3-(4-氰基苄氧基)苯甲酸 | 169605-19-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(4-氰基苄氧基)苯甲酸
• 英文名称: 3-((4-cyanobenzyl)oxy)benzoic acid
• 英文别名: 3-[(4-Cyanophenyl)methoxy]benzoic acid
• CAS: 169605-19-0
• 化学式: C₁₅H₁₁NO₃
• mdl: MFCD09814102
• 分子量: 253.257
• InChiKey: KQWBKVFVLFWHMO-UHFFFAOYSA-N

物化性质

• 沸点：
  483.9±30.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-氰基苄氧基)苯甲酸 在 氯化亚砜 、 N,N-二甲基甲酰胺 、 盐酸羟胺 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 3.08h， 生成 3-((4-cyanobenzyl)oxy)-N-hydroxybenzamide
  参考文献：
  名称：

  Discovery of N-hydroxy-3-alkoxybenzamides as direct acid sphingomyelinase inhibitors using a ligand-based pharmacophore model

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2018.03.065
• 作为产物：
  描述：

  methyl 3-((4-cyanobenzyl)oxy)benzoate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以5.4 g (100%)的产率得到3-(4-氰基苄氧基)苯甲酸
  参考文献：
  名称：

  Aromatic compounds containing basic and acidic termini useful as

  摘要：

  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。

  公开号：

  US05563158A1

文献信息

• Facile Conversion of Molecularly Complex (Hetero)aryl Carboxylic Acids into Alkynes for Accelerated SAR Exploration
  作者：Ferdinand H. Lutter、Matthieu Jouffroy

  DOI：10.1002/chem.202102130

  日期：2021.10.25

  molecularly complex (hetero)aryl carboxylic acids into the bioisostere world: A functional-group-tolerant and operationally simple decarbonylative alkynylation is reported that allows the synthesis of aryl alkynes from highly functionalized aryl and heteroaryl carboxylic acids. The reaction shows an unmatched substrate scope mainly thanks to its remarkably mild reaction conditions using a homogenous Pd/Cu

  将分子复杂的（杂）芳基羧酸带入生物电子等排世界：据报道，一种具有官能团耐受性且操作简单的脱羰炔基化反应允许从高度官能化的芳基和杂芳基羧酸合成芳基炔烃。该反应显示出无与伦比的底物范围，这主要归功于其使用均质 Pd/Cu 双金属系统的非常温和的反应条件。商业药物吗氯贝胺的三唑类似物的制备展示了该协议的效用。
• 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。
• Discovery of potent benzoxaborole inhibitors against SARS-CoV-2 main and dengue virus proteases
  作者：Nikos Kühl、Johannes Lang、Mila M. Leuthold、Christian D. Klein

  DOI：10.1016/j.ejmech.2022.114585

  日期：2022.10

  The RNA viruses SARS-CoV-2 and dengue pose a major threat to human health worldwide and their proteases (Mpro; NS2B/NS3) are considered as promising targets for drug development. We present the synthesis and biological evaluation of novel benzoxaborole inhibitors of these two proteases. The most active compound achieves single-digit micromolar activity against SARS-CoV-2 Mpro in a biochemical assay

  RNA 病毒 SARS-CoV-2 和登革热对全世界人类健康构成重大威胁，它们的蛋白酶 (M pro ; NS2B/NS3) 被认为是药物开发的有前途的目标。我们介绍了这两种蛋白酶的新型苯并氧硼环抑制剂的合成和生物学评价。在生化测定中，活性最高的化合物对 SARS-CoV-2 M pro具有个位数的微摩尔活性。对登革热 NS2B/NS3 蛋白酶最具活性的物质在细胞中具有亚微摩尔活性 (EC 500.54 μM) 并抑制细胞培养物中的 DENV-2 复制。大多数苯并氧杂硼化合物没有相关的细胞毒性或显着的脱靶抑制作用。此外，该类还展示了被动膜渗透性和对评估蛋白酶的稳定性。该化合物类别可能有助于开发具有抗 DENV 或 SARS-CoV-2 活性的抗病毒剂。
• 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.
• [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.