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

[21] The biochemical basis of anthelmintic action and resistance [J].

Köhler, P .

INTERNATIONAL JOURNAL FOR PARASITOLOGY, 2001, 31 (04) :336-345

[22] Solid phase synthesis of peptides containing novel amino acids, substituted 3-benzimidazolealanines [J].

Koprowska-Ratajska, Malgorzata ;

Kluczyk, Alicja ;

Stefanowicz, Piotr ;

Bartosz-Bechowski, Hubert ;

Szewczuk, Zbigniew .

AMINO ACIDS, 2009, 36 (02) :309-315

[23] Hookworm infection [J].

Loukas, Alex ;

Hotez, Peter J. ;

Diemert, David ;

Yazdanbakhsh, Maria ;

McCarthy, James S. ;

Correa-Oliveira, Rodrigo ;

Croese, John ;

Bethony, Jeffrey M. .

NATURE REVIEWS DISEASE PRIMERS, 2016, 2

[24] Characterisation of benzimidazole binding with recombinant tubulin from Giardia duodenalis, Encephalitozoon intestinalis, and Cryptosporidium parvum [J].

MacDonald, LM ;

Armson, A ;

Thompson, RCA ;

Reynoldson, JA .

MOLECULAR AND BIOCHEMICAL PARASITOLOGY, 2004, 138 (01) :89-96

[25] SYNTHESIS AND BIOLOGICAL-ACTIVITIES OF BENZIMIDAZOLE DERIVATIVES FROM PEPTIDES [J].

MAEKAWA, K ;

OHTANI, J .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1977, 41 (05) :811-818

[26] Mebendazole inhibits growth of human adrenocortical carcinoma cell lines implanted in nude mice [J].

Martarelli, Daniele ;

Pompei, Pierluigi ;

Baldi, Caterina ;

Mazzoni, Giovanni .

CANCER CHEMOTHERAPY AND PHARMACOLOGY, 2008, 61 (05) :809-817

[27] Structure-guided design of peptide-based tryptase inhibitors [J].

McGrath, ME ;

Sprengeler, PA ;

Hirschbein, B ;

Somoza, JR ;

Lehoux, I ;

Janc, JW ;

Gjerstad, E ;

Graupe, M ;

Estiarte, A ;

Venkataramani, C ;

Liu, Y ;

Yee, R ;

Ho, JD ;

Green, MJ ;

Lee, CS ;

Liu, L ;

Tai, V ;

Spencer, J ;

Sperandio, D ;

Katz, BA .

BIOCHEMISTRY, 2006, 45 (19) :5964-5973

[28] Identification of flubendazole as potential anti-neuroblastoma compound in a large cell line screen [J].

Michaelis, Martin ;

Agha, Bishr ;

Rothweiler, Florian ;

Loeschmann, Nadine ;

Voges, Yvonne ;

Mittelbronn, Michel ;

Starzetz, Tatjana ;

Harter, Patrick N. ;

Abhari, Behnaz A. ;

Fulda, Simone ;

Westermann, Frank ;

Riecken, Kristoffer ;

Spek, Silvia ;

Langer, Klaus ;

Wiese, Michael ;

Dirks, Wilhelm G. ;

Zehner, Richard ;

Cinatl, Jaroslav ;

Wass, Mark N. ;

Cinatl, Jindrich, Jr. .

SCIENTIFIC REPORTS, 2015, 5

[29] BENZIMIDAZOLE-5(6)-ALANINE AND RELATED COMPOUNDS .1. SYNTHESIS OF AMINO ACIDS AS INHIBITORS OF NOREPINEPHRINE BIOSYNTHESIS [J].

MILKOWSK.JD ;

MILLER, FM ;

JOHNSON, EM ;

ZENKER, N .

JOURNAL OF MEDICINAL CHEMISTRY, 1970, 13 (04) :741-&

[30] Angiotensin II receptor type 1 (AT1) selective nonpeptidic antagonists-A perspective [J].

Naik, Prashant ;

Murumkar, Prashant ;

Giridhar, Rajani ;

Yadav, Mange Ram .

BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (24) :8418-8456

← 1 2 3 4 →