L-NAME | 50903-99-6

• 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: L-NAME
• 英文别名: Nω-nitro-L-arginine methyl ester；N^G-nitro-L-arginine methyl ester；N-nitro-L-arginine methyl ester；L-N^G-nitroarginine methyl ester；N^w-nitro-L-arginine methyl ester；Nο-nitro-L-arginine methyl ester；N-omega-nitro-L-arginine methyl ester；N^ω-nitro-L-arginine；nitro-L-arginine methyl ester；L-nitroarginine methylester；N^ω-nitro-L-argine methyl ester；N(gamma)-nitro-L-arginine methyl ester；L-N-nitroarginine methyl ester；L-N-arginine methyl ester；N'''-nitro-l-arginine methyl ester；methyl (2S)-2-amino-5-[(N'-nitrocarbamimidoyl)amino]pentanoate
• CAS: 50903-99-6
• 化学式: C₇H₁₅N₅O₄
• mdl: MFCD00273095
• 分子量: 233.227
• InChiKey: KCWZGJVSDFYRIX-YFKPBYRVSA-N

物化性质

• 沸点：
  375.47°C (rough estimate)
• 密度：
  1.3521 (rough estimate)

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：
  0.714
• 拓扑面积：
  149
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 储存条件：
  | 温度范围：2-8°C |

反应信息

• 作为反应物：
  描述：

  L-NAME 在 selenium(IV) oxide 、 水 作用下， 以 1,3-二噁烷 为溶剂， 反应 8.0h， 以51%的产率得到(3beta)-3-羟基羽扇-20(30)-烯-29-醛
  参考文献：
  名称：

  Synthesis of new heterocyclic lupeol derivatives as nitric oxide and pro-inflammatory cytokine inhibitors

  摘要：

  A series of heterocyclic derivatives including indoles, pyrazines along with oximes and esters were synthesized from lupeol and evaluated for anti-inflammatory activity through inhibition of lipopolysaccharide (LPS) induced nitric oxide (NO) production in RAW 264.7 and J774A.1 cells. All the synthesized molecules of lupeol were found to be more active in inhibiting NO production with an IC50 of 18.4-48.7 mu M in both the cell lines when compared to the specific nitric oxide synthase (NOS) inhibitor, L-NAME (IC50 = 69.21 and 73.18 mu M on RAW 264.7 and J774A.1 cells, respectively). The halogen substitution at phenyl ring of indole moiety leads to potent inhibition of NO production with half maximal concentration ranging from 18.4 to 41.7 mu M. Furthermore, alkyl (11, 12) and p-bromo/iodo (15, 16) substituted compounds at a concentration of 20 mu g/mL exhibited mild inhibition (29-42%) of LPS-induced tumor necrosis factor alpha (TNF-alpha) and weak inhibition (10-22%) towards interleukin 1-beta (IL-1 beta) production in both the cell lines. All the derivatives were found to be non-cytotoxic when tested at their IC50 (mu M). These findings suggest that the derivatives of lupeol could be a lead to potent inhibitors of NO. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.032
• 作为产物：
  描述：

  L-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 L-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

• Preparation of l-proline based aeruginosin 298-A analogs: Optimization of the P1-moiety
  作者：Guijun Wang、Navneet Goyal、Branden Hopkinson

  DOI：10.1016/j.bmcl.2009.04.056

  日期：2009.7

  residue. The structure optimization was focused on modification of the P1 position. In choosing the P1 group, an effort was made to avoid using the highly basic guanidine groups present in nearly all naturally occurring aeruginosins. The synthesis and enzyme assays of these aeruginosin analogs against thrombin and trypsin are reported. We found that several compounds with neutral P1 groups exhibit excellent

  铜绿素是一族天然的寡肽，具有共同的双环氨基酸核心结构。该家族中的许多化合物都是丝氨酸蛋白酶的抑制剂，例如凝血酶和胰蛋白酶。凝血酶是凝血级联反应中的重要酶，并且是抗凝药物开发的有希望的靶标。为了了解结构-活性关系（SAR）并找到选择性的凝血酶抑制剂，我们合成了一系列铜绿菌素298-A类似物，其中P 2双环氨基酸被1-脯氨酸残基取代。结构优化的重点是修改P 1位置。在选择P 1时为了避免这种情况，人们努力避免使用几乎所有天然存在的铜绿素酶中都存在的高碱性胍基。报道了这些铜绿素类似物针对凝血酶和胰蛋白酶的合成和酶测定。我们发现几种具有中性P 1基团的化合物相对于胰蛋白酶表现出优异的选择性，并且对凝血酶具有良好的效力。此处获得的P 1基团的SAR数据可用于制备对胰蛋白酶具有更好选择性的其他凝血酶抑制剂。
• Relationship between Structure and Papain Inhibitory Activity of Epoxysuccinyl Amino Acid Derivatives
  作者：Masaharu Tamai、Takashi Adachi、Kiyoshi Oguma、Shigeo Morimoto、Kazunori Hanada、Sadafumi Ohmura、Masahiro Ohzeki

  DOI：10.1080/00021369.1981.10864575

  日期：1981.3

  A number of amino acid derivatives of DL-Zra/w-epoxysuccinic acid, with a general formula of R1O-ES-AA-OR2 (ES, DL-trans-epoxysuccinyl group; AA, amino acid residue) were newly synthesized and used for the study of structure-activity relationships of papain inhibition. Branched-alkyl amino acids, such as Leu, He and Val, as AA and hydrogen or an alkyl group substituted with a phenyl or cycloalkyl group as R1 were desirable for activity, respectively. However, R2 or the optical activities of ES and AA not so much influenced on the activity.

  一些DL-Zra/w-环氧琥珀酸氨基酸衍生物被新合成并用于木瓜蛋白酶抑制的结构-活性关系研究。通式为R1O-ES-AA-OR2（ES，DL-反式环氧琥珀酰基团；AA，氨基酸残基）。AA为支链烷基氨基酸，如Leu、He和Val，R1为氢或被苯基或环烷基取代的烷基，这类衍生物具有较好的活性。但R2或ES和AA的光学活性对活性的影响不大。
• Studies on the Secondary Structure of Bradykinin in Aqueous Solution. Syntheses, Circular Dichroism Spectra, and Biological Activities of Bradykinin Analogs Containing 5-Aminovaleric Acid Residue
  作者：Chikao Hashimoto、Makoto Tamaki、Shosuke Sofuku、Ichiro Muramatsu

  DOI：10.1246/bcsj.64.1533

  日期：1991.5

  of Arg1 and the carboxyl group of Arg9, was proposed for the secondary structure of bradykinin in aqueous solution. The biological activities of these analogs depend on the presence of both Phe residues at positions 5 and 8, and Arg residues at positions 1 and 9. No correlation between the biological activities and the secondary structure could be found.

  通过溶液法合成了八种含有 5-氨基戊酸残基的缓激肽类似物。基于对它们的 CD 谱的考虑，Ser6 的羰基氧和 Phe8 的酰胺质子之间存在分子内 3→1 氢键，Pro2 的羰基氧和 Phe8 的酰胺质子之间存在分子内 4→1 氢键。 Phe5 以及 Arg1 的胍基和 Arg9 的羧基之间的盐桥，被认为是缓激肽在水溶液中的二级结构。这些类似物的生物活性取决于位置 5 和 8 上的 Phe 残基以及位置 1 和 9 上的 Arg 残基的存在。未发现生物活性与二级结构之间的相关性。
• 雷公藤甲素靶向前药及其制备方法和应用
  申请人：郭可点

  公开号：CN109021061B

  公开（公告）日：2019-07-12

  本发明涉及医药技术领域，特别涉及靶向诱生型一氧化氮合酶(iNOS)雷公藤甲素前药及其制备方法和应用。该雷公藤甲素靶向前药的R1为L‑精氨酸、L‑精氨酸甲酯、L‑Nω‑NO‑精氨酸、L‑Nω‑NO‑精氨酸甲酯、L‑胍氨酸、L‑硫代胍氨酸、L‑赖氨酸或L‑鸟氨酸。本发明利用炎症部位诱生型一氧化氮合酶(iNOS)高表达的特点，以iNOS特异性底物(基团)对雷公藤甲素进行半合成制备前药，通过其靶向特性降低雷公藤甲素的毒性、改善其生物利用度，其抗炎效果显著好于雷公藤甲素，可以实现对雷公藤甲素有效开发和利用。
• Novel Derivatives of 3.5-Seco-4-Norcholestane and Use Thereof
  申请人：Bordet Thierry

  公开号：US20080275130A1

  公开（公告）日：2008-11-06

  The invention relates to compounds of formula (I): where X+Y=keto, or X=OH and Y=H, or X+Y=oxime or methyloxime, B=OH and C+D=H, or C+D=C1-C4 linear or branched alkyl, or C=H and D=C1-C4 linear or branched alkyl, or B+C=keto and D=methyl, hydroxyl, or methylamino, or B and C=H and D=methylamino, or B+C=oxime and D=methyl and R=C1-C10 linear or branched alkyl, the salts, esters, or salts of esters thereof as medicament, in particular as neuroprotectors, novel compounds of formula (I) and pharmaceutical compositions.

  该发明涉及以下式（I）的化合物：其中X+Y=keto，或X=OH且Y=H，或X+Y=oxime或methyloxime，B=OH且C+D=H，或C+D=C1-C4直链或支链烷基，或C=H且D=C1-C4直链或支链烷基，或B+C=keto且D=甲基、羟基或甲基氨基，或B和C=H且D=甲基氨基，或B+C=oxime且D=甲基，以及R=C1-C10直链或支链烷基的盐、酯或其盐酯作为药物，特别是作为神经保护剂，以及该式（I）的新化合物和药物组合物。