5-azido-1H-indazole | 20376-99-2

• 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: 5-azido-1H-indazole
• CAS: 20376-99-2
• 化学式: C₇H₅N₅
• 分子量: 159.15
• InChiKey: LYOBLOSSFBVVFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-azido-1H-indazole 在 氢氧化钾 、 碘 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以95.5%的产率得到5-叠氮基-3-碘-1H-吲唑
  参考文献：
  名称：

  The design and synthesis of YC-1 analogues as probes for soluble guanylate cyclase

  摘要：

  Soluble guanylate cyclase (sGC) is highly activated in the presence of both YC-1 (1-benzyl-3-(5'-hydroxymethyl-2'-furyl)indazole) and CO. In this report, the design, synthesis, and activity (i.e., sGC activation) of photolabile analogues of 3-(5'-hydroxymethyl-2'-furyl)-1-benzylindazole (YC-1) are presented. Initial results with 6-azido-3-(5'-hydroxymethyl-2-furyl)-1-benzylindazole led to the synthesis of a tritium-labeled analogue. When photoactivated, this analogue labeled the alpha-subunit of sGC. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.093
• 作为产物：
  描述：

  在 sodium azide 、 亚硝酸特丁酯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 5-azido-1H-indazole
  参考文献：
  名称：

  Discovery and structure-activity relationship studies of 1-aryl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives as potent dual inhibitors of indoleamine 2,3-dioxygenase 1 (IDO1) and trytophan 2,3-dioxygenase (TDO)

  摘要：

  Indoleamine 2,3-dioxygenase 1 (IDO1) and tryptophan 2,3-dioxygenase (TDO), which mediate kynurenine pathway of tryptophan degradation, have emerged as potential new targets in immunotherapy for treatment of cancer because of their critical role in immunosuppression in the tumor microenvironment. In this investigation, we report the structural optimization and structure-activity relationship studies of 1-phenyl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione derivatives as a new class of IDO1/TDO dual inhibitors. Among all the obtained dual inhibitors, 1-(3-chloro-4-fluorophenyl)-6-fluoro-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione (38) displayed the most potent IDO1 and TDO inhibitory activities with IC₅₀ (half-maximal inhibitory concentration) values of 5 nM for IDO1 and 4 nM for TDO. It turned out that compound 38 was not a PAINS compound. Compound 38 could efficiently inhibit the biofunction of IDO1 and TDO in intact cells. In LL2 (Lewis lung cancer) and Hepa1-6 (hepatic carcinoma) allograft mouse models, this compound also showed considerable in vivo anti-tumor activity and no obvious toxicity was observed. Therefore, 38 could be a good lead compound for cancer immunotherapy and deserving further investigation.

  DOI：

  10.1016/j.ejmech.2020.112703

文献信息

• Syntheses of heterocyclic compounds, part XXI. Oxazoles from pyrolysis of aryl and heterocyclic azides in a mixture of acetic and polyphosphoric acid
  作者：E. B. Mullock、H. Suschitzky

  DOI：10.1039/j39680001937

  日期：——

  Pyrolysis of 2-azido-naphthalene, -anthraquinone, and various azido-heterocycles in a mixture of polyphosphoric and acetic acid results in fusion of an oxazolo-moiety on to the parent system. The scope of this convenient oxazole synthesis in its widest sense is discussed.

  在多磷酸和乙酸的混合物中2-叠氮基萘，蒽醌和各种叠氮基杂环的热解导致恶唑基部分融合到母体系统上。从最广泛的意义上讨论了这种方便的恶唑合成的范围。
• Heterocyclic modulators of PKB
  申请人：ZENG Qingping

  公开号：US20090275592A1

  公开（公告）日：2009-11-05

  The invention relates to heterocyclic compounds of Formula I and compositions thereof useful for treating diseases mediated by protein kinase B (PKB) where the variables have the definitions provided herein. The invention also relates to the therapeutic use of such compounds and compositions thereof in treating disease states associated with abnormal cell growth, cancer, inflammation, and metabolic disorders.

  本发明涉及一种公式I的杂环化合物及其组合物，其中变量具有本文所提供的定义，其在治疗由蛋白激酶B（PKB）介导的疾病方面具有用途。本发明还涉及这种化合物和组合物在治疗与异常细胞生长、癌症、炎症和代谢紊乱相关的疾病状态方面的治疗用途。
• [EN] HETEROCYCLIC MODULATORS OF PKB<br/>[FR] MODULATEURS HÉTÉROCYCLIQUES DE PKB
  申请人：AMGEN INC

  公开号：WO2009011880A3

  公开（公告）日：2009-04-02
• (1,2,3-Triazol-4-yl)benzenamines: Synthesis and activity against VEGF receptors 1 and 2
  作者：Alexander S. Kiselyov、Marina Semenova、Victor V. Semenov

  DOI：10.1016/j.bmcl.2009.01.046

  日期：2009.3

  Derivatives of (1,2,3-triazol-4-yl) benzenamines are described as potent and ATP-competitive inhibitors of vascular endothelial growth factor receptors I and II (VEGFR-1/2). A number of compounds exhibited VEGFR-2 and VEGFR-1 inhibitory activity comparable to that of Vatalanib (TM) in both HTRF enzymatic and cellular assays. (C) 2009 Elsevier Ltd. All rights reserved.
• Novel VEGFR-2 kinase inhibitors identified by the back-to-front approach
  作者：Kingkan Sanphanya、Suvara K. Wattanapitayakul、Suwadee Phowichit、Valery V. Fokin、Opa Vajragupta

  DOI：10.1016/j.bmcl.2013.03.042

  日期：2013.5

  We report a novel VEGFR-2 inhibitor, developed by the back-to-front approach. Docking experiments indicated that the 3-chloromethylphenylurea motif of the lead compound occupied the back pocket of VEGFR-2 kinase. An attempt was made to enhance the binding affinity of 1 by expanding the structure to access the front pocket using a triazole linker. A library of 1,4-(disubstituted)-1H-1,2,3-triazoles were screened in silico, and one compound (VH02) was identified with an IC50 against VEGFR-2 of 0.56 mu M. VH02 showed antiangiogenic effects, inhibiting tube formation in HUVEC cells (EA.hy926) at 0.3 mu M, 13 times lower than its cytotoxic dose. These enzymatic and cellular activities suggest that VH02 has potential as a lead for further optimization. (C) 2013 Elsevier Ltd. All rights reserved.