Boc-Arg(NO2)-Pro-OBzl | 54046-53-6

• 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: Boc-Arg(NO2)-Pro-OBzl
• 英文别名: Boc-Arg(NO2)-Pro-OBn；Boc-Arg(NO₂)-Pro-OBzl；benzyl (2S)-1-[(2S)-5-[[amino(nitramido)methylidene]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]pyrrolidine-2-carboxylate
• CAS: 54046-53-6
• 化学式: C₂₃H₃₄N₆O₇
• 分子量: 506.559
• InChiKey: UIBQDBBDQFGJFL-ROUUACIJSA-N

物化性质

• 熔点：
  45-46 °C(Solv: ethyl ether (60-29-7); ligroine (8032-32-4))
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  36.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  175.99
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Boc-Arg(NO2)-Pro-OBzl 在 palladium on activated charcoal N-甲基吗啉 、 盐酸 、 ammonium formate 、 三氟乙酸 、 氯甲酸异丁酯 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 3.5h， 生成 Ile-Pro-Arg-Pro
  参考文献：
  名称：

  Abiraj; Sachidananda; Gowda, A. S. Prakasha, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 3, p. 649 - 654

  摘要：

  DOI：
• 作为产物：
  描述：

  N-Boc-N'-硝基-L-精氨酸 、 L-脯氨酸苄酯 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 N-甲基吗啉 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以86%的产率得到Boc-Arg(NO2)-Pro-OBzl
  参考文献：
  名称：

  Identification, synthesis and bioassay for the metabolites of P6A

  摘要：

  The metabolites Ala-Arg-Pro-Ala-OH, Ala-Arg-Pro-OH, Arg-Pro-Ala-Lys-OH and Pro-Ala-Lys-OH were identified by HPLC/ESI/MS from the in vivo blood of Ala-Arg-Pro-Ala-Lys-OH (M) received mice. The in vitro incubation of P6A in the blood of mice the same metabolites were also found by use of the Prep LC System. The protective intermediates of these metabolites were prepared via the solution method using the stepwise synthesis in 77.4, 90, 88, and 80% yield, respectively. After deprotection with catalytic hydrogenation the intermediates were converted into the corresponding sequences Arg-Pro-Ala-Lys-OH Pro-Ala-Lys-OH, Ala-Arg-Pro-Ala-OH, and Ala-Arg-Pro-OH in 90, 95, 85% and 86% yield, respectively. In the thrombolysis in vivo assay the synthetic Ala-Arg-Pro-Ala-OH, and Ala-Arg-Pro-OH exhibited no activity. On the other hand the thrombolytic activity of Arg-Pro-Ala-Lys-OH was comparable to P6A, and an enhanced thrombolytic activity was observed for Pro-Ala-Lys-OH. In the in vitro fibrinolytic lysis tests the approximate results were obtained and an enhanced activity was also observed for Pro-Ala-Lys-OH. In the euglobulin clot lysis time tests P6A, Arg-Pro-Ala-Lys-OH and Pro-Ala-Lys-OH gave significantly shorter time than that given by UK, demonstrating their fast action. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.09.021

文献信息

• Amino acids and peptides. XIII. Synthetic studies on N-terminal tripeptide amide analogs of fibrin .ALPHA.-chain.
  作者：Koichi KAWASAKI、Toshiki TSUJI、Katsuhiko HIRASE、Masanori MIYANO、Yoshinori IMOTO、Masahiro IWAMOTO

  DOI：10.1248/cpb.39.584

  日期：——

  N-Terminal tripeptide analogs of fibrin alpha-chain were synthesized and their inhibitory effect on fibrinogen/thrombin clotting was examined. A new water-soluble active ester, 3-pyridinium ester, was used for the synthesis. Among the synthetic peptides, H-Gly-Pro-Arg-hexamethyleneimine exhibited the highest inhibitory effect on fibrinogen-thrombin clotting.

  合成纤维蛋白α-链的N-末端三肽类似物，并检查其对纤维蛋白原/凝血酶凝血的抑制作用。一种新的水溶性活性酯3-吡啶鎓酯被用于合成。在合成肽中，H-Gly-Pro-Arg-六亚甲基亚胺对纤维蛋白原-凝血酶的凝结表现出最高的抑制作用。
• Synthesis of Quinazolinone Conjugated Shorter Analogues of Bactenecin7 as Potent Antimicrobials
  作者：R. Suhas、S. Chandrashekar、S. M. Anil、D. Channe Gowda

  DOI：10.2174/092986613804725235

  日期：2013.2.1

  A series of shorter peptide analogues of Bactenecin7 (RP, PRP, GPRP and RPRP) were synthesized and conjugated to 3-(4-oxo-3,4-dihydroquinazolin-2-yl)propanoic acid to study the effect of conjugation. All the peptides and their conjugates were characterized by analytical and spectroscopic techniques. The synthesized compounds viz., peptides, heterocyclic conjugates and the hydrogenolyzed products were

  合成了一系列Bactenecin7的短肽类似物（RP，PRP，GPRP和RPRP），并将其与3-（4-氧代-3,4-二氢喹唑啉-2-基）丙酸偶联，以研究偶联作用。通过分析和光谱技术表征所有肽及其缀合物。评价了合成的化合物，即肽，杂环缀合物和氢解产物对一组病原体的抗微生物活性。结果显示，所有缀合物均显示出比其同行更高的活性。此外，氢解四肽结合物（10和13）的活性比使用的标准药物高出近3-4倍。
• Nosho, Jasuharu; Otagiri, Ken; Shinoda, Ichizo, Agricultural and Biological Chemistry, 1985, vol. 49, # 6, p. 1829 - 1838
  作者：Nosho, Jasuharu、Otagiri, Ken、Shinoda, Ichizo、Okai, Hideo

  DOI：——

  日期：——
• Narendra Babu; Rangappa, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 2, p. 297 - 304
  作者：Narendra Babu、Rangappa

  DOI：——

  日期：——