(4Z)-4-benzylidene-2-(2-chlorophenyl)-1,3-oxazol-5(4H)-one | 849770-52-1

• 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
• 英文名称: (4Z)-4-benzylidene-2-(2-chlorophenyl)-1,3-oxazol-5(4H)-one
• 英文别名: (4Z)-4-benzylidene-2-(2-chlorophenyl)oxazol-5(4H)-one；4-Benzylidene-2-(2-chlorophenyl)oxazol-5(4H)-one；(4Z)-4-benzylidene-2-(2-chlorophenyl)-1,3-oxazol-5-one
• CAS: 849770-52-1
• 化学式: C₁₆H₁₀ClNO₂
• 分子量: 283.714
• InChiKey: GIHHWZDCEABATP-UVTDQMKNSA-N

物化性质

• 熔点：
  109-111 °C(Solv: ethanol (64-17-5))
• 沸点：
  417.2±55.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4Z)-4-benzylidene-2-(2-chlorophenyl)-1,3-oxazol-5(4H)-one 在 aluminum (III) chloride 作用下， 以 1,1,2,2-四氯乙烷 为溶剂， 反应 1.5h， 以35%的产率得到1-(2-氯苯基)异喹啉-3-羧酸
  参考文献：
  名称：

  WO2008/23357

  摘要：

  公开号：
• 作为产物：
  描述：

  methyl (2Z)-2-(2-chlorobenzamido)-3-phenylprop-2-enoate 在 三氯氧磷 作用下， 以 甲苯 为溶剂， 以95%的产率得到(4Z)-4-benzylidene-2-(2-chlorophenyl)-1,3-oxazol-5(4H)-one
  参考文献：
  名称：

  Synthesis of 4-benzylidene-oxazol-5(4H)-imines, structural analogs of PK11195, under Bischler-Napieralski conditions

  摘要：

  A simple and convenient one-pot procedure to prepare 4-benzylidene-2-aryl-1,3-oxazol-5(4H)-imines from phenyl pyruvic acid and a series of arylamides, under classical Bischler-Napieralski (B-N) conditions and microwave heating (MW) has been developed. The structures of the prepared compounds were unambiguously assigned through single crystal X-ray diffraction studies. The compounds thus prepared can be used to synthesize bioactive compounds with different molecular architectures. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.01.047

文献信息

• HETEROCYCLIC DERIVATIVES, PHARMACEUTICAL COMPOSITIONS AND METHODS OF USE THEREOF
  申请人：Gavish Moshe

  公开号：US20100029658A1

  公开（公告）日：2010-02-04

  The present invention relates to novel quinoxaline, quinazoline and phthalazine derivatives as well as multimeric derivatives, methods for their preparation, pharmaceutical compositions including such compounds, and methods of using these compounds for the treatment and prevention of brain damage resulting from brain injury, especially secondary brain damage due to traumatic brain injury (TBI). The compounds of the invention are also useful in treating and preventing neurodegenerative diseases.

  本发明涉及新型喹喔啉、喹喔啉和邻苯二甲酰苯胺衍生物，以及多聚衍生物，其制备方法，包括这些化合物的制药组合物，以及利用这些化合物治疗和预防由脑损伤引起的脑损伤，特别是由创伤性脑损伤（TBI）引起的继发性脑损伤的方法。本发明的化合物还可用于治疗和预防神经退行性疾病。
• Synthesis and anticholinesterase activity of 2-(dimethylamino)ethyl and choline esters of n-substituted α, β-dehydroamino acids
  作者：A. A. Grigoryan、A. A. Ambartsumyan、M. V. Mkrtchyan、V. O. Topuzyan、G. P. Alebyan、R. S. Asatryan

  DOI：10.1007/s11094-006-0077-8

  日期：2006.3

  A new method for the synthesis of tertiary and quaternary aminoesters of N-substituted α,β-dehydroamino acids is described. Aseries of 16 dehydroamino acids esterified to choline or to its tertiary analog have been synthesized by the proposed method with a yield of 84–93%, and their interactions with human erythrocyte acetylcholinesterase (ACE) and human plasma butyrylcholinesterase (BCE) has been studied. The half-inhibiting concentrations IC50 of the synthesized compounds (determined with respect to cholinesterase hydrolysis of a model substrate, 0.1 mM ATC) vary within a broad range (0.16–1840 µM). The values of traditional parameters of the wave functions of ligands estimated using the Hartree-Fock method do not explain the observed pattern of the anticholinesterase activity. The specific properties of the molecules, especially in their quaternary ammonium salt forms, are probably related to their structural features, in particular, to the ability of the inhibitors to form cyclic conformations (so-called crown structures). Such structures are probably stabilized as a result of the formation of intramolecuar hydrogen bonds between protons of the choline residue and oxygen of the terminal peptide group.

  本文介绍了一种合成 N-取代的 α、β-脱氢氨基酸的三级和四级氨基酯的新方法。通过所提出的方法合成了 16 种与胆碱或其三级类似物酯化的脱氢氨基酸系列，产率为 84-93%，并研究了它们与人红细胞乙酰胆碱酯酶（ACE）和人血浆丁酰胆碱酯酶（BCE）的相互作用。合成化合物的半抑制浓度 IC50（根据胆碱酯酶水解模型底物 0.1 mM ATC 测定）在很宽的范围内变化（0.16-1840 µM）。使用哈特里-福克方法估算的配体波函数的传统参数值并不能解释所观察到的抗胆碱酯酶活性模式。分子的特殊性质，尤其是季铵盐形式的分子，可能与它们的结构特征有关，特别是与抑制剂形成环状构象（所谓的冠状结构）的能力有关。这种结构的稳定可能是胆碱残基的质子与末端肽基的氧之间形成分子内氢键的结果。
• Heterocyclic derivatives binding to the peripheral-type benzodiazepine receptor (PBR)
  申请人：Technion Research & Development Foundation

  公开号：EP2589597A2

  公开（公告）日：2013-05-08

  The present invention relates to quinazoline derivatives as well as multimeric derivatives, methods for their preparation, pharmaceutical compositions including such compounds, and methods of using these compounds for the treatment and prevention of brain damage resulting from brain injury, especially secondary brain damage due to traumatic brain injury (TBI). The compounds of the invention are also useful in treating and preventing neurodegenerative diseases.

  本发明涉及喹唑啉衍生物以及多聚衍生物、其制备方法、包括此类化合物的药物组合物，以及使用这些化合物治疗和预防脑损伤导致的脑损伤，特别是创伤性脑损伤（TBI）导致的继发性脑损伤的方法。本发明的化合物还可用于治疗和预防神经退行性疾病。
• ISLAM A. M.; HANNOUT I. B.; SOUKA L. M.; AREF H., EGYPT. J. CHEM., 1977(1980), 20, NO 5, 473-482
  作者：ISLAM A. M.、 HANNOUT I. B.、 SOUKA L. M.、 AREF H.

  DOI：——

  日期：——
• Palcut, Marian; Benko, Jan; Mueller, Norbert, Journal of Chemical Research, 2004, # 10, p. 649 - 653
  作者：Palcut, Marian、Benko, Jan、Mueller, Norbert、Hritzova, Ol'ga、Vollarova, Ol'ga、Melikian, Gaugik S.

  DOI：——

  日期：——