5-叠氮基-1H-吲唑 | 20377-00-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 5-叠氮基-1H-吲唑
• 英文名称: 5-azido-1H-indazole
• 英文别名: 6-azido-1H-indazole；6-azidoindazole；6-azido-1H-indazole；6-Azido-1H-indazol
• CAS: 20377-00-8
• 化学式: C₇H₅N₅
• 分子量: 159.15
• InChiKey: CXCLSRHPGZIRJB-UHFFFAOYSA-N

物化性质

• 熔点：
  157-159 °C(Solv: benzene (71-43-2))

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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-叠氮基-1H-吲唑 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6-azido-3-iodoindazole
  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：

  6-氨基吲唑 在 盐酸 、 sodium acetate 、 sodium nitrite 、 sodium azide 作用下， 以 水 为溶剂， 反应 1.0h， 以90%的产率得到5-叠氮基-1H-吲唑
  参考文献：
  名称：

  Novel VEGFR-2 kinase inhibitors identified by the back-to-front approach

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2013.03.042

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。
• On the mechanism for the photooxidation of aromatic azides containing a secondary N–H bond: A sequence of intramolecular transformations with the formation of heterocyclic oximes
  作者：Ekaterina Chainikova、Sergey Khursan、Alfia Yusupova、Alexander Lobov、Marat Abdullin、Rustam Safiullin

  DOI：10.1016/j.tetlet.2018.07.034

  日期：2018.8

  During the photooxidation of aromatic azides containing a secondary N–H bond at the para-position, a sequence of intramolecular transformations of nitroso oxides led to the formation of heterocyclic oximes along with the corresponding nitroso and nitro compounds.

  期间包含在二次N-H键的芳族叠氮化物的光氧化对-位，导致与相应的亚硝基和硝基化合物沿着杂环肟的形成亚硝基氧化物的分子内的变换的序列。
• Synthesis and photolysis of azido-benzo[b]thiophens, -benzothiazoles, -benzimidazoles, and -indazoles: novel 6,7-diamino-benzothiazoles, -benzimidazoles, and -indazoles and 6-diethylamino-8H-thiazolo [5,4-c]azepines
  作者：Peter T. Gallagher、Brian Iddon、Hans Suschitzky

  DOI：10.1039/p19800002362

  日期：——

  an excess of a secondary amine gave either the corresponding 6,7-diaminobenzothiazole (14)–(20), a 6-amino-8H-thiazolo[5,4-c]azepine (21)–(24), a mixture of both, or intractable material [as in the case of azide (9)]. Irradiation of 7-azido-3-methylbenzo[b]thiophen in an excess of diethylamine gave 7-amino-3-methylbenzo[b]thiophen and a trace of 3,3′-dimethyl-7,7′-azobenzo[b]thiophen. 6-Azidoindazole

  在过量仲胺存在下照射6-叠氮基苯并噻唑（4）-（9）（参见方案），得到相应的6,7-二氨基苯并噻唑（14）-（20），即6-氨基-8 H-噻唑并[5,4- c ]氮杂（21）-（24），两者的混合物或难处理的物质[如叠氮化物（9）的情况]。7-叠氮基-3-甲基苯并[照射b ]在过量的二乙胺的噻吩，得到7-氨基-3-甲基苯并[ b ]噻吩和3,3'-二甲基-7,7'- azobenzo痕量[ b]噻吩。6-叠氮基吲唑生成7-氨基-6-二乙基氨基吲唑（32）和5（6）-叠氮基苯并咪唑生成4（7）-氨基-5（6）-二乙基氨基苯并咪唑（33）和5（6）-氨基-4的混合物（7）-二乙氨基苯并咪唑（34）。将6-叠氮基苯并噻唑或其2-甲基衍生物在甲醇氧化物甲醇-二恶烷混合物中进行光解，分别得到相应的6-甲氧基-8 H-噻唑并[5,4- c ] a庚因，分别为（30）或（31）。
• [EN] APPLICATION OF FSO2N3 IN PREPARATION OF AZIDE<br/>[FR] UTILISATION DE FSO2N3 DANS LA PRÉPARATION D'AZIDE<br/>[ZH] FSO 2N 3在制备叠氮化合物中的应用
  申请人：SHANGHAI INSITITUTE OF ORGANIC CHEMISTRY CHINESE ACAD OF SCIENCES

  公开号：WO2019238057A1

  公开（公告）日：2019-12-19

  一种FSO2N3在制备叠氮化合物中的应用，使用FSO2N3进行重氮转移反应(diazo transfer)，可从一级胺基化合物(包括一级烷基胺类化合物(R-NH2)，(杂)芳基胺类化合物(Ar-NH2)或磺酰胺类化合物(RSO2NH2))快速、安全、高收率地制备对应的叠氮化合物(R-N3，Ar-N3或RSO2N3)；且操作简单、高效。
• GALLAGHER P. T.; IDDON B.; SUSCHITZKY H., J. CHEM. SOC. PERKIN TRANS., PART 1, 1980, NO 11, 2362-2370
  作者：GALLAGHER P. T.、 IDDON B.、 SUSCHITZKY H.

  DOI：——

  日期：——