6-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine | 1334217-93-4

• 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: 6-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine
• 英文别名: 6-Nitro-1-(oxan-2-yl)indazol-5-amine
• CAS: 1334217-93-4
• 化学式: C₁₂H₁₄N₄O₃
• 分子量: 262.268
• InChiKey: NTDGISVXKBQIDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  98.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine 在 盐酸 、 platinum(IV) oxide 、 copper(l) iodide 、 四(三苯基膦)钯 、 氢气 、 碘 、 铜 、 sodium carbonate 、 potassium carbonate 作用下， 以 乙醇 、 二丁醚 、 水 、 二甲基亚砜 、 乙酸乙酯 、 甲苯 为溶剂， 反应 67.0h， 生成 9-methoxy-3,6-dihydropyrazolo[3,4-c]carbazol-5-amine
  参考文献：
  名称：

  Identification of 1,6-dihydropyrazolo[4,3-c]carbazoles and 3,6-dihydropyrazolo[3,4-c]carbazoles as new Pim kinase inhibitors

  摘要：

  New 1,6-dihydropyrazolo[4,3-c]carbazoles and 3,6-dihydropyrazolo[3,4-c]carbazoles were prepared and evaluated for their Pim kinase inhibitory potencies as well as their antiproliferative activities toward two prostatic cancer cell lines. Pyrazolocarbazole 15a was found to be a potent Pim kinase modulator with inhibitory potency toward the three isoforms. Compound 6c strongly inhibited Pim-3 with weaker effect toward Pim-1 and Pim-2, and thus could be used as an interesting molecular tool to study Pim-3 biological functions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.011
• 作为产物：
  描述：

  5-溴-6-硝基-1H-吲唑 在 盐酸 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 水 、 对甲苯磺酸 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 6.5h， 生成 6-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine
  参考文献：
  名称：

  Identification of 1,6-dihydropyrazolo[4,3-c]carbazoles and 3,6-dihydropyrazolo[3,4-c]carbazoles as new Pim kinase inhibitors

  摘要：

  New 1,6-dihydropyrazolo[4,3-c]carbazoles and 3,6-dihydropyrazolo[3,4-c]carbazoles were prepared and evaluated for their Pim kinase inhibitory potencies as well as their antiproliferative activities toward two prostatic cancer cell lines. Pyrazolocarbazole 15a was found to be a potent Pim kinase modulator with inhibitory potency toward the three isoforms. Compound 6c strongly inhibited Pim-3 with weaker effect toward Pim-1 and Pim-2, and thus could be used as an interesting molecular tool to study Pim-3 biological functions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.011

文献信息

• Synthesis of 1,6-dihydropyrrolo[2,3-g]indazoles using Larock indole annulation
  作者：Laurent Gavara、Fabrice Anizon、Pascale Moreau

  DOI：10.1016/j.tet.2011.07.029

  日期：2011.9

  The synthesis of 1,6-dihydropyrrolo[2,3-g]indazole derivatives is described. The indolic ring system is constructed via a Larock palladium-catalyzed annulation using terminal and internal alkynes. Additionally, when using internal alkynes for this reaction, we found that a directing effect on regioselectivity was mediated by the ester group of alkyl 3-substituted propiolate derivatives. (C) 2011 Elsevier Ltd. All rights reserved.