5-oxo-8-cyclopropyl-7-(2-(1,3,5,7-tetramethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene-8-yl)ethyl)-3,5-dihydro-2H-thiazolo[3,2-a]pyridine-3-carboxylic acid | 1487164-52-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-oxo-8-cyclopropyl-7-(2-(1,3,5,7-tetramethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene-8-yl)ethyl)-3,5-dihydro-2H-thiazolo[3,2-a]pyridine-3-carboxylic acid
• 英文别名: 8-Cyclopropyl-7-[2-(2,2-difluoro-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-8-yl)ethyl]-5-oxo-2,3-dihydro-[1,3]thiazolo[3,2-a]pyridine-3-carboxylic acid
• CAS: 1487164-52-2
• 化学式: C₂₆H₂₈BF₂N₃O₃S
• 分子量: 511.4
• InChiKey: GCPWPAATVFGDLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  90.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-oxo-8-cyclopropyl-7-(2-(1,3,5,7-tetramethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene-8-yl)ethyl)-3,5-dihydro-2H-thiazolo[3,2-a]pyridine-3-carboxylic acid 、 3-甲基苯胺 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 以14 mg的产率得到8-cyclopropyl-7-((2-(1,3,5,7-tetramethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene-8-yl)ethyl))-5-oxo-N-(3-methylphenyl)-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyridine-3-carboxamide
  参考文献：
  名称：

  Thiazolino 2-Pyridone Amide Inhibitors ofChlamydia trachomatisInfectivity

  摘要：

  The bacterial pathogen Chlamydia trachomatis is a global health burden currently treated with broad-spectrum antibiotics which disrupt commensal bacteria. We recently identified a compound through phenotypic screening that blocked infectivity of this intracellular pathogen without host cell toxicity (compound 1, KSK 120). Herein, we present the optimization of 1 to a class of thiazolino 2-pyridone amides that are highly efficacious (EC50 <= 100 nM) in attenuating infectivity across multiple serovars of C. trachomatis without host cell toxicity. The lead compound 21a exhibits reduced lipophilicity versus 1 and did not affect the growth or viability of representative commensal flora at 50 mu M. In microscopy studies, a highly active fluorescent analogue 37 localized inside the parasitiphorous inclusion, indicative of a specific targeting of bacterial components. In summary, we present a class of small molecules to enable the development of specific treatments for C. trachomatis.

  DOI：

  10.1021/acs.jmedchem.5b01759
• 作为产物：
  描述：

  4-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-4-hydroxybutyric acid benzyl ester 在 草酰氯 、 1,4-环己二烯 、 10 wt% Pd(OH)2 on carbon 、 水 、 三乙胺 、 三氟乙酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 28.21h， 生成 5-oxo-8-cyclopropyl-7-(2-(1,3,5,7-tetramethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene-8-yl)ethyl)-3,5-dihydro-2H-thiazolo[3,2-a]pyridine-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of Fluorescent Ring-Fused 2-Pyridone Peptidomimetics

  摘要：

  Thiazolino fused 2-pyridone peptidomimetics are of significant biological importance due to their ability to interfere with adhesive fiber formation in uropathogenic Escherichia coli and oligomerization of amyloid fibers. We have developed an efficient synthetic route to fluorescent BODIPY analogues, with structural diversification from a key intermediate enabling introduction of C-2 substituents and late incorporation of the BODIPY moiety. A mild lithium halide mediated hydrolysis enabled preparation of peptidomimetic fluorophores with useful photophysical properties for further chemical biology applications.

  DOI：

  10.1021/jo401844y