L-精氨酸苄酯 | 57177-89-6

• 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
• 中文名称: L-精氨酸苄酯
• 英文名称: L-Arg-OBzl
• 英文别名: Arg-CO₂Bn；H₂N-R-OBn；H-Arg-OBzl；L-arginine benzyl ester；L-Arginin-benzylester；benzyl L-argininate；benzyl (2S)-2-amino-5-(diaminomethylideneamino)pentanoate
• CAS: 57177-89-6
• 化学式: C₁₃H₂₀N₄O₂
• 分子量: 264.327
• InChiKey: JSCSSJKVVXQJON-NSHDSACASA-N

物化性质

• 沸点：
  411.2±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-精氨酸苄酯 在 N-甲基吗啉 、 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， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Design, synthesis and evaluation of inhibitor of apoptosis protein (IAP) antagonists that are highly selective for the BIR2 domain of XIAP

  摘要：

  We recently reported the systematic ligand-based rational design and synthesis of monovalent Smac mimetics that bind preferentially to the BIR2 domain of the anti-apoptotic protein XIAP. Expanded structure-activity relationship (SAR) studies around these peptidomimetics led to compounds with significantly improved selectivity (>60-fold) for the BIR2 domain versus the BIR3 domain of XIAP. The potent and highly selective IAP antagonist 8q (ML183) sensitized TRAIL-resistant prostate cancer cells to apoptotic cell death, highlighting the merit of this probe compound as a valuable tool to investigate the biology of XIAP. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.096
• 作为产物：
  描述：

  Tos-Arg-OCH2Ph 在 N-甲基吗啉 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 L-精氨酸苄酯
  参考文献：
  名称：

  一类新的取代嘌呤与Gly-AA-OBzl的偶联物：口服镇痛活性的合成和评价

  摘要：

  针对慢性疼痛的化学疗法，通过五步反应方法和19种新型缀合物N- [2-氯-9-（四氢吡喃-2-）偶联了两种止痛药，取代的嘌呤和Gly-AA-OBzl。提供了（yl）-9 H-嘌呤-6-yl] -N-环丙基糖基氨基酸苄酯。在鼠尾轻弹模型上，测定了它们的体内止痛活性。结果表明，将Gly-OC 2 H 5引入取代的嘌呤的6-位导致镇痛活性的模棱两可的增加，而将Gly-AA-OBzl引入该位置导致镇痛活性的显着增加。

  DOI：

  10.1016/j.bmcl.2009.05.077

文献信息

• Method of treating tumors
  申请人：Svendsen John Sigurd

  公开号：US09115169B2

  公开（公告）日：2015-08-25

  The invention provides a method of treating tumors by adminstering to a human or animal patient an effective amount of a molecule of 2 to 4 amino acids or equivalent subunits in length, which incorporates a bulky and lipophilic group comprising at least 13 non-hydrogen atoms and containing no more than 2 polar functional groups, in which the bulky and lipophilic group incorporates one or more closed rings of 5 or more non-hydrogen atoms, and in which the molecule further has at least two more cationic than anionic moieties.

  这项发明提供了一种治疗肿瘤的方法，通过向人类或动物患者施用含有2至4个氨基酸或等效亚单位的分子的有效量，该分子包含至少13个非氢原子的庞大和亲脂基团，并且不含有超过2个极性功能团，在这种庞大和亲脂基团中包含了一个或多个由5个或更多个非氢原子组成的闭环，并且该分子还具有至少两个阳离子基团多于阴离子基团。
• [EN] PREPARATIONS CONTAINING AMINO ACIDS AND OROTIC ACID<br/>[FR] PRÉPARATIONS CONTENANT DES ACIDES AMINÉS ET DE L'ACIDE OROTIQUE
  申请人：IOVATE T & P INC

  公开号：WO2009076743A1

  公开（公告）日：2009-06-25

  The present invention describes compounds produced from an orotic acid molecule and an ammo acid molecule The compounds, which include an amide linkage, are represented by the general Formula (I), wherein R is selected from the group consisting of (CH3)2CHCH2-, (CH3)2CH-, CH3CH2CH(CH3)-, H2NC(=NH)NH(CH2)3-, and C6H5CH2- Formula (I). The compounds are produced by one of two disclosed methods 1) reacting orotic acid or derivatives thereof with a thionyl halide, and then combining the acyl halide with an ammo acid in the presence of dichloromethane and a dimethylammopyπdme (DMAP) catalyst, or 2) protecting the carboxylic acid of an ammo acid with a benzyl group, and then combining the benzyl-protected ammo acid with a dicyclohexylcarbodiimide (DCC) activated orotic acid, followed by removal of the protecting group. The resulting ammo acid orotate amide compounds are aimed at providing enhanced stability in solution compared with the related esters.

  该发明描述了由乳酸分子和氨基酸分子产生的化合物。这些化合物包括酰胺键，由通用式(I)表示，其中R选自(CH3)2CHCH2-、(CH3)2CH-、CH3CH2CH(CH3)-、H2NC(=NH)NH(CH2)3-和C6H5CH2-。这些化合物由两种方法之一制备：1）将乳酸或其衍生物与硫酰卤反应，然后在二氯甲烷和二甲基氨基吡啶(DMAP)催化剂存在下将酰卤与氨基酸结合；2）用苄基保护氨基酸的羧基，然后将苄基保护的氨基酸与二环己基碳二亚胺（DCC）活化的乳酸结合，然后去除保护基。最终产生的氨基酸乳酸酰胺化合物旨在在溶液中提供比相关酯更强的稳定性。
• Novel peptide
  申请人：Ajinomoto Co., Inc.

  公开号：US04670540A1

  公开（公告）日：1987-06-02

  Peptides represented by the formula: ##STR1## wherein: X represents Met, Met(O), Nle, or Ile; Y represents a cystine residue or an .alpha.-amino suberic acid residue; Z represents Gly or Ala; m, n, and p each represent 0 or 1; A represents Ser, Ser-Ser, Arg-Ser-Ser, Arg-Arg-Ser-Ser, Leu-Arg-Arg-Ser-Ser, or Ser-Leu-Arg-Arg-Ser-Ser; and B represents Asn, Asn-Ser, Asn-Ser-Phe, Asn-Ser-Phe-Arg, or Asn-Ser-Phe-Arg-Tyr; with the proviso that .alpha.-hANP(1-28), .alpha.-rANP(1-28), .alpha.-rANP(4-28), .alpha.-rANP(5-27), .alpha.-rANP(5-25), and .alpha.-rANP(3-28) are excluded from the compounds represented by the formula are disclosed along with methods of using these compounds.

  公式所代表的肽类：##STR1## 其中：X代表Met，Met（O），Nle或Ile; Y代表半胱氨酸残基或α-氨基戊二酸残基; Z代表Gly或Ala; m，n和p每个表示0或1; A代表Ser，Ser-Ser，Arg-Ser-Ser，Arg-Arg-Ser-Ser，Leu-Arg-Arg-Ser-Ser或Ser-Leu-Arg-Arg-Ser-Ser; B代表Asn，Asn-Ser，Asn-Ser-Phe，Asn-Ser-Phe-Arg或Asn-Ser-Phe-Arg-Tyr; 前提是α-hANP（1-28），α-rANP（1-28），α-rANP（4-28），α-rANP（5-27），α-rANP（5-25）和α-rANP（3-28）由该公式所代表的化合物中排除，并公开了使用这些化合物的方法。
• Antimicrobial compounds and formulations
  申请人：——

  公开号：US20030195144A1

  公开（公告）日：2003-10-16

  The invention relates to the use of a molecule comprising a backbone of 2 to 35 non-hydrogen atoms in length, having covalently attached thereto at least two bulky and lipoophilic groups and having at least one more cationic than anionic moiety, in the manufacture of a medicament for destabilising microbial cell membranes and the use as a membrane acting antimicrobial agent of a molecule comprising a backbone of 2 to 35 non-hydrogen atoms in length, having covalently attached thereto a super bulky and lipophilic group comprising at least 9 non-hydrogen atoms and having at least two more cationic than anionic moieties and to methods of treatment involving such molecules, in particular peptides including peptide derivatives, and peptidomimetics.

  本发明涉及使用分子制造药物，该分子包括长度为2至35个非氢原子的骨架，至少连接有两个笨重和亲脂性基团，并且具有至少一个阳离子多于阴离子的基团，用作破坏微生物细胞膜的药物，并且涉及使用包括长度为2至35个非氢原子的骨架的分子，该分子共价连接有一个超级笨重和亲脂性基团，包括至少9个非氢原子，并且具有至少两个阳离子多于阴离子的基团，作为膜作用抗微生物药物的用途，以及涉及此类分子的治疗方法，特别是包括肽衍生物和肽类似物的肽。
• Antimicrobial Compounds and Formulations
  申请人：Svendsen John Sigurd

  公开号：US20120108520A1

  公开（公告）日：2012-05-03

  The invention relates to the use of a molecule comprising a backbone of 2 to 35 non-hydrogen atoms in length, having covalently attached thereto at least two bulky and lipophilic groups and having at least one more cationic than anionic moiety, in the manufacture of a medicament for destabilising microbial cell membranes and the use as a membrane acting antimicrobial agent of a molecule comprising a backbone of 2 to 35 non-hydrogen atoms in length, having covalently attached thereto a super bulky and lipophilic group comprising at least 9 non-hydrogen atoms and having at least two more cationic than anionic moieties and to methods of treatment involving such molecules, in particular peptides including peptide derivatives, and peptidomimetics.

  本发明涉及使用一种分子，其包含长度为2至35个非氢原子的骨架，并且至少连接有两个笨重和亲脂性基团，并且具有至少一个阳离子大于阴离子的基团，在制造破坏微生物细胞膜的药物方面使用该分子。另外，本发明还涉及使用一种分子作为膜作用抗微生物剂，该分子包括长度为2至35个非氢原子的骨架，并且共价连接有一个超大的、亲脂性的基团，包括至少9个非氢原子，并且具有至少两个阳离子大于阴离子的基团。本发明还涉及涉及这样的分子的治疗方法，特别是包括肽衍生物和肽类似物的肽。