2-hydroxy-5-nitro-N-(1(2)H-tetrazol-5-yl)-benzamide | 67127-27-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-hydroxy-5-nitro-N-(1(2)H-tetrazol-5-yl)-benzamide
• 英文别名: 2-hydroxy-5-nitro-N-(tetrazol-5-yl)-benzamide；2-hydroxy-5-nitro-N-(2H-tetrazol-5-yl)benzamide
• CAS: 67127-27-9
• 化学式: C₈H₆N₆O₄
• 分子量: 250.173
• InChiKey: QYAYAEMWJUHHBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 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：
  150
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-硝基水杨酸 在 氯化亚砜 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 2-hydroxy-5-nitro-N-(1(2)H-tetrazol-5-yl)-benzamide
  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

• Benzamide derivatives
  申请人：May & Baker Limited

  公开号：US04146631A1

  公开（公告）日：1979-03-27

  Benzamide derivatives of the formula:- ##STR1## wherein R.sup.1 represents a fluorine, chlorine or bromine atom, or an alkyl, alkoxy, alkylthio, alkylsulphonyl, alkanoylamino, alkylamino or alkylsulphamoyl group, each such group containing from 1 to 6 carbon atoms, a dialkylsulphamoyl, dialkylamino or dialkylcarbamoyl group (wherein the two alkyl groups may be the same or different and each contains from 1 to 4 carbon atoms), an alkanoyl, alkoxycarbonyl, alkoxycarbonylamino or alkylcarbamoyl group containing from 2 to 6 carbon atoms, or a hydroxy, formyl, nitro, trifluoromethyl, aryl, benzyloxycarbonylamino, amino, sulphamoyl, cyano, tetrazol-5-yl, carboxy, carbamoyl or aroyl group, and n represents an integer 1, 2 or 3, are new compounds possessing pharmacological properties, in particular properties of value in the treatment of respiratory disorders manifested by the interaction of tissue-fixed antibodies with specific antigens.

  Benzamide衍生物的公式为：-##STR1##其中R.sup.1代表氟、氯或溴原子，或者是含有1到6个碳原子的烷基、烷氧基、烷硫基、烷基磺酰、烷酰胺基、烷基氨基或烷基磺酰胺基的基团，或者是含有2到6个碳原子的二烷基磺酰胺基、二烷基氨基或二烷基氨基甲酰基（其中两个烷基可能相同或不同，每个烷基都含有1到4个碳原子），或者是含有2到6个碳原子的烷酰基、烷氧羰基、烷氧羰基胺基或烷基甲酰胺基的基团，或者是羟基、甲酰基、硝基、三氟甲基、芳基、苄氧羰基胺基、氨基、磺酰基、氰基、四唑-5-基、羧基、氨基甲酰基或芳酰基基团，n表示整数1、2或3，是具有药理学特性的新化合物，特别是在治疗通过组织固定抗体与特定抗原相互作用表现出的呼吸系统疾病方面具有价值的特性。
• 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：——
• US4146631A
  申请人：——

  公开号：US4146631A

  公开（公告）日：1979-03-27
• 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.