Boc-Phe-NHTs | 1187922-70-8

• 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-Phe-NHTs
• 英文别名: (S)-tert-butyl (1-(4-methylphenylsulfonamido)-1-oxo-3-phenylpropan-2-yl)carbamate
• CAS: 1187922-70-8
• 化学式: C₂₁H₂₆N₂O₅S
• 分子量: 418.514
• InChiKey: CMKZLHPTKGXKMR-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  101.57
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Boc-Phe-NHTs 在 盐酸 、 N,N-二异丙基乙胺 、 O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 生成 (S)-1-(4-bromobenzyl)-N-{1-[(4-methylphenyl)sulfonamido]-1-oxo-3-phenylpropan-2-yl}-1H-indazole-3-carboxamide
  参考文献：
  名称：

  Design, Synthesis, Biological Evaluation, and Molecular Docking Studies of Indazole Derivatives as Bcl-2/Mcl-1 Dual Inhibitors

  摘要：

  DOI：

  10.1134/s1070363222060238
• 作为产物：
  描述：

  S-(tert-butyl) (2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanethioate 在 2,6-二甲基吡啶 、 15-冠醚-5 、 sodium thiophenolate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 Boc-Phe-NHTs
  参考文献：
  名称：

  肽硫代酸叠氮化连接反应的的Fmoc为基础的合成通过2-氰基乙基硫酯

  摘要：

  从2-氰基乙基肽硫代酸酯快速有效地制备肽硫代酸已经完成。无需使用3-巯基丙腈作为亲核试剂从树脂结合的叔丁基肽硫代酸酯中纯化，即可纯净地获得S -2-氰乙基肽硫代酸酯。在温和的条件下，2-氰基乙基的消除迅速进行（t 1/2 <8分钟），并提供了高达16-mer大小的肽硫代酸。可以分离或原位形成肽硫代酸，并使之与缺电子的叠氮化物平稳反应，生成酰胺作为连接产物。

  DOI：

  10.1021/ol302247h

文献信息

• N-Pyrrolidine-based α/β-peptides incorporating ABOC, a constrained bicyclic β-amino acid, for asymmetric aldol reaction catalysis
  作者：Pierre Milbeo、Kelly Maurent、Laure Moulat、Aurélien Lebrun、Claude Didierjean、Emmanuel Aubert、Jean Martinez、Monique Calmès

  DOI：10.1016/j.tet.2016.02.027

  日期：2016.3

  A series of N-pyrrolidine-based α,β-peptide catalysts incorporating a constrained 2-aminobicyclo[2.2.2]octane carboxylic acid (ABOC) residue were synthesized and evaluated in the asymmetric aldol reaction from acetone and some p-substituted benzaldehydes. Their catalytic properties were shown to be highly dependent on the amino acid sequences and on the absolute configuration of the ABOC residue that

  合成了一系列结合了约束的2-氨基双环[2.2.2]辛烷羧酸（ABOC）残基的N-吡咯烷基α，β-肽催化剂，并在丙酮和一些对位取代的苯甲醛的不对称羟醛反应中进行了评估。结果表明，它们的催化性能高度依赖于氨基酸序列以及起决定性作用的ABOC残基的绝对构型。在所测试的肽中，固态的转手构型的杂手性三肽H-Pro-（R）-ABOC-Asp-OCH 3 13被证明是最有效的催化剂，可高产率地提供β-羟基酮和良好的对映选择性（高达87％）。
• <i>Se</i>-(9-Fluorenylmethyl) Selenoesters; Preparation, Reactivity, and Use as Convenient Synthons for Selenoacids
  作者：Fabien Fécourt、Bernard Delpech、Oleg Melnyk、David Crich

  DOI：10.1021/ol401677a

  日期：2013.7.19

  Se-(9-Fluorenylmethyl) selenoesters are readily prepared, stable precursors to selenocarboxylates, which they liberate on treatment with DBU. Fm selenoesters are compatible with the use of TFA for the removal of Boc groups and with simple peptide bond forming reactions. Amino acid derived selenocarboxylates condense directly with amines to give amides, react smoothly with isocyanates and isothiocyanates to give amides, and couple with electron-deficient azides also to give amides.
• Design, synthesis and preliminary biological studies of pyrrolidine derivatives as Mcl-1 inhibitors
  作者：Yichao Wan、Junhua Wang、Feng’e Sun、Minglu Chen、Xuben Hou、Hao Fang

  DOI：10.1016/j.bmc.2015.11.014

  日期：2015.12

  Anti-apoptotic proteins, such as B-cell lymphoma (Bcl-2) protein, myeloid cell leukemia sequence 1 (Mcl-1) protein, are potential targets for cancer treatment. In the studies, a series of pyrrolidine derivatives were developed as potent Mcl-1 inhibitors. The preliminary biological studies suggested that most of target compounds exhibit good abilities for targeting Mcl-1 protein. Among them, compound 21 (K-i = 0.53 mu M) exhibited equal inhibitory activities towards Mcl-1 protein compared to positive control gossypol (K-i = 0.39 mu M). This compound also possessed good antiproliferative activities against MDA-MB-231 and PC-3 cancer cells. (c) 2015 Elsevier Ltd. All rights reserved.
• An improved practical synthesis of protected α-amino selenocarboxylates and its application to the synthesis of N-(α-aminoacyl)sulfonamides
  作者：Xinghua Wu、Yu Chen、Longqin Hu

  DOI：10.1016/j.tetlet.2009.07.080

  日期：2009.10

  An improved practical synthetic method was developed for the preparation of selenocarboxylates of amino acids through the reaction of the corresponding activated esters with sodium hydrogen selenide in alcoholic or aqueous medium. The protected cc-amino selenocarboxylates reacted readily with sulfonyl azide to form N-(alpha-aminoacyl)sulfonamides in high yields. The commonly used protecting groups in amino acid and peptide chemistries are well tolerated under these reaction conditions. No protecting groups are needed for the side chains of Arg, Met, Set, Tyr, and Trp. (C) 2009 Published by Elsevier Ltd.
• Discovery and development of thiazolidine-2,4-dione derivatives as Bcl-2/Mcl-1 dual inhibitors
  作者：Jiabing Long、Hongjuan Chen、Zixue Yan、Le Zhou、Ritian Deng、Jie Wang、Zilong Tang、Yichao Wan

  DOI：10.1016/j.bioorg.2024.107687

  日期：2024.10