1,2-Pentamethylene-5-nitro-1,2-dihydro-3H-indazol-3-one | 106158-03-6

• 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: 1,2-Pentamethylene-5-nitro-1,2-dihydro-3H-indazol-3-one
• 英文别名: 2-nitro-7,8,9,10-tetrahydro-6H,12H-<1,2>diazepino<1,2-a>indazol-12-one；2-nitro-7,8,9,10-tetrahydro-[1,2]diazepino[1,2-a]indazol-12(6H)-one；2-nitro-7,8,9,10-tetrahydro-6H,12H-[1,2]diazepino[1,2-a]indazol-12-one；2-nitro-7,8,9,10-tetrahydro-6H-diazepino[1,2-a]indazol-12-one
• CAS: 106158-03-6
• 化学式: C₁₂H₁₃N₃O₃
• 分子量: 247.254
• InChiKey: FXWLITZBMJHUCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-nitro-1H-indazole-1-spiro-1'-piperidin-3-ylio oxide 生成 1,2-Pentamethylene-5-nitro-1,2-dihydro-3H-indazol-3-one
  参考文献：
  名称：

  Stable indazol-3-ylio oxides by intramolecular cyclization of N',N'-disubstituted 2-halobenzohydrazides

  摘要：

  DOI：

  10.1016/s0040-4039(00)80187-2

文献信息

• Study of 5-nitroindazoles' anti-Trypanosoma cruzi mode of action: Electrochemical behaviour and ESR spectroscopic studies
  作者：Jorge Rodríguez、Alejandra Gerpe、Gabriela Aguirre、Ulrike Kemmerling、Oscar E. Piro、Vicente J. Arán、Juan Diego Maya、Claudio Olea-Azar、Mercedes González、Hugo Cerecetto

  DOI：10.1016/j.ejmech.2008.07.018

  日期：2009.4

  New indazole derivatives have been developed to know about structural requirements for adequate anti-Trypanosoma cruzi activity. In relation to position 1 of indazole ring, we have observed that a butylaminopentyl substituent (14) affords good activity, but N-oxidation of omega-tertiary amino moiety yields completely inactive compounds (17,18); the substituent at position 3 of indazole ring affects drastically the in vitro activity, 3-OH derivative 13 being completely inactive. On the other hand, since compound 22, denitro-analogue of active compound 4, does not show activity, the 5-nitro substituent of indazole ring seems to be essential. Intramolecular cyclization of side chain at position 1 also affords inactive compounds (19, 20). The electrochemical studies showed that the trypanocidal 5-nitroindazole derivatives yielded nitro-anion radical via one-electron process at physiological pH. This electrochemical behaviour occurs in the parasite according to ESR experiment with the T cruzi microsomal fraction showing that 5-nitroindazole derivatives suffer bio-reduction without reactive oxygen species generation. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Aran, Vicente J.; Asensio, Juan L.; Ruiz, Jose R., Journal of the Chemical Society. Perkin transactions I, 1993, # 10, p. 1119 - 1128
  作者：Aran, Vicente J.、Asensio, Juan L.、Ruiz, Jose R.、Stud, Manfred

  DOI：——

  日期：——
• Aran, V. J.; Stud, M.; Foces-Foces, C., Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 1743 - 1745
  作者：Aran, V. J.、Stud, M.、Foces-Foces, C.、Cano, F. H.、Martinez-Ripoll, M.

  DOI：——

  日期：——
• ARAN, V. J.;STUD, M.;FOCES-FOCES, C.;CANO, F. H.;MARTINEZ-RIPOLL, M., J. HETEROCYCL. CHEM., 1985, 22, N 6, 1743-1745
  作者：ARAN, V. J.、STUD, M.、FOCES-FOCES, C.、CANO, F. H.、MARTINEZ-RIPOLL, M.

  DOI：——

  日期：——
• RUIZ, JOSE R.;ARAN, VICENTE J.;STUD, MANFRED, TETRAHEDRON LETT., 29,(1988) N 6, 697-700
  作者：RUIZ, JOSE R.、ARAN, VICENTE J.、STUD, MANFRED

  DOI：——

  日期：——