4-((dibenzylamino)methyl)benzoic acid | 271243-24-4

• 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-((dibenzylamino)methyl)benzoic acid
• 英文别名: 4-[(Dibenzylazaniumyl)methyl]benzoate
• CAS: 271243-24-4
• 化学式: C₂₂H₂₁NO₂
• mdl: MFCD09722714
• 分子量: 331.414
• InChiKey: LVLFRFFNPLOMON-UHFFFAOYSA-N

物化性质

• 沸点：
  477.5±33.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.136
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-((dibenzylamino)methyl)benzoic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 C₂₂H₂₀ClNO
  参考文献：
  名称：

  Discovery of novel PTP1B inhibitors via pharmacophore-oriented scaffold hopping from Ertiprotafib

  摘要：

  An integrated molecular design strategy combining pharmacophore recognition and scaffold hopping was exploited to discover novel PTP1B inhibitors based on the known PTP1B inhibitor Ertiprotafib. A composite pharmacophore model was proposed from the interaction mode of Ertiprotafib, and 21 diverse molecules from five distinct structural classes were designed and synthesized accordingly. New compounds with considerable inhibition against PTP1B were identified from each series, and the most active compound 3a showed IC50 value of 1.3 mu mol L-1 against human recombinant PTP1B. Docking study indicated that the new inhibitors assumed binding modes similar to that of Ertiprotafib. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.002
• 作为产物：
  描述：

  methyl 4-[(dibenzylamino)methyl]benzoate 在 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 4-((dibenzylamino)methyl)benzoic acid
  参考文献：
  名称：

  Discovery of novel PTP1B inhibitors via pharmacophore-oriented scaffold hopping from Ertiprotafib

  摘要：

  An integrated molecular design strategy combining pharmacophore recognition and scaffold hopping was exploited to discover novel PTP1B inhibitors based on the known PTP1B inhibitor Ertiprotafib. A composite pharmacophore model was proposed from the interaction mode of Ertiprotafib, and 21 diverse molecules from five distinct structural classes were designed and synthesized accordingly. New compounds with considerable inhibition against PTP1B were identified from each series, and the most active compound 3a showed IC50 value of 1.3 mu mol L-1 against human recombinant PTP1B. Docking study indicated that the new inhibitors assumed binding modes similar to that of Ertiprotafib. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.002

文献信息

• Chemokine receptor modulators
  申请人：Clark Michael P.

  公开号：US20080261978A1

  公开（公告）日：2008-10-23

  The invention provides compounds of Formula (I) and pharmaceutical compositions comprising compounds of Formula (I). These compounds are useful treating or preventing HIV infections, and in treating proliferative disorders such as inhibiting the metastasis of various cancers

  该发明提供了式（I）的化合物及包含该化合物的药物组合物。这些化合物可用于治疗或预防HIV感染，并用于治疗增殖性疾病，如抑制各种癌症的转移。
• WO2008/109154
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and pharmacological characterization of benzenesulfonamides as dual species inhibitors of human and murine mPGES-1
  作者：Thomas Hanke、Florian Rörsch、Theresa M. Thieme、Nerea Ferreiros、Gisbert Schneider、Gerd Geisslinger、Ewgenij Proschak、Sabine Grösch、Manfred Schubert-Zsilavecz

  DOI：10.1016/j.bmc.2013.10.006

  日期：2013.12

  The microsomal prostaglandin E-2 synthase 1 (mPGES-1) became a desirable target in recent years for the research of new anti-inflammatory drugs. Even though many potent inhibitors of human mPGES-1, tested in vitro assay systems, have been synthesized, they all failed in preclinical trials in rodent models of inflammation, due to the lack of activity on rodent enzyme. Within this work we want to present a new class of mPGES-1 inhibitors derived from a benzenesulfonamide scaffold with inhibitory potency on human and murine mPGES-1. Starting point with an IC50 of 13.8 mu M on human mPGES-1 was compound 1 (4-benzyl[(4-methoxyphenyl) methyl] sulfamoyl} benzoic acid; FR4), which was discovered by a virtual screening approach. Optimization during a structure-activity relationship (SAR) process leads to compound 28 (4-[(cyclohexylmethyl)[(4-phenylphenyl) methyl] sulfamoyl] benzoic acid) with an improved IC50 of 0.8 mu M on human mPGES-1. For the most promising compounds a broad pharmacological characterization has been carried out to estimate their anti-inflammatory potential. (C) 2013 Elsevier Ltd. All rights reserved.
• [EN] CHEMOKINE RECEPTOR MODULATORS<br/>[FR] MODULATEURS DE RÉCEPTEUR DE CHIMIOKINE
  申请人：METASTATIX INC

  公开号：WO2008109154A1

  公开（公告）日：2008-09-12

  [EN] The invention provides compounds of Formula (I) and pharmaceutical composi tions comprising compounds of Formula (I). These compounds are useful treating or preventing HIV infections, and in treating proliferative disorders such as inhibiting the metastasis of various cancers
  [FR] L'invention concerne des composés de la formule (I) et des compositions pharmaceutiques comprenant des composés de la formule (I). Ces composés sont utiles pour traiter ou prévenir des infections par le VIH, et pour traiter des troubles prolifératifs par l'inhibition de la métastase de divers cancers, par exemple.
• Discovery of novel PTP1B inhibitors via pharmacophore-oriented scaffold hopping from Ertiprotafib
  作者：Jun-Zheng Liu、Shu-En Zhang、Feilin Nie、Ying Yang、Yan-Bo Tang、Wenwen Yin、Jin-Ying Tian、Fei Ye、Zhiyan Xiao

  DOI：10.1016/j.bmcl.2013.10.002

  日期：2013.12

  An integrated molecular design strategy combining pharmacophore recognition and scaffold hopping was exploited to discover novel PTP1B inhibitors based on the known PTP1B inhibitor Ertiprotafib. A composite pharmacophore model was proposed from the interaction mode of Ertiprotafib, and 21 diverse molecules from five distinct structural classes were designed and synthesized accordingly. New compounds with considerable inhibition against PTP1B were identified from each series, and the most active compound 3a showed IC50 value of 1.3 mu mol L-1 against human recombinant PTP1B. Docking study indicated that the new inhibitors assumed binding modes similar to that of Ertiprotafib. (C) 2013 Elsevier Ltd. All rights reserved.