2,3-dihydrothiazolo[3,2-b]indazole | 27006-94-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 2,3-dihydrothiazolo[3,2-b]indazole
• 英文别名: 2,3-Dihydro-[1,3]thiazolo[3,2-b]indazole
• CAS: 27006-94-6
• 化学式: C₉H₈N₂S
• 分子量: 176.242
• InChiKey: QSKICCHAGXIDGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dihydrothiazolo[3,2-b]indazole 在 sodium tungstate (VI) dihydrate 、 双氧水 作用下， 以 水 、 乙酸乙酯 为溶剂， 以99%的产率得到2,3-dihydrothiazolo[3,2-b]indazole 1,1-dioxide
  参考文献：
  名称：

  Davis–Beirut Reaction: Route to Thiazolo-, Thiazino-, and Thiazepino-2H-indazoles

  摘要：

  Methods for the construction of thiazolo-, thiazino-, and thiazepino-2H-indazoles from o-nitrobenzaldehydes or o-nitrobenzyl bromides and S-trityl-protected 1 degrees-aminothioalkanes are reported. The process consists of formation of the requisite N-(2-nitrobenzyl) (tritylthio)alkylamine, subsequent deprotection of the trityl moiety with TFA, and immediate treatment with aq. KOH in methanol under Davis-Beirut reaction conditions to deliver the target thiazolo-, thiazino-, or thiazepino-2H-indazole in good overall yield. Subsequent S-oxidation gives the corresponding sulfone.

  DOI：

  10.1021/jo501014e
• 作为产物：
  描述：

  在 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以92 mg的产率得到2,3-dihydrothiazolo[3,2-b]indazole
  参考文献：
  名称：

  Inhibition of myeloperoxidase: Evaluation of 2H-indazoles and 1H-indazolones

  摘要：

  Myeloperoxidase (MPO) produces hypohalous acids as a key component of the innate immune response; however, release of these acids extracellularly results in inflammatory cell and tissue damage. The twostep, one-pot Davis-Beirut reaction was used to synthesize a library of 2H-indazoles and 1H-indazolones as putative inhibitors of MPO. A structure-activity relationship study was undertaken wherein compounds were evaluated utilizing taurine-chloramine and MPO-mediated H2O2 consumption assays. Docking studies as well as toxicophore and Lipinski analyses were performed. Fourteen compounds were found to be potent inhibitors with IC50 values < 1 mu M, suggesting these compounds could be considered as potential modulators of pro-oxidative tissue injury pertubated by the inflammatory MPO/H2O2/HOCl/HOBr system. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.09.044