4-(4-aminobenzoyl)benzoic acid methyl ester | 349443-22-7

• 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-aminobenzoyl)benzoic acid methyl ester
• 英文别名: Methyl 4-[(4-aminophenyl)carbonyl]benzoate；methyl 4-(4-aminobenzoyl)benzoate
• CAS: 349443-22-7
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: JCIJQBHESSRAOT-UHFFFAOYSA-N

物化性质

• 熔点：
  135 °C
• 沸点：
  451.1±30.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 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：
  69.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-aminobenzoyl)benzoic acid methyl ester 在 水 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 4-[4-(benzylamino)benzoyl]benzoic acid
  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 、 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 4-(4-aminobenzoyl)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

• MULTIBINDING AGENTS THAT MODULATE PPARgamma AND RXR RECEPTORS
  申请人：Advanced Medicine, Inc.

  公开号：EP1083888A1

  公开（公告）日：2001-03-21
• [EN] MULTIBINDING AGENTS THAT MODULATE PPAR gamma AND RXR RECEPTORS<br/>[FR] AGENTS A LIAISONS MULTIPLES MODULANT LES RECEPTEURS PPAR gamma ET RXR
  申请人：——

  公开号：WO1999063983A9

  公开（公告）日：2000-03-23

  [EN] Disclosed are novel multi-binding compounds (agents) which bind to PPAR gamma receptors. The compounds of this invention comprise a plurality of ligands each of which can bind to such receptors thereby modulating the biological processes and/or functions thereof. The ligands are capable of binding to either a PPAR gamma receptor or a RXR receptor, so long as at least one ligand of the multi-binding compound binds to a PPAR gamma receptor. Each of the ligands is covalently attached to a linker or linkers which may be the same or different to provide for the multi-binding compound. The linker is selected such that the multi-binding compound so constructed demonstrates increased modulation of the biological processes mediated by the PPAR gamma receptor.
  [FR] L'invention concerne de nouveaux composés (agents) à liaisons multiples qui se lient aux récepteurs PPAR gamma . Les composés de cette invention renferment plusieurs ligands, chacun de ces ligands pouvant se lier à ces récepteurs de manière à moduler les processus et/ou les fonctions biologiques de ceux-ci. Ces ligands sont par ailleurs capables de se lier soit à un récepteur PPAR gamma , soit à un récepteur RXR, pour autant qu'au moins un ligand desdits composés à liaisons multiples se lie à un récepteur PPAR gamma . Chaque ligand est en outre fixé par covalence à un segment de liaison ou à plusieurs segments de liaison, lesquels peuvent être identiques ou différents afin de former ledit composé à liaisons multiples. Le segment de liaison est choisi de sorte que le composé à liaisons multiples ainsi construit présente une modulation améliorée des processus biologiques ayant pour origine ledit récepteur PPAR gamma .
• Novel 5α-Reductase Inhibitors:  Synthesis, Structure−Activity Studies, and Pharmacokinetic Profile of Phenoxybenzoylphenyl Acetic Acids
  作者：Ola I. A. Salem、Martin Frotscher、Christiane Scherer、Alexander Neugebauer、Klaus Biemel、Martina Streiber、Ruth Maas、Rolf W. Hartmann

  DOI：10.1021/jm050728w

  日期：2006.1.1

  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.