(S)-prop-2-yn-1-yl 2-((tert-butoxycarbonyl)amino)-4-methylpentanoate

• 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: (S)-prop-2-yn-1-yl 2-((tert-butoxycarbonyl)amino)-4-methylpentanoate
• 英文别名: prop-2-yn-1-yl (tert-butoxycarbonyl)leucinate；(S)-prop-2-ynyl 2-(tert-butoxycarbonylamino)-4-methyl-pentanoate；prop-2-ynyl (2S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• 化学式: C₁₄H₂₃NO₄
• 分子量: 269.341
• InChiKey: DRVTVGVKXOEGDX-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-prop-2-yn-1-yl 2-((tert-butoxycarbonyl)amino)-4-methylpentanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  疏水性定向手性自组装和聚集诱导发光：以联乙炔为核心的伪肽手性掺杂剂

  摘要：

  具有刚性二炔核心的设计伪肽显示出疏水驱动的 AIE 手性自组装。它们在乙腈中自组装成囊泡，而在 90% H 2 O/DMSO 中自组装成超分子螺旋。这些没有 LC 特性的自组装假肽充当手性掺杂剂，将非手性 LC 基质引导到螺旋组装中。

  DOI：

  10.1002/anie.202209806
• 作为产物：
  描述：

  L-亮氨酸 在 potassium carbonate 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (S)-prop-2-yn-1-yl 2-((tert-butoxycarbonyl)amino)-4-methylpentanoate
  参考文献：
  名称：

  Synthesis, antimicrobial potency with in silico study of Boc-leucine-1,2,3-triazoles

  摘要：

  A library of N-Boc protected Leucine-linked 1,4-disubstituted 1,2,3-triazoles was synthesized and fully characterized, in high yield via copper-catalyzed alkyne-azide cycloaddition (CuAAC) reaction. In vitro antibacterial activity showed that compound 4h found to be more potent than the reference drug Ciprofloxacin (MIC: 0.0196 mu mol/mL) against tested bacterial strains S. entrica, B. subtilis, S. aureus, E. coli and P. auroginosa with MIC: 0.0148, 0.0074, 0.0148, 0.0074, and 0.0074 mu mol/mL, respectively and antifungal activity with MIC: 0.0148 mu mol/mL as compared to reference drug Fluconazole (MIC: 0.0102 mu mol/mL) against A. niger and C. albicans fungal strains. Further, the molecular docking study on 4h and its predecessor alkyne 3 by choosing E. coli topoisomerase II, DNA Gyrase (PDB ID: 1KZN) showed better binding with triazole than alkyne and these results were supported by DFT study using B3LYP/6-311G(d,p) basis set.

  DOI：

  10.1016/j.steroids.2020.108675

文献信息

• Design and synthesis of cyclic depsipeptides containing triazole (CDPT) rings
  作者：Sumit K. Agrawal、Piyush Panini、Manisha Sathe、Deepak Chopra、M. P. Kaushik

  DOI：10.1039/c3ra45100c

  日期：——

  We report the synthesis of cyclic depsipeptides containing triazole (CDPT) rings using click chemistry. 1,3-Dipolar cyclization via CuI-catalyzed alkyne–azide coupling gave the CDPT ring in a 58–64% yield.

  我们报告了利用点击化学合成含有咪唑环的环状依赖肽（CDPT）。通过CuI催化的炔烃-叠氮化合物的1,3-双极环化反应，获得了CDPT环，产率为58-64%。
• Synthesis of <i>C</i>-Propargylic Esters of N-Protected Amino Acids and Peptides
  作者：Sean P. Bew、Glyn D. Hiatt-Gipson

  DOI：10.1021/jo100537q

  日期：2010.6.4

  critical importance of amino acids in organic synthesis as well as their myriad of applications in “click” chemistry it is interesting to note that the synthesis of C-propargyl derived amino acid esters has not been particularly well served. We report a convenient, straightforward, and high-yielding synthesis of structurally diverse C-propargyl-derived N-protected amino acid esters.

  近年来，人们对将炔烃衍生的基元用于所谓的“点击”化学反应产生了极大的兴趣。鉴于氨基酸在有机合成中的至关重要性及其在“点击”化学中的众多应用，值得注意的是，C-炔丙基衍生的氨基酸酯的合成并未得到很好的服务。我们报道了结构多样的C-炔丙基衍生的N-保护的氨基酸酯的方便，直接和高产率的合成。
• A one-pot synthesis of [1,2,3]triazolo[1,5-a]quinoxalines from 1-azido-2-isocyanoarenes with high bond-forming efficiency
  作者：Dengke Li、Tingting Mao、Jinbo Huang、Qiang Zhu

  DOI：10.1039/c6cc08543a

  日期：——

  An efficient approach to prepare 1,2,3-triazolo[1,5-a]quinoxaline scaffolds, starting from 1-azido-2-isocyanoarenes and terminal acetylenes or substituted acetaldehydes, has been developed.

  一种高效的方法，从1-叠氮基-2-异氰基芳烃和末端炔烃或取代的乙醛出发，制备1,2,3-三唑[1,5-a]喹喔啉骨架已经被开发出来。
• Simultaneous Protection and Activation of Amino Acids Using Propargyl Pentafluorophenyl Carbonate
  作者：Ramapanicker Ramesh、Sakthidevi Rajasekaran、Rohit Gupta、Srinivasan Chandrasekaran

  DOI：10.1021/ol060494q

  日期：2006.4.1

  A very efficient method for the simultaneous protection of the amino group and activation of the carboxyl group of amino acids is reported using propargyl pentafluorophenyl carbonate (PocOPfp). The amino group is protected as a propargyloxycarbonyl (Poc) derivative, and the carboxyl group is activated as a pentafluorophenyl ester. The yields obtained are good to excellent ranging from 60 to 87%.
• New Colchicine-Derived Triazoles and Their Influence on Cytotoxicity and Microtubule Morphology
  作者：Persefoni Thomopoulou、Julia Sachs、Nicole Teusch、Aruljothi Mariappan、Jay Gopalakrishnan、Hans-Günther Schmalz

  DOI：10.1021/acsmedchemlett.5b00418

  日期：2016.2.11

  A series of new colchicinoids with a variable triazole unit at C-7 was synthesized through Cu(I)-catalyzed 1,3-dipolar cycloaddition (click-chemistry) of a colchicine-derived azide with various alkynes and the cytotoxicity against THP-1 and Jurkat cancer cell lines was used for structural optimization. Three particularly active compounds (IC50 <= 5 nM) were additionally investigated with respect to their efficacy against relevant solid tumor cell lines (HeLa, A549, and SK MES 1). Besides distorting the microtubule morphology by tubulin depolymerization, one compound also exhibited a pronounced centrosome declustering effect in triple negative breast cancer cells (MDA-MB-231) and nonsmall cell lung cancer cells (H1975).