(E)-4-(2-硝基苯基)-4-氧代-2-丁烯酸 | 80937-24-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (E)-4-(2-硝基苯基)-4-氧代-2-丁烯酸
• 中文别名: (2E)-4-(2-硝基苯基)-4-羰基丁-2-烯酸
• 英文名称: 4-(2-nitrophenyl)-4-oxo-2-butenoic acid
• 英文别名: 4-(2-nitrophenyl)-4-oxobut-2-enoic acid；(E)-4-(2'-nitrophenyl)-4-oxobut-2-enoic acid；4-(2-nitro-phenyl)-4-oxo-trans-crotonic acid；4-(2-Nitro-phenyl)-4-oxo-trans-crotonsaeure；(E) 4-(2-nitrophenyl)-4-oxo-2-butenoic acid；3-(2-nitrobenzoyl)acrylic acid；(E)-4-(2-Nitrophenyl)-4-oxo-2-butenoic acid；(E)-4-(2-nitrophenyl)-4-oxobut-2-enoic acid
• CAS: 80937-24-2
• 化学式: C₁₀H₇NO₅
• 分子量: 221.169
• InChiKey: PBLUZBCDLSSYAR-AATRIKPKSA-N

物化性质

• 熔点：
  169 °C
• 沸点：
  437.4±45.0 °C(Predicted)
• 密度：
  1.435±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-4-(2-硝基苯基)-4-氧代-2-丁烯酸 在 platinum(IV) oxide 氢气 作用下， 以 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 22.0h， 以41%的产率得到4-(2-氨基苯基)-4-氧代丁酸
  参考文献：
  名称：

  Novel human lens metabolites from normal and cataractous human lenses

  摘要：

  4-(2-Aminophenyl)-4-oxobutanoic acid, 4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid and glutathionyl-kynurenine have been identified as novel metabolites in normal and cataractous human lenses following total synthesis and comparison with authentic human lens samples. Their structures are consistent with those derived from the major human lens UV filters kynurenine and 3-hydroxykynurenine, and it is proposed that these compounds also play a role as UV filters. These metabolites were isolated in pmol/mg levels (dry mass) in lenses. 4-(2-Amino-3-hydroxyphenyl)-4-oxobutanoic acid and glutathionyl-kynurenine were found to be unstable at physiological pH. Other potential metabolites, glutathionyl-3-hydroxykynurenine, kynurenine yellow and 3-hydroxykynurenine yellow, were not detected in either normal or cataractous lenses. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.133
• 作为产物：
  描述：

  邻硝基苯乙酮 在 1,4-二氧六环 、 吡啶 、 selenium(IV) oxide 作用下， 生成 (E)-4-(2-硝基苯基)-4-氧代-2-丁烯酸
  参考文献：
  名称：

  The Selenium Dioxide Oxidation of Substituted Acetophenones

  摘要：

  DOI：

  10.1246/bcsj.28.480

文献信息

• [EN] N-(4-(PIPERAZIN-1-YL)-PHENYL-2-OXAZOLIDINONE-5-CARBOXAMIDE DERIVATES AND RELATED COMPOUNDS AS ANTIBACTERIAL AGENTS<br/>[FR] DERIVES DE N-(4-(PIPERAZINE-1-YL)-PHENYL-2-OXAZOLIDINONE-5-CARBOXAMIDES ET COMPOSES ASSOCIES SERVANT D'AGENTS ANTIBACTERIENS
  申请人：UPJOHN CO

  公开号：WO2004045616A1

  公开（公告）日：2004-06-03

  The present invention provides antibacterial agents having the formula I described herein. or-pharmaceutically acceptable salts thereof wherein: A is a structure i, ii, iii, or iv, W is N(H)C(X)-R,. Het, or -Y HET, in which the Hot or Y HET is optionally substituted with =S or '0, provided that when A is structure iv, W is not - Y--1-MT or Het;

  本发明提供了具有以下式I的抗菌剂，或其药学上可接受的盐，其中：A是结构i、ii、iii或iv，W是N(H)C(X)-R、Het或-Y HET，在其中Hot或Y HET可以选择地被=S或'0取代，但当A是结构iv时，W不是-Y--1-MT或Het。
• Design, synthesis, and bioevaluation of a novel class of (E)-4-oxo-crotonamide derivatives as potent antituberculosis agents
  作者：Jinfeng Ren、Jian Xu、Guoning Zhang、Changliang Xu、LiLi Zhao、XueFu You、Yucheng Wang、Yu Lu、Liyan Yu、Juxian Wang

  DOI：10.1016/j.bmcl.2019.01.001

  日期：2019.2

  A series of novel (E)-4-oxo-2-crotonamide derivatives were designed and synthesized to find potent antituberculosis agents. All the target compounds were evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv(MTB). Results reveal that 4-phenyl moiety at part A and short methyl group at part C were found to be favorable. Most of the derivatives displayed promising activity against

  设计并合成了一系列新颖的（E）-4-氧代-2-巴豆酰胺衍生物，以寻找有效的抗结核药。评价所有目标化合物的抗结核分枝杆菌H37Rv（MTB）的体外活性。结果表明，发现A部分的4-苯基部分和C部分的短甲基是有利的。大多数衍生物显示出对MTB有希望的活性，MIC为0.125至4 µg / mL。尤其是，发现化合物IIIa16对MTB的MIC最佳活性为0.125μg/ mL，对耐药性临床MTB分离株的MIC最佳为0.05-0.48μg/ mL。
• First total synthesis of the antifungal antibiotic thiobutacin
  作者：Narayan Chakor、Sabrina Dallavalle、Loana Musso、Maddalena Moretti

  DOI：10.1016/j.tetlet.2008.06.036

  日期：2008.8

  The first total synthesis of thiobutacin, a butanoic acid with antifungal activity recently isolated from the culture broth of a soil actinomycete, Lechevalieria aerocolonigenes strain VK-A9, is described. The five-step procedure involves readily available and cheap starting materials and can easily be transposed to the large scale. Fungal growth inhibition of thiobutacin is mediated by the pH of the

  描述了硫丁酸的首次全合成，该丁酸是最近从土壤放线菌的产气杆结肠假单胞菌菌株VK-A9的培养液中分离出来的，具有抗真菌活性的丁酸。五步法涉及容易获得且便宜的起始原料，并且可以容易地大规模转移。硫代丁星的真菌生长抑制作用是由生长培养基的pH介导的。在pH 6和7之间获得最大的抑制活性。
• CoA Adducts of 4-Oxo-4-phenylbut-2-enoates: Inhibitors of MenB from the <i>M. tuberculosis</i> Menaquinone Biosynthesis Pathway
  作者：Xiaokai Li、Nina Liu、Huaning Zhang、Susan E. Knudson、Huei-Jiun Li、Cheng-Tsung Lai、Carlos Simmerling、Richard A. Slayden、Peter J. Tonge

  DOI：10.1021/ml200141e

  日期：2011.11.10

  A high-throughput screen led to the discovery of 2-amino-4-oxo-4-phenylbutanoate inhibitors of the 1,4-dihydroxy-2-naphthoyl-CoA synthase (MenB) from the menaquinone biosynthesis pathway in Mycobacterium tuberculosis. However, these compounds are unstable in solution and eliminate to form the corresponding 4-oxo-4-phenylbut-2-enoates that then react with CoA in situ to form nanomolar inhibitors of MenB. The potency of these compounds results from interaction of the CoA adduct carboxylate with the MenB oxyanion hole, a conserved structural motif in the crotonase superfamily. 4-Oxo-4-chlorophenylbutenoyl methyl ester has minimum inhibitory concentrations of 0.6 and 1.5 mu g/mL against replicating and nonreplicating M. tuberculosis, respectively, and it is proposed that the methyl ester penetrates the cell where it is hydrolyzed and reacts with CoA to generate the active antibacterial. The CoA adducts thus represent an important foundation for the development of novel MenB inhibitors and suggest a general approach to the development of potent inhibitors of acyl-CoA binding enzymes.
• Inhibition of human cytomegalovirus protease by enedione derivatives of thieno[2,3-d]oxazinones through a novel dual acylation/alkylation mechanism
  作者：Ivan L. Pinto、Richard L. Jarvest、Brian Clarke、Christine E. Dabrowski、Ashley Fenwick、Michele M Gorczyca、L.John Jennings、Patrick Lavery、Edmund J Sternberg、David G. Tew、Andrew West

  DOI：10.1016/s0960-894x(99)00005-0

  日期：1999.2

  Enedione derivatives of thieno[2,3-d]oxazinones are nanomolar inhibitors of CMV protease which act through a novel dual acylation of the catalytic serine and alkylation of the protease cysteine 161 via a Michael addition to the enedione moiety of the inhibitor. (C) 1999 Elsevier Science Ltd. All rights reserved.