D-NAME | 141968-19-6

• 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: D-NAME
• 英文别名: N-nitro-D-arginine methyl ester；methyl (2R)-2-amino-5-[[(E)-N'-nitrocarbamimidoyl]amino]pentanoate
• CAS: 141968-19-6
• 化学式: C₇H₁₅N₅O₄
• 分子量: 233.227
• InChiKey: KCWZGJVSDFYRIX-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  149
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  D-NAME 在 N-甲基吗啉 、 lithium hydroxide 、 三甲基铝 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (2R)-N-(2-(((2S)-1-cyclohexyl-3-hydroxy-4-oxo-4-(phenethylamino)butan-2-yl)amino)-2-oxoethyl)-N-methyl-5-((E)-2-nitroguanidino)-2-((phenylmethyl)sulfonamido)pentanamide
  参考文献：
  名称：

  Novel, potent and selective chimeric FXa inhibitors featuring hydrophobic p1-ketoamide moieties

  摘要：

  Judicious combination of P-region sequences of highly potent anticoagulant proteins including NAPS, NAP6, Ecotin, and Antistasin with SAR from small molecule FXa inhibitors led to a series of chimeric inhibitors of formula 1a-j. We report herein the design, synthesis, and biological activity of this novel family of FXa inhibitors that express both high in vitro potency and superb selectivity against related serine proteases. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00458-3
• 作为产物：
  描述：

  D-精氨酸盐酸盐 在 氯化亚砜 、 硫酸 、 三氧化硫 、 硝酸 、 二氧化氮 作用下， 生成 D-NAME
  参考文献：
  名称：

  Gibian,H.; Schroeder,E., Justus Liebigs Annalen der Chemie, 1961, vol. 642, p. 145 - 162

  摘要：

  DOI：

文献信息

• Selective Inhibition of Neuronal Nitric Oxide Synthase by <i>N</i>^ω-Nitroarginine- and Phenylalanine-Containing Dipeptides and Dipeptide Esters
  作者：Richard B. Silverman、Hui Huang、Michael A. Marletta、Pavel Martasek

  DOI：10.1021/jm970200u

  日期：1997.8.1

  A series of N-omega-nitroarginine (Arg(NO2))-and phenylalanine-containing dipeptides and dipeptide esters were synthesized as potential selective inhibitors of neuronal nitric oxide synthase (nNOS). All of the dipeptides and dipeptide esters are competitive inhibitors of nNOS, macrophage nitric oxide synthase (iNOS), and endothelial nitric oxide synthase (eNOS), except for the ones that contain D-Arg(NO2) (8-10, 12, 13), which are uncompetitive inhibitors of iNOS but competitive inhibitors of nNOS and eNOS. None of the dipeptides or dipeptide esters tested (1, 2, 12, 13) exhibited time-dependent inhibition of any of the NOS isoforms, unlike N-omega-nitro-L-arginine itself, which does, although it is reversible. The order of the amino acids in the dipeptide or dipeptide ester is important to selectivity, and the selectivity depends on the chirality of the amino acids. In the case of the corresponding benzyl esters (5 vs 6), both dipeptides favor iNOS over nNOS and eNOS inhibition. All of the dipeptide methyl esters containing a D-amino acid, however, exhibit an inhibitary preference for nNOS over iNOS and eNOS. The most impressive selectivities observed are 1800- and 800-fold for 12 and 13, respectively, in favour of nNOS over iNOS, unfortunately, the selectivities of these compounds for nNOS over eNOS are only 2.5 and 5.3, respectively.
• Novel, potent and selective chimeric FXa inhibitors featuring hydrophobic p1-ketoamide moieties
  作者：J.Edward Semple、Odile E Levy、Nathaniel K Minami、Timothy D Owens、Daniel V Siev

  DOI：10.1016/s0960-894x(00)00458-3

  日期：2000.10

  Judicious combination of P-region sequences of highly potent anticoagulant proteins including NAPS, NAP6, Ecotin, and Antistasin with SAR from small molecule FXa inhibitors led to a series of chimeric inhibitors of formula 1a-j. We report herein the design, synthesis, and biological activity of this novel family of FXa inhibitors that express both high in vitro potency and superb selectivity against related serine proteases. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Gibian,H.; Schroeder,E., Justus Liebigs Annalen der Chemie, 1961, vol. 642, p. 145 - 162
  作者：Gibian,H.、Schroeder,E.

  DOI：——

  日期：——