methyl 3-((4-cyanobenzyl)oxy)benzoate | 169605-18-9

• 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: methyl 3-((4-cyanobenzyl)oxy)benzoate
• 英文别名: Methyl 3-(4-cyanobenzyloxy)benzoate；methyl 3-[(4-cyanophenyl)methoxy]benzoate
• CAS: 169605-18-9
• 化学式: C₁₆H₁₃NO₃
• 分子量: 267.284
• InChiKey: NHNKMGDEPNUWGW-UHFFFAOYSA-N

物化性质

• 沸点：
  434.4±30.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-((4-cyanobenzyl)oxy)benzoate 在 lithium hydroxide 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 Methyl N-(3-(4-cyanobenzyloxy)benzoyl)-DL-3-amino-4,4,4-trifluorobutyrate
  参考文献：
  名称：

  Design, synthesis, and in vitro activities of benzamide-core glycoprotein IIb/IIIa antagonists: 2,3-Diaminopropionic acid derivatives as surrogates of aspartic acid

  摘要：

  In an effort to discover novel nonpeptide glycoprotein IIb/IIIa (GPIIb/lIIa, alpha(IIb)/beta 3) inhibitors, we investigated RGD mimetics featuring a 3-substituted benzoic acid as the core, benzamidine as the basic moiety, and a series of beta- and alpha-substituted beta-alanine derivatives as aspartic acid surrogates. It was found that the use of beta-methyl beta-alanine slightly improved the anti-aggregant potency in human platelet-rich plasma over the unsubstituted beta-alanine compound, while alpha-substitution with a trifluoromethyl group resulted in considerable loss in activity. Significant enhancement (up to 100-fold) in potency was obtained when the beta-alanine was replaced with N-2-substituted L-2,3-diaminopropionic acid derivatives. Among the three types of cc-substituents (carbamate, amide, and sulfonamide) investigated, no apparent preference was observed with respect to in vitro potency. However, alkyl groups were more favorable than arylalkyl groups (Cbz) in the carbamate analogues. We also investigated piperidine, piperazine, and N-formamidinopiperidine as replacements for the benzamidine moiety. The former two replacements led to a drop in potency while the latter replacement resulted in maintenance of activity as compared with the corresponding benzamidine analogue. (C) 1997 The DuPont Merck Pharmaceutical Company. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00013-8
• 作为产物：
  描述：

  3-羟基苯甲酸甲酯 、 对氰基溴化苄 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 4.0h， 生成 methyl 3-((4-cyanobenzyl)oxy)benzoate
  参考文献：
  名称：

  发现具有抗抑郁活性的有效，选择性和直接酸性鞘氨醇酶抑制剂。

  摘要：

  最近对鞘脂的研究表明，在主要抑郁症的发病机理中起着重要作用的酸性鞘磷脂酶（ASM）逐渐成为开发抗抑郁药的新靶标。在本文中，我们首先描述了基于异羟肟酸的ASM直接抑制剂的设计，合成和生物学评估，以验证它们在体内的抗抑郁作用。结果，使用基于结构的方法开发了一系列新颖的ASM抑制剂。我们的研究表明，施用21b可以改善大鼠的抑郁样行为。重要的是，该阳性结果与抑制ASM和增加海马神经发生有关。据我们所知，

  DOI：

  10.1021/acs.jmedchem.9b00739

文献信息

• Aromatic compounds containing basic and acidic termini useful as
  申请人：The Dupont Merck Pharmaceutical Company

  公开号：US05563158A1

  公开（公告）日：1996-10-08

  This invention relates to novel compounds containing basic and acidic termini, pharmaceutical compositions containing such compounds, processes for preparing such compounds, and to methods of using these compounds, alone or in combination with other therapeutic agents, for the inhibition of platelet aggregation, as thrombolytics, and/or for the treatment of thromboembolic disorders.

  这项发明涉及含有碱性和酸性末端的新化合物，包含这些化合物的药物组合物，制备这些化合物的方法，以及使用这些化合物的方法，单独或与其他治疗剂结合，用于抑制血小板聚集，作为溶栓剂，和/或用于治疗血栓栓塞性疾病。
• Compounds containing basic and acidic termini useful as fibrinogen
  申请人：The DuPont Merck Pharmaceutical Company

  公开号：US05691329A1

  公开（公告）日：1997-11-25

  This invention relates to novel compounds containing basic and acidic termini, pharmaceutical compositions containing such compounds, processes for preparing such compounds, and to methods of using these compounds, alone or in combination with other therapeutic agents, for the inhibition of platelet aggregation, as thrombolytics, and/or for the treatment of thromboembolic disorders.

  本发明涉及一种含有碱性和酸性末端的新化合物，包含这种化合物的制药组合物、制备这种化合物的方法，以及使用这些化合物的方法，单独或与其他治疗剂联合使用，用于抑制血小板聚集，作为溶栓剂，和/或用于治疗血栓栓塞性疾病。
• Discovery of N-hydroxy-3-alkoxybenzamides as direct acid sphingomyelinase inhibitors using a ligand-based pharmacophore model
  作者：Kan Yang、Keyi Nong、Qinlan Gu、Jibin Dong、Jinxin Wang

  DOI：10.1016/j.ejmech.2018.03.065

  日期：2018.5

  Acid sphingomyelinase (ASM) has been shown to be involved in many physiological processes, emerging to be a promising drug target. In this study, we constructed a ligand-based pharmacophore model of ASM inhibitors and applied this model to optimize the lead compound alpha-mangostin, a known inhibitor of ASM. 23 compounds were designed and evaluated in vitro for ASM inhibition, of these, 10 compounds were found to be more potent than alpha-mangostin. This high hit ratio confirmed that the presented model is very effective and practical. The most potent hit, 1c, was found to selectively and competitively inhibit the enzyme and inhibit the generation of ceramide in a dose-dependent manner. Furthermore, 1c showed favorable anti-apoptosis and anti-inflammatory activity. Interactions with key residues and the Zn2+ cofactor of 1c were found by docking simulation. These results provide promising leads and important guidance for further development of efficient ASM inhibitors and drug candidates. (C) 2018 Elsevier Masson SAS. All rights reserved.
• [EN] GRAM-NEGATIVE SPECIFIC ANTIBIOTICS SPARING EFFECT ON GUT MICROBIOME<br/>[FR] EFFET ÉPARGNANT DES ANTIBIOTIQUES SPÉCIFIQUES À GRAM NÉGATIF SUR MICROBIOME INTESTINAL
  申请人：[en]THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS

  公开号：WO2023091873A1

  公开（公告）日：2023-05-25

  Small molecule inhibitors of the localization of lipoprotein CDE (LolCDE) complex that is found in the membrane of bacteria. Searches for suitable candidates for the LolCDE complex led to the discovery of an inhibitor named lolamycin. Lolamycin specifically targets Gram-negative bacteria such asEscherichia coli,Klebsiella pneumoniae,Enterobacter cloacae, andSalmonella typhimurium, and is selective over Gram-negative and Gram-positive commensal bacteria, thereby avoiding perturbation of the gut microbiome.
• Design, synthesis, and in vitro activities of benzamide-core glycoprotein IIb/IIIa antagonists: 2,3-Diaminopropionic acid derivatives as surrogates of aspartic acid
  作者：Chu-Biao Xue、John Roderick、Sharon Jackson、Maria Rafalski、Arlene Rockwell、Shaker Mousa、Richard E. Olson、William F. DeGrado

  DOI：10.1016/s0968-0896(97)00013-8

  日期：1997.4

  In an effort to discover novel nonpeptide glycoprotein IIb/IIIa (GPIIb/lIIa, alpha(IIb)/beta 3) inhibitors, we investigated RGD mimetics featuring a 3-substituted benzoic acid as the core, benzamidine as the basic moiety, and a series of beta- and alpha-substituted beta-alanine derivatives as aspartic acid surrogates. It was found that the use of beta-methyl beta-alanine slightly improved the anti-aggregant potency in human platelet-rich plasma over the unsubstituted beta-alanine compound, while alpha-substitution with a trifluoromethyl group resulted in considerable loss in activity. Significant enhancement (up to 100-fold) in potency was obtained when the beta-alanine was replaced with N-2-substituted L-2,3-diaminopropionic acid derivatives. Among the three types of cc-substituents (carbamate, amide, and sulfonamide) investigated, no apparent preference was observed with respect to in vitro potency. However, alkyl groups were more favorable than arylalkyl groups (Cbz) in the carbamate analogues. We also investigated piperidine, piperazine, and N-formamidinopiperidine as replacements for the benzamidine moiety. The former two replacements led to a drop in potency while the latter replacement resulted in maintenance of activity as compared with the corresponding benzamidine analogue. (C) 1997 The DuPont Merck Pharmaceutical Company. Published by Elsevier Science Ltd.