5-amino-4-cyano-2-(4-nitrophenyl)-1,3-oxazole | 53657-73-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-amino-4-cyano-2-(4-nitrophenyl)-1,3-oxazole
• 英文别名: 5-Amino-2-(4-nitrophenyl)-1,3-oxazole-4-carbonitrile
• CAS: 53657-73-1
• 化学式: C₁₀H₆N₄O₃
• 分子量: 230.183
• InChiKey: ZACZWSYZWBDCTP-UHFFFAOYSA-N

物化性质

• 熔点：
  288 °C(Solv: acetone (67-64-1))
• 沸点：
  508.6±60.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  异硫氰酸己酯 、 5-amino-4-cyano-2-(4-nitrophenyl)-1,3-oxazole 在 三乙烯二胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以58%的产率得到7-amino-6-hexyl-2-(4-nitrophenyl)-oxazolo[5,4-d]pyrimidine-5(4H)-thione
  参考文献：
  名称：

  Synthesis and Heterocyclization of 5-Amino-4-cyano-1, 3-oxazoles

  摘要：

  本文描述了一种便捷的一锅法合成新型氧杂并嘧啶[5,4-d]的工艺，该方法通过碱催化的异环化反应，将2-取代的5-氨基-4-氰基-1,3-氧杂唑与多种异硫氰酸酯反应。

  DOI：

  10.14233/ajchem.2013.14633
• 作为产物：
  描述：

  2-cyano-3-(4-nitro-phenyl)-1-phthalimido-aziridine-2-carboxylic acid amide 以 苯 为溶剂， 生成 5-amino-4-cyano-2-(4-nitrophenyl)-1,3-oxazole
  参考文献：
  名称：

  Person,H. et al., Bulletin de la Societe Chimique de France, 1976, p. 1989 - 1992

  摘要：

  DOI：

文献信息

• DBU: An Efficient Base Catalyst for Synthesis of the New Oxazolo[5,4-d]pyrimidine Derivatives
  作者：Ahmad Nikseresht、Mehdi Bakavoli、Samad Shoghpour Bayraq

  DOI：10.1080/00397911.2014.910527

  日期：2014.9.17

  Abstract New types of oxazolo[5,4-d]pyrimidines were synthesized via 1,8-diazabicyclo[5,4,0]undec-7-ene-catalyzed heteroannulation of 2-substituted 5-amino-4-cyano-1,3-oxazoles with various isothiocyanates. GRAPHICAL ABSTRACT

  摘要 通过1,8-二氮杂双环[5,4,0]undec-7-烯催化2-取代5-氨基-4-氰基-1杂环化合成了新型恶唑并[5,4-d]嘧啶， 3-恶唑与各种异硫氰酸酯。图形概要
• Preparation of 2-alkyl- and 2-aryl-5-amino-4-cyano-1,3-oxazoles
  作者：Fillmore Freeman、Darrick S.H.L. Kim

  DOI：10.1016/s0040-4039(00)99083-x

  日期：1989.1
• Synthesis, biological evaluation and molecular modelling of diversely functionalized heterocyclic derivatives as inhibitors of acetylcholinesterase/butyrylcholinesterase and modulators of Ca2+ channels and nicotinic receptors
  作者：José L Marco、Cristóbal de los Rı́os、Antonio G Garcı́a、Mercedes Villarroya、M.Carmo Carreiras、Carla Martins、Ana Eleutério、Antonio Morreale、M Orozco、F.Javier Luque

  DOI：10.1016/j.bmc.2004.02.017

  日期：2004.5

  The synthesis and the biological activity of compounds 5-40 as inhibitors of acetyleholinesterase (AChE) and butyrylcholinesterase (BuChE), as well as modulators of voltage-dependent Ca2+ channels and nicotinic receptors, are described. These molecules are tacrine analogues, which have been prepared from polyfunctionalized 6-amino-5-cyano-4H-pyrans, 6-amino-5-cyano-pyridines and 5-amino-2-aryl-3-cyano-1,3-oxazoles via Friedlander reaction with selected cycloalkanones. These compounds are moderate acetylcholinesterase and butyrylcholinesterase inhibitors, the BuChE/AChE selectivity of the most active molecules ranges from 10.0 (compound 29) to 76.9 (compound 16). Interestingly, the 'oxazolo-tacrine' derivatives are devoid of any activity. All compounds showed an important inhibitory effect on the nicotinic acetylcholine receptor. Most of them also blocked L-type Ca2+ channels, and three of them, 64, 19 and 67, the non-L type of Ca2+ channels. Molecular modelling studies suggest that these compounds might bind at the peripheral binding site of AChE, which opens the possibility to design inhibitors able to bind at both, the catalytic and peripheral binding sites of the enzyme. (C) 2004 Elsevier Ltd. All rights reserved.
• FREEMAN, FILLMORE;KIM, DARRICK S. H. L., TETRAHEDRON LETT., 30,(1989) N0, C. 2631-2632
  作者：FREEMAN, FILLMORE、KIM, DARRICK S. H. L.

  DOI：——

  日期：——
• PERSON H.; LUANGLATH K.; BAUDRU M.; FOUCAND A., BULL. SOC. CHIM. FRANCE, 1976, NO 11-12, PART. 2, 1989-1992
  作者：PERSON H.、 LUANGLATH K.、 BAUDRU M.、 FOUCAND A.

  DOI：——

  日期：——