4-(4-nitrobenzoyl)benzoic acid methyl ester | 79859-23-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(4-nitrobenzoyl)benzoic acid methyl ester
• 英文别名: methyl 4-(4-nitrobenzoyl)benzoate；Benzoic acid, 4-(4-nitrobenzoyl)-, methyl ester
• CAS: 79859-23-7
• 化学式: C₁₅H₁₁NO₅
• 分子量: 285.256
• InChiKey: ZJBHPLPTDLRKCU-UHFFFAOYSA-N

物化性质

• 熔点：
  174-175 °C
• 沸点：
  465.3±30.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(4-nitrobenzoyl)benzoic acid methyl ester 在 tin(ll) chloride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 4-[4-(benzylamino)benzoyl]benzoic acid methyl ester
  参考文献：
  名称：

  Novel 5α-Reductase Inhibitors:  Synthesis, Structure−Activity Studies, and Pharmacokinetic Profile of Phenoxybenzoylphenyl Acetic Acids

  摘要：

  Novel substituted benzoyl benzoic acids and phenylacetic acids 1-14 have been synthesized and evaluated for inhibition of rat and human steroid 5 alpha- reductase isozymes I and 2. The compounds turned out to be potent and selective human type 2 enzyme inhibitors, exhibiting IC50 values in the nanomolar range. The phenylacetic acid derivatives were more potent than the analogous benzoic acids. Bromination in the 4-position of the phenoxy moiety led to the strongest inhibitor in this class (12; IC50 = 5 nM), which was equipotent to finasteride. Since oral absorption is essential for a potential drug, 12 was further examined. In the parallel artificial membrane permeation assay (PAMPA) it turned out to be a good permeator, whereas it was a medium permeator in Caco2 cells. After oral administration (40 mg/kg) to rats a high bioavailability and a biological half-life of 5.5 h were observed, making it a promising candidate for clinical evaluation.

  DOI：

  10.1021/jm050728w
• 作为产物：
  描述：

  (4-甲基苯基)-(4-硝基苯基)甲酮 在 chromium(VI) oxide 、 硫酸 、 溶剂黄146 作用下， 反应 7.0h， 生成 4-(4-nitrobenzoyl)benzoic acid methyl ester
  参考文献：
  名称：

  Novel 5α-Reductase Inhibitors:  Synthesis, Structure−Activity Studies, and Pharmacokinetic Profile of Phenoxybenzoylphenyl Acetic Acids

  摘要：

  Novel substituted benzoyl benzoic acids and phenylacetic acids 1-14 have been synthesized and evaluated for inhibition of rat and human steroid 5 alpha- reductase isozymes I and 2. The compounds turned out to be potent and selective human type 2 enzyme inhibitors, exhibiting IC50 values in the nanomolar range. The phenylacetic acid derivatives were more potent than the analogous benzoic acids. Bromination in the 4-position of the phenoxy moiety led to the strongest inhibitor in this class (12; IC50 = 5 nM), which was equipotent to finasteride. Since oral absorption is essential for a potential drug, 12 was further examined. In the parallel artificial membrane permeation assay (PAMPA) it turned out to be a good permeator, whereas it was a medium permeator in Caco2 cells. After oral administration (40 mg/kg) to rats a high bioavailability and a biological half-life of 5.5 h were observed, making it a promising candidate for clinical evaluation.

  DOI：

  10.1021/jm050728w

文献信息

• Kinetically Controlled, Highly Chemoselective Acylation of Functionalized Grignard Reagents with Amides by N−C Cleavage
  作者：Guangchen Li、Michal Szostak

  DOI：10.1002/chem.201904678

  日期：2020.1.13

  (iPrMgCl⋅LiCl) permits excellent substrate scope with respect to both the amide and Grignard coupling partners. These reactions enable facile, operationally simple and chemoselective access to tetrahedral intermediates from amides under significantly milder conditions than chelation-controlled intermediates. This novel direct two-component coupling sets the stage for using amides as acylating reagents

  在动力学控制下，通过高度化学选择性的NC裂解，已实现了酰胺与功能化格氏试剂的直接无过渡金属酰化反应。该方法提供了通过瞬态四面体中间体快速收敛的官能化联芳基酮的途径。通用的Turbo-Grignard试剂（iPrMgCl·LiCl）促进了通过原位卤素-镁交换而直接获得功能化Grignard试剂的优点，因此，相对于酰胺和Grignard偶合剂，都具有出色的底物范围。与螯合控制的中间体相比，这些反应能够在较温和的条件下从酰胺中轻松，操作简单且化学选择性地接近酰胺的四面体中间体。
• Chemokine receptor binding compounds
  申请人：Zhou Yuanxi

  公开号：US20050277670A1

  公开（公告）日：2005-12-15

  The present invention relates to chemokine receptor binding compounds, pharmaceutical compositions and their use. More specifically, the present invention relates to modulators of chemokine receptor activity, preferably modulators of CCR5. These compounds demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).

  本发明涉及化学因子受体结合化合物、制药组合物及其使用。更具体地，本发明涉及化学因子受体活性调节剂，优选为CCR5的调节剂。这些化合物表现出对人类免疫缺陷病毒（HIV）感染靶细胞的保护作用。
• CHEMOKINE RECEPTOR BINDING COMPOUNDS
  申请人：ANORMED INC.

  公开号：EP1708703A2

  公开（公告）日：2006-10-11
• EP1708703A4
  申请人：——

  公开号：EP1708703A4

  公开（公告）日：2008-04-09
• US7491735B2
  申请人：——

  公开号：US7491735B2

  公开（公告）日：2009-02-17