8-cyclopropyl-2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-7-naphthalen-1-ylmethyl-5-oxo-5H-thiazolo[3,2-a]pyridine-3-carboxylic acid methyl ester | 1235550-98-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-cyclopropyl-2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-7-naphthalen-1-ylmethyl-5-oxo-5H-thiazolo[3,2-a]pyridine-3-carboxylic acid methyl ester
• 英文别名: Methyl 8-cyclopropyl-2-(2,3-dihydro-1,4-benzodioxin-6-yl)-7-(naphthalen-1-ylmethyl)-5-oxo-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate
• CAS: 1235550-98-7
• 化学式: C₃₁H₂₅NO₅S
• 分子量: 523.609
• InChiKey: ZYKWNVKPPCVFPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  90.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8-cyclopropyl-2-(2,3-dihydrobenzo[b][1,4]dioxin-6-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78%的产率得到5-cyclopropyl-8-(1,4-dioxa-2,3-dihydronaphth-6-yl)-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
• 作为产物：
  描述：

  2-bromo-8-cyclopropyl-7-(naphthalen-1-yl)methyl-5-oxo-5H-thiazolo[3,2-a]pyridine-3-carboxylic acid methyl ester 、 苯并-1,4-二氧六环-6-硼酸 在 potassium fluoride 、 palladium diacetate 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以94%的产率得到8-cyclopropyl-2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-7-naphthalen-1-ylmethyl-5-oxo-5H-thiazolo[3,2-a]pyridine-3-carboxylic acid methyl ester
  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