Literature DB >> 24064500

Lead optimization of an acylhydrazone scaffold possessing antiviral activity against Lassa virus.

James R Burgeson1, Dima N Gharaibeh, Amy L Moore, Ryan A Larson, Sean M Amberg, Tove' C Bolken, Dennis E Hruby, Dongcheng Dai.   

Abstract

Previously we reported the optimization of antiviral scaffolds containing benzimidazole and related heterocycles possessing activity against a variety of arenaviruses. These series of compounds were discovered through an HTS campaign of a 400,000 small molecule library using lentivirus-based pseudotypes incorporated with the Lassa virus envelope glycoprotein (LASV GP). This screening also uncovered an alternate series of very potent arenavirus inhibitors based upon an acylhydrazone scaffold. Subsequent SAR analysis of this chemical series involved various substitutions throughout the chemical framework along with assessment of the preferred stereochemistry. These studies led to an optimized analog (ST-161) possessing subnanomolar activity against LASV and submicromolar activity against a number of other viruses in the Arenaviridae family.
Copyright © 2013 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Antiviral; Arenavirus; Lassa fever; Lassa virus; SAR

Mesh:

Substances:

Year:  2013        PMID: 24064500      PMCID: PMC3836667          DOI: 10.1016/j.bmcl.2013.08.103

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  12 in total

1.  Design, synthesis, and pharmacological evaluation of N-acylhydrazones and novel conformationally constrained compounds as selective and potent orally active phosphodiesterase-4 inhibitors.

Authors:  Arthur E Kümmerle; Martine Schmitt; Suzana V S Cardozo; Claire Lugnier; Pascal Villa; Alexandra B Lopes; Nelilma C Romeiro; Hélène Justiniano; Marco A Martins; Carlos A M Fraga; Jean-Jacques Bourguignon; Eliezer J Barreiro
Journal:  J Med Chem       Date:  2012-08-30       Impact factor: 7.446

2.  Interaction of HIV-1 reverse transcriptase ribonuclease H with an acylhydrazone inhibitor.

Authors:  Qingguo Gong; Lakshmi Menon; Tatiana Ilina; Lena G Miller; Jinwoo Ahn; Michael A Parniak; Rieko Ishima
Journal:  Chem Biol Drug Des       Date:  2010-11-29       Impact factor: 2.817

3.  Antibody conjugates with morpholinodoxorubicin and acid-cleavable linkers.

Authors:  B M Mueller; W A Wrasidlo; R A Reisfeld
Journal:  Bioconjug Chem       Date:  1990 Sep-Oct       Impact factor: 4.774

4.  New class of potent antitumor acylhydrazone derivatives containing furan.

Authors:  Zining Cui; Ying Li; Yun Ling; Juan Huang; Jingrong Cui; Ruiqing Wang; Xinling Yang
Journal:  Eur J Med Chem       Date:  2010-09-17       Impact factor: 6.514

5.  Synthesis, antitubercular activity, and SAR study of N-substituted-phenylamino-5-methyl-1H-1,2,3-triazole-4-carbohydrazides.

Authors:  Alessandro K Jordão; Plínio C Sathler; Vitor F Ferreira; Vinícius R Campos; Maria C B V de Souza; Helena C Castro; Andressa Lannes; André Lourenco; Carlos R Rodrigues; Murilo L Bello; Maria C S Lourenco; Guilherme S L Carvalho; Maria C B Almeida; Anna C Cunha
Journal:  Bioorg Med Chem       Date:  2011-07-24       Impact factor: 3.641

6.  Design and synthesis of a novel series of N-alkyl isatin acylhydrazone derivatives that act as selective cannabinoid receptor 2 agonists for the treatment of neuropathic pain.

Authors:  Philippe Diaz; Jijun Xu; Fanny Astruc-Diaz; Hao-Min Pan; David L Brown; Mohamed Naguib
Journal:  J Med Chem       Date:  2008-07-31       Impact factor: 7.446

7.  Novel cationic lipids incorporating an acid-sensitive acylhydrazone linker: synthesis and transfection properties.

Authors:  Abderrahim Aissaoui; Benjamin Martin; Erwan Kan; Noufissa Oudrhiri; Michelle Hauchecorne; Jean-Pierre Vigneron; Jean-Marie Lehn; Pierre Lehn
Journal:  J Med Chem       Date:  2004-10-07       Impact factor: 7.446

8.  Discovery and optimization of potent broad-spectrum arenavirus inhibitors derived from benzimidazole and related heterocycles.

Authors:  James R Burgeson; Amy L Moore; Dima N Gharaibeh; Ryan A Larson; Natasha R Cerruti; Sean M Amberg; Dennis E Hruby; Dongcheng Dai
Journal:  Bioorg Med Chem Lett       Date:  2012-12-01       Impact factor: 2.823

9.  Discovery and optimization of potent broad-spectrum arenavirus inhibitors derived from benzimidazole.

Authors:  Dongcheng Dai; James R Burgeson; Dima N Gharaibeh; Amy L Moore; Ryan A Larson; Natasha R Cerruti; Sean M Amberg; Tove' C Bolken; Dennis E Hruby
Journal:  Bioorg Med Chem Lett       Date:  2012-12-01       Impact factor: 2.823

10.  Identification of a broad-spectrum arenavirus entry inhibitor.

Authors:  Ryan A Larson; Dongcheng Dai; Virginia T Hosack; Ying Tan; Tove' C Bolken; Dennis E Hruby; Sean M Amberg
Journal:  J Virol       Date:  2008-08-20       Impact factor: 5.103

View more
  10 in total

1.  Tractable synthesis of multipurpose screening compounds with under-represented molecular features for an open access screening platform.

Authors:  Felix Wilde; Edgar Specker; Martin Neuenschwander; Marc Nazaré; Anja Bodtke; Andreas Link
Journal:  Mol Divers       Date:  2014-04-01       Impact factor: 2.943

2.  Identification of Clotrimazole Derivatives as Specific Inhibitors of Arenavirus Fusion.

Authors:  Sylvia Rothenberger; Christian Widmann; Stefan Kunz; Giulia Torriani; Evgeniya Trofimenko; Jennifer Mayor; Chiara Fedeli; Hector Moreno; Sébastien Michel; Mathieu Heulot; Nadja Chevalier; Gert Zimmer; Neeta Shrestha; Philippe Plattet; Olivier Engler
Journal:  J Virol       Date:  2019-03-05       Impact factor: 5.103

3.  Microwave-assisted synthesis and evaluation of acylhydrazones as potential inhibitors of bovine glutathione peroxidase.

Authors:  Felix Wilde; Heidi Lemmerhirt; Thomas Emmrich; Patrick J Bednarski; Andreas Link
Journal:  Mol Divers       Date:  2014-01-19       Impact factor: 2.943

4.  Substituted tetrazoles as multipurpose screening compounds.

Authors:  Nicole Rüger; Georg Michael Fassauer; Christian Bock; Thomas Emmrich; Anja Bodtke; Andreas Link
Journal:  Mol Divers       Date:  2016-12-27       Impact factor: 2.943

5.  Computer aided drug discovery of highly ligand efficient, low molecular weight imidazopyridine analogs as FLT3 inhibitors.

Authors:  Brendan Frett; Nick McConnell; Catherine C Smith; Yuanxiang Wang; Neil P Shah; Hong-yu Li
Journal:  Eur J Med Chem       Date:  2015-02-28       Impact factor: 6.514

6.  Small-Molecule Fusion Inhibitors Bind the pH-Sensing Stable Signal Peptide-GP2 Subunit Interface of the Lassa Virus Envelope Glycoprotein.

Authors:  Sundaresh Shankar; Landon R Whitby; Hedi E Casquilho-Gray; Joanne York; Dale L Boger; Jack H Nunberg
Journal:  J Virol       Date:  2016-07-11       Impact factor: 5.103

7.  Characterizing the Lassa Virus Envelope Glycoprotein Membrane Proximal External Region for Its Role in Fusogenicity.

Authors:  Junyuan Cao; Guangshun Zhang; Minmin Zhou; Yang Liu; Gengfu Xiao; Wei Wang
Journal:  Virol Sin       Date:  2020-09-08       Impact factor: 4.327

8.  Recombinant Lassa Virus Expressing Green Fluorescent Protein as a Tool for High-Throughput Drug Screens and Neutralizing Antibody Assays.

Authors:  Yíngyún Caì; Masaharu Iwasaki; Brett F Beitzel; Shuīqìng Yú; Elena N Postnikova; Beatrice Cubitt; Lisa Evans DeWald; Sheli R Radoshitzky; Laura Bollinger; Peter B Jahrling; Gustavo F Palacios; Juan C de la Torre; Jens H Kuhn
Journal:  Viruses       Date:  2018-11-20       Impact factor: 5.818

9.  Structure-activity relationship optimization for lassa virus fusion inhibitors targeting the transmembrane domain of GP2.

Authors:  Guangshun Zhang; Junyuan Cao; Yan Cai; Yang Liu; Yanli Li; Peilin Wang; Jiao Guo; Xiaoying Jia; Mengmeng Zhang; Gengfu Xiao; Yu Guo; Wei Wang
Journal:  Protein Cell       Date:  2019-02       Impact factor: 14.870

10.  Screening and Identification of Lassa Virus Entry Inhibitors from an FDA-Approved Drug Library.

Authors:  Peilin Wang; Yang Liu; Guangshun Zhang; Shaobo Wang; Jiao Guo; Junyuan Cao; Xiaoying Jia; Leike Zhang; Gengfu Xiao; Wei Wang
Journal:  J Virol       Date:  2018-07-31       Impact factor: 5.103

  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.