to p75(ext) with IC50 values in the low micromolar range. Other amino-substituted kynurenic acids also possessed activity at slightly higher concentrations. Several structural features seem to be essential, including the carboxylic acid, a polar group on the benzene ring (or thiophene ring, in the case of analogues of 16), and the C-4 carbonyl group in the pyridinone ring. These compounds were also found to inhibit the binding of [I-125]NGF to its receptors in membranes from PC12 cells (which express p75 as well as trk(a) receptors for NGF) and DG44-CHO cells (transfected with full length p75 NGFR). The available data for 5h and 16 do not allow the determination of whether the effects of these compounds are mediated by their interaction with NGF or the NGF receptors.

  DOI：

  10.1021/jm00022a008
• 作为产物：
  描述：

  S,S-dimethyl-N-(p-nitrophenyl)sulfilimine 、 丁炔二酸二甲酯 在 水 作用下， 以 氯仿 为溶剂， 生成 2-((4-硝基苯基)氨基)-2-丁烯二酸二甲酯
  参考文献：
  名称：

  亚氨基磺脲类与乙酰二羧酸二甲酯的反应

  摘要：

  DOI：

  10.1016/s0040-4039(01)82409-6

文献信息

• Amide derivatives and nociceptin antagonists
  申请人：Japan Tobacco Inc.

  公开号：US06410561B1

  公开（公告）日：2002-06-25

  The present invention relates to a compound of the formula [1′] wherein R2 is lower alkyl optionally substituted by hydroxy, amino and the like, ring B is phenyl, thienyl and the like, E is a single bond, —O—, —S— and the like, ring G is aryl, heterocyclic group and the like, R5 is halogen atom, hydroxy, lower alkyl optionally substituted by halogen atom etc., and the like, t is 0 or an integer of 1 to 5, when t is an integer of 2 to 5, each R5 may be the same or different, m is 0 or an integer of 1 to 8, and n is 0 or an integer of 1 to 4, and a nociceptin antagonist containing compound [1′] as an active ingredient. The compound [1′] shows, due to nociceptin antagonistic action, analgesic effect against sharp pain such as postoperative pain and the like. The present invention also relates to the use of certain amide derivative inclusive of compound [1′] as a nociceptin antagonist or analgesic.

  本发明涉及一种化合物的公式为[1′]，其中R2是可选择地由羟基、氨基等取代的较低烷基，环B是苯基、噻吩基等，E是单键，—O—，—S—等，环G是芳基、杂环基等，R5是卤原子、羟基、可选择地由卤原子等取代的较低烷基等，t为0或1至5的整数，当t为2至5的整数时，每个R5可以相同或不同，m为0或1至8的整数，n为0或1至4的整数，以及包含化合物[1′]作为活性成分的一种痛觉受体拮抗剂。该化合物[1′]由于痛觉受体拮抗作用，对于术后疼痛等剧痛具有镇痛效果。本发明还涉及某些酰胺衍生物的使用，包括化合物[1′]作为痛觉受体拮抗剂或镇痛剂。
• CuCl₂-Mediated Reaction of [60]Fullerene with Amines in the Presence or Absence of Dimethyl Acetylenedicarboxylate: Preparation of Fulleropyrroline or Aziridinofullerene Derivatives
  作者：Hai-Tao Yang、Xi-Chen Liang、Yan-Hong Wang、Yang Yang、Xiao-Qiang Sun、Chun-Bao Miao

  DOI：10.1021/jo402043p

  日期：2013.12.6

  The CuCl2-mediated three-component reaction of C60 with amines and dimethyl acetylenedicarboxylate afforded the fulleropyrrolines in moderate yields. Furthermore, the CuCl2-mediated oxidative [2 + 1] reaction of C60 with aromatic amines bearing a strong electron-withdrawing group provided the aziridinofullerenes and the selective cis-1-bisaziridinofullerenes.

  C 60与胺和乙炔二羧酸二甲酯的CuCl 2介导的三组分反应以中等收率得到了全吡咯啉。此外，氯化亚铜2介导的氧化[2 + 1]的C反应60与芳族胺带有强吸电子基团提供的aziridinofullerenes和选择性的顺式-1- bisaziridinofullerenes。
• AMIDE DERIVATIVES AND NOCICEPTIN ANTAGONISTS
  申请人：Japan Tobacco Inc.

  公开号：EP1072263A1

  公开（公告）日：2001-01-31

  The present invention relates to a compound of the formula [1' ] wherein R2 is lower alkyl optionally substituted by hydroxy, amino and the like, ring B is phenyl, thienyl and the like, E is a single bond, -O-,-S- and the like, ring G is aryl, heterocyclic group and the like, R5 is halogen atom, hydroxy, lower alkyl optionally substituted by halogen atom etc., and the like, t is 0 or an integer of 1 to 5, when t is an integer of 2 to 5, each R5 may be the same or different, m is 0 or an integer of 1 to 8, and n is 0 or an integer of 1 to 4, and a nociceptin antagonist containing compound [1' ] as an active ingredient The compound [1' ] shows, due to nociceptin antagonistic action, analgesic effect against sharp pain such as postoperative pain and the like. The present invention also relates to the use of certain amide derivative inclusive of compound [1' ] as a nociceptin antagonist or analgesic.

  本发明涉及一种式 [1' ]的化合物。 其中 R2 是任选被羟基、氨基等取代的低级烷基，环 B 是苯基、噻吩基等，E 是单键、-O-、-S- 等，环 G 是芳基、杂环基等，R5 是卤素原子、羟基、任选被卤素原子等取代的低级烷基，t 是 0 或 1 至 5 的整数，当 t 是 2 至 5 的整数时，每个 R5 可以是相同的、等，t 为 0 或 1 至 5 的整数，当 t 为 2 至 5 的整数时，每个 R5 可以相同或不同，m 为 0 或 1 至 8 的整数，n 为 0 或 1 至 4 的整数，以及含有化合物[1']作为活性成分的痛觉素拮抗剂。本发明还涉及包含化合物[1' ]的某些酰胺衍生物作为痛觉素拮抗剂或镇痛剂的用途。
• Vernon, John M.; Carr, Richard M.; Sukari, Mohamed A., Journal of Chemical Research, Miniprint, 1982, # 5, p. 1310 - 1334
  作者：Vernon, John M.、Carr, Richard M.、Sukari, Mohamed A.

  DOI：——

  日期：——
• Quinoline derivatives as antiallergy agents
  作者：Charles M. Hall、Herbert G. Johnson、John B. Wright

  DOI：10.1021/jm00253a006

  日期：1974.7