L-苯丙氨酸酰胺三氟乙酸酯 | 81092-89-9

• 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-苯丙氨酸酰胺三氟乙酸酯
• 英文名称: L-phenylalanine amide trifluoroacetate
• 英文别名: PheNH2 trifluoroacetic salt；(S)-2-Amino-3-phenylpropanamide 2,2,2-trifluoroacetate；(2S)-2-amino-3-phenylpropanamide;2,2,2-trifluoroacetic acid
• CAS: 81092-89-9
• 化学式: C₂HF₃O₂*C₉H₁₂N₂O
• 分子量: 278.231
• InChiKey: FUYYFIGVJAJEMM-QRPNPIFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.68
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  L-苯丙氨酸酰胺三氟乙酸酯 在 palladium 10% on activated carbon 、 氢气 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 72.0h， 生成 (2S,4S)-tert-butyl 2-((S)-1-amino-1-oxo-3-phenylpropan-2-ylcarbamoyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Peptidomimetics of Arg-Phe-NH2 as small molecule agonists of Mas-related gene C (MrgC) receptors

  摘要：

  A series of Arg-Phe-NH2 peptidomimetics containing an Arg mimetic were synthesized and tested as agonists of human MrgX1, rat MrgC, and mouse MrgC11 receptors. As predicted from the previously established species specificity, these peptidomimetics were found to be devoid of MrgX1 agonist activity. In contrast, these compounds acted as agonists of MrgC and/or MrgC11 with varying degrees of potency. These new peptidomimetics should complement the existing small molecule human MrgX1 agonists and enhance our ability to assess the therapeutic utility of targeting Mrg receptors in rodent models. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.09.025
• 作为产物：
  描述：

  Boc-Phe-O-COO-isoBu 在 ammonium hydroxide 、 苯甲醚 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 L-苯丙氨酸酰胺三氟乙酸酯
  参考文献：
  名称：

  Design of Plasma Kallikrein Inhibitors: Functional and Structural Requirements of Plasma Kallikrein Inhibitors.

  摘要：

  合成血浆激肽释放酶（PK）抑制剂反式-4-氨基甲基环己烷羰基苯丙氨酸-4-羧甲基苯甲酰胺（PKSI-527）由三个部分组成。尝试用类似物替换每个部分，以提高PKSI-527的效力和选择性。在检测的肽中，反式-4-氨基甲基环己烷羰基苯丙氨酸-4-羧基苯甲酰胺（肽16）对PK具有高度选择性，IC50值为2.7μM，与PKSI-527效力相当。

  DOI：

  10.1248/cpb.46.452

文献信息

• Conformational analysis and μ-opioid receptor affinity of short peptides, endomorphin models in a low polarity solvent
  作者：Giuliana Cardillo、Luca Gentilucci、Alessandra Tolomelli、Ahmed R. Qasem、Santi Spampinato、Maria Calienni

  DOI：10.1039/b306161m

  日期：——

  Peptide carbamates containing the sequence H-Pro-Trp-PheNH2 showed in CDCl3 restricted conformations stabilized by the presence of a gamma-turn. To test the reliability of the peptides as endomorphin conformational models, we measured the affinities for mu-receptors labelled with [3H]-DAMGO. In particular, Cbz-Pro-Trp-PheNH2 displayed a nanomolar affinity.

  含有序列H-Pro-Trp-PheNH2的氨基甲酸酯肽在CDCl3限制的构象中显示，可通过存在伽马转角来稳定。为了测试作为内啡肽构象模型的肽的可靠性，我们测量了用[3H] -DAMGO标记的mu受体的亲和力。特别地，Cbz-Pro-Trp-PheNH2显示出纳摩尔亲和力。
• Investigation of peripheral cholecystokinin receptor heterogeneity by cyclic and related linear analogs of CCK26-33. Synthesis and biological properties
  作者：Bruno Charpentier、Christiane Durieux、Isabelle Menant、Bernard P. Roques

  DOI：10.1021/jm00389a002

  日期：1987.6

  by a D-Lys residue in Boc[Nle28,31]CCK27-33, a derivative as active as CCK8. The linear peptide Boc-Asp-Tyr(SO3H)-Nle-D-Lys-Trp-Nle-Asp-Phe-NH2 was cyclized through amide bond formation between the side chains of Asp26 and D-Lys29 to give the peptide Boc-Asp-Tyr(SO3H)-Nle-D-Lys-Trp-Nle-Asp-Phe-NH2. Analogues 1 and 2 were shown to stimulate secretion of amylase from rat pancreas with a potency that

  通过替换柔性Gly29残基，研究了CCK26-33 [Asp-Tyr（SO3H）-Met-Gly-Trp-Met-Asp-Phe-NH2]（CCK8）周围受体的可能异质性在CCK8折叠中，通过Boc [Nle28，31] CCK27-33中的D-Lys残基，具有与CCK8同样活性的衍生物。线性肽Boc-Asp-Tyr（SO3H）-Nle-D-Lys-Trp-Nle-Asp-Phe-NH2通过Asp26和D-Lys29侧链之间的酰胺键形成环化，得到肽Boc-Asp -Tyr（SO3H）-Nle-D-Lys-Trp-Nle-Asp-Phe-NH2。已显示类似物1和2刺激大鼠胰腺淀粉酶的分泌，其效力分别比CCK8低40和80倍。相反，两种肽均作为CCK8诱导的豚鼠回肠收缩的弱拮抗剂（EC50约为10（-5）M）。尽管它们的C末端Asp32残基发生酰胺化，但从1和2中除去苯丙氨酸获得的肽3和4在所
• BENZIMIDAZOLE DERIVATIVES
  申请人：Munchhof Michael John

  公开号：US20100029615A1

  公开（公告）日：2010-02-04

  The present invention relates to a compound of the formula (I) or a pharmaceutically acceptable salt thereof, wherein R 1, R 2 , R 3 , R 4 , R 5 , A, X, n, and are as defined herein. Such novel benzamidazole derivatives are useful in trv treatment of abnormal cell growth, such as cancer, in mammals. This invention ate relates to a method of using such compounds in the treatment of abnormal cell growth in mammals, especially humans, and to pharmaceutical compositions containing sue compounds.

  本发明涉及式(I)的化合物或其药学上可接受的盐，其中R1、R2、R3、R4、R5、A、X、n和如此定义的。这些新型苯并咪唑衍生物在哺乳动物中治疗异常细胞生长，如癌症方面具有用途。本发明还涉及使用这些化合物治疗哺乳动物，特别是人类的异常细胞生长的方法，以及含有这些化合物的制药组合物。
• Elucidation and synthesis of selected pentapeptides
  申请人：ARIZONA BOARD OF REGENTS

  公开号：EP0612762A1

  公开（公告）日：1994-08-31

  The sea hare Dolabella auricularia has yielded many structurally distinct peptides which possess antineoplastic activity. Presently the compound denominated "dolastatin 10" represents the most important of such peptides because of its demonstrated potential as an anticancer drug. The present invention relates to the systematic creation of five unique pentapeptides by selectively coupling a tripeptide - trifluoro-acetate salt with a preselected dipeptide-trifluoroacetate salt which provide active molecules capable of emulating the measured therapeutic effect of dolastatin 10. The pentapeptides hereof have the structure shown below: wherein R is selected from the following group of substituents:

  海兔多拉贝拉（Dolabella auricularia）产生了许多结构独特的多肽，具有抗肿瘤活性。目前，被称为 "多拉他汀 10 "的化合物是此类肽中最重要的一种，因为它具有作为抗癌药物的潜力。 本发明涉及通过选择性地将三肽-三氟乙酸盐与预选的二肽-三氟乙酸盐偶联，系统地制造出五种独特的五肽，这些五肽提供的活性分子能够模拟多拉他汀 10 的实测治疗效果。五肽的结构如下所示： 其中 R 选自以下一组取代基：
• Pharmaceutically relevant aromatic-cationic peptides
  申请人：Stealth BioTherapeutics Corp.

  公开号：US10221213B2

  公开（公告）日：2019-03-05

  The present technology provides peptides, methods of generating the peptides, and pharmaceutically acceptable salts of the peptides. In some embodiments, the peptide is D-Arg-2′6′-Dmt-Lys-Phe-NH2.

  本技术提供了多肽、生成多肽的方法以及多肽的药学上可接受的盐。在某些实施方案中，多肽是D-Arg-2′6′-Dmt-Lys-Phe-NH2。