414
Views
17
CrossRef citations to date
0
Altmetric
Research Articles

Designing, synthesis, and antimicrobial action of oxazoline and thiazoline derivatives of fatty acid esters

, , , , , , & show all
Pages 3412-3431 | Received 19 Aug 2016, Accepted 24 Oct 2016, Published online: 28 Nov 2016

References

  • Ahmad, A., & Khan, A. U. (2009). Prevalence of Candida species and potential risk factors for vulvovaginal candidiasis in Aligarh, India. European Journal of Obstetrics & Gynecology and Reproductive Biology, 144, 68–71.10.1016/j.ejogrb.2008.12.020
  • Balikci, H., Acikgoz, Z. C., Guvenman, S., Celikbilek, N., & Ozdem, B. (2014). Detection of plasmid-mediated AmpC beta-lactamase production in Escherichia coli and Klebsiella spp. isolates. Mikrobiyoloji Bülteni, 48, 82–93.
  • Bergstrom, K. S., Sham, H. P., Zarepour, M., & Vallance, B. A. (2012). Innate host responses to enteric bacterial pathogens: A balancing act between resistance and tolerance. Cellular Microbiology, 14, 475–484.10.1111/j.1462-5822.2012.01750.x
  • Butcu, M., Akcay, S. S., Aksaray, S., Calisici, G., Inan, A. S., & Engin, D. O. (2011). In vitro susceptibility of enterococci strains isolated from urine samples to fosfomycin and other antibiotics. Journal of Infection and Chemotherapy, 17, 575–578.10.1007/s10156-011-0212-7
  • Cheng, A., & Dixon, S. L. (2003). In silico models for the prediction of dose-dependent human hepatotoxicity. Journal of Computer-Aided Molecular Design, 17, 811–823.10.1023/B:JCAM.0000021834.50768.c6
  • Cheng, A., & Merz, K. M., Jr (2003). Prediction of aqueous solubility of a diverse set of compounds using quantitative structure−property relationships. Journal of Medicinal Chemistry, 46, 3572–3580.10.1021/jm020266b
  • Chowdhary, A., Randhawa, H. S., Sundar, G., Kathuria, S., Prakash, A., Khan, Z., Sun, S., & Xu, J. (2011). In vitro antifungal susceptibility profiles and genotypes of 308 clinical and environmental isolates of Cryptococcus neoformans var. grubii and Cryptococcus gattii serotype B from north-western India. Journal of Medical Microbiology, 60, 961–967.10.1099/jmm.0.029025-0
  • Clark, D. E. (1999). Rapid calculation of polar molecular surface area and its application to the prediction of transport phenomena. 1. Prediction of intestinal absorption. Journal of Pharmaceutical Sciences, 88, 807–814.10.1021/js9804011
  • Collins, A. H. (1976). Microbiological Methods. London: Butterworth (p. 24).
  • Colmenarejo, G., Alvarez-Pedraglio, A., & Lavandera, J. L. (2001). Cheminformatic models to predict binding affinities to human serum albumin. Journal of Medicinal Chemistry, 44, 4370–4378.10.1021/jm010960b
  • Crane, L., Anastassiadou, M., Hage, S., Stigliani, J. L., Baziard-Mouysset, G., Payard, M., … Renard, P. (2006). Design and synthesis of novel imidazoline derivatives with potent antihyperglycemic activity in a rat model of type 2 diabetes. Bioorganic & Medicinal Chemistry, 14, 7419–7433.10.1016/j.bmc.2006.07.026
  • Cruickshank, R., Duguid, J., Marmion, B., & Swain, R. (1975). Medical Microbiology: The Practice of Medical Microbiology. Churchill Livingstone, London, 2, 196–202.
  • Daoud, N. N., Dickinson, N. A., & Gilbert, P. (1983). Anti-microbial activity and physicochemical properties of some alkyldimethylbenzylammonium chlorides. Microbios, 37, 73–85.
  • Davyt, D., & Serra, G. (2010). Thiazole and oxazole alkaloids: Isolation and synthesis. Marine Drugs, 8, 2755–2780.10.3390/md8112755
  • DeLeo, F. R., Otto, M., Kreiswirth, B. N., & Chambers, H. F. (2010). Community-associated meticillin-resistant Staphylococcus aureus. The Lancet, 375, 1557–1568.10.1016/S0140-6736(09)61999-1
  • Dombek, K. M., & Ingram, L. O. (1984). Effects of ethanol on the Escherichia coli plasma membrane. Journal of Bacteriology, 157, 233–239.
  • Egan, W. J., Merz, K. M., Jr, & Baldwin, J. J. (2000). Prediction of drug absorption using multivariate statistics. Journal of Medicinal Chemistry, 43, 3867–3877.10.1021/jm000292e
  • Ertl, P., Rohde, B., & Selzer, P. (2000). Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties. Journal of Medicinal Chemistry, 43, 3714–3717.10.1021/jm000942e
  • Espinel-Ingroff, A., Boyle, K., & Sheehan, D. J. (2001). In vitro antifungal activities of voriconazole and reference agents as determined by NCCLS methods: Review of the literature. Mycopathologia, 150, 101–115.10.1023/A:1010954803886
  • Farshori, N. N., Ahmad, A., Khan, A. U., & Rauf, A. (2011). A facile, one-pot synthesis, characterization and antimicrobial activity of o-hydroxy anilide derivatives and 1-substituted-1,3-dicyclohexylurea analogs of long chain carboxylic acids. European Journal of Medicinal Chemistry, 46, 1433–1438.10.1016/j.ejmech.2011.01.070
  • Farshori, N. N., Banday, M. R., Ahmad, A., Khan, A. U., & Rauf, A. (2010). Synthesis, characterization, and in vitro antimicrobial activities of 5-alkenyl/hydroxyalkenyl-2-phenylamine-1,3,4-oxadiazoles and thiadiazoles. Bioorganic & Medicinal Chemistry Letters, 20, 1933–1938.10.1016/j.bmcl.2010.01.126
  • França, T. C. C., Guimarães, A. P., Cortopassi, W. A., Oliveira, A. A., & Ramalho, T. C. (2013). Applications of docking and molecular dynamic studies on the search for new drugs against the biological warfare agents bacillus anthracis and Yersinia pestis. Current Computer-Aided Drug Design, 9, 507–517.10.2174/15734099113099990033
  • Gabathuler, R. (2010). Approaches to transport therapeutic drugs across the blood-brain barrier to treat brain diseases. Neurobiology of Disease, 37, 48–57.10.1016/j.nbd.2009.07.028
  • Ghose, A. K., Viswanadhan, V. N., & Wendoloski, J. J. (1999). A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases. Journal of Combinatorial Chemistry, 1, 55–68.10.1021/cc9800071
  • Giacoppo, J. O. S., Franca, T. C. C., Kuča, K., Cunha, E. F. F., Abagyan, R., Mancini, D. T., & Ramalho, T. C. (2015). Molecular modeling and in vitro reactivation study between the oxime BI-6 and acetylcholinesterase inhibited by different nerve agents. Journal of Biomolecular Structure & Dynamics, 33, 2048–2058.10.1080/07391102.2014.989408
  • Gunstone, F. D. (1954). Fatty acids. Part II. The nature of the oxygenated acid present in Vernonia anthelmintica(Willd.) seed oil. Journal of the Chemical Society (Resumed), 2, 1611–1616.10.1039/jr9540001611
  • Gunstone, F. D. (1972). Fatty acids, Part 35 the preparation and properties of the complete series of methyl epoxyoctadecanoates. Chemistry and Physics of Lipids, 9, 26–34.10.1016/0009-3084(72)90031-X
  • Hansch, C., & Fujita, T. (1964). p-σ-π analysis. A method for the correlation of biological activity and chemical structure. Journal of the American Chemical Society, 86, 1616–1626.10.1021/ja01062a035
  • Hunt, W. A. (1975). The effects of aliphatic alcohols on the biophysical and biochemical correlates of membrane function. Advances in Experimental Medicine and Biology, 56, 195–210.10.1007/978-1-4684-7529-6
  • Husain, S., Abdul, Y., Singh, S., Ahmad, A., & Husain, M. (2014). Regulation of nitric oxide production by δ-opioid receptors during glaucomatous injury. PLoS ONE, 9, e110397.10.1371/journal.pone.0110397
  • Jubie, S., Ramesh, P. N., Dhanabal, P., Kalirajan, R., Muruganantham, N., & Antony, A. S. (2012). Synthesis, antidepressant and antimicrobial activities of some novel stearic acid analogues. European Journal of Medicinal Chemistry, 54, 931–935.10.1016/j.ejmech.2012.06.025
  • Kelder, J., Grootenhuis, P. D., Bayada, D. M., Delbressine, L. P., & Ploemen, J. P. (1999). Polar molecular surface as a dominating determinant for oral absorption and brain penetration of drugs. Pharmaceutical Research, 16, 1514–1519.10.1023/A:1015040217741
  • Kempe, K., Lobert, M., Hoogenboom, R., & Schubert, U. S. (2009). Screening the synthesis of 2-substituted-2-oxazolines. Journal of Combinatorial Chemistry, 11, 274–280.10.1021/cc800174d
  • Kubinyi, H. (1993). QSAR: Hansch analysis and related approaches. New York, NY: VCH.10.1002/SERIES6138
  • Kubo, I., Muroi, H., & Kubo, A. (1993). Antibacterial activity of long-chain alcohols against Streptococcus mutans. Journal of Agricultural and Food Chemistry, 41, 2447–2450.10.1021/jf00036a045
  • Kubo, I., Muroi, H., & Kubo, A. (1995). Structural functions of antimicrobial long-chain alcohols and phenols. Bioorganic & Medicinal Chemistry, 3, 873–880.10.1016/0968-0896(95)00081-Q
  • Kubo, I., Muroi, H., Masaki, H., & Kubo, A. (1993). Antibacterial activity of long-chain alcohols: The role of hydrophobic alkyl groups. Bioorganic & Medicinal Chemistry Letters, 3, 1305–1308.10.1016/S0960-894X(00)80336-4
  • Lagunin, A., Filimonov, D., & Poroikov, V. (2010). Multi-targeted natural products evaluation based on biological activity prediction with PASS. Current Pharmaceutical Design, 16, 1703–1717.10.2174/138161210791164063
  • Leucuta, S. E. (2014). Selecting oral bioavailability enhancing formulations during drug discovery and development. Expert Opinion on Drug Discovery, 9, 139–150.10.1517/17460441.2014.877881
  • Lien, E. J., Hansch, C., & Anderson, S. M. (1968). Structure-activity correlations for antibacterial agents on gram-positive and gram-negative cells. Journal of Medicinal Chemistry, 11, 430–441.10.1021/jm00309a004
  • Lipinski, C. A., Lombardo, F., Dominy, B. W., & Feeney, P. J. (2001). Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Advanced Drug Delivery Reviews, 46, 3–26.10.1016/S0169-409X(00)00129-0
  • McIsaac, W. J., & Hunchak, C. L. (2011). Overestimation error and unnecessary antibiotic prescriptions for acute cystitis in adult women. Medical Decision Making, 31, 405–411.10.1177/0272989X10391671
  • McKarns, S. C., Hansch, C., Caldwell, W. S., Morgan, W. T., Moore, S. K., & Doolittle, D. J. (1997). Correlation between hydrophobicity of short-chain aliphatic alcohols and their ability to alter plasma membrane integrity. Fundamental and Applied Toxicology, 36, 62–70.10.1006/faat.1996.2252
  • Muegge, I. (2003). Selection criteria for drug-like compounds. Medicinal Research Reviews, 23, 302–321.10.1002/(ISSN)1098-1128
  • Örnek, K., Apan, T., Oğurel, R., & Örnek, N. (2014). Comparison of the antimicrobial effect of heavy silicone oil and conventional silicone oil against endophthalmitis-causing agents. Indian Journal of Ophthalmology, 62, 388–391.10.4103/0301-4738.126994
  • Padmavathi, V., Venkatesh, B. C., Muralikrishna, A., & Padmaja, A. (2012). The reactivity of gem cyanoester ketene dithiolates towards the development of potent antioxidant heterocycles. Chemical and Pharmaceutical Bulletin, 60, 449–458.10.1248/cpb.60.449
  • Parvez, A., Jyotsna, M., & Youssoufi, M. H. (2010). Theoretical calculations and experimental verification of the antibacterial potential of some monocyclic β-lactams containing two synergetic buried antibacterial pharmacophore sites. Phosphorus, Sulfur, and Silicon and the Related Elements, 185, 1500–1510.10.1080/10426500903095556
  • Parvez, A., Meshram, J., Tiwari, V., Sheik, J., Dongre, R., Youssoufi, M. H., & Ben Hadda, T. (2010). Pharmacophores modeling in terms of prediction of theoretical physico-chemical properties and verification by experimental correlations of novel coumarin derivatives produced via Betti’s protocol. European Journal of Medicinal Chemistry, 45, 4370–4378.10.1016/j.ejmech.2010.06.004
  • Pellegatti, M., Pagliarusco, S., Solazzo, L., & Colato, D. (2011). Plasma protein binding and blood-free concentrations: Which studies are needed to develop a drug? Expert Opinion on Drug Metabolism & Toxicology, 7, 1009–1020.10.1517/17425255.2011.586336
  • Pospieszny, T., Koenig, H., Kowalczyk, I., & Brycki, B. (2014). Synthesis, spectroscopic and theoretical studies of new quasi-podands from bile acid derivatives linked by 1,2,3-triazole rings. Molecules, 19, 2557–2570.10.3390/molecules19022557
  • Remko, M., Swart, M., & Bickelhaupt, F. M. (2006). Theoretical study of structure, pKa, lipophilicity, solubility, absorption, and polar surface area of some centrally acting antihypertensives. Bioorganic & Medicinal Chemistry, 14, 1715–1728.10.1016/j.bmc.2005.10.020
  • Settimo, L., Bellman, K., & Knegtel, R. M. (2014). Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds. Pharmaceutical Research, 31, 1082–1095.
  • Sravani, M., Duganath, N., Gade, D., & Sandeep Reddy, C. (2012). Insilico analysis and docking of imatinib derivatives targeting BCR-ABL oncoprotein for chronic myeloid leukemia. Asian Journal of Research in Chemistry, 5, 153–158.
  • Susnow, R. G., & Dixon, S. L. (2003). Use of robust classification techniques for the prediction of human cytochrome P450 2D6 inhibition. Journal of Chemical Information and Computer Sciences, 43, 1308–1315.10.1021/ci030283p
  • Suter, C. M. (1941). Relationships between the structure and the bactericidal properties of phenols. Chemical Reviews, 28, 269–299.10.1021/cr60090a004
  • Vassilev, L. T., Vu, B. T., Graves, B., Carvajal, D., Podlaski, F., Filipovic, Z., … Liu, E. A. (2004). In vivo activation of the p53 pathway by small-molecule antagonists of MDM2. Science, 303, 844–848.10.1126/science.1092472
  • Veber, D. F., Johnson, S. R., Cheng, H. Y., Smith, B. R., Ward, K. W., & Kopple, K. D. (2002). Molecular properties that influence the oral bioavailability of drug candidates. Journal of Medicinal Chemistry, 45, 2615–2623.10.1021/jm020017n
  • Williams, A. A., Sugandhi, E. W., Macri, R. V., Falkinham, J. O., 3rd, & Gandour, R. D. (2007). Antimicrobial activity of long-chain, water-soluble, dendritic tricarboxylato amphiphiles. Journal of Antimicrobial Chemotherapy, 59, 451–458.10.1093/jac/dkl503
  • Wipf, P., Reeves, J. T., Balachandran, R., & Day, B. W. (2002). Synthesis and biological evaluation of structurally highly modified analogues of the antimitotic natural product curacin A. Journal of Medicinal Chemistry, 45, 1901–1917.10.1021/jm0105171
  • Xia, X., Maliski, E. G., Gallant, P., & Rogers, D. (2004). Classification of kinase inhibitors using a Bayesian model. Journal of Medicinal Chemistry, 47, 4463–4470.10.1021/jm0303195
  • Xu, W., Ling, P., & Zhang, T. (2013). Polymeric micelles, a promising drug delivery system to enhance bioavailability of poorly water-soluble drugs. Journal of Drug Delivery, 2013, 340315.
  • Yoshida, T., Jono, K., & Okonogi, K. (1997). Modified agar dilution susceptibility testing method for determining in vitro activities of antifungal agents, including azole compounds. Antimicrobial Agents and Chemotherapy, 41, 1349–1351.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.