tert-butyl (S)-(1-oxo-1-(phenethylamino)-3-phenylpropan-2-yl)carbamate | 126770-48-7

• 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: tert-butyl (S)-(1-oxo-1-(phenethylamino)-3-phenylpropan-2-yl)carbamate
• 英文别名: tert-butyl(S)-1-(phenethylcarbamoyl)-2-phenylethylcarbamate；Boc-Phe-PEA；N-tert-butoxycarbonyl-L-phenylalanine-β-phenethylamide；N-(Boc-L-phenylalanyl)-2-phenylethylamine；tert-butyl N-[(2S)-1-oxo-3-phenyl-1-(2-phenylethylamino)propan-2-yl]carbamate
• CAS: 126770-48-7
• 化学式: C₂₂H₂₈N₂O₃
• 分子量: 368.476
• InChiKey: CNYYLCDGLCSSGJ-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-(1-oxo-1-(phenethylamino)-3-phenylpropan-2-yl)carbamate 在 三氟乙酸 作用下， 生成 (S)-2-amino-N-phenethyl-3-phenylpropanamide
  参考文献：
  名称：

  Structure−Activity Relationships on Phenylalanine-Containing Inhibitors of Histone Deacetylase:  In Vitro Enzyme Inhibition, Induction of Differentiation, and Inhibition of Proliferation in Friend Leukemic Cells

  摘要：

  Inhibitors of histone deacetylases (HDACs) are a new class of anticancer agents that affect gene regulation. We had previously reported the first simple synthetic HDAC inhibitors with in vitro activity at submicromolar concentrations. Here, we present structure-activity data on modifications of a phenylalanine-containing lead compound including amino acid amides as well as variations of the amino acid part. The compounds were tested for inhibition of maize HD-2, rat liver HDAC, and for the induction of terminal cell differentiation and inhibition of proliferation in Friend leukemic cells. In the amide series, in vitro inhibition was potentiated up to 15-fold, but the potential to induce cell differentiation decreased. Interestingly, an HDAC class selectivity was indicated among some of these amides. In the amino acid methyl ester series, a biphenylalanine derivative was identified as a good enzyme inhibitor, which blocks proliferation in the submicromolar range and is also a potent inducer of terminal cell differentiation.

  DOI：

  10.1021/jm0208119
• 作为产物：
  描述：

  在 9-azanoradamantane N-oxyl 、 potassium tert-butylate 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 生成 tert-butyl (S)-(1-oxo-1-(phenethylamino)-3-phenylpropan-2-yl)carbamate
  参考文献：
  名称：

  通过铜（I）催化的硼氢化/氧化反应由醛简单合成醛基三氟硼酸钾

  摘要：

  酰基三氟硼酸钾（KAT）是通过铜（I）催化的醛化硼化和随后的氧化反应制得的。这种合成路线的特点是可利用的醛类广泛，有利的步骤经济性，温和的反应条件以及对各种官能团的耐受性，并且能够轻松生成各种KAT，例如带有卤化物，硫化物，乙缩醛，或酯部分。此外，通过使用天然氨基酸作为起始原料，该方法应用于三步合成各种在C末端带有KAT部分的α-氨基酸类似物。

  DOI：

  10.1002/anie.201901748

文献信息

• Photocyclization of Tetra- and Pentapeptides Containing Adamantylphthalimide and Phenylalanines: Reaction Efficiency and Diastereoselectivity
  作者：Margareta Sohora、Mario Vazdar、Irena Sović、Kata Mlinarić-Majerski、Nikola Basarić

  DOI：10.1021/acs.joc.8b01785

  日期：2018.12.21

  the linear peptides disclosed conformational reasons for the observed diastereoselectivity, being due to the peptide backbone spatial orientation imposed by the Phe amino acids. The photochemical efficiency for the decarboxylation and cyclization is not dependent on the peptide length, but it depends on the oxidation potential of the amino acid at the C-terminus. The results described herein are particularly

  合成了一系列四肽和五肽，其在N端带有邻苯二甲酰亚胺发色团。肽的C末端被氨基酸Phe，Phe（OMe）或Phe（OMe）2战略性地取代具有不同的氧化电位。通过制备性辐射和光产物的分离以及激光闪光光解研究了肽的光化学反应性。光激发后，这些肽会经历光诱导电子转移（PET）和脱羧作用，然后进行非对映选择性环化，保留四肽构型或五肽构型反转。分子动力学（MD）模拟和NOE实验支持分配环状肽的立体化学。线性肽的MD模拟公开了观察到的非对映选择性的构象原因，这是由于Phe氨基酸施加的肽主链空间取向。脱羧和环化的光化学效率不取决于肽的长度，而是取决于C末端氨基酸的氧化电位。本文所述的结果对于合理设计有效光化学反应以制备具有所需选择性的环肽特别重要。
• Method for preserving quaternary ammonium salt
  申请人：——

  公开号：US20030153785A1

  公开（公告）日：2003-08-14

  A method of improving the stability of a quaternary ammonium salt and a method of efficiently preparing the quaternary ammonium salt having improved stability.

  一种提高季铵盐稳定性的方法和一种高效制备稳定性提高的季铵盐的方法。
• N,N′-disubstituted cinnamamide derivatives potentiate ciprofloxacin activity against overexpressing NorA efflux pump Staphylococcus aureus 1199B strains
  作者：Sylvie Radix、Anne Doléans Jordheim、Luc Rocheblave、Serge N'Digo、Anne-Laure Prignon、Carine Commun、Serge Michalet、Marie-Geneviève Dijoux-Franca、Angélique Mularoni、Nadia Walchshofer

  DOI：10.1016/j.ejmech.2018.03.028

  日期：2018.4

  A multi-step procedure has been described which afforded satisfactory yields of N,N′-disubstituted cinnamamides derived from N-Boc-protected amino acids (Boc-Gly, Boc-Val, Boc-Phe). The key step of this synthesis was a regioselective RedAl reduction of an amide function in presence of a carbamate group. Next, these cinnamamides were evaluated in co-admnistration with ciprofloxacin as efflux pump inhibitors

  已经描述了多步程序，其提供了令人满意的得自N -Boc保护的氨基酸（Boc-Gly，Boc-Val，Boc-Phe）的N，N'-二取代的肉桂酰胺的产率。该合成的关键步骤是在氨基甲酸酯基团存在下，区域选择性的RedA1还原酰胺功能。接下来，将这些肉桂酰胺与环丙沙星作为两种泵的金黄色葡萄球菌菌株，即过表达SA1199B和野生型SA1199的金黄色葡萄球菌菌株的外排泵抑制剂共同评估。同时，它们对人肺成纤维细胞MRC5细胞的内在毒性得到了赞赏。因此，发现结合氨基甲酸酯基和吲哚-3-基基团的肉桂酰胺是最有效的，也是毒性较小的EPI之一，构成了有希望的产品。
• Aziridine derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05668128A1

  公开（公告）日：1997-09-16

  The present invention relates to a compound of the formula: ##STR1## wherein R.sub.1 and Q are independently an optionally esterified or amidated carboxyl group; R.sub.2 is hydrogen, an acyl group or an optionally substituted hydrocarbon residue; X is a divalent hydrocarbon residue which may be substituted; or a salt thereof, which is useful as prophylactic and therapeutic agents of bone diseases and as agents for inhibiting thiol protease.

  本发明涉及一种化合物，其化学式为：##STR1## 其中R.sub.1和Q分别为可选的酯化或酰胺化的羧基；R.sub.2为氢、酰基或可选的取代的碳氢残基；X为可选的取代的二价碳氢残基；或其盐。该化合物可用作预防和治疗骨疾病的药物和抑制巯基蛋白酶的药物。
• PROCESS FOR PRODUCING CARBOXYLIC ACID DERIVATIVE AND CONDENSING AGENT COMPRISING QUATERNARY AMMONIUM SALT
  申请人：TOKUYAMA CORPORATION

  公开号：EP1085000A1

  公开（公告）日：2001-03-21

  A process for producing a carboxylic acid derivative characterized by mixing a quaternary ammonium salt having a specific triazine ring in the molecule, a carboxylic acid compound, and a compound having a nucleophilic functional group to conduct the condensation reaction of the carboxylic acid compound with the compound having a nucleophilic functional group; and a condensing agent comprising the quaternary ammonium salt. By the process, the condensation reaction can be conducted under mild conditions and a carboxylic acid derivative, especially an amide or ester compound, can be obtained in high yield.

  一种生产羧酸衍生物的工艺，其特征在于将分子中含有特定三嗪环的季铵盐、羧酸化合物和具有亲核官能团的化合物混合，以进行羧酸化合物与具有亲核官能团的化合物的缩合反应；以及由季铵盐组成的缩合剂。通过该工艺，可在温和条件下进行缩合反应，并以高产率获得羧酸衍生物，特别是酰胺或酯类化合物。