benzyl N-{2-[(4,6-dimethyl-2-pyridinyl)amino]-2-oxoethyl}carbamate | 162103-60-8

• 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-[(4,6-dimethyl-2-pyridinyl)amino]-2-oxoethyl}carbamate
• 英文别名: benzyl N-[2-[(4,6-dimethylpyridin-2-yl)amino]-2-oxoethyl]carbamate
• CAS: 162103-60-8
• 化学式: C₁₇H₁₉N₃O₃
• 分子量: 313.356
• InChiKey: WQCUMJLETPAWDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  80.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl N-{2-[(4,6-dimethyl-2-pyridinyl)amino]-2-oxoethyl}carbamate 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， 生成 L-alanyl-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：

  N-苄氧羰基甘氨酸 以 四氢呋喃 为溶剂， 反应 11.0h， 生成 benzyl N-{2-[(4,6-dimethyl-2-pyridinyl)amino]-2-oxoethyl}carbamate
  参考文献：
  名称：

  Synthesis and hypolipidemic activity of N-pyridinyl borodipeptidylamides

  摘要：

  A series of borodipeptide derivatives 7-9, which contain a 6-amino-2,4-dimethylpyridine moiety, was prepared in 3 steps. They were evaluated as hypolipidemic agents in rodents at 20 mg/kg per day. The methioninamide and phenylalaninamide derivatives were the most potent compounds demonstrating hypocholesterolemic and hypotriglyceridemic activities in rats. After 14 days, the activity of these compounds was superior to that of clofibrate, at a dose of 200 mg/kg per day.

  DOI：

  10.1016/0223-5234(94)90111-2

文献信息

• (α-Aminoacyl)amino-Substituted Heterocycles and Related Compounds
  作者：Alan R. Katritzky、Bahaa El-Dien M. El-Gendy、Ekaterina Todadze、Ashraf A. A. Abdel-Fattah

  DOI：10.1021/jo8007379

  日期：2008.7.1

  N-Protected-(aminoacyl)benzotriazoles 1a−e,g,i,j,1a′−c′ convert heterocyclic amines of the following series: thiazoles (3a and 3a′), benzothiazoles (3b and 3b′), benzimidazoles (3c and 3c′), thiadiazoles (3d), pyrimidones (9a,b,a′), pyrazoles (11a,b), and pyridines (13a−g, 13d′) under microwave irradiation, into N-substituted amides in yields of 40−98% (average 76%). N-Protected peptidoylbenzotriazoles

  N-保护的（氨基酰基）苯并三唑1a - e，g，i，j，1a' - c'转换以下系列的杂环胺：噻唑（3a和3a'），苯并噻唑（3b和3b'），苯并咪唑（3c和3c'），噻二唑（3d），嘧啶酮（9a，b，a'），吡唑（11a，b）和吡啶（13a - g，13d'）在微波辐射下转化为N-取代的酰胺，产率为40-98％（平均76％）。N-保护的peptidoylbenzotriazoles 6A，b同样，得到Ç -末端的N-保护的酰胺dipeptidoyl 7A，b（52-60％）。
• 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.
• Synthesis and hypolipidemic activity of N-pyridinyl borodipeptidylamides
  作者：M DUFLOS、S ROBERTPIESSARD、J ROBERT、M ANDRIAMANAMIHAJA、G LEBAUT、B ROBERT、F MAINARD

  DOI：10.1016/0223-5234(94)90111-2

  日期：——

  A series of borodipeptide derivatives 7-9, which contain a 6-amino-2,4-dimethylpyridine moiety, was prepared in 3 steps. They were evaluated as hypolipidemic agents in rodents at 20 mg/kg per day. The methioninamide and phenylalaninamide derivatives were the most potent compounds demonstrating hypocholesterolemic and hypotriglyceridemic activities in rats. After 14 days, the activity of these compounds was superior to that of clofibrate, at a dose of 200 mg/kg per day.