2-(1-(4-(((4-([1,1'-biphenyl]-4-yl)-5-cyano-6-oxo-1,6-dihydropyrimidin-2-yl)thio)methyl)phenyl)-1H-1,2,3-triazol-4-yl)acetic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-(1-(4-(((4-([1,1'-biphenyl]-4-yl)-5-cyano-6-oxo-1,6-dihydropyrimidin-2-yl)thio)methyl)phenyl)-1H-1,2,3-triazol-4-yl)acetic acid
• 英文别名: 2-[1-[4-[[5-cyano-6-oxo-4-(4-phenylphenyl)-1H-pyrimidin-2-yl]sulfanylmethyl]phenyl]triazol-4-yl]acetic acid
• 化学式: C₂₈H₂₀N₆O₃S
• 分子量: 520.571
• InChiKey: UKHDWZZRWCPBMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  159
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5-cyano-6-(biphenyl-4-yl)-2-thiouracil 在 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 16.0h， 生成 2-(1-(4-(((4-([1,1'-biphenyl]-4-yl)-5-cyano-6-oxo-1,6-dihydropyrimidin-2-yl)thio)methyl)phenyl)-1H-1,2,3-triazol-4-yl)acetic acid
  参考文献：
  名称：

  Design, syntheses and evaluation of 4-oxo-5-cyano thiouracils as SecA inhibitors

  摘要：

  Protein translocation is essential for bacterial survival and the most important translocation mechanism is the secretion (Sec) pathway in which SecA is a central core driving force. Thus targeting SecA is a promising strategy for developing novel antibacterial therapeutics. Herein, we report the syntheses and evaluation of a series of nearly 60 4-oxo-5-cyano thiouracil derivatives based upon our previously reported core pyrimidine structure. Introduction of polar group such as -N-3 and linker groups such as -CH2-O- enhanced the potency several fold. Apart from being potential antibacterial agents, these inhibitors can be indispensable tools for biologists to probe the mechanism of protein translocation via the SecA machinery in bacteria. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2014.11.017

文献信息

• SecA Inhibitors and Methods of Making and Using Thereof
  申请人：Georgia State University Research Foundation, Inc.

  公开号：US20150152077A1

  公开（公告）日：2015-06-04

  Inhibitors of SecA, and methods of making and using thereof, are described herein. The compounds described herein can be used to treat or prevent microbial infections, such as bacterial infections.

  本文介绍了SecA的抑制剂及其制备和使用方法。本文所描述的化合物可用于治疗或预防微生物感染，如细菌感染。
• SecA INHIBITORS AND METHODS OF MAKING AND USING THEREOF
  申请人：Wang Binghe

  公开号：US20180222880A1

  公开（公告）日：2018-08-09

  Inhibitors of SecA, and methods of making and using thereof, are described herein. The compounds described herein can be used to treat or prevent microbial infections, such as bacterial infections.
• US9957247B2
  申请人：——

  公开号：US9957247B2

  公开（公告）日：2018-05-01
• Design, syntheses and evaluation of 4-oxo-5-cyano thiouracils as SecA inhibitors
  作者：Arpana S. Chaudhary、Jinshan Jin、Weixuan Chen、Phang C. Tai、Binghe Wang

  DOI：10.1016/j.bmc.2014.11.017

  日期：2015.1

  Protein translocation is essential for bacterial survival and the most important translocation mechanism is the secretion (Sec) pathway in which SecA is a central core driving force. Thus targeting SecA is a promising strategy for developing novel antibacterial therapeutics. Herein, we report the syntheses and evaluation of a series of nearly 60 4-oxo-5-cyano thiouracil derivatives based upon our previously reported core pyrimidine structure. Introduction of polar group such as -N-3 and linker groups such as -CH2-O- enhanced the potency several fold. Apart from being potential antibacterial agents, these inhibitors can be indispensable tools for biologists to probe the mechanism of protein translocation via the SecA machinery in bacteria. Published by Elsevier Ltd.