7-(naphthalen-1-ylmethyl)-8-cyclopropyl-5-oxo-2-(phenylcarbamoyl)-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylic acid | 1235550-92-1

• 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: 7-(naphthalen-1-ylmethyl)-8-cyclopropyl-5-oxo-2-(phenylcarbamoyl)-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylic acid
• 英文别名: 8-cyclopropyl-7-naphthalen-1-ylmethyl-5-oxo-2-phenylcarbamoyl-5H-thiazolo[3,2-a]pyridine-3-carboxylic acid；8-Cyclopropyl-7-(naphthalen-1-ylmethyl)-5-oxo-2-(phenylcarbamoyl)-[1,3]thiazolo[3,2-a]pyridine-3-carboxylic acid
• CAS: 1235550-92-1
• 化学式: C₂₉H₂₂N₂O₄S
• 分子量: 494.571
• InChiKey: UEAFFNFTOKKPIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  8-cyclopropyl-7-(naphthalen-1-yl)methyl-5-oxo-2-phenylcarbamoyl-5H-thiazolo[3,2-a]pyridine-3-carboxylic acid methyl ester 在 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.42h， 以88%的产率得到7-(naphthalen-1-ylmethyl)-8-cyclopropyl-5-oxo-2-(phenylcarbamoyl)-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxylic acid
  参考文献：
  名称：

  Design and Synthesis of C-2 Substituted Thiazolo and Dihydrothiazolo Ring-Fused 2-Pyridones: Pilicides with Increased Antivirulence Activity

  摘要：

  Pilicides block pili formation by binding to pilus chaperones and blocking their function in the chaperone/usher pathway in E. coli. Various C-2 substituents were introduced on the pilicide scaffold by design and synthetic method developments. Experimental evaluation showed that proper substitution of this position affected the biological activity of the compound. Aryl substituents resulted in pilicides with significantly increased potencies as measured in pili-dependent biofilm and hemagglutination assays. The structural basis of the PapD chaperone-pilicide interactions was determined by X-ray crystallography.

  DOI：

  10.1021/jm100470t

文献信息

• [EN] COMPOUNDS AND METHODS FOR TREATMENT OF CHLAMYDIA INFECTIONS<br/>[FR] COMPOSÉS ET MÉTHODES POUR LE TRAITEMENT D'INFECTIONS À CHLAMYDIA
  申请人：QURETECH BIO AB

  公开号：WO2014185853A1

  公开（公告）日：2014-11-20

  The present invention provides new compounds, pharmaceutical compositions and methods for the treatment and diagnosis of Chlamydia infections. The compounds are substituted ring-fused 2-pyridones and are shown to reduce the infectivity of Chlamydia. The invention further identifies the membrane-localized hexose-phosphate permease (UhpC)of Chlamydia as drug target and provides methods for the identification and development of new anti-Chlamydia compounds

  本发明提供了用于治疗和诊断沙眼感染的新化合物、药物组合物和方法。这些化合物是取代环融合的2-吡啶酮，并且已被证明可以减少沙眼的传染性。该发明进一步确定了沙眼的膜定位己糖磷酸透过酶（UhpC）作为药物靶标，并提供了用于识别和开发新的抗沙眼化合物的方法。