(R)-3-phenyl-5-(pyrrolidin-2-yl)-1,2,4-oxadiazole | 871208-88-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (R)-3-phenyl-5-(pyrrolidin-2-yl)-1,2,4-oxadiazole
• 英文别名: 3-phenyl-5-[(2R)tetrahydro-1H-pyrrol-2-yl]-1,2,4-oxadiazole；3-phenyl-5-[(2R)-pyrrolidin-2-yl]-1,2,4-oxadiazole
• CAS: 871208-88-7
• 化学式: C₁₂H₁₃N₃O
• 分子量: 215.255
• InChiKey: RJBMVNYIOPXWKS-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  51
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-3-phenyl-5-(pyrrolidin-2-yl)-1,2,4-oxadiazole 、 对氯苯异氰酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以59%的产率得到(R)-N-(4-chlorophenyl)-2-(3-phenyl-1,2,4-oxadiazol-5-yl)pyrrolidine-1-carboxamide
  参考文献：
  名称：

  Synthesis and structure-activity relationship study of pyrrolidine-oxadiazoles as anthelmintics against Haemonchus contortus

  摘要：

  Parasitic roundworms (nematodes) are significant pathogens of humans and animals and cause substantive socioeconomic losses due to the diseases that they cause. The control of nematodes in livestock animals relies heavily on the use of anthelmintic drugs. However, their extensive use has led to a widespread problem of drug resistance in these worms. Thus, the discovery and development of novel chemical entities for the treatment of parasitic worms of humans and animals is needed. Herein, we describe our medicinal chemistry optimization efforts of a phenotypic hit against Haemonchus contortus based on a pyrrolidine-oxadiazole scaffold. This led to the identification of compounds with potent inhibitory activities (IC50 = 0.78-22.4 mu M) on the motility and development of parasitic stages of H. contortus, and which were found to be highly selective in a mammalian cell counter-screen. These compounds could be used as suitable chemical tools for drug target identification or as lead compounds for further optimization. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112100
• 作为产物：
  描述：

  苯甲酰胺肟 在 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (R)-3-phenyl-5-(pyrrolidin-2-yl)-1,2,4-oxadiazole
  参考文献：
  名称：

  Synthesis and structure-activity relationship study of pyrrolidine-oxadiazoles as anthelmintics against Haemonchus contortus

  摘要：

  Parasitic roundworms (nematodes) are significant pathogens of humans and animals and cause substantive socioeconomic losses due to the diseases that they cause. The control of nematodes in livestock animals relies heavily on the use of anthelmintic drugs. However, their extensive use has led to a widespread problem of drug resistance in these worms. Thus, the discovery and development of novel chemical entities for the treatment of parasitic worms of humans and animals is needed. Herein, we describe our medicinal chemistry optimization efforts of a phenotypic hit against Haemonchus contortus based on a pyrrolidine-oxadiazole scaffold. This led to the identification of compounds with potent inhibitory activities (IC50 = 0.78-22.4 mu M) on the motility and development of parasitic stages of H. contortus, and which were found to be highly selective in a mammalian cell counter-screen. These compounds could be used as suitable chemical tools for drug target identification or as lead compounds for further optimization. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112100

文献信息

• Dpp-IV Inhibitors
  申请人：Edwards John Paul

  公开号：US20080015146A1

  公开（公告）日：2008-01-17

  The invention relates to compounds of formula (I) wherein Z, R 1-9 , n, A, X and R b have the meaning as cited in the description and the claims. Said compounds are useful as DPP-IV inhibitors. The invention also relates to the preparation of such compounds as well as the production and use thereof as medicament.

  本发明涉及公式(I)的化合物，其中Z、R1-9、n、A、X和Rb的含义如所述描述和权利要求中所述。所述化合物可用作DPP-IV抑制剂。本发明还涉及制备这些化合物的方法，以及作为药物的生产和使用。
• [EN] DPP-IV INHIBITORS<br/>[FR] INHIBITEURS DE LA DPP-IV
  申请人：SANTHERA PHARMACEUTICALS DEUTS

  公开号：WO2005121131A1

  公开（公告）日：2005-12-22

  The invention relates to compounds of formula (I); wherein Z, R1-9, n, A, X and Rb have the meaning as cited in the description and the claims. Said compounds are useful as DPP-IV inhibitors. The invention also relates to the preparation of such compounds as well as the production and use thereof as medicament.
• Synthesis and structure-activity relationship study of pyrrolidine-oxadiazoles as anthelmintics against Haemonchus contortus
  作者：Banfeng Ruan、Yuezhou Zhang、Solomon Tadesse、Sarah Preston、Aya C. Taki、Abdul Jabbar、Andreas Hofmann、Yaqing Jiao、Jose Garcia-Bustos、Jitendra Harjani、Thuy Giang Le、Swapna Varghese、Silvia Teguh、Yiyue Xie、Jephthah Odiba、Min Hu、Robin B. Gasser、Jonathan Baell

  DOI：10.1016/j.ejmech.2020.112100

  日期：2020.3

  Parasitic roundworms (nematodes) are significant pathogens of humans and animals and cause substantive socioeconomic losses due to the diseases that they cause. The control of nematodes in livestock animals relies heavily on the use of anthelmintic drugs. However, their extensive use has led to a widespread problem of drug resistance in these worms. Thus, the discovery and development of novel chemical entities for the treatment of parasitic worms of humans and animals is needed. Herein, we describe our medicinal chemistry optimization efforts of a phenotypic hit against Haemonchus contortus based on a pyrrolidine-oxadiazole scaffold. This led to the identification of compounds with potent inhibitory activities (IC50 = 0.78-22.4 mu M) on the motility and development of parasitic stages of H. contortus, and which were found to be highly selective in a mammalian cell counter-screen. These compounds could be used as suitable chemical tools for drug target identification or as lead compounds for further optimization. (C) 2020 Elsevier Masson SAS. All rights reserved.