5-氨基-1-苯基-1H-1,2,3-三唑-4-甲酰胺 | 20317-25-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-氨基-1-苯基-1H-1,2,3-三唑-4-甲酰胺
• 英文名称: 5-amino-1-phenyl-1,2,3-triazole-4-carboxamide
• 英文别名: 1-Phenyl-5-amino-1,2,3-triazol-carbonsaeure-(4)-amid；5-amino-1-phenyl-1H-1,2,3-triazole-4-carboxamide；5-amino-1-phenyltriazole-4-carboxamide
• CAS: 20317-25-3
• 化学式: C₉H₉N₅O
• mdl: MFCD00721182
• 分子量: 203.203
• InChiKey: OHURUUSZJHIVTO-UHFFFAOYSA-N

物化性质

• 熔点：
  170-171 °C (decomp)
• 沸点：
  472.6±48.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  99.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-氨基-1-苯基-1H-1,2,3-三唑-4-甲酰胺 在 magnesium oxide 、 palladium dichloride 氢气 、 N,N-二甲基苯胺 、 三氯氧磷 作用下， 以 乙醇 、 乙酸乙酯 、 苯 为溶剂， 反应 20.5h， 生成 5-methyl-3-phenyl-3H-1,2,3-triazolo<4,5-d>pyrimidine
  参考文献：
  名称：

  Higashino, Takeo; Sato, Susumu; Miyashita, Akira, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 12, p. 4803 - 4812

  摘要：

  DOI：
• 作为产物：
  描述：

  苯胺 在 盐酸 、 sodium azide 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 生成 5-氨基-1-苯基-1H-1,2,3-三唑-4-甲酰胺
  参考文献：
  名称：

  Design and synthesis of a novel class of carbonic anhydrase-IX inhibitor 1-(3-(phenyl/4-fluorophenyl)-7-imino-3H-[1,2,3]triazolo[4,5d]pyrimidin 6(7H)yl)urea

  摘要：

  Carbonic anhydrase IX (CAIX) is a promising target in cancer therapy especially in the case of hypoxia-induced tumors. The selective inhibition of CA isozymes is a challenging task in drug design and discovery process. Here, we performed fluorescence-binding studies and inhibition assay combined with molecular docking and molecular dynamics (MD) simulation analyses to determine the binding affinity of two synthesized triazolo-pyrimidine urea derived (TPUI and TPUII) compounds with CAIX and CAN. Fluorescence binding results are showing that molecule TPUI has an excellent binding-affinity for CAIX (k(D) = 0.048 mu M). The TPUII also exhibits an appreciable binding affinity (k(D) = 7.521 mu M) for CAIX. TPUI selectively inhibits CAIX as compared to TPUII in the 4-NPA assay. Docking studies show that TPUI is spatially well-fitted in the active site cavity of CAIX, and is involve in H-bond interactions with His94, His96, His119, Thr199 and Thr200. MD simulation studies revealed that TPUI efficiently binds to CAIX and essential active site residual interaction is consistent during the entire simulation of 40 ns. These studies suggest that TPUI appeared as novel class of CAIX inhibitor, and may be used as a lead molecule for the development of potent and selective CAIX inhibitor for the hypoxia-induced cancer therapy. (C) 2016 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jmgm.2016.01.006

文献信息

• Selective Synthesis of Functionally Substituted 1,2,3-Triazoles
  作者：T. V. Golobokova、A. G. Proidakov、V. N. Kizhnyaev

  DOI：10.1134/s1070428020030136

  日期：2020.3

  AbstractDifferent conditions were used to achieve selective formation of 4.5-disubstituted 1-aryl(hetaryl)-1,2,3-triazoles via cycloaddition of the corresponding enolates and aryl or hetaryl azides. Optimal conditions were found for the bromination of 1-(5-methyl-1-phenyl-1,2,3-triazol-4-yl)ethanone to obtain 2-bromo-1-(5-methyl-1-phenyl-1,2,3-triazol-4-yl)ethanone.

  摘要通过相应的烯醇化物和芳基或杂芳基叠氮化物的环加成反应，使用不同的条件来实现4.5-二取代的1-芳基（杂芳基）-1,2,3-三唑的选择性形成。找到了最佳的条件来溴化1-（5-甲基-1-苯基-1,2,3-三唑-4-基）乙酮以获得2-溴-1-（5-甲基-1-苯基-1） ，2,3-三唑-4-基）乙酮。
• Synthesis of Fused Pyrimidinones by Reaction of Aminoarenecarboxamide with Esters; Preparation of Pyrrolo[2,3-d]-, Thieno[2,3-d]-, Isoxazolo[5,4-d]-, and 1,2,3-Triazolo[4,5-d]-pyrimidinones, and Quinazoles
  作者：Akira Miyashita、Katsuhiro Fujimoto、Tomomi Okada、Takeo Higashino

  DOI：10.3987/com-95-s75

  日期：——

  Several fused pyrimidinones were synthesized by reaction of aminoarenecarboxamide with esters in moderate to good yields. In the presence of sodium ethoxide, treatments of 2-amino-1-phenyl-3-pyrrolecarboxamide(4, 5, and 6), 2-amino-3-thiophene-carboxamide (14), 3-amino-4-isoxazolecarboxamide (10 and 11), 4-amino-1,2,3-triazole-5-carboxamide (16), and o-aminobenzamide (18) with esters (3) such as ethyl formate (3a) and ethyl acetate (3b) led to the corresponding pyrrolo[2,3-d]- (7, 8, and 9), and thieno[2,3-d]pyrimidin-4(3H)-ones (15), isoxazolo[5,4-d]pyrimidin-4(5H)-ones (12 and 13), 1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-ones (17), and 4(3H)-quinazolones (19), respectively.
• Yamada et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1957, vol. 77, p. 452,455
  作者：Yamada et al.

  DOI：——

  日期：——
• Notes - Synthesis of Potential Anticancer Agents. V. Convenient Synthesis of 4(5)-Amino-5(4)-Carboxamido-1,2,3-Triazole
  作者：L. Bennett, Jr.、Harry Baker

  DOI：10.1021/jo01357a617

  日期：1957.6
• Synthesis and thermolysis of 4-substituted 5-azido-l-phenyl-l,2,3-triazoles
  作者：Gerrit L'abbé、Anna Vandendriessche、Suzanne Toppet

  DOI：10.1016/s0040-4020(01)85991-3

  日期：1988.1