5-cyclopropyl-8-(2-furyl)-4-[(1-naphthyl)methyl]-2-oxo-7-thia-1-azabicyclo[4.3.0]nona-3,5,8-triene-9-carboxylic acid | 1235551-15-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-cyclopropyl-8-(2-furyl)-4-[(1-naphthyl)methyl]-2-oxo-7-thia-1-azabicyclo[4.3.0]nona-3,5,8-triene-9-carboxylic acid
• 英文别名: 8-cyclopropyl-2-furan-2-yl-7-naphthalen-1-ylmethyl-5-oxo-5H-thiazolo[3,2-a]pyridine-3-carboxylic acid；8-Cyclopropyl-2-(furan-2-yl)-7-(naphthalen-1-ylmethyl)-5-oxo-[1,3]thiazolo[3,2-a]pyridine-3-carboxylic acid
• CAS: 1235551-15-1
• 化学式: C₂₆H₁₉NO₄S
• 分子量: 441.507
• InChiKey: OJWSXOQDEQZLIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  96
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  8-cyclopropyl-2-(furan-2-yl)-7-naphthalen-1-ylmethyl-5-oxo-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50%的产率得到5-cyclopropyl-8-(2-furyl)-4-[(1-naphthyl)methyl]-2-oxo-7-thia-1-azabicyclo[4.3.0]nona-3,5,8-triene-9-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] RING-FUSED THIAZOLINO 2-PYRIDONES, METHODS FOR PREPARATION THEREOF AND THEIR USE IN THE TREATMENT AND/OR PREVENTION OF A DISEASE INVOLVING GRAM-POSITIVE BACTERIA<br/>[FR] THIAZOLINO 2-PYRIDONES À CYCLES FUSIONNÉS, LEURS PROCÉDÉS DE PRÉPARATION ET LEUR UTILISATION DANS LE TRAITEMENT ET/OU LA PRÉVENTION DE MALADIE IMPLIQUANT DES BACTÉRIES À GRAM POSITIF
  申请人：QURETECH BIO AB

  公开号：WO2018229141A1

  公开（公告）日：2018-12-20

  The present disclosure provides a compound of Formula I, or a pharmaceutically acceptable salt thereof, optionally in combination with a drug against a disease involving gram-positive bacteria.

  本公开提供一种I式化合物，或其药学上可接受的盐，可选地与一种针对涉及革兰氏阳性细菌疾病的药物组合使用。
• RING-FUSED THIAZOLINO 2-PYRIDONES, METHODS FOR PREPARATION THEREOF AND THEIR USE IN THE TREATMENT AND/OR PREVENTION OF A DISEASE INVOLVING GRAM-POSITIVE BACTERIA
  申请人：Quretech Bio AB

  公开号：EP3638681A1

  公开（公告）日：2020-04-22