Synthesis, characterization, antimicrobial activity, and QSAR studies on substituted oxadiazaboroles

被引:0
作者
Meryem Pir
Hikmet Agirbas
Fatma Budak
Merve Ilter
机构
[1] Kocaeli University,Department of Chemistry
[2] Kocaeli University,Department of Microbiology
来源
Medicinal Chemistry Research | 2016年 / 25卷
关键词
Oxadiazaborole derivatives; Antimicrobial activity; QSAR;
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中图分类号
学科分类号
摘要
This paper presents the synthesis and in vitro antimicrobial activity studies of 3,4,5-trisubstituted 4,5-dihydro-1,2,4,5-oxadiazaboroles (4) and 3,5-disubstituted 4,5-dihydro-1,2,4,5-oxadiazaboroles (7). The antimicrobial activities of the compounds were assessed against a panel of microorganisms including Staphylococcus aureus, Enterococcus faecalis, Pseudomonas aeruginosa, Escherichia coli, Streptococcus mutans, and Candida albicans. Some of the oxadiazaboroles exhibited fair activities against these microorganisms. The pMIC values of the compounds were first correlated with Hammett polar substituent constant (σ) and lipophilic constant (π) and statistically significant correlations were obtained. Additionally, the pMIC values of the compounds were correlated with σ, π, and some theoretical descriptors and fair 2D-quantitative structure–activity relationship models with clogP, surface area approx, ELUMO, µ, and EHOMO as independent variables were obtained. Application of training and test sets to quantitative structure–activity relationship models gave good results. Squared correlation matrix of the theoretical descriptors used in the quantitative structure–activity relationship study showed no correlation between the descriptors.
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页码:1794 / 1812
页数:18
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  • [1] Agirbas A(2015)The use of digital fabrication as a sketching tool in the architectural design process−a case study eCAADe 2 319-324
  • [2] Akama T(2009)Discovery and structure–activity study of a novel benzoxaborole anti-inflammatory agent (AN2728) for the potential topical treatment of psoriasis and atopic dermatitis Bioorg Med Chem Lett 19 2129-2132
  • [3] Baker SJ(2006)Identification of a novel boron-containing antibacterial agent (AN0128) with anti-inflammatory activity, for the potential treatment of cutaneous diseases Bioorg Med Chem Lett 16 5963-5967
  • [4] Zhang YK(2014)Heterocyclic aminoboron compounds as antituberculosis agents Heteroat Chem 25 100-106
  • [5] Hernandez V(2013)An assessment of the genetic toxicology of novel boron-containing therapeutic agents Environ Mol Mutagen 54 338-346
  • [6] Zhou H(2012)Design and synthesis of 3,5-disubstituted boron-containing 1,2,4-oxadiazoles as potential combretastatin A-4 (CA-4) analogs Tetrahedron Lett 53 3947-3950
  • [7] Sanders V(2007)Potentiometric study of acid-base equilibria of 3,5-disubstituted 1,2,4,5-oxadiazaboroles in nonaqueous media J Chem Eng Data 52 718-720
  • [8] Freund Y(2009)Quantitative structure–activity relationship (QSAR) for a series of novel cannabinoid derivatives using descriptors derived from semi-empirical quantum-chemical calculations Bioorg Med Chem 17 2598-2606
  • [9] Kimura R(2013)The design, synthesis, and antioxidant activity of amphiphilic oximes and amidoximes Acta Chim Slov 60 310-322
  • [10] Maples KR(1991)A survey of Hammett substituent constants and resonance and field parameters Chem Rev 91 165-195