Preliminary antifungal and cytotoxic evaluation of synthetic cycloalkyl[b]thiophene derivatives with PLS-DA analysis

Acta Pharmaceutica

Volumn 62, Issue 2, 2012, Pages 221-236

  Souza, Beatriz ^a   De Oliveira, Tiago ^a   Aquino, Thiago ^a   De Lima, Maria ^a   Pitta, Ivan ^a   Galdino, Suely ^a   Lima, Edeltrudes ^b   Gonçalves Silva, Teresinha ^a   Militão, Gardênia ^a   Scotti, Luciana ^b   Scotti, Marcus ^b   Mendonça Jr , Francisco ^c  

^a FEDERAL UNIVERSITY OF PERNAMBUCO   (Brazil)

^b FEDERAL UNIVERSITY OF PARAÍBA   (Brazil)

^c STATE UNIVERSITY OF PARAÍBA   (Brazil)

Author keywords

antifungal activity; antiproliferative activity; cycloalkyl b thiophene derivatives; Pentacle program; PLS DA

Indexed keywords

2 AMINOTHIOPHENE DERIVATIVE; 2 [(1H INDOL 2 YLMETHYLIDENE)AMINO] 5,6,7,8 TETRAHYDRO 4H CYCLOHEPTA[B]THIOPHENE 3 CARBONITRILE; ANTIFUNGAL AGENT; ANTINEOPLASTIC AGENT; CYCLOALKYL[B]THIOPHENE DERIVATIVE; FLUCYTOSINE; MICONAZOLE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; CANCER CELL CULTURE; CANDIDA KRUSEI; CARBON NUCLEAR MAGNETIC RESONANCE; CELL PROLIFERATION; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMOMETRICS; COLON CARCINOMA; COMPUTER PROGRAM; CONTROLLED STUDY; CRYPTOCOCCUS NEOFORMANS; DISCRIMINANT ANALYSIS; DRUG CYTOTOXICITY; DRUG SYNTHESIS; GROWTH INHIBITION; HUMAN; HUMAN CELL; INFRARED SPECTROSCOPY; LARYNX CARCINOMA; LUNG CANCER; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PARTIAL LEAST SQUARES REGRESSION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 84863453722     PISSN: 13300075     EISSN: 18469558     Source Type: Journal    
DOI: 10.2478/v10007-012-0017-y     Document Type: Article

References (21)

1. Z. Puterová, A. Krutošíková and D. Végh, Gewalg reactions: synthesis, properties and applications of substituted 2-aminothiophenes, Arkivoc i (2010) 209-246.
2. K. Balamurugan, S. Perumal, A. S. K. Reddy, P. Yogeeswari and D. Sriram, A facile domino protocol for the regioselective and discovery of novel 2-amino-5-arylthieno-[2,3-b]thiophenes as anti-mycobacterial agents, Tetrahedron Lett. 50 (2009) 6191-6195; DOI: 10.1016/j.tetlet.2009.08.085.
3. I. M. I. Fakhr, M. A. A. Radwan, S. El-Batran, M. E. Omar, A. El-Salam and S. M. El-Shenawy, Synthesis and pharmacological evaluation of 2-substituted benzo[b]thiophenes as anti-inflammatory and analgesic agents, Eur. J. Med. Chem. 44 (2009) 1718-1725; DOI: 10.1016/j.ejmech.2008. 02.034.
4. A. M. Isloor, B. Kalluraya and K. S. Pai, Synthesis, characterization and biological activities of some new benzo[b]thiophene derivatives, Eur. J. Med. Chem. 45 (2010) 825-830; DOI: 10.1016/j. ejmech.2009.11.015.
5. A. E. G. E. Amr, M. H. Sherif, M. G. Assy, M. A. Al-Omar and I. Raga, Antiarrhythmic, serotonin antagonist and antianxiety activities of novel substituted thiophene derivatives synthesized from 2-amino-4,5,6,7-tetrahydro-N- phenylbenzo[b]thiophene-3-carboxamide, Eur. J. Med. Chem. 45 (2010) 5935-5942; DOI: 10.1016/j.ejmech.2010.09.059.
6. M. Gütschow, L. Kuerschner, U. Neumann, M. Pietsch, R. Löser, N. Koglin and K. Eger, 2-(Di-ethylamino)thieno[1,3]oxazin-4-ones as stable inhibitors of human leukocyte elastaze, J. Med. Chem. 42 (1999) 5437-5447; DOI: 10.1021/jm991108w.
7. A. B. Pinkerton, T. T. Lee, T. Z. Hoffman, Y. Wang, M. Kahraman, T. G. Cook, D. Severance, T. C. Gahman, S. A. Noble, A. K. Shiau and R. I. Davis, Synthesis and SAR of thiophene containing kinesin spindle protein (KSP) inhibitors, Bioorg. Med. Chem. Lett. 17 (2007) 3562-3569; DOI: 10.1016/j.bmcl.2007.04.076.
8. L. Aurelio, C. Valant, H. Figler, B. L. Flynn, J. Linden, P. M. Sexton, A. Christopoulos and P. J. Scammells, 3-and 6-Substituted 2-amino-4,5,6,7- tethahydrothieno[2,3-c]pyridines as A1 adeno-sine receptor allosteric modulators and antagonists, Bioorg. Med. Chem. 17 (2009) 7353-7361; DOI: 10.1016/j.bmc.2009.08.024. 9.
9. F. J. B. Mendonça Jr., R. G. Lima-Neto, T. B. Oliveira, M. C. A. Lima, I. R. Pitta, S. L. Galdino, R. M. D. Cruz, R. S. A. Araújo and R. P. Neves, Synthesis and evaluation of the antifungal activity of 2-(substituted-amino)-4,5-dialkyl-thiophene-3-carbonitrile derivatives, Lat. Am. J. Pharm. 30 (2011) 1492-1499.
10. A. A. Abu-Hashem, M. F. El-Shehry and F. A. Badria, Design and synthesis of novel thiophe-necarbohydrazide, thienopyrazole and thienopyrimidine derivatives as antioxidant and antitu-mor agents, Acta Pharm. 60 (2010) 311-323; DOI: 10.2478/v10007-010-0030-y
11. National Committee for Clinical and Laboratory Standards: Method M27-A2, NCCLS, Wayne (PA), Villanova, Pennsylvania, USA, 2002, pp. 1-29.
12. J. A. Barnett, R. W. Paire and D. Yarrow, Yeasts: Characteristics and Identification, Cambridge University Press, Cambridge 2000.
13. E. L. Souza, T. L. M. Stamford, E. O. Lima and V. N. Trajano, Effectiveness of Origanum vulgare L. essential oil to inhibit the growth of food spoiling yeasts, Food Control 18 (2007) 409-413; DOI: 10.1016/j.foodcont.2005. 11.008.
14. P. J. Houghton, M. J. Howea, C. C. Lee and G. Steventon, Uses and abuses of in vitro tests in ethnopharmacology: visualizing an elephant, J. Ethnopharmacol. 110 (2007) 391-400; DOI: 10.1016/j.jep.2007.01.032.
15. M. R. Boyd and K. D. Paull, Some practical considerations and applications of the national cancer institute in vitro anticancer discovery screen, Drug Develop. Res. 34 (1995) 91-109; DOI: 10.1002/ddr.430340203.
16. M. Kòurková, D. Sabolová, L. Janovec, J. Mike, J. Koval, J. Ungvarský, M. Tefaniinová, P. Federoko, P. Kristian and J. Imrich, Cytotoxic activity of proflavinediureas: synthesis, antitu-mor, evaluation and DNA binding properties of 1',1"-(acridin-3,6-diyl)-3', 3"-dialkyldiureas, Bioorg. Med. Chem.16 (2008) 3976-3984; DOI: 10.1016/j.bmc.2008.01.026.
17. N. L. Allinger, A hydrocarbon force-field utilizing V1 and V2 torsional terms, J. Am. Chem. Soc. 99 (1977) 8127-8134; DOI: 10.1021/ja00467a001.
18. M. J. S. E. Dewar, G. Zoebisch, E. F. Healy and J. J. P. Stewart, AM1: a new general purpose quantum mechanical molecular model, J. Am. Chem. Soc. 107 (1985) 3902-3909; DOI: 10.1021/ja00299a024.
19. N. C. Cohen, Guidebook on Molecular Modeling, in Drug Design, Academic Press, San Diego 1996, p. 361.
20. http://www.moldiscovery.com/soft-pentacle.php, access date 4/12/2012.
21. C. A. Boateng, S. V. K. Eyunni, X, Y. Zhu, J. R. Etukala, B. A. Bricker, M. K. Ashfaq, M. R. Jacob, S. I. Khan, L. A. Walker and S. Y. Ablordeppey, Synthesis and evaluation against opportunistic fungal pathogens, Bioorg. Med. Chem. 19 (2011) 458-470; DOI: 10.1016/j.bmc.2010.11.008.