Benzyl (2S)-N-(tert-butoxycarbonyl)phenylalanyl-β-alaninate ester | 88574-38-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: Benzyl (2S)-N-(tert-butoxycarbonyl)phenylalanyl-β-alaninate ester
• 英文别名: Boc-Phe-β-Ala-OBzl；3-[[(S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxo-3-phenylpropyl]amino]propanoic acid, phenylmethyl ester；benzyl 3-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]propanoate
• CAS: 88574-38-3
• 化学式: C₂₄H₃₀N₂O₅
• 分子量: 426.513
• InChiKey: QKQKFJGFUBBRDT-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Benzyl (2S)-N-(tert-butoxycarbonyl)phenylalanyl-β-alaninate ester 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.92h， 生成
  参考文献：
  名称：

  Mehrotra, Amit P.; Webster, Kerri L.; Gani, David, Journal of the Chemical Society. Perkin transactions I, 1997, # 17, p. 2495 - 2511

  摘要：

  DOI：
• 作为产物：
  描述：

  BOC-L-苯丙氨酸 在 N-甲基吗啉 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.08h， 生成 Benzyl (2S)-N-(tert-butoxycarbonyl)phenylalanyl-β-alaninate ester
  参考文献：
  名称：

  Mehrotra, Amit P.; Webster, Kerri L.; Gani, David, Journal of the Chemical Society. Perkin transactions I, 1997, # 17, p. 2495 - 2511

  摘要：

  DOI：

文献信息

• Studies on analgesic oligopeptides. V. Structure-activity relationship of tripeptide alkylamides, Tyr-D-Arg-Phe-X.
  作者：KENJI SUZUKI、HIROKI FUJITA、YUSUKE SASAKI、MIKI SHIRATORI、SHINOBU SAKURADA、KENSUKE KISARA

  DOI：10.1248/cpb.36.4834

  日期：——

  Twenty-one analogs based on the structure Tyr-D-Arg-Phe-X (X=OH, alkyl ester, alkylamide or amino acid having a different carbon chain) were synthesized by the solution method and their analgesic activities were tested after subcutaneous (s. c.) administration in mice. Most tripeptide alkylamides showed no analgesia at a dose of 10 mg/kg, s. c. However, some tripeptide alkylamides having the hydroxyl group on the alkyl moiety showed greater activity than morphine. Introduction of the carboxyl group on the alkyl moiety also led to tetrapeptide analogs with potent analgesia, e. g., the compound with X=β-alanine is 33 times more potent than morphine on a molar basis. These results suggest that proper carbon chain lengths and the presence of an oxygen atom at the fourth position are important for high analgesic activity in the series of D-Arg2-dermorphin analogs.

  通过溶液法合成了基于结构Tyr-D-Arg-Phe-X（X=OH，烷基酯，烷基酰胺或具有不同碳链的氨基酸）的21种类似物，并在小鼠皮下（s.c.）给药后测试了它们的镇痛活性。大多数三肽烷基酰胺在10 mg/kg，s.c.剂量下没有镇痛作用。然而，一些在烷基部分具有羟基的三肽烷基酰胺显示出比吗啡更大的活性。在烷基部分引入羧基也导致具有强效镇痛作用的四肽类似物，例如，X=β-丙氨酸的化合物在摩尔基础上比吗啡强33倍。这些结果表明，适当的碳链长度和在第四位存在氧原子对于D-Arg2-dermorphin类似物系列中的高镇痛活性是重要的。
• Synthesis of functionalised cyclic pentapeptide analogues of the serine-threonine protein phosphatase inhibitor nodularin
  作者：Amit P Mehrotra、David Gani

  DOI：10.1016/0040-4039(96)01515-8

  日期：1996.9

  A generic synthesis of cyclic peptidic analogues of nodularin incorporating suitable functionality for synthetic elaboration is described, providing access to new protein phosphatase inhibitors.

  描述了具有适当合成合成加工功能的结核菌素环状肽类似物的通用合成方法，为获得新的蛋白质磷酸酶抑制剂提供了可能。
• Atrial natriuretic peptide derivative
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05159061A1

  公开（公告）日：1992-10-27

  A peptide derivative of the formula ##STR1## wherein A is hydrogen or a hydrocarbon acyl having 2 to 18 carbon atoms which is substituted by an amino group at the .alpha.-position; B is F-Gly wherein F is a neutral .alpha.-amino acid residue, or NH-(CH.sub.2)nCO wherein n is an integer of 1 to 4; C is a neutral .alpha.-amino acid residue; and E is L-Arg or D-Arg; when A, B and C are hydrogen, Gly-Gly, and Met or Ile, respectively, E is D-Arg, or its pharmacologically acceptable salt has strong hypotensive and natriuretic activity; therefore it is useful as a therapeutic drug for hypertension, a diuretic, and a therapeutic drug for cardiac and cerebral circulatory diseases.

  一种肽衍生物的公式为 ##STR1## 其中A是氢或具有2至18个碳原子的烃基酰基，该烃基酰基在α位上被氨基取代; B是F-Gly，其中F是中性的α-氨基酸残基，或NH-(CH.sub.2)nCO，其中n是1至4的整数; C是中性的α-氨基酸残基; 而E是L-Arg或D-Arg; 当A、B和C为氢、Gly-Gly和Met或Ile时，E为D-Arg，或其药理学上可接受的盐具有强烈的降压和利尿活性; 因此，它可用作治疗高血压、利尿剂、心脏和脑循环疾病的治疗药物。
• Phosphonate and phosphonamide endopeptidase inhibitors
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04963539A1

  公开（公告）日：1990-10-16

  Compounds of the formula ##STR1## wherein Y is O or NH and X is ##STR2## will inhibit the action of neutral endopeptidase. As a result, such compounds produce diuresis, natriuresis, and lower blood pressure as well as being useful in the treatment of congestive heart failure, relieving pain, and diarrhea when administered to a mammalian host.

  式子为##STR1##的化合物，其中Y为O或NH，X为##STR2##，将抑制中性内肽酶的作用。因此，这些化合物产生利尿、利钠和降低血压的作用，同时在给哺乳动物宿主施用时，对治疗充血性心力衰竭、缓解疼痛和腹泻也有用处。
• Pro-drugs for CCK antagonists
  申请人：Warner-Lambert Company

  公开号：US05554643A1

  公开（公告）日：1996-09-10

  Novel pro-drugs to new and unnatural depeptoids of .alpha.-substituted Trp-Phe derivatives useful as agents in the treatment of obesity, hypersecretion of gastric acid in the gut, gastrin-dependent tumors, or as antipsychotics are disclosed. Further, the dipeptoids are antianxiety agents and antiulcer agents. They are agents useful for preventing the response to the withdrawal from chronic treatment or with use of nicotine, diazepam, alcohol, cocaine, caffeine, or opioids. The pro-drugs are also useful in treating and/or preventing panic attacks. Also disclosed are pharmaceutical compositions and methods of treatment using the pro-drugs as well as processes for preparing them and novel intermediates useful in their preparation. An additional feature of the invention is the use of the subject pro-drug compounds in diagnostic compositions.

  本发明揭示了一种新型和非天然的α-取代Trp-Phe衍生物的前药，用作治疗肥胖症、肠道中胃酸的高分泌、胃泌素依赖性肿瘤或作为抗精神病药物。此外，二肽类化合物是抗焦虑剂和抗溃疡剂。它们是有用的药物，可用于预防慢性治疗或使用尼古丁、地西泮、酒精、可卡因、咖啡因或阿片类药物的戒断反应。这些前药也可用于治疗和/或预防惊恐发作。本发明还揭示了使用前药的制药组合物和治疗方法，以及制备它们的新型中间体。本发明的另一个特点是将主题前药化合物用于诊断组合物。