3,4-Dihydro-2H-<1,3>oxazino<2,3-b>indazole | 106662-02-6

• 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: 3,4-Dihydro-2H-<1,3>oxazino<2,3-b>indazole
• 英文别名: 3,4-dihydro-2H-[1,3]oxazino[3,2-b]indazole；3,4-Dihydro-2H-[1,3]oxazino[2,3-b]indazole
• CAS: 106662-02-6
• 化学式: C₁₀H₁₀N₂O
• 分子量: 174.202
• InChiKey: VDSSYOZEQFVSDT-UHFFFAOYSA-N

物化性质

• 熔点：
  148-150 °C
• 沸点：
  360.5±11.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-Dihydro-2H-<1,3>oxazino<2,3-b>indazole 在 硫酸 作用下， 以 甲醇 为溶剂， 以52%的产率得到2-(3-hydroxypropyl)-1,2-dihydro-3H-indazol-3-one
  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
• 作为产物：
  描述：

  3-(2-nitrobenzylamino)propan-1-ol 在 potassium hydroxide 作用下， 以 水 为溶剂， 反应 24.0h， 生成 3,4-Dihydro-2H-<1,3>oxazino<2,3-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

文献信息

• Umsetzung von 1,2-Dihydro-3-indazolon mit ω-Dialkylaminoalkylhalogeniden und α,ω-Dihalogenalkanen
  作者：Herbert Oelschläger、Uwe Matthiesen、Mohammed Al Shaik

  DOI：10.1002/ardp.19863191012

  日期：——

  2‐Dihydro‐3‐indazolons in trockenem Dioxan mit ω‐Dialkylaminoalkylhalogeniden zu den analgetisch wirkenden basischen Lactimethern reagiert, entstehen bei der Umsetzung mit α, ω‐Dihalogenpropanen zwei basische Verbindungen, die als 3,4‐Dihydro‐2H‐(1,3)oxazino[2,2‐b]indazol (1) und 2,3‐Dihydro‐1H‐pyrazolo[1,2‐a]indazol‐9‐on (2) identifiziert wurden. 2 läßt sich mit LiAlH4 zu 2,3‐Dihydro‐1H, 9H‐pyrazolo [1

  1,2-二氢-3-吲唑酮的 K 盐在干燥的二恶烷中与 ω-二烷基氨基烷基卤化物反应形成具有镇痛作用的碱性内酯，而与 α, ω-二卤丙烷的反应产生两种碱性化合物，称为3,4-二氢-2H-(1,3)恶嗪基[2,2-b]吲唑(1)和2,3-二氢-1H-吡唑并[1,2-a]吲唑-9-酮(2)被识别。2 可以用 LiAlH4 还原为 2,3-二氢-1H, 9H-吡唑并 [1, 2-a] 吲唑 (5)。
• An Oxazolo[3,2-<i>b</i>]indazole Route to 1<i>H</i>-Indazolones
  作者：James S. Oakdale、Danielle M. Solano、James C. Fettinger、Makhluf J. Haddadin、Mark J. Kurth

  DOI：10.1021/ol900891s

  日期：2009.7.2

  The novel heterocycle 2,3-dihydrooxazolo[3,2-b]indazole has been synthesized and utilized to provide easy access to 1H-indazolones, particularly the previously unreported 2-(2-alkoxyethyl)-1H-indazol-3(2H)-ones. Mechanistic as well as optimization and reaction scope studies are reported.
• Nucleophilic Substitution of Oxazino-/Oxazolino-/Benzoxazin [3,2-<i>b</i>]indazoles: An Effective Route to 1<i>H</i>-Indazolones
  作者：Michael B. Donald、Wayne E. Conrad、James S. Oakdale、Jeffrey D. Butler、Makhluf J. Haddadin、Mark J. Kurth

  DOI：10.1021/ol100751n

  日期：2010.6.4

  A variety of nucleophiles, thiolates, alkoxides, amines, iodide, and cyanide, react with oxazino-, oxazolino-, and benzoxazin[3,2-b]indazoles under microwave conditions to yield a diverse set of 2-substituted 1H-indazolones. The synthetic utility of these indazoles is further demonstrated by ANRORC (addition of the nucleophile, ring-opening, and ring closure) reactions to yield isomeric pyrazoloindazolones by a process wherein iodide acts first as a nucleophile and subsequently as a leaving group.
• OELSCHLAEGER H.; MATTHIESEN U.; SHAIK M. AL., ARCH. PHARM., 319,(1986) N 10, 939-944
  作者：OELSCHLAEGER H.、 MATTHIESEN U.、 SHAIK M. AL.

  DOI：——

  日期：——