N-stearoyl-L-arginine

• 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-stearoyl-L-arginine
• 英文别名: N-stearoylarginine；(2S)-5-(diaminomethylideneamino)-2-(octadecanoylamino)pentanoic acid
• 化学式: C₂₄H₄₈N₄O₃
• 分子量: 440.67
• InChiKey: NKGQJPIKJYXDCX-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  31
• 可旋转键数：
  22
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  131
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  阿糖胞苷 、 N-stearoyl-L-arginine 在 吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 生成 N-((S)-1-((1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)amino)-5-guanidino-1-oxopentan-2-yl)stearamide
  参考文献：
  名称：

  Synthesis and evaluation of anti-tumor activities of N4 fatty acyl amino acid derivatives of 1-β-arabinofuranosylcytosine

  摘要：

  1-beta-D-Arabinofuranosylcytosine (Ara-C, Cytarabine) is one of the drugs used for acute nonlympbocytic leukemia (ANLL). However, the bioavailability of Ara-C is relatively low due to its low lipophilicity. In order to improve the lipophilicity and bioavailability of Ara-C, a series of N-4 derivatives of Ara-C, i.e., (fatty acid)-(amino acid)-Ara-C analogues, were prepared. The 15 derivatives synthesized were characterized by their melting points, optical rotations and partition coefficients. It was found that the Ara-C derivatives synthesized in this study were more lipophilic than Ara-C as determined by their partition coefficients. Their in vitro cytotoxicity and in vivo anti-tumor activity were determined and compared with that of Ara-C. It was found that the derivatives were more active than Ara-C in Hela cells, but not in HL-60 cells. The in vivo results showed that some of the derivatives were more effective than Ara-C in mice bearing S-180 tumor while others showed a decreased activity in comparison with Ara-C. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.02.028
• 作为产物：
  描述：

  Nα-stearoyl-L-arginine methyl ester 在 sodium hydroxide 作用下， 生成 N-stearoyl-L-arginine
  参考文献：
  名称：

  Synthesis and evaluation of anti-tumor activities of N4 fatty acyl amino acid derivatives of 1-β-arabinofuranosylcytosine

  摘要：

  1-beta-D-Arabinofuranosylcytosine (Ara-C, Cytarabine) is one of the drugs used for acute nonlympbocytic leukemia (ANLL). However, the bioavailability of Ara-C is relatively low due to its low lipophilicity. In order to improve the lipophilicity and bioavailability of Ara-C, a series of N-4 derivatives of Ara-C, i.e., (fatty acid)-(amino acid)-Ara-C analogues, were prepared. The 15 derivatives synthesized were characterized by their melting points, optical rotations and partition coefficients. It was found that the Ara-C derivatives synthesized in this study were more lipophilic than Ara-C as determined by their partition coefficients. Their in vitro cytotoxicity and in vivo anti-tumor activity were determined and compared with that of Ara-C. It was found that the derivatives were more active than Ara-C in Hela cells, but not in HL-60 cells. The in vivo results showed that some of the derivatives were more effective than Ara-C in mice bearing S-180 tumor while others showed a decreased activity in comparison with Ara-C. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.02.028

文献信息

• Cosmetic composition
  申请人：AJINOMOTO CO., INC.

  公开号：US20030165448A1

  公开（公告）日：2003-09-04

  A cosmetic composition for skin and/or hair, which comprises at least one kind of substance selected from the group consisting of an N &agr; ,N G -di-acylarginine, for example, a compound represented by the following general formula (I): 1 wherein R 1 and R 2 each independently represents a straight or branched-chain alkyl group having 1 to 21 carbon atoms or a straight or branched-chain alkenyl group having 2 to 21 carbon atoms. The cosmetic composition imparts much moistness and superior conditioning effects such as body or elasticity to hair, and to skin, said composition does not impart tackiness and blocked feeling, whilst imparts superior feeling of use such as moistness.

  一种用于皮肤和/或头发的化妆品组合物，其包含以下所述组中选择的至少一种物质，即N&agr;，NG-二酰基精氨酸，例如，由下述一般式（I）表示的化合物：其中R1和R2各自独立地表示具有1至21个碳原子的直链或支链烷基或具有2至21个碳原子的直链或支链烯基。该化妆品组合物为头发提供了很多湿润和优越的调理效果，例如体积或弹性，而对于皮肤，该组合物不会产生黏腻和堵塞感，同时提供了优越的使用感，例如湿润感。
• Cosmetic compositions
  申请人：——

  公开号：US20040052747A1

  公开（公告）日：2004-03-18

  A cosmetic composition which comprises one or more kinds of mono-N &agr; -long-chain acylarginines and/or one or more kinds of powders selected from powders subjected to a surface treatment with a mono-N &agr; -long-chain acylarginine and (B) a silicone compound for cosmetics and/or an amphoteric surfactant and is preferably applied to hair or skin. The composition has a feature of imparting gloss and elasticity to hair and skin, whilst little sliminess to skin and scalp during rinsing and little tackiness after drying.

  一种化妆品组合物，包括一种或多种单一的N&agr;-长链酰基精氨酸和/或一种或多种经过表面处理的粉末，其中表面处理使用了一种单一的N&agr;-长链酰基精氨酸，以及（B）一种用于化妆品的硅氧烷化合物和/或一种两性表面活性剂，最好用于头发或皮肤。该组合物具有赋予头发和皮肤光泽和弹性的特点，而在冲洗时对皮肤和头皮几乎没有黏滑感，干后几乎没有粘性。
• Arginine derivatives and cosmetic compositions comprising the same
  申请人：AJINOMOTO CO., INC.

  公开号：EP0320976A1

  公开（公告）日：1989-06-21

  The arginine derivative of this invention can emulsify the oily and aqueous components uniformly to form a stable emulsion. It can form an O/W or W/O emulsion as desired, if the proportions of the oily and aqueous com­ponents are appropriately varied, or if another appropriate emulsifier is added. The emulsifier composition contain­ing the arginine derivative of this invention provides, for example, cosmetics for the skin such as a milky lotion and a cream, medicines for external use such as an ointment, cosmetics for the hair such as a shampoo, a rinse, a hair treatment solution and a hair conditioner, and softeners. It is particularly useful when employed for cosmetics for the hair or softeners, since the arginine derivative is adsorbed by the hair, or fibers, such as of wool or cotton, and exhibits, among others, the following effects: (1) It removes the roughness of the hair or fibers and renders them soft to the touch; (2) It smoothens the hair or fibers and renders them easy to comb; (3) It prevents the generation of static electricity which would otherwise cause the loosening of e.g. the hair; (4) It gives a pleasant handle and an oily feel, such as a smooth or moist feel; and (5) It is hardly irritating to the skin of the head or the eyes.

  本发明的精氨酸衍生物可均匀地乳化油性和水性成分，形成稳定的乳液。如果适当改变油性成分和水性成分的比例，或添加另一种适当的乳化剂，它可以根据需要形成 O/W 或 W/O 型乳液。例如，含有本发明精氨酸衍生物的乳化剂组合物可提供乳状乳液和乳霜等皮肤用化妆品、软膏等外用药物、洗发水、洗发露、头发护理液和护发素等头发用化妆品以及软化剂。精氨酸衍生物可被头发或纤维（如羊毛或棉花）吸附，除其他外，还具有以下功效，因此特别适用于头发化妆品或柔顺剂： (1) 它能去除头发或纤维的粗糙感，使其触感柔软； (2) 抚平头发或纤维，使其易于梳理； (3) 防止产生静电，否则静电会导致头发等松散； (4) 手感舒适，有油腻感，如光滑或湿润的感觉；以及 (5) 对头部皮肤或眼睛几乎没有刺激。
• COSMETIC COMPOSITIONS
  申请人：Ajinomoto Co., Inc.

  公开号：EP1269969A1

  公开（公告）日：2003-01-02

  A cosmetic composition which comprises one or more kinds of mono-Nα-long-chain acylarginines and/or one or more kinds of powders selected from powders subjected to a surface treatment with a mono-Nα-long-chain acylarginine and (B) a silicone compound for cosmetics and/or an amphoteric surfactant and is preferably applied to hair or skin. The composition has a feature of imparting gloss and elasticity to hair and skin, whilst little sliminess to skin and scalp during rinsing and little tackiness after drying.

  一种化妆品组合物，它包含一种或多种单-Nα-长链酰基精氨酸和/或一种或多种粉末，这些粉末选自经过单-Nα-长链酰基精氨酸表面处理的粉末和 (B) 化妆品用硅氧烷化合物和/或两性表面活性剂，最好用于头发或皮肤。该组合物的特点是能赋予头发和皮肤光泽和弹性，同时在冲洗时皮肤和头皮不会变得纤细，干燥后也不会产生粘腻感。
• Preparation, characterization, and surface and biological properties of<i>N</i>-stearoyl amino acids
  作者：A. Sivasamy、M. Krishnaveni、P. G. Rao

  DOI：10.1007/s11746-001-0361-5

  日期：2001.9

  AbstractSeveral lipoamino acids were synthesized, in which n‐octadecanoic acid (stearic acid) was coupled with the α‐amino group of an amino acid. The products were characterized and their identities confirmed by advanced analytical techniques like Fourier transform infrared 1H nuclear magnentic resonance spectroscopy, and differential scanning, calorimetry. Their surface properties, such as critical micelle concentration (CMC) and foaming properties, biodegradability, and antimicrobial activity were also evaluated. The N‐stearoyl amino acids (NSA) had low CMC values, and some of them showed good foaming properties. They were screened for antimicrobial activity against the gram‐positive bacteria Staphylococcus aureus, Micrococcus luteus, and Bacillus cerceus, the gram‐negative bacteria Escherichia coli and Pseudomonas aeruginosa, and the yeast Candida albicans. All the compounds inhibited at least one of these organisms. N‐Stearoyl proline was the most effective, the order of antimicrobial activity being aromatic NSA> acidic NSA>basic NSA. However, the effective inhibition by all the compounds indicates the desirability of more thorough investigation and suggests that some of these compounds may have potential utility as biostatic additives in commercial products. All NSA are highly biodegradable and can readily be removed under conditions of normal secondary sewage treatment.