L-Arg-OBzl hydrochloride | 108246-37-3

• 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-Arg-OBzl hydrochloride
• 英文别名: L-arginine benzyl ester; hydrochloride；L-Arginin-benzylester; Hydrochlorid；l-Arginine benzyl ester hydrochloride；benzyl (2S)-2-amino-5-(diaminomethylideneamino)pentanoate;hydrochloride
• CAS: 108246-37-3
• 化学式: C₁₃H₂₀N₄O₂*ClH
• 分子量: 300.788
• InChiKey: XGFPTLNYBCKNCV-MERQFXBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.53
• 重原子数：
  20
• 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：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-Arg-OBzl hydrochloride 、 BOC-L-1,2,3,4-四氢-Β-咔啉-3-羧酸 在 N-甲基吗啉 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以85%的产率得到N-[(3S)-N-Boc-1,2,3,4-tetrahydro-β-carboline-3-carboxyl]-L-arginine benzyl ester
  参考文献：
  名称：

  一类新的抗血栓形成的六氢吡嗪-[1'，2'：1,6]吡啶基-[3,4-b]-吲哚-1,4-dion：设计，合成，logK测定和QSAR分析。

  摘要：

  基于N-[（3S）]-1,2,3,4-四氢-β-咔啉-3-羧基] -1-赖氨酸在乙酸水溶液（5％）和大鼠中的环化血浆给出了相同的产物，并假设环化产物具有抗血栓活性，我们报道了20种六氢吡嗪并[1'，2'：1,6]吡啶并[ 3,4-b]吲哚-1,4-dion（5a-t）作为潜在的抗血栓形成剂。制备了两种中间体（四氢-β-咔啉-3-羧基-1-氨基酸苄酯，2-氨基酰基四氢-β-咔啉-3-羧酸苄酯），并用于环化形成5a-t。在已报道的文献中，四氢-β-咔啉-3-羧酸酯的盐酸盐与Boc-氨基酸的偶联通常产生非常低的收率产物，并伴随着消旋作用。然而，在我们的情况下，四氢-β-咔啉-3-羧酸苄酯的游离碱以高收率且没有外消旋作用产生了所需的产物。来自体外和体内研究的抗血栓形成结果表明，5a-t可能是一类新型的抗血栓形成剂，口服有效有效浓度为0.5μmol/ kg。此外，使用e-dragon服务器生成的分子

  DOI：

  10.1016/j.bmc.2007.06.012
• 作为产物：
  描述：

  L-精氨酸 、 苯甲醇 在 盐酸 作用下， 反应 0.25h， 以58%的产率得到L-Arg-OBzl hydrochloride
  参考文献：
  名称：

  Inhibitory effects of l-arginine derivatives on endothelium-dependent vasorelaxing response to acetylcholine of the rat aorta

  摘要：

  N-omega-nitro-L-arginine alkyl esters (A-1-A-B) and L-arginine alkyl esters (E-I-E-B) were synthesized, and the vasorelaxing effects of acetylcholine were studied in the absence or presence of these compounds in rat aortic rings with intact endothelium that was precontracted with phenylephrine. These compounds revealed that the nitro group is an essential inhibiting group of these inhibitors, and that hydrophobic functional groups can fine-tune the binding effects. Among them, A-3 is the most potent inhibitor. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.02.012

文献信息

• Synthesis and cytotoxic activities of β-carboline amino acid ester conjugates
  作者：Ming Zhao、Lanrong Bi、Wei Wang、Chao Wang、Michèle Baudy-Floc’h、Jingfang Ju、Shiqi Peng

  DOI：10.1016/j.bmc.2006.06.021

  日期：2006.10

  beta-Carboline represents a class of compounds with potent anti-tumor activity by intercalating with DNA. To further enhance the cytotoxic potency and bioavailability of beta-carboline, a series of novel beta-carboline amino acid ester conjugates were designed and synthesized, and the cytotoxic activities of these compounds were tested using a panel of human tumor cell lines. In addition, the membrane permeability of these compounds was evaluated in vitro using a Caco-2 cell monolayer model. The P-carboline amino acid ester conjugates demonstrated improved cytotoxic activity compared to the parental beta-carbolines. In particular, the Lys/Arg conjugates were the most potent analogs with an IC50 value of 4 and 1 mu M against human cervical carcinoma cells. The low interaction energy of Arg conjugate based on molecular modeling may contribute to its enhanced cytotoxicity. Taken together, this study provided new insights into structure-activity relationships in the beta-carboline amino acid ester conjugates and identified the beta-carboline Lys/Arg conjugates as promising lead compounds for further in vivo biological and molecular evaluation. (c) 2006 Elsevier Ltd. All rights reserved.