1(2)H-tetrazole-5-carboxylic acid 3-acetyl-5-cyano-2-hydroxy-anilide | 70977-44-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1(2)H-tetrazole-5-carboxylic acid 3-acetyl-5-cyano-2-hydroxy-anilide
• 英文别名: 3'-acetyl-5'-cyano-2'-hydroxytetrazole-5-carboxanilide；3'-Acetyl-5'-cyano-2'-hydroxytetrazol-5-carboxanilid；N-(3-acetyl-5-cyano-2-hydroxyphenyl)-2H-tetrazole-5-carboxamide
• CAS: 70977-44-5
• 化学式: C₁₁H₈N₆O₃
• 分子量: 272.223
• InChiKey: VTZCCDKZXZLZTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  145
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-乙酰基-4-氰基苯酚 在 palladium on activated charcoal 吡啶 、 草酰氯 、 硫酸 、 氢气 、 硝酸 作用下， 以 乙醇 为溶剂， 反应 0.83h， 生成 1(2)H-tetrazole-5-carboxylic acid 3-acetyl-5-cyano-2-hydroxy-anilide
  参考文献：
  名称：

  Synthesis and quantitative structure-activity relationships of antiallergic 2-hydroxy-N-(1H-tetrazol-5-yl)benzamides and N-(2-hydroxyphenyl)-1H-tetrazole-5-carboxamides

  摘要：

  The synthesis and antiallergic activity of a series of 2-hydroxy-N-1H-tetrazol-5-ylbenzamides and isomeric N-(2-hydroxyphenyl)-1H-tetrazole-5-carboxamides is described. A relationship between structure and intravenous antiallergic activity in the rat passive cutaneous anaphylaxis (PCA) test has been established using a Hansch/Free-Wilson model and used to direct studies toward potent derivatives. The contribution of physicochemical properties to activity is discussed. One member of this series, N-(3-acetyl-5-fluoro-2-hydroxyphenyl)-1H-tetrazole-5-carboxamide (3f), which was selected for further evaluation, has an ID50 value of 0.16 mg/kg po and is 130 times more potent than disodium cromoglycate (DSCG) on intravenous administration.

  DOI：

  10.1021/jm00154a019

文献信息

• New chemical process
  申请人：MAY & BAKER LIMITED

  公开号：EP0323885A1

  公开（公告）日：1989-07-12

  A process for the preparation of a di(alkali metal) salt of tetrazole-5-carboxylic acid comprises the reaction, in an anhydrous tertiary amine base medium containing a strong acid, of an alkali metal azide with an alkyl cyanoformate followed, without isolation of the alkyl tetrazole-5-carboxylate thus produced, by reaction in situ with an alkali metal hydroxide: the alkali metal salt of tetrazole-5-carboxylic acid obtained can be used to prepare pharmaceuticals.

  制备四氮唑-5-羧酸二（碱金属）盐的工艺包括：在含有强酸的无水叔胺碱介质中，碱金属叠氮化物与氰基甲酸烷基酯反应，然后与碱金属氢氧化物就地反应，而不分离由此生成的四氮唑-5-羧酸烷基酯：得到的四氮唑-5-羧酸碱金属盐可用于制备药物。
• FORD, E.;KNOWLES, PH.;LUNT, E.;MARSHALL, S. M.;PENROSE, A. J.;RAMSDEN, A.+, J. MED. CHEM., 1986, 29, N 4, 538-549
  作者：FORD, E.、KNOWLES, PH.、LUNT, E.、MARSHALL, S. M.、PENROSE, A. J.、RAMSDEN, A.+

  DOI：——

  日期：——
• US4442115A
  申请人：——

  公开号：US4442115A

  公开（公告）日：1984-04-10
• Synthesis and quantitative structure-activity relationships of antiallergic 2-hydroxy-N-(1H-tetrazol-5-yl)benzamides and N-(2-hydroxyphenyl)-1H-tetrazole-5-carboxamides
  作者：Roger E. Ford、Phillip Knowles、Edward Lunt、Stuart M. Marshall、Audrey J. Penrose、Christopher A. Ramsden、Anthony J. H. Summers、Joyce L. Walker、Derek E. Wright

  DOI：10.1021/jm00154a019

  日期：1986.4

  The synthesis and antiallergic activity of a series of 2-hydroxy-N-1H-tetrazol-5-ylbenzamides and isomeric N-(2-hydroxyphenyl)-1H-tetrazole-5-carboxamides is described. A relationship between structure and intravenous antiallergic activity in the rat passive cutaneous anaphylaxis (PCA) test has been established using a Hansch/Free-Wilson model and used to direct studies toward potent derivatives. The contribution of physicochemical properties to activity is discussed. One member of this series, N-(3-acetyl-5-fluoro-2-hydroxyphenyl)-1H-tetrazole-5-carboxamide (3f), which was selected for further evaluation, has an ID50 value of 0.16 mg/kg po and is 130 times more potent than disodium cromoglycate (DSCG) on intravenous administration.