4-(5-bromopyridin-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one | 380380-71-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-(5-bromopyridin-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one
• 英文别名: 2-[2-oxo-(2,3)-dihydro-(1,3,4)-triazol-1-yl]-5-bromopyridine；4-(5-Bromo-2-pyridinyl)-2,4-dihydro-3H-1,2,4-triazol-3-one；4-(5-bromopyridin-2-yl)-1H-1,2,4-triazol-5-one
• CAS: 380380-71-2
• 化学式: C₇H₅BrN₄O
• 分子量: 241.047
• InChiKey: PLGBXHHISWCQPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(5-bromopyridin-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one 在 tris-(dibenzylideneacetone)dipalladium(0) 、 lithium perchlorate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Design and synthesis of novel antifungal triazole derivatives with good activity and water solubility

  摘要：

  In order to find novel antifungal agents with good activity and aqueous solubility, a series of SYN-2869 analogues containing a pyridine ring were synthesized and evaluated for their in vitro antifungal activity and water solubility. The results indicated that some compounds showed potent activity against six pathogenic fungi. In particular, the analogue 17a having an isobutyl substitution on the triazolone exhibited significant broad spectrum antifungal activity. In addition, the water solubility of compound 17a was sufficiently improved over SYN-2869. (C) 2013 Yu-She Yang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.01.047
• 作为产物：
  描述：

  N-(5-bromopyridin-2-yl)hydrazinecarboxamide 、 醋酸甲脒 以 N,N-二甲基甲酰胺 为溶剂， 以50%的产率得到4-(5-bromopyridin-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one
  参考文献：
  名称：

  具有改进的抗真菌活性、水溶性和生物利用度的吡啶取代的伊曲康唑类似物的设计和合成

  摘要：

  设计并合成了一系列含伊曲康唑吡啶环的新型类似物。大多数化合物显示出比母体伊曲康唑更有效的抗真菌活性。特别是，类似物、、、和表现出比伊曲康唑更高的溶解度和生物利用度。其生物利用度（42.2%）比伊曲康唑（8%）高5倍，并且在Ames试验中遗传毒理学呈阴性。

  DOI：

  10.1016/j.bmcl.2011.06.062

文献信息

• Novel oxazolidinone derivatives and a process for the preparation thereof
  申请人：——

  公开号：US20030166620A1

  公开（公告）日：2003-09-04

  The present invention relates to novel oxazolidinone derivatives, their pharmaceutically acceptable salts and a process for the preparation thereof. More particularly, the present invention relates to oxazolidinone derivatives having pyridine or pyrimidine moeity substituted by heterocycle and heteroaromaticcycle at 4-position of phenyl ring. The compounds of the present invention have wide antibacterial spectrum, superior antibacterial activity and low toxicity, such that the compound of this invention can be used as an antibacterial agent.

  本发明涉及新颖的噁唑烷酮衍生物，其药用盐以及其制备方法。更具体地，本发明涉及在苯环的4位被杂环和杂芳环取代的噁唑烷酮衍生物。本发明的化合物具有广泛的抗菌谱、优越的抗菌活性和低毒性，因此本发明的化合物可用作抗菌剂。
• Design and synthesis of pyridine-substituted itraconazole analogues with improved antifungal activities, water solubility and bioavailability
  作者：Yu Liu、Zining Liu、Xufeng Cao、Xin Liu、Huili He、Yushe Yang

  DOI：10.1016/j.bmcl.2011.06.062

  日期：2011.8

  series of novel analogues of itraconazole-containing pyridine rings were designed and synthesized. Most of the compounds showed more potent antifungal activities than that of the parent itraconazole. In particular, the analogues , , , and exhibited much higher solubility and bioavailability than did itraconazole. The bioavailability of (42.2%) was five times higher than that of itraconazole (8%) and was

  设计并合成了一系列含伊曲康唑吡啶环的新型类似物。大多数化合物显示出比母体伊曲康唑更有效的抗真菌活性。特别是，类似物、、、和表现出比伊曲康唑更高的溶解度和生物利用度。其生物利用度（42.2%）比伊曲康唑（8%）高5倍，并且在Ames试验中遗传毒理学呈阴性。
• Aryl or heteroaryl triazolone derivatives or salts thereof, or pharmaceutical compositions comprising the same
  申请人：YUHAN CORPORATION

  公开号：US10562865B2

  公开（公告）日：2020-02-18

  The present technology provides aryl or heteroaryl triazolone derivatives or pharmaceutically acceptable salts thereof, preparation processes thereof, pharmaceutical compositions comprising the same, and the use thereof. The aryl or heteroaryl triazolone derivatives or their pharmaceutically acceptable salts exhibit selective inhibitory activity on VAP-1 and therefore can be usefully applied, e.g., for the treatment and prophylaxis of nonalcoholic hepatosteatosis (NASH).

  本技术提供了芳基或杂芳基三唑酮衍生物或其药学上可接受的盐、其制备工艺、包含这些衍生物的药物组合物及其用途。芳基或杂芳基三唑酮衍生物或其药学上可接受的盐类对 VAP-1 具有选择性抑制活性，因此可用于治疗和预防非酒精性肝病（NASH）等。
• NOVEL ARYL OR HETEROARYL TRIAZOLONE DERIVATIVES OR SALTS THEREOF, OR PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
  申请人：Yuhan Corporation

  公开号：EP3768663A1

  公开（公告）日：2021-01-27
• ARYL OR HETEROARYL TRIAZOLONE DERIVATIVES OR SALTS THEREOF, OR PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
  申请人：YUHAN CORPORATION

  公开号：US20210147368A1

  公开（公告）日：2021-05-20

  The present technology provides aryl or heteroaryl triazolone derivatives or pharmaceutically acceptable salts thereof, preparation processes thereof, pharmaceutical compositions comprising the same, and the use thereof. The aryl or heteroaryl triazolone derivatives or their pharmaceutically acceptable salts exhibit selective inhibitory activity on VAP-1 and therefore can be usefully applied, e.g., for the treatment and prophylaxis of nonalcoholic hepatosteatosis (NASH).