title: New Non-Toxic Semi-Synthetic Derivatives from Natural Diterpenes Displaying Anti-Tuberculosis Activity.
abstract: We report herein the synthesis of six diterpene derivatives, three of which are new, generated through known organic chemistry reactions that allowed structural modification of the existing natural products kaurenoic acid (1) and copalic acid (2). The new compounds were fully characterized using high resolution mass spectrometry, infrared spectroscopy, ¹H- and (13)C-NMR experiments. We also report the evaluation of the anti-tuberculosis potential for all compounds, which showed some promising results for Micobacterium tuberculosis inhibition. Moreover, the toxicity for each of the most active compounds was also assessed.
authors.affiliation: Pesquisas em Ciências Exatas e Tecnológicas, Universidade de Franca, Franca 14404-600, Brazil. pcxpm1@nottingham.ac.uk.
authors.forename: Priscilla M
authors.initials: PM
authors.lastname: Matos
authors.affiliation: School of Chemistry, University of East Anglia, Norwich Research Park, Norwich, NR4 7TJ, UK. mahoneybri@gmail.com.
authors.forename: Brian
authors.initials: B
authors.lastname: Mahoney
authors.affiliation: School of Chemistry, University of East Anglia, Norwich Research Park, Norwich, NR4 7TJ, UK. y.chan@uea.ac.uk.
authors.forename: Yohan
authors.initials: Y
authors.lastname: Chan
authors.affiliation: School of Chemistry, University of East Anglia, Norwich Research Park, Norwich, NR4 7TJ, UK. ddukbr@gmail.com.
authors.forename: David P
authors.initials: DP
authors.lastname: Day
authors.affiliation: Pesquisas em Ciências Exatas e Tecnológicas, Universidade de Franca, Franca 14404-600, Brazil. mirela@com4.com.br.
authors.forename: Mirela M W
authors.initials: MM
authors.lastname: Cabral
authors.affiliation: Pesquisas em Ciências Exatas e Tecnológicas, Universidade de Franca, Franca 14404-600, Brazil. carlos.martins@unifran.edu.br.
authors.forename: Carlos H G
authors.initials: CH
authors.lastname: Martins
authors.affiliation: Pesquisas em Ciências Exatas e Tecnológicas, Universidade de Franca, Franca 14404-600, Brazil. raquel.santos@unifran.edu.br.
authors.forename: Raquel A
authors.initials: RA
authors.lastname: Santos
authors.affiliation: Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto 14040-903, Brazil. jkbastos@fcfrp.usp.br.
authors.forename: Jairo K
authors.initials: JK
authors.lastname: Bastos
authors.affiliation: School of Chemistry, University of East Anglia, Norwich Research Park, Norwich, NR4 7TJ, UK. p.page@uea.ac.uk.
authors.forename: Philip C Bulman
authors.initials: PC
authors.lastname: Page
authors.affiliation: Pesquisas em Ciências Exatas e Tecnológicas, Universidade de Franca, Franca 14404-600, Brazil. vladimir.heleno@unifran.edu.br.
authors.forename: Vladimir C G
authors.initials: VC
authors.lastname: Heleno
mesh_terms: D000995:Antitubercular Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000995:Antitubercular Agents; D001688:Biological Products; D004224:Diterpenes; C556511:copalic acid; C051436:kaurenoic acid
keywords: Mycobacterium tuberculosis; anti-tuberculosis activity; copalic acid; cytotoxicity; diterpene derivatives; kaurenoic acid; structural modification