Conformational space and vibrational spectra of 2-[(2,4-dimethoxyphenyl) amino]-1,3-thiazolidin-4-one

Journal of Molecular Modeling

Volumn 20, Issue 8, 2014, Pages

  Nowaczyk, Alicja ^a   Kowiel, Marcin ^b   Gzella, Andrzej ^b   Fijałkowski, Łukasz ^a   Horishny, Volodymyr ^c   Lesyk, Roman ^c  

^a NICOLAUS COPERNICUS UNIVERSITY   (Poland)

^b POZNAN UNIVERSITY OF MEDICAL SCIENCES   (Poland)

^c DANYLO HALYTSKY LVIV NATIONAL MEDICAL UNIVERSITY   (Ukraine)

Author keywords

1,3 thiazolidin 4 one; Ab initio calculations; FTIR spectral characteristics; Tautomerism; X ray analysis

Indexed keywords

2 [(2,4 DIMETHOXYPHENYL)AMINO] 1,3 THIAZOLIDIN 4 ONE; THIAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG; 2-((2,4-DIMETHOXYPHENYL)AMINO)-1,3-THIAZOLIDIN-4-ONE;

AB INITIO CALCULATION; ARTICLE; BIOLOGICAL ACTIVITY; CRYSTAL STRUCTURE; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; SOLID STATE; TAUTOMER; X RAY CRYSTALLOGRAPHY; CHEMISTRY; CONFORMATION; DIMERIZATION; HYDROGEN BOND; STATIC ELECTRICITY; STEREOISOMERISM; THERMODYNAMICS; VIBRATION;

CRYSTALLOGRAPHY, X-RAY; DIMERIZATION; HYDROGEN BONDING; MOLECULAR CONFORMATION; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STATIC ELECTRICITY; STEREOISOMERISM; THERMODYNAMICS; THIAZOLIDINES; VIBRATION;

EID: 84905649971     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-014-2366-6     Document Type: Article

References (46)

1. Jain AK, Vaidya A, Ravichandran V, Kashaw SK (2012) Recent developments and biological activities of thiazolidinone derivatives: a review. Bioorg Med Chem 20(11):3378-3395
2. Tripathi AC, Gupta SJ, Fatima GN, Sonar PK, Verma A, Saraf SK (2014) 4-Thiazolidinones: the advances continue. Eur J Med Chem 72:52-77
3. Devinyak O, Zimenkovsky B, Lesyk R (2013) Biologically active 4-thiazolidinones: a review of QSAR studies and QSAR modeling of antitumor activity. Curr Top Med Chem 12(24):2763-2784
4. Verma A, Saraf SK (2008) 4-thiazolidinone - a biologically active scaffold. Eur J Med Chem 43(5):897-905
5. Prabhakar YS, Solomon VR, Gupta MK, Katti SB (2006) QSAR studies on thiazolidines: a biologically privileged scaffold. QSAR and molecular modeling studies in heterocyclic Drugs II. Springer, Berlin, pp 161-249
6. Singh SP, Parmar SS, Raman K, Stenberg VI (1981) Chemistry and biological activity of thiazolidinones. Chem Rev 81(2):175-203
7. Havrylyuk D, Mosula L, Zimenkovsky B, Vasylenko O, Gzella A, Lesyk R (2010) Synthesis and anticancer activity evaluation of 4-thiazolidinones containing benzothiazole moiety. Eur J Med Chem 45(11):5012-5021
8. Havrylyuk D, Zimenkovsky B, Vasylenko O, Gzella A, Lesyk R (2012) Synthesis of new4-thiazolidinone, pyrazoline and isatin based conjugates with promising antitumor activity. J Med Chem 55(20):8630-8641
9. Havrylyuk D, Zimenkovsky B, Vasylenko O, Lesyk R (2013) Synthesis and anticancer and antiviral activities of new 2-pyrazoline-substituted 4-thiazolidinones. J Heterocycl Chem 50:E55-E62
10. Lesyk RB, Zimenkovsky BS, Kaminskyy DV, Kryshchyshyn AP, Havryluk DY, Atamanyuk DV, Subtel'na IY, Khyluk DV (2011) Thiazolidinone motif in anticancer drug discovery. Experience of DH LNMU medicinal chemistry scientific group. Biopolym Cell 27(2):107-117
11. Taylor PJ (1970) The infra-red spectroscopy of some 2-substituted thiazolid-4-ones, a new class of enamino-ketone. Elucidation of structure. Spectrochim Acta A-M 26(1):153-163
12. Taylor PJ (1976) The IR spectroscopy of some highly conjugated systems. Rationale of the investigation. Spectrochim Acta A-M 32(8):1471-1476
13. Enchev V, Chorbadjiev S, Jordanov B (2002) Comparative study of the structure of rhodanine, isorhodanine, thiazolidine-2, 4-dione, and thiorhodanine. Chem Heterocycl Compd 38(9):1110-1120
14. Khovratovich NN, Chizhevskaya II (1967) The problem of the tautomerism of 2-iminothiazolidin-4-one and some of its derivatives. Chem Heterocycl Compd 3(2):513-515
15. Akerblom E (1967) 2-Aminothiazoline-4-one and 2-imnothiazolidine-4-one derivatives. Part I The reaction of chloroacetic acid with Nmonoalkylthiourea. Acta Chem Scand 21:843-848
16. Akerblom E (1967) 2-Aminothiazoline-4-one and 2-imnothiazolidine-4-one derivatives. Part II Tautomerism. Acta Chem Scand 21:1437-1442
17. Taylor PJ (1970) The infra-red spectroscopy of some 2-substituted thiazolid-4-ones, a new class of enamino-ketone: infra-red assignments and chemical implications. Spectrochim Acta A-M 26(1):165-194
18. Brown FC (1961) 4-Thiazolidinones. Chem Rev 61(5):463-521
19. Liebermann C (1881) Zur Constitution der Sulfhydantoine und Sulfurethane. Ann Chem 207:121-167
20. Liebermann C, Lange A (1879) Ueber die Formeln der Sulfhydantoine. Ber Dtsch Chem Ges 12:1588-1595
21. Ramsh SM, Smorygo NA, Ginak AI (1984) Structure of 2-amino-4- thiazolinone. Chem Heterocycl Compd 20(8):865-869
22. Metwally MA, Farahat AA, Abdel-Wahab BF (2010) 2-Amino-4-thiazolidinones: synthesis and reactions. J Sulfur Chem 31(4):315-349
23. Subtelna I, Atamanyuk D, Szymanska E, Kiec-Kononowicz K, Zimenkovsky B, Vasylenko O, Gzella A, Lesyk R (2010) Synthesis of 5-arylidene-2-amino-4- azolones and evaluation of their anticancer activity. Bioorg Med Chem 18(14):5090-5102
24. Sharpe SW, Johnson TJ, Sams RL, Chu PM, Rhoderick GC, Johnson PA (2004) Gas-phase databases for quantitative infrared spectroscopy. Appl Spectrosc 58(12):1452-1461
25. Parr RG, Weitao Y (1994) Density-functional theory of atoms and molecules, vol 16. Oxford University Press, USA
26. Becke AD (1993) Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648
27. Vosko SH, Wilk L, Nusair M (1980) Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis. Can J Phys 58(8):1200-1211
28. Lee C, Yang W, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37:785
29. Ditchfield R, Hehre WJ, Pople JA (1971) Self-consistent molecularorbital methods. IX An extended Gaussian-type basis for molecularorbital studies of organic molecules. J Chem Phys 54:724-728
30. Frisch MJ, Pople JA, Binkley JS (1984) Self-consistent molecular orbital methods 25. Supplementary functions for Gaussian basis sets. J Chem Phys 80:3265-3269
31. Steel PJ, Guard JAM (1994) Heterocyclic tautomerism. VI. A redetermination and reassignment of the structure of 2-aminothiazol-4 (5H)-one (pseudothiohydantoin). Acta Cryst C 50(11):1721-1723
32. Lesyk R, Vladzimirska O, Holota S, Zaprutko L, Gzella A (2007) New 5-substituted thiazolo [3, 2- b][1, 2, 4] triazol-6-ones: synthesis and anticancer evaluation. Eur J Med Chem 42(5):641-648
33. Ostapiuk YV, Obushak MD, Matiychuk VS, Naskrent M, Gzella AK (2012) A convenient method for the synthesis of 2-[(5-benzyl-1, 3-thiazol-2-yl) imino]-1, 3-thiazolidin-4-one derivatives. Tetrahedron Lett 53(5):543-545
34. Kaminskyy D, Gzella AK, Lesyk R (2014) Cyclocondensation of thioamides and haloacetic acid derivatives provides inly 4-thiazolidinones; isomeric 5-thiazolidinones were not observed. Synth Commun 44:231-236
35. Allen FH (2002) The Cambridge Structural Database: a quarter of a million crystal structures and rising. Acta Cryst B 58(3):380-388
36. Haynes WM, Lide DR, Bruno TJ (2012) CRC handbook of chemistry and physics 2012-2013. CRC, Boca Raton
37. Allen FH, Kennard O, Watson DG, Brammer L, Orpen AG, Taylor R (1987) Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds. J Chem Soc Perkin Trans 2(12):S1-S19
38. Lin JF, Wu CC, Lien MH (1995) Ab initio study on the imineenamine tautomerism of the. alpha-substituted imines (XH2CCH: NH, X=H, BH2, CH3, NH2, OH, F, Cl, CN, NO). J Phys Chem 99(46):16903-16908
39. Katritzky AR, Hall CD, El-Gendy BE-DM, Draghici B (2010) Tautomerism in drug discovery. J Comput-Aided Mol Des 24(6-7):475-484
40. Bonde CG, Gaikwad NJ (2004) Synthesis and preliminary evaluation of some pyrazine containing thiazolines and thiazolidinones as antimicrobial agents. Bioorg Med Chem 12(9):2151-2161
41. Chohan ZH, Youssoufi MH, Jarrahpour A, Ben Hadda T (2010) Identification of antibacterial and antifungal pharmacophore sites for potent bacteria and fungi inhibition: indolenyl sulfonamide derivatives. Eur J Med Chem 45(3):1189-1199
42. Yoshida H, Takeda K, Okamura J, Ehara A, Matsurra H (2002) A new approach to vibrational analysis of large molecules by density functional theory: wavenumber-linear scaling method. J Phys Chem A 106(14):3580-3586
43. Anderluh M, Jukic M, Petric R (2009) Three-component one-pot synthetic route to 2-amino-5-alkylidene-thiazol-4-ones. Tetrahedron 65(1):344-350
44. Abhinit M, Ghodke M, Pratima NA (2009) Exploring potential of 4-thiazolidinone: a brief review. Int J Pharm Pharm Sci 1:57-64
45. Socrates G, Socrates G (2001) Infrared and Raman characteristic group frequencies: tables and charts. John Wiley & Sons Inc, Chichester
46. Coates J (2000) Interpretation of infrared spectra, a practical approach. Encyclopedia of analytical chemistry. Wiley, New York