5-nitro-3-(tetrahydro-2H-pyran-2-yl)-3,6-dihydropyrazolo[3,4-c]carbazole | 1445376-72-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-nitro-3-(tetrahydro-2H-pyran-2-yl)-3,6-dihydropyrazolo[3,4-c]carbazole
• 英文别名: indazole
• CAS: 1445376-72-6
• 化学式: C₁₈H₁₆N₄O₃
• 分子量: 336.35
• InChiKey: NVGYNVRCCUUVHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  85.98
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-nitro-3-(tetrahydro-2H-pyran-2-yl)-3,6-dihydropyrazolo[3,4-c]carbazole 在 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 以82%的产率得到5-nitro-3,6-dihydropyrazolo[3,4-c]carbazole
  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 、 copper(l) iodide 、 四(三苯基膦)钯 、 水 、 碘 、 铜 、 sodium carbonate 、 potassium carbonate 、 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 、 乙醇 、 二氯甲烷 、 二丁醚 、 水 、 二甲基亚砜 、 甲苯 为溶剂， 反应 32.5h， 生成 5-nitro-3-(tetrahydro-2H-pyran-2-yl)-3,6-dihydropyrazolo[3,4-c]carbazole
  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 and biological activity of pyrazole analogues of the staurosporine aglycon K252c
  作者：Yannick J. Esvan、Francis Giraud、Elisabeth Pereira、Virginie Suchaud、Lionel Nauton、Vincent Théry、Lyubov G. Dezhenkova、Dmitry N. Kaluzhny、Vsevolod N. Mazov、Alexander A. Shtil、Fabrice Anizon、Pascale Moreau

  DOI：10.1016/j.bmc.2016.05.032

  日期：2016.7

  isoforms 1–3 whereas it did not impair the activity of two known targets of K252c, protein kinase C isoforms α and γ. Compound 3 exhibited moderate cytotoxic activity toward human leukemia and colon carcinoma cell lines (K562 and HCT116), strongly suggesting that this new scaffold deserves further investigations for treatment of malignancies associated with Pim activity.

  合成了星形孢菌素糖苷配基（K252c）的衍生物，其中内酰胺环被吡唑部分取代。生成的吲哚并吡唑并咔唑（3）抑制了Pim同工型1-3，但并未损害K252c的两个已知靶标蛋白激酶C同工型α和γ的活性。化合物3对人白血病和结肠癌细胞系（K562和HCT116）表现出中等的细胞毒活性，强烈表明这种新支架值得进一步研究以治疗与Pim活性相关的恶性肿瘤。