Lys(TmG)-OMe | 1372712-15-6

• 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: Lys(TmG)-OMe
• 英文别名: methyl (2S)-2-amino-6-[bis(dimethylamino)methylideneamino]hexanoate
• CAS: 1372712-15-6
• 化学式: C₁₂H₂₆N₄O₂
• 分子量: 258.364
• InChiKey: YAJVBCHPUHKMPV-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  71.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N6-((苄氧基)羰基)-N2-(叔丁氧基羰基)-L-赖氨酸甲酯 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙腈 为溶剂， 反应 2.0h， 生成 Lys(TmG)-OMe
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of Novel Arginine Analogs as Potential Inhibitors of Acetylcholine-Induced Relaxation in Rat Thoracic Aortic Rings

  摘要：

  It is widely appreciated that the vascular endothelium is capable of modulating vascular smooth muscle tone suiting it well for its role as an important regulator of a number of diverse biological processes. Endothelial dysfunction is an early manifestation of atherothrombosis and a consequence of the established disease. Although several arginine derivatives alkylated at one of the guanidino nitrogen were found to inhibit vasorelaxation induced by acetylcholine, activity of the corresponding arginine esters is not reported. The present work was therefore designed to synthesize and evaluate series of novel arginine derivatives to obtain further insight into structure–activity relationship in this series of compounds. Present study involves assessment of activity of these novel compounds on the vascular tone of rat thoracic aorta in comparison with l‐arginine analog, that is, l‐nitro‐arginine methyl ester (l‐NAME). Results from the present study showed that full reversal of phenylephrine‐mediated contraction was achieved by cumulative applications of acetylcholine (3 nm–300 μm), which were abolished when the aortic rings were pretreated with l‐NAME (300 μm). Results from the present study demonstrated that these novel arginine derivatives cause significant yet reversible reduction in acetylcholine‐mediated relaxation, similar to that of l‐NAME.

  DOI：

  10.1111/j.1747-0285.2011.01286.x

文献信息

• Synthesis and Pharmacological Evaluation of Novel Arginine Analogs as Potential Inhibitors of Acetylcholine-Induced Relaxation in Rat Thoracic Aortic Rings
  作者：Manish Jain、Manoj Kumar Barthwal、Wahajul Haq、Seturam B. Katti、Madhu Dikshit

  DOI：10.1111/j.1747-0285.2011.01286.x

  日期：2012.4

  It is widely appreciated that the vascular endothelium is capable of modulating vascular smooth muscle tone suiting it well for its role as an important regulator of a number of diverse biological processes. Endothelial dysfunction is an early manifestation of atherothrombosis and a consequence of the established disease. Although several arginine derivatives alkylated at one of the guanidino nitrogen were found to inhibit vasorelaxation induced by acetylcholine, activity of the corresponding arginine esters is not reported. The present work was therefore designed to synthesize and evaluate series of novel arginine derivatives to obtain further insight into structure–activity relationship in this series of compounds. Present study involves assessment of activity of these novel compounds on the vascular tone of rat thoracic aorta in comparison with l‐arginine analog, that is, l‐nitro‐arginine methyl ester (l‐NAME). Results from the present study showed that full reversal of phenylephrine‐mediated contraction was achieved by cumulative applications of acetylcholine (3 nm–300 μm), which were abolished when the aortic rings were pretreated with l‐NAME (300 μm). Results from the present study demonstrated that these novel arginine derivatives cause significant yet reversible reduction in acetylcholine‐mediated relaxation, similar to that of l‐NAME.