N-(4-Nitrobenzoyl)-L-proline methyl ester | 91807-78-2

• 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: N-(4-Nitrobenzoyl)-L-proline methyl ester
• 英文别名: methyl (4-nitrobenzoyl)-L-prolinate；N-(4-Nitrobenzoyl)-L-prolin-methylester；methyl (2S)-1-(4-nitrobenzoyl)pyrrolidine-2-carboxylate
• CAS: 91807-78-2
• 化学式: C₁₃H₁₄N₂O₅
• 分子量: 278.265
• InChiKey: KEQHFDMJTZQKDN-NSHDSACASA-N

物化性质

• 沸点：
  455.4±40.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(4-Nitrobenzoyl)-L-proline methyl ester 在 草酰氯 、 palladium on activated charcoal 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 36.0h， 生成 (4-(4,5-dibromo-1H-pyrrole-2-carboxamido)benzoyl)-L-proline
  参考文献：
  名称：

  New N -phenyl-4,5-dibromopyrrolamides and N -Phenylindolamides as ATPase inhibitors of DNA gyrase

  摘要：

  Following the withdrawal of novobiocin, the introduction of a new ATPase inhibitor of DNA gyrase to the clinic would add the first representative of this mechanistic class to the antibacterial pipeline. This would be of great importance because of the well-known problems associated with antibacterial resistance. Using structure-based design and starting from the recently determined crystal structure of the N-phenyl-4,5-dibromopyrrolamide inhibitor-DNA gyrase B complex, we have prepared 28 new N-phenyl-4,5-dibromopyrrolamides and N-phenylindolamides and evaluated them against DNA gyrase from Escherichia coli. The most potent compound was 2-((4-(4,5-dibromo-1H-pyrrole-2-carboxamido)phenyl) amino)-2-oxoacetic acid (9a), with an IC50 of 0.18 mu M against E. coli gyrase. A selected set of compounds was evaluated against DNA gyrase from Staphylococcus aureus and against topoisomerase IV from E. coli and S. aureus, but the activities were weaker. The binding affinity of 2-((4-(4,5-dibromo-1H-pyrrole-2carboxamido)phenyl)amino)-2-oxoacetic acid (9a) to E. coli gyrase was studied using surface plasmon resonance. In the design of the present series, the focus was on the optimisation of biological activities of compounds especially by varying their size, the position and orientation of key functional groups, and their acid base properties. The structure activity relationship (SAR) was examined and the results were rationalised with molecular docking. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.03.079
• 作为产物：
  描述：

  L-脯氨酸甲酯盐酸盐 、 4-硝基苯酰肼 在 thallium(III) nitrate trihydrate 、 三乙胺 作用下， 以 乙腈 为溶剂， 以91%的产率得到N-(4-Nitrobenzoyl)-L-proline methyl ester
  参考文献：
  名称：

  An Efficient and Simple Thallium(III)-Induced Cleavage of the Hydrazino Moiety

  摘要：

  DOI：

  10.1021/jo00110a059

文献信息

• Polymer-Supported Mukaiyama Reagent:  A Useful Coupling Reagent for the Synthesis of Esters and Amides
  作者：Stefano Crosignani、Jerome Gonzalez、Dominique Swinnen

  DOI：10.1021/ol0480372

  日期：2004.11.1

  Polymer-supported N-alkyl-2-chloro pyridinium triflate was synthesized in one step from Wang resin. This reagent proved to be a very effective coupling reagent for the synthesis of esters or amides from carboxylic acids and alcohols or amines (primary and secondary). [reaction: see text]

  由Wang树脂一步合成了聚合物负载的N-烷基-2-氯吡啶鎓三氟甲磺酸盐。该试剂被证明是从羧酸和醇或胺（伯和仲）合成​​酯或酰胺的非常有效的偶联剂。[反应：看文字]
• [EN] ALBICIDIN DERIVATIVES, THEIR USE AND SYNTHESIS<br/>[FR] DÉRIVÉS D'ALBICIDINE, LEUR UTILISATION ET LEUR SYNTHÈSE
  申请人：TECH UNIVERSITÄT BERLIN

  公开号：WO2014125075A1

  公开（公告）日：2014-08-21

  The present invention relates to a antibiotically active compounds characterized by general formula (I), wherein X1, BB, BC, BD, BE and X2 are building blocks with D1, D2, D3, D4 or D5 being linkers which comprise carbon, sulphur, nitrogen, phosphor and/or oxygen atoms and which are covalently connecting the moities BA and BB, BB and BC, BC and BD, BD and BE and BE and BF, respectively, and wherein in particular the building block BC comprises an amino acid derivative. The invention relates further to said compounds for use in a method of treatment of diseases, in particular for use in a method of treatment of bacterial infections.

  本发明涉及一种抗生素活性化合物，其特征在于一般式（I），其中X1、BB、BC、BD、BE和X2是具有D1、D2、D3、D4或D5为连接物的构建块，该连接物包括碳、硫、氮、磷和/或氧原子，并以共价键连接BA和BB、BB和BC、BC和BD、BD和BE以及BE和BF的基团，特别是构建块BC包括氨基酸衍生物。该发明还涉及上述化合物用于治疗疾病的方法，特别是用于治疗细菌感染的方法。
• ALBICIDIN DERIVATIVES, THEIR USE AND SYNTHESIS
  申请人：TECHNISCHE UNIVERSITÄT BERLIN

  公开号：US20150376120A1

  公开（公告）日：2015-12-31

  Antibiotically active compounds characterized by general formula (I), wherein X1, BB, BC, BD, BE and X2 are building blocks with D1, D2, D3, D4 or D5 being linkers which include carbon, sulphur, nitrogen, phosphor and/or oxygen atoms and which are covalently connecting the moities BA and BB, BB and BC, BC and BD, BD and BE and BE and BF, respectively, and wherein in particular the building block BC comprises an amino acid derivative. The compounds for use in a method of treatment of diseases, in particular for use in a method of treatment of bacterial infections are also disclosed.

  具有一般式（I）的抗生素活性化合物的特征，其中X1、BB、BC、BD、BE和X2是具有D1、D2、D3、D4或D5连接器的构建块，包括碳、硫、氮、磷和/或氧原子，并且共价连接BA和BB、BB和BC、BC和BD、BD和BE以及BE和BF的基团，其中特别是构建块BC包括一种氨基酸衍生物。该化合物用于治疗疾病的方法，特别是用于治疗细菌感染的方法。
• An Efficient and Simple Thallium(III)-Induced Cleavage of the Hydrazino Moiety
  作者：Marijan Kocevar、Polona Mihorko、Slovenko Polanc

  DOI：10.1021/jo00110a059

  日期：1995.3
• New N -phenyl-4,5-dibromopyrrolamides and N -Phenylindolamides as ATPase inhibitors of DNA gyrase
  作者：Nace Zidar、Tihomir Tomašič、Helena Macut、Anja Sirc、Matjaž Brvar、Sofia Montalvão、Päivi Tammela、Janez Ilaš、Danijel Kikelj

  DOI：10.1016/j.ejmech.2016.03.079

  日期：2016.7

  Following the withdrawal of novobiocin, the introduction of a new ATPase inhibitor of DNA gyrase to the clinic would add the first representative of this mechanistic class to the antibacterial pipeline. This would be of great importance because of the well-known problems associated with antibacterial resistance. Using structure-based design and starting from the recently determined crystal structure of the N-phenyl-4,5-dibromopyrrolamide inhibitor-DNA gyrase B complex, we have prepared 28 new N-phenyl-4,5-dibromopyrrolamides and N-phenylindolamides and evaluated them against DNA gyrase from Escherichia coli. The most potent compound was 2-((4-(4,5-dibromo-1H-pyrrole-2-carboxamido)phenyl) amino)-2-oxoacetic acid (9a), with an IC50 of 0.18 mu M against E. coli gyrase. A selected set of compounds was evaluated against DNA gyrase from Staphylococcus aureus and against topoisomerase IV from E. coli and S. aureus, but the activities were weaker. The binding affinity of 2-((4-(4,5-dibromo-1H-pyrrole-2carboxamido)phenyl)amino)-2-oxoacetic acid (9a) to E. coli gyrase was studied using surface plasmon resonance. In the design of the present series, the focus was on the optimisation of biological activities of compounds especially by varying their size, the position and orientation of key functional groups, and their acid base properties. The structure activity relationship (SAR) was examined and the results were rationalised with molecular docking. (C) 2016 Elsevier Masson SAS. All rights reserved.