3-methyl-2,3-dihydrooxazolo[3,2-b]indazole | 1227927-45-8

• 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-methyl-2,3-dihydrooxazolo[3,2-b]indazole
• 英文别名: 3-Methyl-2,3-dihydro-[1,3]oxazolo[3,2-b]indazole
• CAS: 1227927-45-8
• 化学式: C₁₀H₁₀N₂O
• 分子量: 174.202
• InChiKey: VFDUJYBGFGFBLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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-methyl-2,3-dihydrooxazolo[3,2-b]indazole 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 33.0h， 生成 1-((3-isopropylisoxazol-5-yl)methyl)-2-(1-(4-propyl-1H-1,2,3-triazol-1-yl)propan-2-yl)-1H-indazol-3(2H)
  参考文献：
  名称：

  戴维斯-贝鲁特反应：N1,N2-二取代-1H-吲唑酮通过1,6-亲电加成到3-烷氧基-2H-吲唑

  摘要：

  多种亲电子试剂（酸酐、酰氯、碳氯化物、磺酰氯和烷基溴）与 3-甲氧基-2 H-吲唑 ( 1a )、苯并恶嗪[3,2- b ]吲唑 ( 1d ) 和恶唑并 [3] 发生反应,2- b ]吲唑 ( 1e ) — 戴维斯-贝鲁特反应可用的底物 — 产生多种N 1 , N 2 -二取代-1 H-吲唑酮。对于某些亲电子试剂，吲唑1d的 AERORC（亲电子试剂的添加、开环和闭环）过程会导致形成吲唑并吲唑酮。这些N 1 的一个有趣方面, N 2 -二取代-1 H -吲唑酮是通过例如此处报道的叠氮-炔环加成化学实现多样化。

  DOI：

  10.1021/ol2010424
• 作为产物：
  描述：

  2-硝基苄溴 在 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 水 、 异丙醇 为溶剂， 反应 24.0h， 生成 3-methyl-2,3-dihydrooxazolo[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

文献信息

• 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.
• 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.
• The Davis–Beirut Reaction: <i>N</i>¹,<i>N</i>²-Disubstituted-1<i>H</i>-Indazolones via 1,6-Electrophilic Addition to 3-Alkoxy-2<i>H</i>-Indazoles
  作者：Wayne E. Conrad、Ryo Fukazawa、Makhluf J. Haddadin、Mark J. Kurth

  DOI：10.1021/ol2010424

  日期：2011.6.17

  A variety of electrophiles (anhydrides, acid chlorides, carbonochloridates, sulfonyl chlorides, and alkyl bromides) react with 3-methoxy-2H-indazole (1a), benzoxazin[3,2-b]indazole (1d), and oxazolino[3,2-b]indazole (1e) — substrates available by the Davis–Beirut reaction — to yield a diverse set of N1,N2-disubstituted-1H-indazolones. With certain electrophiles, an AERORC (Addition of the Electrophile

  多种亲电子试剂（酸酐、酰氯、碳氯化物、磺酰氯和烷基溴）与 3-甲氧基-2 H-吲唑 ( 1a )、苯并恶嗪[3,2- b ]吲唑 ( 1d ) 和恶唑并 [3] 发生反应,2- b ]吲唑 ( 1e ) — 戴维斯-贝鲁特反应可用的底物 — 产生多种N 1 , N 2 -二取代-1 H-吲唑酮。对于某些亲电子试剂，吲唑1d的 AERORC（亲电子试剂的添加、开环和闭环）过程会导致形成吲唑并吲唑酮。这些N 1 的一个有趣方面, N 2 -二取代-1 H -吲唑酮是通过例如此处报道的叠氮-炔环加成化学实现多样化。