7,8-dihydro-[1,3]dioxolo[4,5-f]thiazolo[3,2-b]indazole | 1620514-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 7,8-dihydro-[1,3]dioxolo[4,5-f]thiazolo[3,2-b]indazole
• 英文别名: 7,8-Dihydro-[1,3]dioxolo[4,5-f]thiazolo[3,2-b]indazole；4,6-dioxa-11-thia-14,15-diazatetracyclo[7.6.0.03,7.010,14]pentadeca-1(15),2,7,9-tetraene
• CAS: 1620514-67-1
• 化学式: C₁₀H₈N₂O₂S
• 分子量: 220.252
• InChiKey: FKXVOMMOWFNETA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7,8-dihydro-[1,3]dioxolo[4,5-f]thiazolo[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91%的产率得到7,8-dihydro-[1,3]dioxolo[4,5-f]thiazolo[3,2-b]indazole 9,9-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：

  6-硝基胡椒醛 在 三乙基硅烷 、 sodium cyanoborohydride 、 三氟乙酸 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 0.5h， 生成 7,8-dihydro-[1,3]dioxolo[4,5-f]thiazolo[3,2-b]indazole
  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

文献信息

• Inhibition of myeloperoxidase: Evaluation of 2H-indazoles and 1H-indazolones
  作者：Aaron Roth、Sean Ott、Kelli M. Farber、Teresa A. Palazzo、Wayne E. Conrad、Makhluf J. Haddadin、Dean J. Tantillo、Carroll E. Cross、Jason P. Eiserich、Mark J. Kurth

  DOI：10.1016/j.bmc.2014.09.044

  日期：2014.11

  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.
• Davis–Beirut Reaction: Route to Thiazolo-, Thiazino-, and Thiazepino-2<i>H</i>-indazoles
  作者：Kelli M. Farber、Makhluf J. Haddadin、Mark J. Kurth

  DOI：10.1021/jo501014e

  日期：2014.8.1

  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.