(3R)-7-(benzo[d][1,3]dioxol-5-ylmethyl)-8-methoxy-5-oxo-3,5-dihydro-2H-thiazolo[3,2-a]pyridine-3-carboxylic acid | 1374967-57-3

• 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[d][1,3]dioxol-5-ylmethyl)-8-methoxy-5-oxo-3,5-dihydro-2H-thiazolo[3,2-a]pyridine-3-carboxylic acid
• 英文别名: (3R)-7-(1,3-benzodioxol-5-ylmethyl)-8-methoxy-5-oxo-2,3-dihydro-[1,3]thiazolo[3,2-a]pyridine-3-carboxylic acid
• CAS: 1374967-57-3
• 化学式: C₁₇H₁₅NO₆S
• 分子量: 361.375
• InChiKey: SULNWOVGSSWEEF-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (3R)-7-(benzo[d][1,3]dioxol-5-ylmethyl)-8-methoxy-5-oxo-3,5-dihydro-2H-thiazolo[3,2-a]pyridine-3-carboxylic acid
  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

• [EN] 2,3-DIHYDRO-THIAZOLO[3,2-A]PYRIDIN-5-ONE DERIVATIVES, INTERMEDIATES THEREOF, AND THEIR USE AS ANTIBACERIAL AGENTS<br/>[FR] DÉRIVÉS DE 2,3-DIHYDRO-THIAZOLO [3,2-A] PYRIDIN-5-ONE, LEURS INTERMÉDIAIRES ET LEUR UTILISATION COMME AGENTS ANTIBACTÉRIENS
  申请人：QURETECH BIO AB

  公开号：WO2016075296A1

  公开（公告）日：2016-05-19

  The disclosure relates to certain novel substituted ring-fused thiazolino 2- pyridones of Formula I, to processes for preparing such compounds, to their use in treating a bacterial infection such as a Chlamydia infection, to methods for their therapeutic use and to pharmaceutical compositions containing them.

  该披露涉及某些新型取代环融合噻唑烷基吡啶酮化合物，其化学式为I，涉及制备这类化合物的过程，以及它们在治疗细菌感染，如沙眼衣原体感染中的用途，涉及它们的治疗用途方法以及含有它们的药物组合物。
• 2,3-dihydro-thiazolo[3,2-A]pyridin-5-one derivatives, intermediates thereof, and their use as antibacterial agents
  申请人：Quretech Bio AB

  公开号：US10294244B2

  公开（公告）日：2019-05-21

  The disclosure relates to certain novel substituted ring-fused thiazolino 2-pyridines of Formula I, to processes for preparing such compounds, to their use in treating a bacterial infection such as Chlamydia infection, to methods for their therapeutic use and to pharmaceutical compositions containing them.

  本公开涉及式 I 的某些新型取代环融噻唑 2-吡啶、制备此类化合物的工艺、它们在治疗衣原体感染等细菌感染中的用途、它们的治疗方法以及含有它们的药物组合物。
• 2,3-DIHYDRO-THIAZOLO[3,2-A]PYRIDIN-5-ONE DERIVATIVES, INTERMEDIATES THEREOF, AND THEIR USE AS ANTIBACERIAL AGENTS
  申请人：Quretech Bio AB

  公开号：EP3218382A1

  公开（公告）日：2017-09-20
• 2,3-Dihydro-Thiazolo[3,2-A]Pyridin-5-One Derivatives, Intermediates Thereof, and Their Use as Antibacterial Agents
  申请人：Quretech Bio AB

  公开号：US20170334931A1

  公开（公告）日：2017-11-23

  The disclosure relates to certain novel substituted ring-fused thiazolino 2-pyridines of Formula I, to processes for preparing such compounds, to their use in treating a bacterial infection such as Chlamydia infection, to methods for their therapeutic use and to pharmaceutical compositions containing them.