benzyl N-[2-[[2-[(4,6-dimethylpyridin-2-yl)amino]-2-oxoethyl]amino]-2-oxoethyl]carbamate | 167370-27-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl N-[2-[[2-[(4,6-dimethylpyridin-2-yl)amino]-2-oxoethyl]amino]-2-oxoethyl]carbamate
• CAS: 167370-27-6
• 化学式: C₁₉H₂₂N₄O₄
• 分子量: 370.408
• InChiKey: QJLDVLBXKXRIFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl N-[2-[[2-[(4,6-dimethylpyridin-2-yl)amino]-2-oxoethyl]amino]-2-oxoethyl]carbamate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以62%的产率得到glycyl-glycine-N-(4,6-dimethylpyridin-2-yl)amide
  参考文献：
  名称：

  6-Amino-2,4-lutidine carboxamides: α-aminoamide derivatives as systemic and topical inflammation inhibitors

  摘要：

  The development of new potential anti-inflammatory compounds resulting from the incorporation of alpha-aminoacid residues into 6-amino-2,3-lutidine afforded (N-protected) aminoamides with interesting inhibitory activity. Out of 28 tested compounds, 10 (5a, 5b, 7d, 8a, 8b, 8d, 10a, 11b, 12a and 12b) exerted potent (> 90%) inhibition in the carrageenan foot edema (CFE) rat model after oral administration of 0.4 mmol kg(-1). Except for Cbz-glycyl, Cbz-alanyl, Fmoc-valyl and Cbz-alanyl-glycyl derivatives (5a, 5b, 7d and 11b), N-deprotection afforded more active compounds. Introduction of a glycyl residue in the previously studied highly active 3-fluorobenzamide 2, which led to 10a, maintained potent peripheral edema inhibition but had a detrimental effect in the acute TPA-induced mouse ear-swelling model. Glycylglycinamide 12a, which had an ID50 of 9.0 mg kg(-1) in the CFE test, appeared to be the most efficient compound tested in this new series of non-carboxylic nonsteroidal anti-inflammatory drugs. Glycinamide 8a, although less potent in the same assay (14.3 mg kg(-1)), exerted a significant inhibitory effect in acute and chronic ear-swelling tests after topical application of 3 mg/ear. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80022-6
• 作为产物：
  描述：

  2-氨基-4,6-二甲基吡啶 在 palladium on activated charcoal 氢气 、 N,N'-羰基二咪唑 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 生成 benzyl N-[2-[[2-[(4,6-dimethylpyridin-2-yl)amino]-2-oxoethyl]amino]-2-oxoethyl]carbamate
  参考文献：
  名称：

  6-Amino-2,4-lutidine carboxamides: α-aminoamide derivatives as systemic and topical inflammation inhibitors

  摘要：

  The development of new potential anti-inflammatory compounds resulting from the incorporation of alpha-aminoacid residues into 6-amino-2,3-lutidine afforded (N-protected) aminoamides with interesting inhibitory activity. Out of 28 tested compounds, 10 (5a, 5b, 7d, 8a, 8b, 8d, 10a, 11b, 12a and 12b) exerted potent (> 90%) inhibition in the carrageenan foot edema (CFE) rat model after oral administration of 0.4 mmol kg(-1). Except for Cbz-glycyl, Cbz-alanyl, Fmoc-valyl and Cbz-alanyl-glycyl derivatives (5a, 5b, 7d and 11b), N-deprotection afforded more active compounds. Introduction of a glycyl residue in the previously studied highly active 3-fluorobenzamide 2, which led to 10a, maintained potent peripheral edema inhibition but had a detrimental effect in the acute TPA-induced mouse ear-swelling model. Glycylglycinamide 12a, which had an ID50 of 9.0 mg kg(-1) in the CFE test, appeared to be the most efficient compound tested in this new series of non-carboxylic nonsteroidal anti-inflammatory drugs. Glycinamide 8a, although less potent in the same assay (14.3 mg kg(-1)), exerted a significant inhibitory effect in acute and chronic ear-swelling tests after topical application of 3 mg/ear. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80022-6

文献信息

• 6-Amino-2,4-lutidine carboxamides: α-aminoamide derivatives as systemic and topical inflammation inhibitors
  作者：Muriel Duflos、Jacqueline Courant、Guillaume Le Baut、Nicole Grimaud、Pierre Renard、Dominique Manechez、Daniel-Henri Caignard

  DOI：10.1016/s0223-5234(98)80022-6

  日期：1998.7

  The development of new potential anti-inflammatory compounds resulting from the incorporation of alpha-aminoacid residues into 6-amino-2,3-lutidine afforded (N-protected) aminoamides with interesting inhibitory activity. Out of 28 tested compounds, 10 (5a, 5b, 7d, 8a, 8b, 8d, 10a, 11b, 12a and 12b) exerted potent (> 90%) inhibition in the carrageenan foot edema (CFE) rat model after oral administration of 0.4 mmol kg(-1). Except for Cbz-glycyl, Cbz-alanyl, Fmoc-valyl and Cbz-alanyl-glycyl derivatives (5a, 5b, 7d and 11b), N-deprotection afforded more active compounds. Introduction of a glycyl residue in the previously studied highly active 3-fluorobenzamide 2, which led to 10a, maintained potent peripheral edema inhibition but had a detrimental effect in the acute TPA-induced mouse ear-swelling model. Glycylglycinamide 12a, which had an ID50 of 9.0 mg kg(-1) in the CFE test, appeared to be the most efficient compound tested in this new series of non-carboxylic nonsteroidal anti-inflammatory drugs. Glycinamide 8a, although less potent in the same assay (14.3 mg kg(-1)), exerted a significant inhibitory effect in acute and chronic ear-swelling tests after topical application of 3 mg/ear. (C) Elsevier, Paris.