5-ethoxy-3-(3-phenoxyphenyl)-1,3,4-oxadiazol-2(3H)-one

• 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: 5-ethoxy-3-(3-phenoxyphenyl)-1,3,4-oxadiazol-2(3H)-one
• 英文别名: EmPPOX；3-(3-phenoxyphenyl)-5-ethoxy-3H-(1,3,4)oxadiazol-2-one；3-(3-Phenoxyphenyl)-5-ethoxy-1,3,4-oxadiazol-2-one；5-Ethoxy-3-(3-phenoxyphenyl)-1,3,4-oxadiazol-2-one
• 化学式: C₁₆H₁₄N₂O₄
• 分子量: 298.298
• InChiKey: OPUUTKNZIZBSCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  、 氯甲酸三氯甲酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 以283 mg的产率得到5-ethoxy-3-(3-phenoxyphenyl)-1,3,4-oxadiazol-2(3H)-one
  参考文献：
  名称：

  恶唑酮选择性抑制胃脂肪分解的恶二唑酮抑制剂减慢脂肪的消化和吸收

  摘要：

  基于先前的研究，并在硅片分子对接实验中，我们设计并合成了一系列新的10 5 -烷氧基Ñ -3-（3- P苯氧基P -苯基）-1,3,4-牛adiazol-2（3H）一衍生物（R m PPOX）。这些分子被进一步评估为哺乳动物消化脂肪酶的选择性和有效抑制剂：纯化的狗胃脂肪酶（DGL）和豚鼠胰腺脂肪酶相关蛋白2（GPLRP2），以及其中所含的猪（PPL）和人（HPL）胰腺脂肪酶猪胰腺提取物（PPE）和人胰液（HPJ）。发现这些化合物能将经典的胰腺脂肪酶（抑制不良）与胃脂肪酶（完全抑制）区分开。其中，5-（2-（Be nzyloxy）ethoxy）-3-（3- P henoxy P henyl ）-1,3,4- Ox adiazol-2（3H）-one（Be m PPOX）被确认为DGL最有效的抑制剂，甚至比FDA批准的药物Orlistat更有活性。来米PPOX和奥利司他进行进一步比较的体外中试

  DOI：

  10.1016/j.ejmech.2016.08.009

文献信息

• Use of substituted 3-phenyl-5-alkoxy-3H-(1,3,4)-oxadizol-2-ones for inhibiting pancreatic lipase
  申请人：——

  公开号：US20030236288A1

  公开（公告）日：2003-12-25

  The invention relates to a method for inhibiting pancreatic lipase, or the prophylaxis or treatment of obesity or diabetes mellitus of type 1 and 2, in a patient in need thereof, comprising administering to the patient a pharmaceutically effective amount of substituted 3-phenyl-5-alkoxy-3H-(1,3,4)-oxadiazol-2-ones of formula 1: 1 wherein R 1 , R 2 , R 3 , R 4 and R 5 are as defined herein, or a prodrug, solvate, pharmacologically acceptable salt or acid addition salt thereof.

  本发明涉及一种用于抑制胰腺脂肪酶，或预防或治疗1型和2型糖尿病或肥胖症的方法，适用于需要的患者，包括向患者投给药理有效量的取代的3-苯基-5-烷氧基-3H-(1,3,4)-恶二唑-2-酮，其化学式为1：1，其中R1、R2、R3、R4和R5如本文所述定义，或其前药、溶剂化物、药理上可接受的盐或酸性加成盐。
• Oxadiazolone derivatives, new promising multi-target inhibitors against M. tuberculosis
  作者：Phuong Chi Nguyen、Vincent Delorme、Anaïs Bénarouche、Alexandre Guy、Valérie Landry、Stéphane Audebert、Matthieu Pophillat、Luc Camoin、Céline Crauste、Jean-Marie Galano、Thierry Durand、Priscille Brodin、Stéphane Canaan、Jean-François Cavalier

  DOI：10.1016/j.bioorg.2018.08.025

  日期：2018.12

  A set of 19 oxadiazolone (OX) derivatives have been investigated for their antimycobacterial activity against two pathogenic slow-growing mycobacteria, Mycobacterium marinum and Mycobacterium bovis BCG, and the avirulent Mycobacterium tuberculosis (M. tb) mc(2)6230. The encouraging minimal inhibitory concentrations (MIC) values obtained prompted us to test them against virulent M. tb H37Rv growth either in broth medium or inside macrophages. The OX compounds displayed a diversity of action and were found to act either on extracellular M. tb growth only with moderated MIC50, or both intracellularly on infected macrophages as well as extracellularly on bacterial growth. Of interest, all OX derivatives exhibited very low toxicity towards host macrophages. Among the six potential OXs identified, HPDX, a selective inhibitor of extracellular M. tb growth, was selected and further used in a competitive labelling/enrichment assay against the activity-based probe Desthiobiotin-FP, in order to identify its putative target(s). This approach, combined with mass spectrometry, identified 18 potential candidates, all being serine or cysteine enzymes involved in M. tb lipid metabolism and/or in cell wall biosynthesis. Among them, Ag85A, CaeA, TesA, KasA and MetA have been reported as essential for in vitro growth of M. tb and/or its survival and persistence inside macrophages. Overall, our findings support the assumption that OX derivatives may represent a novel class of multi-target inhibitors leading to the arrest of M. tb growth through a cumulative inhibition of a large number of Ser- and Cys-containing enzymes involved in various important physiological processes.
• SUBSTITUIERTE 3-PHENYL-5-ALKOXI-1,3,4-OXDIAZOL-2-ONE UND IHRE VERWENDUNG ALS LIPASE-HEMMER
  申请人：Aventis Pharma Deutschland GmbH

  公开号：EP1214302B1

  公开（公告）日：2003-10-29
• VERWENDUNG SUBSTITUIERTER 3-PHENYL-5-ALKOXY-1,3,4-OXDIAZOL-2-ONE ZUR HERSTELLUNG VON ARZNEIMITTELN MIT HEMMENDER WIRKUNG AN DER PANKREATISCHEN LIPASE
  申请人：Aventis Pharma Deutschland GmbH

  公开号：EP1482929A1

  公开（公告）日：2004-12-08
• US6596742B1
  申请人：——

  公开号：US6596742B1

  公开（公告）日：2003-07-22