3-Phenyl-2-(5-propylthiophen-2-yl)-1,2-dihydroquinazolin-4-one | 1429192-07-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-Phenyl-2-(5-propylthiophen-2-yl)-1,2-dihydroquinazolin-4-one
• 英文别名: 3-phenyl-2-(5-propylthiophen-2-yl)-1,2-dihydroquinazolin-4-one
• CAS: 1429192-07-3
• 化学式: C₂₁H₂₀N₂OS
• 分子量: 348.469
• InChiKey: SEOPTNNPNXQCLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  60.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-phenyl-2-[(5-propylthiophen-2-yl)methylideneamino]benzamide 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以341 mg的产率得到3-Phenyl-2-(5-propylthiophen-2-yl)-1,2-dihydroquinazolin-4-one
  参考文献：
  名称：

  N-Methyldihydroquinazolinone Derivatives of Retro-2 with Enhanced Efficacy against Shiga Toxin

  摘要：

  The Retro-2 molecule protects cells against Shiga toxins by specifically blocking retrograde transport from early endosomes to the trans-Golgi network A SAR study has been carried out to identify more potent compounds. Cyclization and modifications of Retro-2 led to a compound with roughly 100 fold improvement of the EC50 against Shiga toxin cytotoxicity measured in a cell protein synthesis assay. We also demonstrated that only one enantiomer of the dihydroquinazolinone reported herein is bioactive.

  DOI：

  10.1021/jm4002346

文献信息

• [EN] COMPOUNDS FOR THE TREATMENT AND PREVENTION OF INFECTIONS<br/>[FR] COMPOSÉS DESTINÉS AU TRAITEMENT ET À LA PRÉVENTION D'INFECTIONS
  申请人：UNIV BROWN

  公开号：WO2014014814A1

  公开（公告）日：2014-01-23

  Provided herein are compounds of Formula (I) or (II): (I) (II) harmaceutically acceptable salts, tautomers, prodrugs, and stereoisomers thereof, and pharmaceutical compositions thereof, wherein X, RN, R1,R3,R4, p, and m are as defined herein. Such compounds and compositions have been found useful in the treatment or prevention of viral infections, e.g., polyomaviral infections, and are further envisioned useful in treatment or prevention of other pathogenic conditions associated with endosomal trafficking. Methods of treating or preventing an infection by a pathogen secreting an AB5 toxin is also contemplated.

  本文提供了化合物的公式(I)或(II)：(I) (II) 其药用可接受的盐、互变异构体、前药和立体异构体，以及药物组合物，其中X、RN、R1、R3、R4、p和m如本文所定义。已发现这些化合物和组合物在治疗或预防病毒感染，例如聚病毒感染方面具有用处，并且进一步被认为在治疗或预防与溶酶体运输相关的其他病原体条件方面有用。还考虑了通过治疗或预防分泌AB5毒素的病原体感染的方法。
• COMPOUNDS FOR THE TREATMENT AND PREVENTION OF INFECTIONS
  申请人：Brown University

  公开号：US20150166517A1

  公开（公告）日：2015-06-18

  Provided herein are compounds of Formula (I) or (II): (I) (II) pharmaceutically acceptable salts, tautomers, prodrugs, and stereoisomers thereof, and pharmaceutical compositions thereof, wherein X, R N , R 1 , R 3 , R 4 , p, and m are as defined herein. Such compounds and compositions have been found useful in the treatment or prevention of viral infections, e.g., polyomaviral infections, and are further envisioned useful in treatment or prevention of other pathogenic conditions associated with endosomal trafficking. Methods of treating or preventing an infection by a pathogen secreting an AB 5 toxin is also contemplated.
• US9695156B2
  申请人：——

  公开号：US9695156B2

  公开（公告）日：2017-07-04
• <i>N</i>-Methyldihydroquinazolinone Derivatives of Retro-2 with Enhanced Efficacy against Shiga Toxin
  作者：Romain Noel、Neetu Gupta、Valérie Pons、Amélie Goudet、Maria Daniela Garcia-Castillo、Aurélien Michau、Jennifer Martinez、David-Alexandre Buisson、Ludger Johannes、Daniel Gillet、Julien Barbier、Jean-Christophe Cintrat

  DOI：10.1021/jm4002346

  日期：2013.4.25

  The Retro-2 molecule protects cells against Shiga toxins by specifically blocking retrograde transport from early endosomes to the trans-Golgi network A SAR study has been carried out to identify more potent compounds. Cyclization and modifications of Retro-2 led to a compound with roughly 100 fold improvement of the EC50 against Shiga toxin cytotoxicity measured in a cell protein synthesis assay. We also demonstrated that only one enantiomer of the dihydroquinazolinone reported herein is bioactive.