(3R)-7-(benzo[b]thiophen-3-ylmethyl)-8-cyclopropyl-5-oxo-3,5-dihydro-2H-thiazolo[3,2-a]pyridine-3-carboxylate lithium salt | 1374967-38-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3R)-7-(benzo[b]thiophen-3-ylmethyl)-8-cyclopropyl-5-oxo-3,5-dihydro-2H-thiazolo[3,2-a]pyridine-3-carboxylate lithium salt
• 英文别名: lithium;(3R)-7-(1-benzothiophen-3-ylmethyl)-8-cyclopropyl-5-oxo-2,3-dihydro-[1,3]thiazolo[3,2-a]pyridine-3-carboxylate
• CAS: 1374967-38-0
• 化学式: C₂₀H₁₆NO₃S₂*Li
• 分子量: 389.425
• InChiKey: LSBKERUNBRWIPP-RSAXXLAASA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.07
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  环丙乙腈 在 盐酸 、 三乙胺 、 三氟乙酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 0.03h， 生成 (3R)-7-(benzo[b]thiophen-3-ylmethyl)-8-cyclopropyl-5-oxo-3,5-dihydro-2H-thiazolo[3,2-a]pyridine-3-carboxylate lithium salt
  参考文献：
  名称：

  Mapping pilicide anti-virulence effect in Escherichia coli, a comprehensive structure–activity study

  摘要：

  Pilicides prevent pili formation and thereby the development of bacterial biofilms in Escherichia coli. We have performed a comprehensive structure activity relationship (SAR) study of the dihydrothiazolo ring-fused 2-pyridone pilicide central fragment by varying all open positions. Orthogonal projections to latent structures discriminant analysis (OPLS-DA) was used to distinguish active from inactive compounds in which polarity proved to be the most important factor for discrimination. A quantitative SAR (QSAR) partial least squares (PLS) model was calculated on the active compounds for prediction of biofilm inhibition activity. In this model, compounds with high inhibitory activity were generally larger, more lipophilic, more flexible and had a lower HOMO. Overall, this resulted in both highly valuable SAR information and potent inhibitors of type 1 pili dependent biofilm formation. The most potent biofilm inhibitor had an EC50 of 400 nM. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2012.01.048

文献信息

• Mapping pilicide anti-virulence effect in Escherichia coli, a comprehensive structure–activity study
  作者：Erik Chorell、Jerome S. Pinkner、Christoffer Bengtsson、Thomas Sainte-Luce Banchelin、Sofie Edvinsson、Anna Linusson、Scott J. Hultgren、Fredrik Almqvist

  DOI：10.1016/j.bmc.2012.01.048

  日期：2012.5

  Pilicides prevent pili formation and thereby the development of bacterial biofilms in Escherichia coli. We have performed a comprehensive structure activity relationship (SAR) study of the dihydrothiazolo ring-fused 2-pyridone pilicide central fragment by varying all open positions. Orthogonal projections to latent structures discriminant analysis (OPLS-DA) was used to distinguish active from inactive compounds in which polarity proved to be the most important factor for discrimination. A quantitative SAR (QSAR) partial least squares (PLS) model was calculated on the active compounds for prediction of biofilm inhibition activity. In this model, compounds with high inhibitory activity were generally larger, more lipophilic, more flexible and had a lower HOMO. Overall, this resulted in both highly valuable SAR information and potent inhibitors of type 1 pili dependent biofilm formation. The most potent biofilm inhibitor had an EC50 of 400 nM. (C) 2012 Published by Elsevier Ltd.