N^G-cyclopropyl-L-arginine | 139299-32-4

• 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: N^G-cyclopropyl-L-arginine
• 英文别名: N5-[(cyclopropylamino)iminomethyl]-L-ornithine；Nw-cyclopropyl-L-arginine；(2S)-2-amino-5-[[amino-(cyclopropylamino)methylidene]amino]pentanoic acid
• CAS: 139299-32-4
• 化学式: C₉H₁₈N₄O₂
• 分子量: 214.268
• InChiKey: HXGYVYKZSPFEOY-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  114
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 三氟乙酸 作用下， 反应 1.0h， 生成 N^G-cyclopropyl-L-arginine
  参考文献：
  名称：

  A General Procedure for Synthesis ofN^G-Alkyl, andN^G-Aryl-L-Arginines as Potential Nitric Oxide Synthase inhibitors

  摘要：

  AbstractA general procedure for the synthesis of NG‐alkyl, and NG‐aryl‐L‐arginines with relatively high overall yield is reported. The key step involved the coupling of protected L‐ornithine 4 with isothiourea 7 to give the fully protected NG‐aryl‐L‐arginine derivative 8. Subsequent deprotection of 8 in acidic condition provided the final target compound 9 with an overall yield of more than 80%.

  DOI：

  10.1002/jccs.199800083

文献信息

• Inhibitors of nitric oxide biosynthesis
  申请人：MERRELL PHARMACEUTICALS INC.

  公开号：EP0446699A1

  公开（公告）日：1991-09-18

  The present invention is directed to a new class of compound which are useful as inhibitors of the biosynthesis of nitric oxide.

  本发明涉及一类可用作一氧化氮生物合成抑制剂的新型化合物。
• Method of treating pruritus and a pharmaceutical composition for the method
  申请人：——

  公开号：US20020156129A1

  公开（公告）日：2002-10-24

  The object of the present invention is to provide a pharmaceutical composition for treatment of pruritus not associated with dermal inflammation such as pruritus caused by the decrease of cutaneous barrier function. Particularly, the object of the present invention is to provide a pharmaceutical composition, comprising at least one substances having the inhibitory function of NO activity in vivo, such as the inhibitory activity for NO biosynthesis and/or at least one substances having the eliminating activity for NO and a pharmaceutically acceptable carrier. Another object of the present invention is to provide a method of treatment of pruritus not associated with dermal inflammation such as pruritus caused by the decrease of skin barrier function. The method comprises the step of administrating the pharmaceutical composition of the present invention.

  本发明的目的是提供一种药物组合物，用于治疗与皮肤炎症无关的瘙痒症，如皮肤屏障功能下降引起的瘙痒症。特别是，本发明的目的是提供一种药物组合物，该组合物包含至少一种具有抑制体内 NO 活性功能的物质，如抑制 NO 生物合成的活性和/或至少一种具有消除 NO 活性的物质和药学上可接受的载体。 本发明的另一个目的是提供一种治疗与皮肤炎症无关的瘙痒症的方法，如皮肤屏障功能下降引起的瘙痒症。该方法包括施用本发明药物组合物的步骤。
• NG-allyl- and NG-cyclopropyl-L-arginine: two novel inhibitors of macrophage nitric oxide synthase
  作者：Norman M. Olken、Michael A. Marletta

  DOI：10.1021/jm00084a020

  日期：1992.3

  N(G)-Methyl-L-arginine has recently been shown to inactivate the inducible murine macrophage nitric oxide (.NO) synthase (Olken, N. M.; Rusche, K. M.; Richards, M. K.; Marletta, M. A. Biochem. Biophys. Res. Commun. 1991, 177, 828-833). N(G)-Allyl-L-arginine and N(G)-cyclopropyl-L-arginine were synthesized as potential mechanism-based enzyme inhibitors to exploit the chemistry presumed to occur at the active site. N(G)-Cyclopropyl-L-arginine was found to be a potent reversible inhibitor with a K(i) = 7.7-mu-M. N(G)-Allyl-L-arginine was found to be both a potent reversible (K(i) = 2.1-mu-M) and irreversible inhibitor of the enzyme. This irreversible inhibition demonstrated pseudo-first-order inactivation kinetics with k(inact) = 0.026 min-1 and K(I) = 3.4-mu-M. Stereospecific protection of the inactivation was afforded by L-arginine, and saturability of the inactivation rate was observed. Our studies indicate that both reversible and irreversible inhibition of the inducible .NO synthease can be achieved with relatively simple modifications of the substrate L-arginine.
• A General Procedure for Synthesis of<i>N</i>^G-Alkyl, and<i>N</i>^G-Aryl-<scp>L</scp>-Arginines as Potential Nitric Oxide Synthase inhibitors
  作者：Bor-Cherng Chen、Shi Shiu、Ding-Yah Yang

  DOI：10.1002/jccs.199800083

  日期：1998.8

  AbstractA general procedure for the synthesis of NG‐alkyl, and NG‐aryl‐L‐arginines with relatively high overall yield is reported. The key step involved the coupling of protected L‐ornithine 4 with isothiourea 7 to give the fully protected NG‐aryl‐L‐arginine derivative 8. Subsequent deprotection of 8 in acidic condition provided the final target compound 9 with an overall yield of more than 80%.