Synthesis of 5-substituted tetrazoles via DNA-conjugated nitrile

被引：14
作者：
Du, Huang-Chi [1 ]
Matzuk, Martin M. [1 ]
Chen, Ying-Chu [1 ]
机构：
[1] Baylor Coll Med, Ctr Drug Discovery, Dept Pathol & Immunol, Houston, TX 77030 USA
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 45期
关键词：
3+2 CYCLOADDITION; 1H-TETRAZOLES; DISCOVERY; AZIDE; CHEMISTRY; LIBRARIES; DESIGN;
D O I：
10.1039/d0ob02021d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A zinc bromide-catalyzed synthesis of 5-substituted tetrazoles via DNA-conjugated nitriles using sodium azide has been developed. The protocol offered moderate to excellent yields of tetrazoles with a broad range of substrates, including a variety of functionalized aromatic, heterocyclic, and aliphatic nitriles. In addition, the electronic effect within the substrate scope was evaluated. DNA fidelity was assessed by ligation efficiency and amplifiability analysis. The ability to generate tetrazoles expands the diversity of heterocycles in the preparation of DNA-encoded chemical libraries.
引用
收藏
页码：9221 / 9226
页数：6
相关论文
共 53 条
  • [1] DNA Compatible Intermolecular Wittig Olefination for the Construction of α, β-Unsaturated Carbonyl Compounds
    An, Yu-Long
    Li, Ke
    Shen, Yanfang
    Hong, Zibing
    Chen, Linlin
    Hu, Yujing
    Zhou, Lichun
    Wang, Disha
    Shi, Xiaodong
    Liu, Shien
    Su, Wenji
    Cui, Weiren
    Kuai, Letian
    Yang, Hongfang
    Peng, Xuanjia
    [J]. ORGANIC LETTERS, 2020, 22 (10) : 3931 - 3935
  • [2] Carboxylic Acid (Bio)Isosteres in Drug Design
    Ballatore, Carlo
    Huryn, Donna M.
    Smith, Amos B., III
    [J]. CHEMMEDCHEM, 2013, 8 (03) : 385 - 395
  • [3] L-Proline: An Efficient Organocatalyst for the Synthesis of 5-Substituted 1H-Tetrazoles via [3+2] Cycloaddition of Nitriles and Sodium Azide
    Bhagat, Saket B.
    Telvekar, Vikas N.
    [J]. SYNLETT, 2018, 29 (07) : 874 - 879
  • [4] Design and synthesis of a novel DNA-encoded chemical library using Diels-Alder cycloadditions
    Buller, Fabian
    Mannocci, Luca
    Zhang, Yixin
    Dumelin, Christoph E.
    Scheuermann, Joerg
    Neri, Dario
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (22) : 5926 - 5931
  • [5] Synthesis of C3-Alkylated Indoles on DNA via Indolyl Alcohol Formation Followed by Metal-Free Transfer Hydrogenation
    Cai, Pinwen
    Yang, Guanyu
    Zhao, Lanzhou
    Wan, Jinqiao
    Li, Jin
    Liu, Guansai
    [J]. ORGANIC LETTERS, 2019, 21 (17) : 6633 - 6637
  • [6] Castañón J, 2018, SLAS DISCOV, V23, P387, DOI 10.1177/2472555217752091
  • [7] C-N Coupling of DNA-Conjugated (Hetero)aryl Bromides and Chlorides for DNA-Encoded Chemical Library Synthesis
    Chen, Ying-Chu
    Faver, John C.
    Ku, Angela F.
    Miklossy, Gabriella
    Riehle, Kevin
    Bohren, Kurt M.
    Ucisik, Melek N.
    Matzuk, Martin M.
    Yu, Zhifeng
    Simmons, Nicholas
    [J]. BIOCONJUGATE CHEMISTRY, 2020, 31 (03) : 770 - 780
  • [8] Novel Autotaxin Inhibitor for the Treatment of Idiopathic Pulmonary Fibrosis: A Clinical Candidate Discovered Using DNA-Encoded Chemistry
    Cuozzo, John W.
    Clark, Matthew A.
    Keefe, Anthony D.
    Kohlmann, Anna
    Mulvihill, Mark
    Ni, Haihong
    Renzetti, Louis M.
    Resnicow, Daniel, I
    Ruebsam, Frank
    Sigel, Eric A.
    Thomson, Heather A.
    Wang, Ce
    Xie, Zhifeng
    Zhang, Ying
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2020, 63 (14) : 7840 - 7856
  • [9] Discovery of potent thrombin inhibitors from a protease-focused DNA-encoded chemical library
    Dawadi, Surendra
    Simmons, Nicholas
    Miklossy, Gabriella
    Bohren, Kurt M.
    Faver, John C.
    Ucisik, Melek Nihan
    Nyshadham, Pranavanand
    Yu, Zhifeng
    Matzuk, Martin M.
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2020, 117 (29) : 16782 - 16789
  • [10] Demko ZP, 2002, ANGEW CHEM INT EDIT, V41, P2110, DOI 10.1002/1521-3773(20020617)41:12<2110::AID-ANIE2110>3.0.CO
123456