4-formyl-N-(2-thiazolyl)benzamide | 147729-75-7

• 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: 4-formyl-N-(2-thiazolyl)benzamide
• 英文别名: 4-formyl-N-(1,3-thiazol-2-yl)benzamide
• CAS: 147729-75-7
• 化学式: C₁₁H₈N₂O₂S
• mdl: MFCD27944987
• 分子量: 232.263
• InChiKey: ZEHWRYDIFIJIKP-UHFFFAOYSA-N

物化性质

• 密度：
  1.427±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-formyl-N-(2-thiazolyl)benzamide 在 sodium hydroxide 、 硫酸 作用下， 以 甲醇 为溶剂， 反应 23.0h， 生成 2-{(E)-3-[4-(Thiazol-2-ylcarbamoyl)-phenyl]-acryloyl}-benzoic acid methyl ester
  参考文献：
  名称：

  2'-Substituted chalcone derivatives as inhibitors of interleukin-1 biosynthesis

  摘要：

  A series of 2'-substituted chalcone derivatives has been found to show potent inhibition of the production of IL-1beta from human peripheral blood monocytes stimulated with lipopolysaccharide (LPS), with IC50 values in the 0.2-5.0-muM range. Some members of the series have also shown inhibition of septic shock induced in mice by injection of LPS, although with low potency. Qualitative structure-activity relationships have shown that the enone is required for activity, which may be mediated by conjugate addition of a biological nucleophile to the chalcone. Electron-poor aromatic rings beta to the ketone give enhanced potency. Although electronic effects in the other ring (directly attached to the ketone) are minimal, this ring must possess an ortho substituent for good activity without cytotoxicity, suggesting a degree of selectivity which would not be expected for simple, nonspecific alkylating agents.

  DOI：

  10.1021/jm00062a016
• 作为产物：
  描述：

  对醛基苯甲酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 4-formyl-N-(2-thiazolyl)benzamide
  参考文献：
  名称：

  2'-Substituted chalcone derivatives as inhibitors of interleukin-1 biosynthesis

  摘要：

  A series of 2'-substituted chalcone derivatives has been found to show potent inhibition of the production of IL-1beta from human peripheral blood monocytes stimulated with lipopolysaccharide (LPS), with IC50 values in the 0.2-5.0-muM range. Some members of the series have also shown inhibition of septic shock induced in mice by injection of LPS, although with low potency. Qualitative structure-activity relationships have shown that the enone is required for activity, which may be mediated by conjugate addition of a biological nucleophile to the chalcone. Electron-poor aromatic rings beta to the ketone give enhanced potency. Although electronic effects in the other ring (directly attached to the ketone) are minimal, this ring must possess an ortho substituent for good activity without cytotoxicity, suggesting a degree of selectivity which would not be expected for simple, nonspecific alkylating agents.

  DOI：

  10.1021/jm00062a016

文献信息

• Amide-type triazole compounds
  申请人：SANKYO COMPANY, LIMITED

  公开号：US20030176480A1

  公开（公告）日：2003-09-18

  A compound of formula (I) or a pharmacologically acceptable prodrug or salt thereof which exhibits excellent antifungal activity: 1 wherein Ar 1 represents a phenyl group or the like; Ar 2 represents a phenylene group or the like. X represents a sulfur atom or a methylene group. R 1 represents a hydrogen atom or a C 1-3 alkyl group; R 2 represents a hydrogen atom or a C 1-3 alkyl group; and R 3 represents an optionally substituted C 6-10 aryl group or the like. Fungal infections may be prevented and/or treated by administering said compound (I) or said prodrug or salt thereof.

  一种具有出色抗真菌活性的化合物，其化学式为（I）或其药理学上可接受的前药或盐：其中Ar1代表苯基或类似物；Ar2代表苯基或类似物。X代表硫原子或亚甲基基团。R1代表氢原子或C1-3烷基基团；R2代表氢原子或C1-3烷基基团；R3代表可选择取代的C6-10芳基基团或类似物。通过给予该化合物（I）或其前药或盐可预防和/或治疗真菌感染。
• TRIAZOLE COMPOUNDS HAVING AMIDE LINKAGE
  申请人：Sankyo Company, Limited

  公开号：EP1284267A1

  公开（公告）日：2003-02-19

  The present invention provides a compound of formula (I) or a pharmacologically acceptable prodrug or salt thereof which exhibits excellent antifungal activity: [wherein Ar1 represents a phenyl group or the like; Ar2 represents a phenylene group or the like; X represents a sulfur atom or a methylene group; R1 represents a hydrogen atom or a C1-3 alkyl group; R2 represents a hydrogen atom or a C1-3 alkyl group; and R3 represents an optionally substituted C6-10 aryl group or the like].

  本发明提供了一种具有优异抗真菌活性的式(I)化合物或其药理学上可接受的原药或盐： [其中 Ar1 代表苯基或类似物；Ar2 代表亚苯基或类似物；X 代表硫原子或亚甲基；R1 代表氢原子或 C1-3 烷基；R2 代表氢原子或 C1-3 烷基；R3 代表任选取代的 C6-10 芳基或类似物]。
• US6653330B2
  申请人：——

  公开号：US6653330B2

  公开（公告）日：2003-11-25
• 2'-Substituted chalcone derivatives as inhibitors of interleukin-1 biosynthesis
  作者：Douglas G. Batt、Robin Goodman、David G. Jones、Janet S. Kerr、Lisa R. Mantegna、Candice McAllister、Robert C. Newton、Sherrill Nurnberg、Patricia K. Welch、Maryanne B. Covington

  DOI：10.1021/jm00062a016

  日期：1993.5

  A series of 2'-substituted chalcone derivatives has been found to show potent inhibition of the production of IL-1beta from human peripheral blood monocytes stimulated with lipopolysaccharide (LPS), with IC50 values in the 0.2-5.0-muM range. Some members of the series have also shown inhibition of septic shock induced in mice by injection of LPS, although with low potency. Qualitative structure-activity relationships have shown that the enone is required for activity, which may be mediated by conjugate addition of a biological nucleophile to the chalcone. Electron-poor aromatic rings beta to the ketone give enhanced potency. Although electronic effects in the other ring (directly attached to the ketone) are minimal, this ring must possess an ortho substituent for good activity without cytotoxicity, suggesting a degree of selectivity which would not be expected for simple, nonspecific alkylating agents.