Expedient on-resin synthesis of peptidic benzimidazoles

被引：10

作者：

Bird, Michael J. ^{[1
]}

Silvestri, Anthony P. ^{[1
]}

Dawson, Philip E. ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2018年 / 28卷 / 16期

基金：

美国国家卫生研究院;

关键词：

Peptide benzimidazoles; SPPS; Benzimidazoles; Peptide therapeutics; Antimicrobials; Antifungals; Anthelmintics; NATIVE CHEMICAL LIGATION; ANTIVIRAL ACTIVITY; AMINO-ACIDS; INHIBITORS; ANTIBACTERIAL; DERIVATIVES; MEBENDAZOLE; DEFORMYLASE; DESIGN; CANCER;

D O I：

10.1016/j.bmcl.2018.04.062

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The benzimidazole moiety is a ubiquitous pharmacophore present in numerous anthelmintic, antibacterial, antiviral, antineoplastic, and antifungal drugs. While the polypharmacology of this heterocycle has spurred the development of numerous solution-phase syntheses, only a handful of disparate and inefficient methods detailing its synthesis on-resin have been reported. Here we report the concise and expedient syntheses of internal and C-terminal peptidic benzimidazoles - an emerging class of peptide deformylase (PDF)-inhibiting antimicrobials. This method benefits from being performed wholly on solid-phase at room temperature resulting in minimal purification and tolerance of temperature-sensitive functionality. (C) 2018 Published by Elsevier Ltd.

引用

页码：2679 / 2681

页数：3

共 39 条

[1] Antiparasitic mebendazole shows survival benefit in 2 preclinical models of glioblastoma multiforme [J].

Bai, Ren-Yuan ;

Staedtke, Verena ;

Aprhys, Colette M. ;

Gallia, Gary L. ;

Riggins, Gregory J. .

NEURO-ONCOLOGY, 2011, 13 (09) :974-982

[2] The therapeutic journey of benzimidazoles: A review [J].

Bansal, Yogita ;

Silakari, Om .

BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (21) :6208-6236

[3] An efficient Fmoc-SPPS approach for the generation of thioester peptide precursors for use in native chemical ligation [J].

Blanco-Canosa, Juan B. ;

Dawson, Philip E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (36) :6851-6855

[4] Chemical Protein Synthesis Using a Second-Generation N-Acylurea Linker for the Preparation of Peptide-Thioester Precursors [J].

Blanco-Canosa, Juan B. ;

Nardone, Brunello ;

Albericio, Fernando ;

Dawson, Philip E. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (22) :7197-7209

[5] Imidazole and benzimidazole derivatives as chemotherapeutic agents [J].

Boiani, M ;

González, M .

MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2005, 5 (04) :409-424

[6] Synthesis and Evaluation of Novel Benzimidazole Conjugates Incorporating Amino Acids and Dipeptide Moieties [J].

Bugday, Nesrin ;

Kucukbay, F. Zehra ;

Apohan, Elif ;

Kucukbay, Hasan ;

Serindag, Ayfer ;

Yesilada, Ozfer .

LETTERS IN ORGANIC CHEMISTRY, 2017, 14 (03) :198-206

[7] Design, synthesis, activity, and structure of a novel class of matrix metalloproteinase inhibitors containing a heterocyclic P-2'-P-3' amide bond isostere [J].

Chen, JJ ;

Zhang, YP ;

Hammond, S ;

Dewdney, N ;

Ho, T ;

Lin, XH ;

Browner, MF ;

Castelhano, AL .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (13) :1601-1606

[8] SYNTHESIS OF PROTEINS BY NATIVE CHEMICAL LIGATION [J].

DAWSON, PE ;

MUIR, TW ;

CLARKLEWIS, I ;

KENT, SBH .

SCIENCE, 1994, 266 (5186) :776-779

[9] Mebendazole induces apoptosis via Bcl-2 inactivation in chemoresistant melanoma cells [J].

Doudican, Nicole ;

Rodriguez, Adrianna ;

Osman, Iman ;

Orlow, Seth J. .

MOLECULAR CANCER RESEARCH, 2008, 6 (08) :1308-1315

[10] Benzimidazole treatment of cystic echinococcosis [J].

El-On, J .

ACTA TROPICA, 2003, 85 (02) :243-252

← 1 2 3 4 →