5-amino-2-(4-methoxyphenyl)[1,3]oxazole-4-carbonitrile | 53657-71-9

• 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-2-(4-methoxyphenyl)[1,3]oxazole-4-carbonitrile
• 英文别名: 5-amino-2-(4-methoxyphenyl)oxazole-4-carbonitrile；2-(4-methoxyphenyl)-5-amino-4-cyano-1,3-oxazole；5-Amino-2-(4-methoxyphenyl)-1,3-oxazole-4-carbonitrile
• CAS: 53657-71-9
• 化学式: C₁₁H₉N₃O₂
• 分子量: 215.211
• InChiKey: VXXJBTXJVPYKBO-UHFFFAOYSA-N

物化性质

• 沸点：
  445.3±55.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  85.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-amino-2-(4-methoxyphenyl)[1,3]oxazole-4-carbonitrile 在 copper dichloride 、 亚硝酸异戊酯 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以13%的产率得到5-chloro-2-(4-methoxyphenyl)oxazole-4-carbonitrile
  参考文献：
  名称：

  在一些选定的杂环系统上的Sandmeyer反应：有用的2-氯杂环-3-腈中间体的合成

  摘要：

  为了制备相应的2-氯-3-腈衍生物作为合成有用的中间体用于进一步开发，已经研究了在一些带有2-氨基-3-腈结构部分的选定杂环上的Sandmeyer反应。 桑德梅尔反应-2-氨基（杂环）-3-腈-2-氨基吡唑-2-氨基恶唑-2-氨基-4 H-吡喃-2-氨基-1,4-二氢吡啶-2-氨基吡啶-2-氯（杂环） ）-3-腈

  DOI：

  10.1055/s-0030-1258149
• 作为产物：
  描述：

  对苯二磺酸氨基丙二酰丁氰 、 对甲氧基苯甲酰氯 以 N-甲基吡咯烷酮 为溶剂， 反应 12.0h， 以51%的产率得到5-amino-2-(4-methoxyphenyl)[1,3]oxazole-4-carbonitrile
  参考文献：
  名称：

  [1,2,3]三唑并[4,5- h ] [1,6]萘啶和[1,3]恶唑并[5,4- h ] [1,6]萘啶的合成及光细胞毒性

  摘要：

  合成[1,2,3]三唑并[4,5- h ] [1,6]萘啶和[1,3]恶唑并[5,4- h ] [1,6]萘并吡啶旨在研究其光细胞毒性活动。辐照后，恶唑-萘吡啶在纳摩尔/低微摩尔浓度（EC 50 0.01–6.59μM）下诱导光依赖性细胞死亡。最photocytotoxic衍生物表现出非常高的选择性和photocytotoxicity指数（SI = 72-86，PTI> 5000），以及三重激发态具有特别长的寿命（18.0微秒）和高摩尔吸光系数（29781±为180 M -1厘米- 1在λ最大315 nm）。光诱导产生的ROS迅速地在肿瘤细胞中选择性地诱导了不可抑制的凋亡过程，线粒体和溶酶体的参与。总而言之，这些结果表明，对于生物应用而言，活性最高的化合物可作为有前途的单线态氧敏化剂。

  DOI：

  10.1016/j.ejmech.2018.10.071

文献信息

• Evolution of the Thienopyridine Class of Inhibitors of IκB Kinase-β:  Part I:  Hit-to-Lead Strategies
  作者：Tina Morwick、Angela Berry、Janice Brickwood、Mario Cardozo、Katrina Catron、Molly DeTuri、Jonathan Emeigh、Carol Homon、Matt Hrapchak、Stephen Jacober、Scott Jakes、Paul Kaplita、Terence A. Kelly、John Ksiazek、Michel Liuzzi、Ronald Magolda、Can Mao、Daniel Marshall、Daniel McNeil、Anthony Prokopowicz、Christopher Sarko、Erika Scouten、Cynthia Sledziona、Sanxing Sun、Jane Watrous、Jiang Ping Wu、Charles L. Cywin

  DOI：10.1021/jm0510979

  日期：2006.5.1

  High-throughput screening is routinely employed as a method for the identification of novel hit structures. Large numbers of active compounds are typically procured in this way and must undergo a rigorous validation process. This process is described in detail for a collection of screening hits identified as inhibitors of I kappa B kinase-beta (IKK beta), a key regulatory enzyme in the nuclear factor-kappa B (NF-kappa B) pathway. From these studies, a promising hit series was selected. Subsequent lead generation activities included the development of a pharmacophore hypothesis and structure-activity relationship (SAR) for the hit series. This led to the exploration of related scaffolds offering additional opportunities, and the various structural classes were comparatively evaluated for enzyme inhibition, selectivity, and drug-like properties. A novel lead series of thienopyridines was thereby established, and this series advanced into lead optimization for further development.
• 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
• Microwave-mediated synthesis and manipulation of a 2-substituted-5-aminooxazole-4-carbonitrile library
  作者：John Spencer、Hiren Patel、Jahangir Amin、Samantha K. Callear、Simon J. Coles、John J. Deadman、Christophe Furman、Roxane Mansouri、Philippe Chavatte、Régis Millet

  DOI：10.1016/j.tetlet.2012.01.081

  日期：2012.3

  A 2-substituted-5-aminooxazole-4-carbonitrile library has been synthesised and modified via microwave-mediated and flow chemistries. One synthesised compound, 5-(1H-pyrrol-1-yl)-4-(1H-tetrazol-5-yl)-2-(thien-2-yl)oxazole, contains three distinct heterocycles attached to the central oxazole core, highlighting the structural diversity of this approach. Three oxazoles had micromolar k(i) values against cannabinoid (CB1/CB2) receptors. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.
• 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：——