Literature DB >> 25013719

Ugi 4-CR Synthesis of γ- and δ-Lactams providing new access to diverse enzyme interactions, a PDB analysis.

André Boltjes1, George P Liao1, Ting Zhao1, Eberhardt Herdtweck2, Alexander Dömling3.   

Abstract

A three step synthesis of N-unsubstituted tetrazolo γ- and δ-lactams involving a key Ugi-4CR is presented. The compounds, otherwise difficult to access, are conveniently synthesized in overall good yields by our route. PDB analysis of the N-unsubstituted γ- and δ-lactam fragment reveals a strongly tri-directional hydrogen bond donor acceptor interaction with the amino acids of the binding sites.

Entities:  

Year:  2014        PMID: 25013719      PMCID: PMC4084911          DOI: 10.1039/C4MD00162A

Source DB:  PubMed          Journal:  Medchemcomm        ISSN: 2040-2503            Impact factor:   3.597


  11 in total

1.  The Protein Data Bank.

Authors:  H M Berman; J Westbrook; Z Feng; G Gilliland; T N Bhat; H Weissig; I N Shindyalov; P E Bourne
Journal:  Nucleic Acids Res       Date:  2000-01-01       Impact factor: 16.971

2.  Structure-assisted design of mechanism-based irreversible inhibitors of human rhinovirus 3C protease with potent antiviral activity against multiple rhinovirus serotypes.

Authors:  D A Matthews; P S Dragovich; S E Webber; S A Fuhrman; A K Patick; L S Zalman; T F Hendrickson; R A Love; T J Prins; J T Marakovits; R Zhou; J Tikhe; C E Ford; J W Meador; R A Ferre; E L Brown; S L Binford; M A Brothers; D M DeLisle; S T Worland
Journal:  Proc Natl Acad Sci U S A       Date:  1999-09-28       Impact factor: 11.205

Review 3.  Recent developments in isocyanide based multicomponent reactions in applied chemistry.

Authors:  Alexander Dömling
Journal:  Chem Rev       Date:  2006-01       Impact factor: 60.622

4.  Rupintrivir is a promising candidate for treating severe cases of enterovirus-71 infection: evaluation of antiviral efficacy in a murine infection model.

Authors:  Xiaonan Zhang; Zhigang Song; Boyin Qin; Xiaoling Zhang; Lixiang Chen; Yunwen Hu; Zhenghong Yuan
Journal:  Antiviral Res       Date:  2013-01-05       Impact factor: 5.970

5.  Concise one-pot preparation of unique bis-pyrrolidinone tetrazoles.

Authors:  Steven Gunawan; Joachim Petit; Christopher Hulme
Journal:  ACS Comb Sci       Date:  2012-02-15       Impact factor: 3.784

6.  Effects of the muscarinic agonist oxotremorine on membrane fluidity in rat lymphocytes.

Authors:  C Tang; A F Castoldi; L G Costa
Journal:  Biochem Mol Biol Int       Date:  1993-04

7.  Tritylamine as an ammonia surrogate in the Ugi tetrazole synthesis.

Authors:  Ting Zhao; André Boltjes; Eberhardt Herdtweck; Alexander Dömling
Journal:  Org Lett       Date:  2013-01-18       Impact factor: 6.005

8.  Design of HIV-1 protease inhibitors with pyrrolidinones and oxazolidinones as novel P1'-ligands to enhance backbone-binding interactions with protease: synthesis, biological evaluation, and protein-ligand X-ray studies.

Authors:  Arun K Ghosh; Sofiya Leshchenko-Yashchuk; David D Anderson; Abigail Baldridge; Marcus Noetzel; Heather B Miller; Yunfeng Tie; Yuan-Fang Wang; Yasuhiro Koh; Irene T Weber; Hiroaki Mitsuya
Journal:  J Med Chem       Date:  2009-07-09       Impact factor: 7.446

9.  Rupintrivir is a promising candidate for treating severe cases of Enterovirus-71 infection.

Authors:  Xiao-Nan Zhang; Zhi-Gang Song; Ting Jiang; Bi-Sheng Shi; Yun-Wen Hu; Zheng-Hong Yuan
Journal:  World J Gastroenterol       Date:  2010-01-14       Impact factor: 5.742

10.  Enabling large-scale design, synthesis and validation of small molecule protein-protein antagonists.

Authors:  David Koes; Kareem Khoury; Yijun Huang; Wei Wang; Michal Bista; Grzegorz M Popowicz; Siglinde Wolf; Tad A Holak; Alexander Dömling; Carlos J Camacho
Journal:  PLoS One       Date:  2012-03-12       Impact factor: 3.240

View more
  2 in total

Review 1.  Tetrazoles via Multicomponent Reactions.

Authors:  Constantinos G Neochoritis; Ting Zhao; Alexander Dömling
Journal:  Chem Rev       Date:  2019-02-01       Impact factor: 60.622

2.  Diverse Isoquinoline Scaffolds by Ugi/Pomeranz-Fritsch and Ugi/Schlittler-Müller Reactions.

Authors:  Yuanze Wang; Pravin Patil; Katarzyna Kurpiewska; Justyna Kalinowska-Tluscik; Alexander Dömling
Journal:  Org Lett       Date:  2019-04-29       Impact factor: 6.005

  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.