2-[(4-氯苯基)氨基甲酰]苯甲酸 | 7142-94-1

• 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: 2-[(4-氯苯基)氨基甲酰]苯甲酸
• 英文名称: N-(4-chlorophenyl)phthalamic acid
• 英文别名: 2-[(4-chlorophenyl)aminocarbonyl]benzoic acid；N-(4-chloro-phenyl)-phthalamic acid；N-(4-Chlor-phenyl)-phthalamidsaeure；Phthalsaeure-mono-(4-chlor-anilid)；2-[(4-Chlorophenyl)carbamoyl]benzoic acid
• CAS: 7142-94-1
• 化学式: C₁₄H₁₀ClNO₃
• 分子量: 275.691
• InChiKey: WJSPLHRLEZJTRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  2-[(4-氯苯基)氨基甲酰]苯甲酸 在 sodium tetrahydroborate 、 sodium acetate 、 乙酸酐 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 2-(4-chlorophenyl)-3-hydroxyisoindolin-1-one
  参考文献：
  名称：

  Aza-Diels–Alder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome

  摘要：

  报告了在路易斯酸催化的无水条件下，通过[4 + 2]亚胺-狄尔斯-阿尔德环化反应，从N-芳基-3-羟基异喹啉酮和N-乙烯基内酰胺合成5-取代-6,6a-二氢异喹诺[2,1-a]喹啉-11(5H)-酮的方法。在相同条件下，N-(2-取代-芳基)-3-羟基异喹啉酮与N-乙烯基吡咯烷酮的反应导致了2-(2-取代-芳基)-3-(2-(2-氧代吡咯烷-1-基)乙烯基)异喹啉-1-酮类似物的形成，表明立体阻碍是导致偏差的原因。基于X射线晶体学和分子建模结果，讨论了反应的可能机制。

  DOI：

  10.3762/bjoc.10.81
• 作为产物：
  描述：

  邻苯二甲酸单甲酯 在 sodium hydroxide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 2-[(4-氯苯基)氨基甲酰]苯甲酸
  参考文献：
  名称：

  Structure-Based Optimization of a Non-β-lactam Lead Results in Inhibitors That Do Not Up-Regulate β-Lactamase Expression in Cell Culture

  摘要：

  Bacterial expression of beta-lactamases is the most widespread resistance mechanism to beta-lactam antibiotics, such as penicillins and cephalosporins. There is a pressing need for novel, non-beta-lactam inhibitors of these enzymes. One previously discovered novel inhibitor of the beta-lactamase AmpC, compound 1, has several favorable properties: it is chemically dissimilar to beta-lactams and is a noncovalent, competitive inhibitor of the enzyme. However, at 26 microM its activity is modest. Using the X-ray structure of the AmpC/1 complex as a template, 14 analogues were designed and synthesized. The most active of these, compound 10, had a K(i) of 1 microM, 26-fold better than the lead. To understand the origins of this improved activity, the structures of AmpC in complex with compound 10 and an analogue, compound 11, were determined by X-ray crystallography to 1.97 and 1.96 A, respectively. Compound 10 was active in cell culture, reversing resistance to the third generation cephalosporin ceftazidime in bacterial pathogens expressing AmpC. In contrast to beta-lactam-based inhibitors clavulanate and cefoxitin, compound 10 did not up-regulate beta-lactamase expression in cell culture but simply inhibited the enzyme expressed by the resistant bacteria. Its escape from this resistance mechanism derives from its dissimilarity to beta-lactam antibiotics.

  DOI：

  10.1021/ja042984o

文献信息

• The cyclisation of substituted phthalanilic acids in acetic acid solution. A kinetic study of substituted N-phenylphthalimide formation
  作者：Christopher J. Perry、Zahida Parveen

  DOI：10.1039/b008399m

  日期：——

  One novel and ten known substituted 3′- and 4′-phthalanilic acids have been prepared. These have been cyclised to two novel and nine known substituted N-phenylphthalimides by heating with glacial acetic acid. Both phthalanilic acids and imides have been characterised in detail and spectroscopic data are given. The kinetics of cyclisation for phthalanilic acids has been examined in detail, and it has

  已经制备了一种新颖的和十种已知的取代的3'-和4'-邻苯二酸。通过加热，将它们环化为两个新的和九个已知的取代的N-苯基邻苯二甲酰亚胺。冰醋酸。邻苯二酸和酰亚胺已经详细描述了特征并给出了光谱数据。的动力学环化对苯二酸的苯酚进行了详细的研究，结果发现一个复杂的机理正在发挥作用。最初涉及的是可逆的溶剂 辅助分子内亲核攻击 酰胺 氮 在 羧酸 羰。明确的证据表明，存在长寿命的中间体可以作为前体酰亚胺编队。使用快速预平衡模型对观察到的动力学进行合理化，然后将中间体缓慢分解为酰亚胺。观察到的用于预平衡的速率常数显示出行为良好的线性Hammett图（ρ  = -1.1），而用于形成酰亚胺 不要。
• Water mediated, environmentally friendly, step-wise, tandem & one-pot syntheses of 2-(1H-benzo[d]imidazole-2-yl)-N-arylbenzamides
  作者：Yervala Dathu Reddy、Chittireddy Venkata Ramana Reddy、Pramod Kumar Dubey

  DOI：10.1039/c3ra44423f

  日期：——

  Water mediated and environmentally friendly, step-wise, tandem & one-pot syntheses of 2-(1H-benzo[d]imidazole-2-yl)-N-arylbenzamide derivatives have been developed by simply combining phthalic anhydride, anilines and phenylenediammonium dihydrogenphosphate. This reaction has an easy workup, provides excellent yields, and uses water as the solvent which is considered to be relatively environmentally benign.

  通过简单地将邻苯二甲酸酐、苯胺和苯二磷酸二氢铵结合在一起，开发出了以水为介质的 2-(1H-苯并[d]咪唑-2-基)-N-芳基苯甲酰胺衍生物的环保型一步串联和一锅合成法。该反应易于操作，产量极高，并使用水作为溶剂，被认为对环境相对无害。
• [EN] PHTHALANILATE COMPOUNDS AND METHODS OF USE<br/>[FR] COMPOSÉS DE PHTALANILATE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：UNIV NOTRE DAME DU LAC

  公开号：WO2011026107A1

  公开（公告）日：2011-03-03

  The invention provides antimicrobial compounds and compositions, and methods of using them. The compounds and compositions include, for example, a compound of any one of Formulas I-X. The invention further provides methods of preparing the compounds, and useful intermediates for their preparation. The compounds can possess highly specific and selective activity, such as antibacterial activity and/or enzymatic inhibitory activity. Accordingly, the compounds and compositions can be used to treat bacterial infections, or to inhibit or kill bacteria, either in vitro or in vivo.

  本发明提供了抗微生物化合物和组合物，以及使用它们的方法。这些化合物和组合物包括，例如，I-X公式中的任何一种化合物。本发明进一步提供了制备这些化合物的方法，并提供了有用的中间体。这些化合物可以具有高度特异性和选择性活性，例如抗菌活性和/或酶抑制活性。因此，这些化合物和组合物可以用于治疗细菌感染，或者在体外或体内抑制或杀死细菌。
• Kumar, Padam Praveen; Rama Devi; Dubey, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 8, p. 1166 - 1171
  作者：Kumar, Padam Praveen、Rama Devi、Dubey

  DOI：——

  日期：——
• Kumar, Padam Praveen; Reddy, Y. Dathu; Kumari, Y. Bharathi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53, # 4, p. 392 - 398
  作者：Kumar, Padam Praveen、Reddy, Y. Dathu、Kumari, Y. Bharathi、Devi, B. Rama、Dubey

  DOI：——

  日期：——