Literature DB >> 18242089

Design, synthesis, and evaluation of novel ethambutol analogues.

Raghunandan Yendapally1, Richard E Lee.   

Abstract

Ethambutol is one of the front-line agents recommended by the World Health Organization for the treatment of tuberculosis. In an effort to develop more potent therapies to treat tuberculosis, novel unsymmetrical ethambutol analogues were successfully synthesized by a new route utilizing novel building blocks synthesized using Ellman's sulfinyl chemistry. The resulting analogues were tested for anti-tuberculosis activity yielding compounds with comparable anti-tuberculosis activity to ethambutol and increased lipophilicity that may instill better tissue penetration and serum half-life.

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Year:  2008        PMID： 18242089      PMCID： PMC2276401          DOI： 10.1016/j.bmcl.2008.01.065

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


  12 in total

1.  A new synthetic compound with antituberculous activity in mice: ethambutol (dextro-2,2'-(ethylenediimino)-di-l-butanol).

Authors:  J P THOMAS; C O BAUGHN; R G WILKINSON; R G SHEPHERD
Journal:  Am Rev Respir Dis       Date:  1961-06

2.  The transcriptional responses of Mycobacterium tuberculosis to inhibitors of metabolism: novel insights into drug mechanisms of action.

Authors:  Helena I M Boshoff; Timothy G Myers; Brent R Copp; Michael R McNeil; Michael A Wilson; Clifton E Barry
Journal:  J Biol Chem       Date:  2004-07-09       Impact factor: 5.157

3.  Combinatorial lead optimization of [1,2]-diamines based on ethambutol as potential antituberculosis preclinical candidates.

Authors:  Richard E Lee; Marina Protopopova; Emma Crooks; Richard A Slayden; Marianne Terrot; Clifton E Barry
Journal:  J Comb Chem       Date:  2003 Mar-Apr

4.  Structure-activity studies leading to ethambutol, a new type of antituberculous compound.

Authors:  R G Shepherd; C Baughn; M L Cantrall; B Goodstein; J P Thomas; R G Wilkinson
Journal:  Ann N Y Acad Sci       Date:  1966-04-20       Impact factor: 5.691

5.  Asymmetric synthesis of protected 1,2-amino alcohols using tert-butanesulfinyl aldimines and ketimines.

Authors:  T P Tang; S K Volkman; J A Ellman
Journal:  J Org Chem       Date:  2001-12-28       Impact factor: 4.354

6.  Ethambutol analogues as potential antimycobacterial agents.

Authors:  H Häusler; R P Kawakami; E Mlaker; W B Severn; A E Stütz
Journal:  Bioorg Med Chem Lett       Date:  2001-07-09       Impact factor: 2.823

7.  [Antituberculous activity of cyclic analogs of ethambutol].

Authors:  A Crémieux; N Baghdadi; P Berthelot; M Debaert
Journal:  Ann Microbiol (Paris)       Date:  1983 Mar-Apr

8.  Discovery of aminothiazole inhibitors of cyclin-dependent kinase 2: synthesis, X-ray crystallographic analysis, and biological activities.

Authors:  Kyoung Soon Kim; S David Kimball; Raj N Misra; David B Rawlins; John T Hunt; Hai-Yun Xiao; Songfeng Lu; Ligang Qian; Wen-Ching Han; Weifang Shan; Toomas Mitt; Zhen-Wei Cai; Michael A Poss; Hong Zhu; John S Sack; John S Tokarski; Chieh Ying Chang; Nikola Pavletich; Amrita Kamath; William G Humphreys; Punit Marathe; Isia Bursuker; Kristen A Kellar; Urvashi Roongta; Roberta Batorsky; Janet G Mulheron; David Bol; Craig R Fairchild; Francis Y Lee; Kevin R Webster
Journal:  J Med Chem       Date:  2002-08-29       Impact factor: 7.446

9.  Identification of a novel arabinofuranosyltransferase (AftA) involved in cell wall arabinan biosynthesis in Mycobacterium tuberculosis.

Authors:  Luke J Alderwick; Mathias Seidel; Hermann Sahm; Gurdyal S Besra; Lothar Eggeling
Journal:  J Biol Chem       Date:  2006-04-04       Impact factor: 5.157

10.  Worldwide emergence of extensively drug-resistant tuberculosis.

Authors:  N Sarita Shah; Abigail Wright; Gill-Han Bai; Lucia Barrera; Fadila Boulahbal; Nuria Martín-Casabona; Francis Drobniewski; Chris Gilpin; Marta Havelková; Rosario Lepe; Richard Lumb; Beverly Metchock; Françoise Portaels; Maria Filomena Rodrigues; Sabine Rüsch-Gerdes; Armand Van Deun; Veronique Vincent; Kayla Laserson; Charles Wells; J Peter Cegielski
Journal:  Emerg Infect Dis       Date:  2007-03       Impact factor: 6.883
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  9 in total

1.  Computational nanochemistry study of the molecular structure and properties of ethambutol.

Authors:  Guillermo Salgado-Morán; Samuel Ruiz-Nieto; Lorena Gerli-Candia; Norma Flores-Holguín; Alejandra Favila-Pérez; Daniel Glossman-Mitnik
Journal:  J Mol Model       Date:  2013-05-26       Impact factor: 1.810

Review 2.  Discovery and development of SQ109: a new antitubercular drug with a novel mechanism of action.

Authors:  Katherine A Sacksteder; Marina Protopopova; Clifton E Barry; Koen Andries; Carol A Nacy
Journal:  Future Microbiol       Date:  2012-07       Impact factor: 3.165

3.  Anticancer activities of a β-amino alcohol ligand and nanoparticles of its copper(ii) and zinc(ii) complexes evaluated by experimental and theoretical methods.

Authors:  Zahra Mardani; Reza Kazemshoar-Duzduzani; Keyvan Moeini; Alireza Hajabbas-Farshchi; Cameron Carpenter-Warren; Alexandra M Z Slawin; J Derek Woollins
Journal:  RSC Adv       Date:  2018-08-13       Impact factor: 4.036

Review 4.  Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models.

Authors:  Nicole D Bartolo; Jacquelyne A Read; Elizabeth M Valentín; K A Woerpel
Journal:  Chem Rev       Date:  2020-01-06       Impact factor: 60.622

5.  Computational finding of potential inhibitor for Cytochrome P450 Mono-oxygenases Enzyme of Mycobacterium tuberculosis.

Authors:  Ashwani Sharma; Krishna K Subbias; Ophélie Robine; Indu Chaturvedi; Anshul Nigam; Nishant Sharma; Prem Prashant Chaudhary
Journal:  Bioinformation       Date:  2012-10-01

6.  (2S,3R)-tert-Butyl N-[4-(N-benzyl-4-fluoro-benzene-sulfonamido)-3-hy-droxy-1-phenyl-butan-2-yl]carbamate.

Authors:  Marcele Moreth; Marcus V N de Souza; James L Wardell; Solange M S V Wardell; Edward R T Tiekink
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-03-21

7.  Crystal structure of (1S,2R)-2-[(3R,4S)-3-methyl-4-phenyl-1,2,3,4-tetra-hydro-isoquinolin-2-yl]-1,2-di-phenyl-ethanol.

Authors:  Karim Ben Ali; Pascal Retailleau
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2019-09-03

8.  Modular synthesis of the pyrimidine core of the manzacidins by divergent Tsuji-Trost coupling.

Authors:  Sebastian Bretzke; Stephan Scheeff; Felicitas Vollmeyer; Friederike Eberhagen; Frank Rominger; Dirk Menche
Journal:  Beilstein J Org Chem       Date:  2016-06-02       Impact factor: 2.883

9.  Synthesis and Application of 1,2-Aminoalcohols with Neoisopulegol-Based Octahydrobenzofuran Core.

Authors:  Fatima Zahra Bamou; Tam Minh Le; Bettina Volford; András Szekeres; Zsolt Szakonyi
Journal:  Molecules       Date:  2019-12-19       Impact factor: 4.411
  9 in total

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