Ukr.Biochem.J. 2016; Том 88, № 4, липень-серпень, c. 57-65
doi: http://dx.doi.org/10.15407/ubj88.04.057
QSAR дослідження та антимікробний потенціал 1,3-тіазолілфосфонієвих солей
M. M. Труш1, В. В. Ковалішин1, В. M. Благодатний2, В. С. Броварець1,
С. Г. Пільо1, В. M. Прокопенко1, Д. M. Година1, Л. O. Метелиця1
1Інститут біоорганічної хімії та нафтохімії НАН України, Київ;
2Національна медична академія післядипломної освіти імені П. Л. Шупика, Київ, Україна;
*e-mail: maria@bpci.kiev.ua
Побудовано регресійні QSAR-моделі для прогнозу антимікробної активності нових похідних тіазолу. Сполуки з високою прогнозованою активністю були синтезовані та тестовані проти грибів та грампозитивних і грамнегативних бактерій. 1,3-тіазол-4-ілфосфонієві солі 4 та 5 виявили значну антибактеріальну та високу протигрибкову активність. Результати прогнозу корелюють з результатами експериментальних досліджень, що свідчить про високу прогнозуючу здатність створених QSAR моделей.
Ключові слова: QSAR, антимікробна активність, тіазолілфосфонієві солі
Посилання:
- Hargrave KD, Hess FK, Oliver JT. N-(4-substituted-thiazolyl)oxamic acid derivatives, a new series of potent, orally active antiallergy agents. J Med Chem. 1983 Aug;26(8):1158-63. PubMed, CrossRef
- Musser JH, Brown RE, Loev B, Bailey K, Jones H, Kahen R, Huang FC, Khandwala A, Leibowitz M, Sonnino-Goldman P. Synthesis of 2-(2,3-dihydro-2-oxo-1,3,4-oxadiazol-5-yl) benzo heterocycles. A novel series of orally active antiallergic agents. J Med Chem. 1984 Feb;27(2):121-5. PubMed, CrossRef
- Patt WC, Hamilton HW, Taylor MD, Ryan MJ, Taylor DG Jr, Connolly CJ, Doherty AM, Klutchko SR, Sircar I, Steinbaugh BA, et al. Structure-activity relationships of a series of 2-amino-4-thiazole-containing renin inhibitors. J Med Chem. 1992 Jul 10;35(14):2562-72. PubMed, CrossRef
- Sharma RN, Xavier FP, Vasu KK, Chaturvedi SC, Pancholi SS. Synthesis of 4-benzyl-1,3-thiazole derivatives as potential anti-inflammatory agents: an analogue-based drug design approach. J Enzyme Inhib Med Chem. 2009 Jun;24(3):890-7. PubMed, CrossRef
- Shelke SH, Mhaske PC, Nandave M, Narkhade S, Walhekar NM, Bobade VD. Synthesis and pharmacological evaluation of a novel series of 3-aryl-2-(2-substituted-4-methylthiazole-5-yl)thiazolidin-4-one as possible anti-inflammatory and antimicrobial agents. Bioorg Med Chem Lett. 2012 Oct 15;22(20):6373-6. PubMed, CrossRef
- Jaen JC, Wise LD, Caprathe BW, Tecle H, Bergmeier S, Humblet CC, Heffner TG, Meltzer LT, Pugsley TA. 4-(1,2,5,6-Tetrahydro-1-alkyl-3-pyridinyl)-2-thiazolamines: a novel class of compounds with central dopamine agonist properties. J Med Chem. 1990 Jan;33(1):311-7. PubMed, CrossRef
- Ergenç N, Capan G, Günay NS, Ozkirimli S, Güngör M, Ozbey S, Kendi E. Synthesis and hypnotic activity of new 4-thiazolidinone and 2-thioxo-4,5-imidazolidinedione derivatives. Arch Pharm (Weinheim). 1999 Oct;332(10):343-7. PubMed, CrossRef
- Carter JS, Kramer S, Talley JJ, Penning T, Collins P, Graneto MJ, Seibert K, Koboldt CM, Masferrer J, Zweifel B. Synthesis and activity of sulfonamide-substituted 4,5-diaryl thiazoles as selective cyclooxygenase-2 inhibitors. Bioorg Med Chem Lett. 1999 Apr 19;9(8):1171-4. PubMed, CrossRef
- Sondhi SM, Singh N, Lahoti AM, Bajaj K, Kumar A, Lozach O, Meijer L. Synthesis of acridinyl-thiazolino derivatives and their evaluation for anti-inflammatory, analgesic and kinase inhibition activities. Bioorg Med Chem. 2005 Jul 1;13(13):4291-9. PubMed, CrossRef
- Kalkhambkar RG, Kulkarni GM, Shivkumar H, Rao RN. Synthesis of novel triheterocyclic thiazoles as anti-inflammatory and analgesic agents. Eur J Med Chem. 2007 Oct;42(10):1272-6. PubMed, CrossRef
- Bell FW, Cantrell AS, Högberg M, Jaskunas SR, Johansson NG, Jordan CL, Kinnick MD, Lind P, Morin JM Jr, Noréen R. Phenethylthiazolethiourea (PETT) compounds, a new class of HIV-1 reverse transcriptase inhibitors. 1. Synthesis and basic structure-activity relationship studies of PETT analogs. J Med Chem. 1995 Dec 8;38(25):4929-36.
PubMed, CrossRef - Rawal RK, Tripathi R, Katti SB, Pannecouque C, De Clercq E. Design and synthesis of 2-(2,6-dibromophenyl)-3-heteroaryl-1,3-thiazolidin-4-ones as anti-HIV agents. Eur J Med Chem. 2008 Dec;43(12):2800-6. PubMed, CrossRef
- Turan-Zitouni G, Özdemir A, Kaplancikli ZA. Synthesis and Antiviral Activity of Some (3,4-Diaryl-3H-thiazol-2-ylidene)pyrimidin-2-yl Amine Derivatives. Phosphorus Sulfur Silicon Relat Elem. 2011;186(2):233-9. CrossRef
- Kumar D, Sundaree S, Johnson EO, Shah K. An efficient synthesis and biological study of novel indolyl-1,3,4-oxadiazoles as potent anticancer agents. Bioorg Med Chem Lett. 2009 Aug 1;19(15):4492-4. PubMed, CrossRef
- Gürsoy E, Güzeldemirci NU. Synthesis and primary cytotoxicity evaluation of new imidazo[2,1-b]thiazole derivatives. Eur J Med Chem. 2007 Mar;42(3):320-6. PubMed, CrossRef
- Shao L, Zhou X, Hu Y, Jin Z, Liu J, Fang J. Synthesis and evaluation of novel ferrocenyl thiazole derivatives as anticancer agents. Synthesis and Reactivity in Inorganic Metal-Org and Nano-Metal Chem. 2006;36(4):325-330. CrossRef
- Abbs TF, Reji F, Devi SKC, Thomas KK, Sreejalekshmi KG, Manju SL, Francis M, Philip SK, Bharathan A, Rajasekharan KN. Synthesis and cytotoxicity studies of thiazole analogs of the anticancer marine alkaloid dendrodoine. Indian J Chem. 2008;47B:1145-1150.
- Hutchinson I, Bradshaw TD, Matthews CS, Stevens MF, Westwell AD. Antitumour benzothiazoles. Part 20: 3′-cyano and 3′-alkynyl-substituted 2-(4′-aminophenyl)benzothiazoles as new potent and selective analogues. Bioorg Med Chem Lett. 2003 Feb 10;13(3):471-4. PubMed, CrossRef
- Luzina EL, Popov AV. Synthesis and anticancer activity of N-bis(trifluoromethyl)alkyl-N’-thiazolyl and N-bis(trifluoromethyl)alkyl-N’-benzothiazolyl ureas. Eur J Med Chem. 2009 Dec;44(12):4944-53. PubMed, CrossRef
- Bondock S, Fadaly W, Metwally MA. Synthesis and antimicrobial activity of some new thiazole, thiophene and pyrazole derivatives containing benzothiazole moiety. Eur J Med Chem. 2010 Sep;45(9):3692-701. PubMed, CrossRef
- Desai NC, Bhatt N, Somani H, Trivedi A. Synthesis, antimicrobial and cytotoxic activities of some novel thiazole clubbed 1,3,4-oxadiazoles. Eur J Med Chem. 2013 Sep;67:54-9. PubMed, CrossRef
- Karegoudar P, Karthikeyan MS, Prasad DJ, Mahalinga M, Holla BS, Kumari NS. Synthesis of some novel 2,4-disubstituted thiazoles as possible antimicrobial agents. Eur J Med Chem. 2008 Feb;43(2):261-7. PubMed, CrossRef
- Karki R, Rao GK, Gupta A, Mariappan G, Adhikari S. Synthesis, Characterization and Antimicrobial Activities of Schiff bases of 2-amino-4-(O-chloroanilino)-1, 3-thiazole. J App Pharm Sci. 2013;3(07):93-96.
- Chimenti F, Bizzarri B, Bolasco A, Secci D, Chimenti P, Granese A, Carradori S, D’Ascenzio M, Lilli D, Rivanera D. Synthesis and biological evaluation of novel 2,4-disubstituted-1,3-thiazoles as anti-Candida spp. agents. Eur J Med Chem. 2011 Jan;46(1):378-82. PubMed, CrossRef
- Sarojini BK, Krishna BG, Darshanraj CG, Bharath BR, Manjunatha H. Synthesis, characterization, in vitro and molecular docking studies of new 2,5-dichloro thienyl substituted thiazole derivatives for antimicrobial properties. Eur J Med Chem. 2010 Aug;45(8):3490-6. PubMed, CrossRef
- Siddiqui N, Arshad MF, Ahsan W, Alam MS. Thiazoles: a valuable insight into the recent advances and biological activities. Int J Pharmaceut Sci Drug Res. 2009;1(3):136-143.
- ChEMBL. Available at https://www.ebi.ac.uk/chembl/
- Granito CE, Rosenberg MD. Chemical Substructure Index (CSI) – a new research tool. J Chem Doc. 1971 Nov;11(4):251-6. CrossRef
- ChemAxon Products. Available at http://www.chemaxon.com/products/
- OCHEM. Available at https://ochem.eu.
- Sushko I, Novotarskyi S, Körner R, Pandey AK, Rupp M, Teetz W, Brandmaier S, Abdelaziz A, Prokopenko VV, Tanchuk VY, Todeschini R, Varnek A, Marcou G, Ertl P, Potemkin V, Grishina M, Gasteiger J, Schwab C, Baskin II, Palyulin VA, Radchenko EV, Welsh WJ, Kholodovych V, Chekmarev D, Cherkasov A, Aires-de-Sousa J, Zhang QY, Bender A, Nigsch F, Patiny L, Williams A, Tkachenko V, Tetko IV. Online chemical modeling environment (OCHEM): web platform for data storage, model development and publishing of chemical information. J Comput Aided Mol Des. 2011 Jun;25(6):533-54. PubMed, PubMedCentral, CrossRef
- Tetko IV. Associative neural network. Methods Mol Biol. 2008;458:185-202. PubMed, CrossRef
- Adriana.CODE. Available at http://docs.ochem.eu/display/MAN/Adriana.CODE.
- Tetko IV, Tanchuk VY. Application of associative neural networks for prediction of lipophilicity in ALOGPS 2.1 program. J Chem Inf Comput Sci. 2002 Sep-Oct;42(5):1136-45. PubMed, CrossRef
- Kier LB, Hall LH. An electrotopological-state index for atoms in molecules. Pharm Res. 1990 Aug;7(8):801-7. PubMed, CrossRef
- Sushko I, Salmina E, Potemkin VA, Poda G, Tetko IV. ToxAlerts: a Web server of structural alerts for toxic chemicals and compounds with potential adverse reactions. J Chem Inf Model. 2012 Aug 27;52(8):2310-6. PubMed, PubMedCentral, CrossRef
- Nantasenamat C, Isarankura-Na-Ayudhya C, Naenna T, Prachayasittikul V. A practical overview of quantitative structure-activity relationship. EXCLI J. 2009;8:74-88.
- Mahobia NK, Patel RD, Sheikh NW, Singh SK, Mishra A, Dhardubey R. Validation method used in quantitative structure activity relationship. Der Pharma Chemica. 2010;2:260-271.
- Sushko I, Novotarskyi S, Körner R, Pandey AK, Cherkasov A, Li J, Gramatica P, Hansen K, Schroeter T, Müller KR, Xi L, Liu H, Yao X, Öberg T, Hormozdiari F, Dao P, Sahinalp C, Todeschini R, Polishchuk P, Artemenko A, Kuz’min V, Martin TM, Young DM, Fourches D, Muratov E, Tropsha A, Baskin I, Horvath D, Marcou G, Muller C, Varnek A, Prokopenko VV, Tetko IV. Applicability domains for classification problems: Benchmarking of distance to models for Ames mutagenicity set. J Chem Inf Model. 2010 Dec 27;50(12):2094-111. PubMed, CrossRef
- Sushko I, Novotarskyi S, Korner R, Pandey AK, Kovalishyn VV, Prokopenko VV, Tetko IV. Applicability domain for in silico models to achieve accuracy of experimental measurements. J Chemometrics. 2010 Apr;24(3-4):202-208. CrossRef
- Lobanov OP, Martynyuk AP, Drach BS. Reactions of (2,2-dichloro-1-acylaminovinil)triphenylphosphonium chloride with nucleophiles. Zhurn Obsh Khim. 1980; 50(10): 2248-2257. (In Russian).
- Brovarets VS, Zyuz KV, Vydzhak RN, Vinogradova TK, Drach BS. Synthesis of 2-acylaminovinylphosphonium salts, their analogues and derivatives based on the chlorine-containing unsaturated azlactones. Rus J Gen Chem. 1994; 64: 1462-1470. (In Russian).
- Brovarets VS, Zyuz KV, Romanenko EA, Drach BS. Transformations of the reaction product of 4-dichloromethylene-2-phenyl-5(4H)-oxazolone with triphenylphosphine to novel derivatives of triazoles and selenazoles. Zhurn Obsh Khim. 1995; 65(12): 1972-1978. (In Russian).
- Bauer AW, Kirby WM, Sherris JC, Turck M. Antibiotic susceptibility testing by a standardized single disk method. Am J Clin Pathol. 1966 Apr;45(4):493-6. PubMed
- CLSI. Performance Standards for Antimicrobial Susceptibility Testing; Twenty-First Informational Supplement. CLSI document M100-S21. Wayne, PA: Clinical and Laboratory Standards Institute; 2011.
- Tropsha A, Gramatica P, Gombar VK. The importance of being earnest: validation is the absolute essential for successful application and interpretation of QSPR models. QSAR Comb Sci. 2003 Apr;22(1):69-77. CrossRef
- Millard M, Pathania D, Shabaik Y, Taheri L, Deng J, Neamati N. Preclinical evaluation of novel triphenylphosphonium salts with broad-spectrum activity. PLoS One. 2010 Oct 4;5(10). pii: e13131. PubMed, PubMedCentral, CrossRef
- Dunn EA, Roxburgh M, Larsen L, Smith RA, McLellan AD, Heikal A, Murphy MP, Cook GM. Incorporation of triphenylphosphonium functionality improves the inhibitory properties of phenothiazine derivatives in Mycobacterium tuberculosis. Bioorg Med Chem. 2014 Oct 1;22(19):5320-8. PubMed, CrossRef
- Gorbunova M. Novel guanidinium and phosphonium polysulfones: synthesis and antimicrobial activity. J Chem Pharm Res. 2013;5:185-192.
- Pugachev MV, Shtyrlin NV, Sysoeva LP, Nikitina EV, Abdullin TI, Iksanova AG, Ilaeva AA, Musin RZ, Berdnikov EA, Shtyrlin YG. Synthesis and antibacterial activity of novel phosphonium salts on the basis of pyridoxine. Bioorg Med Chem. 2013 Jul 15;21(14):4388-95. PubMed, CrossRef
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