2-Cyan-3-<4-methoxy-phenyl>-but-2-en-saeure-ethylester | 20049-36-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-Cyan-3-<4-methoxy-phenyl>-but-2-en-saeure-ethylester
• 英文别名: trans-2-Cyan-3-<4-methoxy-phenyl>-but-2-en-saeure-ethylester；Ethyl 2-cyano-3-(4-methoxyphenyl)-2-butenoate；ethyl (E)-2-cyano-3-(4-methoxyphenyl)but-2-enoate
• CAS: 20049-36-9
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: WJQUTHBBZNRIGS-JLHYYAGUSA-N

物化性质

• 沸点：
  378.0±32.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Cyan-3-<4-methoxy-phenyl>-but-2-en-saeure-ethylester 反应 26.0h， 生成 1,2-dihydro-1-(4-fluorobenzyl)-4-(4-methoxyphenyl)-2-oxopyridine-3-carbonitrile
  参考文献：
  名称：

  Polypharmacological profile of 1,2-dihydro-2-oxo-pyridine-3-carboxamides in the endocannabinoid system

  摘要：

  The endocannabinoid system (ECS) represents one of the major neuromodulatory systems involved in different physiological and pathological processes. Multi-target compounds exert their activities by acting via multiple mechanisms of action and represent a promising pharmacological modulation of the ECS. In this work we report 4-substituted and 4,5-disubstituted 1,2-dihydro-2-oxo-pyridine-3-carboxamide derivatives with a broad spectrum of affinity and functional activity towards both cannabinoid receptors and additional effects on the main components of the ECS. In particular compound B3 showed high affinity for CB1R (K-i = 23.1 nM, partial agonist) and CB2R (K-i = 6.9 nM, inverse agonist) and also significant inhibitory activity (IC50 = 70 nM) on FAAH with moderate inhibition of ABHD12 (IC50 = 2.5 mu M). Compounds B4, B5 and B6 that act as full agonists at CB1R and as partial agonists (B5 and B6) or antagonist (B4) at CB2R, exhibited an additional multi-target property by inhibiting anandamide uptake with sub-micromolar IC50 values (0.28-0.62 mu M). The best derivatives showed cytotoxic activity on U937 lymphoblastoid cells. Finally, molecular docking analysis carried out on the three-dimensional structures of CB1R and CB2R and of FAAH allowed to rationalize the structure-activity relationships of this series of compounds. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.05.019
• 作为产物：
  描述：

  氰乙酸乙酯 、 对甲氧基苯乙酮 在 ammonium acetate 、 溶剂黄146 作用下， 以 苯 为溶剂， 生成 2-Cyan-3-<4-methoxy-phenyl>-but-2-en-saeure-ethylester
  参考文献：
  名称：

  Luu Duc,C. et al., Chimica Therapeutica, 1969, vol. 4, p. 271 - 275

  摘要：

  DOI：

文献信息

• [EN] THIENOPYRIMIDINE DERIVATIVES AS POTASSIUM CHANNEL INHIBITORS<br/>[FR] UTILISATION DE DERIVES DE LA THIENOPYRIMIDINE COMME INHIBITEURS DES CANAUX POTASSIQUES
  申请人：XENTION DISCOVERY LTD

  公开号：WO2004111057A1

  公开（公告）日：2004-12-23

  The present invention provides thienopyrimidine compounds which are potasium channels inhibitors. Pharmaceutical compositions comprising the compounds and their use in the treatment of arrhythmia are also provided.

  本发明提供了硫代嘧啶类化合物，它们是钾通道抑制剂。还提供了包含这些化合物的药物组合物，以及它们在治疗心律失常中的用途。
• Pharmaceutically active compounds and methods of use
  申请人：——

  公开号：US20030073733A1

  公开（公告）日：2003-04-17

  New fused thiophene compounds are provided and methods of using those compounds for a variety of therapeutic indications. Compounds of the invention are particularly useful for treatment of neuropathic pain.

  提供了新的融合噻吩化合物，并提供了使用这些化合物治疗各种治疗适应症的方法。该发明的化合物特别适用于治疗神经病性疼痛。
• The unprecedented reaction of dimethylsulfonium methylide with Michael acceptors: synthesis of 1-substituted vinyl silanes and styrenes
  作者：Sonali M. Date、Rekha Singh、Sunil K. Ghosh

  DOI：10.1039/b509102k

  日期：——

  established leading to functionalized 1-substituted alkenes. In silyl substituted substrates (2a and 2h), where a facile Peterson-type olefination is possible from the adduct; elimination took place instead to give functionalized 1-substituted vinyl silanes. Aryl substituted Michael acceptors (2b-e, 2g and 2i-k) also underwent a similar kind of olefination to give 1-substituted styrene derivatives with moderate

  不同于通常的环丙烷化，已经建立了从二甲基s亚甲基和各种迈克尔受体的加合物进行空前消除反应的条件，从而导致官能化的1-取代的烯烃。在甲硅烷基取代的底物（2a和2h）中，加合物中可能发生容易的Peterson型烯化反应；取而代之，进行消除，得到官能化的1-取代的乙烯基硅烷。芳基取代的Michael受体（2b-e，2g和2i-k）也经历了类似的烯化反应，以中等收率得到1-取代的苯乙烯衍生物以及副产物，副产物是由二甲基ulf甲基化物和亚芳基丙二酸酯。Hammett研究表明，烯化的选择性与 随着芳基取代基变得更缺乏电子，脱甲基化增加。具有β-烷基取代基的亚炔基丙二酸酯（2f和2l）不利于烯烃化过程。将迈克尔受体和卤代烷依次加到二甲基methyl亚甲基和二甲酸钠的混合物中可进行烯化，然后在活性次甲基上进行烷基化。通过对一些sulf甲基化物的研究已经确定了机械途径。
• Compounds
  申请人：Ford John

  公开号：US20050026935A1

  公开（公告）日：2005-02-03

  This invention relates to novel compound of formula (I) or pharmaceutically acceptable salts thereof. The invention is also directed to the uses of compounds having formula (I) in the treatment or prevention of diseases or disorders which requires potassium channel inhibition to an animal, mammal or human in need thereof. The invention is also directed to the use of compounds having formula (I) in the treatment or prevention of arrhythmia to an animal, mammal or human in need thereof.

  本发明涉及公式(I)的新化合物或其药学上可接受的盐。该发明还涉及使用具有公式(I)的化合物在需要钾通道抑制的动物、哺乳动物或人类中治疗或预防疾病或障碍的用途。该发明还涉及使用具有公式(I)的化合物在需要治疗或预防心律失常的动物、哺乳动物或人类中的用途。
• Composition of stabilized synthetic resin
  申请人：ASAHI DENKA KOGYO KABUSHIKI KAISHA

  公开号：EP0336606A1

  公开（公告）日：1989-10-11

  A stabilized synthetic resin composition characterised in that for every 100 parts by weight of synthetic resin, the composition comprises 0.001 to 10 parts by weight of a cyclic alkylphosphite compound of 2,2′-alkylidene-bisphenol having the formula (I) and 0.001 to 10 parts by weight of beta-(3,5-dialkyl-4-­hydroxyphenyl)-propionic acid ester having the formula (II): in which R1 is tertiary-butyl or tertiary-amyl; R2 is an alkyl group having 1 to 9 carbon atoms; R3 is hydrogen or an alkyl group having 1 to 4 carbon atoms: R4 is an alkyl group having 1 to 30 carbon atoms: R5 is an alkyl group having 1 to 4 carbon atoms; R6 is a residual group of a monohydric alcohol, a dihydric alcohol, a trihydric alcohol or a tetrahydric alcohol; and n is a number of 1 to 4.

  一种稳定的合成树脂组合物，其特征在于以每 100 份合成树脂的重量计，该组合物包括 0.001 至 10 份（按重量计）式(I)的 2,2′-亚烷基双酚环状烷基亚磷酸酯化合物和 0.001 至 10 份（按重量计）式(II)的β-(3,5-二烷基-4-羟基苯基)丙酸酯： 其中 R1 是叔丁基或叔戊基；R2 是具有 1 至 9 个碳原子的烷基；R3 是氢或具有 1 至 4 个碳原子的烷基：R4 是具有 1 至 30 个碳原子的烷基：R5 是具有 1 至 4 个碳原子的烷基；R6 是一元醇、二元醇、三元醇或四元醇的残基；n 是 1 至 4 的数字。

表征谱图