Synthesis and crystal structure of some novel 2-aroylimino-3-aryl-4-phenyl- 1,3-thiazolines

Synthetic Communications

Volumn 38, Issue 13, 2008, Pages 2185-2199

  Saeed, Aamer ^a   Zaman, Sabah ^a   Bolte, Michael ^b  

^a QUAID I AZAM UNIVERSITY   (Pakistan)

^b GOETHE UNIVERSITY   (Germany)

Author keywords

1 Aroyl 3 arylthioureas; 2 imino 1,3 thiazolines

Indexed keywords

2 BENZOYLIMINO 3 ALPHA NAPHTHYL 4 PHENYL 1,3 THIAZOLINE; 2 IMINO 1,3 THIAZOLINE; ACETOPHENONE; BROMINE; HETEROCYCLIC COMPOUND; KHG 22394; MELANIN; PS 028; THIOUREA DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; CYCLIZATION; GAS CHROMATOGRAPHY; INFRARED SPECTROSCOPY; MASS SPECTROMETER; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; X RAY DIFFRACTION;

EID: 46749085476     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802026212     Document Type: Article

References (27)

1. Shehata, I. A.; Elsubbagh, H. I.; Abdelal, A. M.; Elsherbeny, M. A.; Alobaid, A. A. Synthesis, Antitumor and Anti-HIV-1 testing of certain thieno[2,3-d]pyrimidine, thieno[2,3-d]imidazo[1,2-c] pyrimidine and thieno[2,3-d][1,3]thiazine derivatives. Med. Chem. Res. 1996, 6, 148.
2. Venkatachalan, T. K.; Sudbeck, E. A.; Mao, C.; Uckun, F. M. Anti-HIV activity of aromatic and heterocyclic thiazolyl thiourea compounds Bioorg. Med. Chem. Lett. 2001, 11, 523.
3. Bonde, C. G.; Gaikwad, N. J. J., Synthesis and preliminary evaluation of some pyrazine containing thiazolines and thiazolidinones as antimicrobial agents. Bioorg. Med. Chem. 2004, 12, 2151.
4. Bondock, S.; Khalifa, W.; Fadda, A. A. Synthesis and antimicrobial evaluation of some new thiazole, thiazolidinone and thiazoline derivatives starting from 1-chloro-3,4-dihydronaphthalene-2-carboxaldehyde. Eur. J. Med. Chem. 2007, 1-7.
5. Eckhardt, S. Recent progress in the development of anticancer agents. Curr. Med. Chem. Anti-Cancer Agents 2002, 2, 419.
6. Lee, C. L.; Sim, M. M., Solid-phase combinatorial synthesis of 5-arylalkylidene rhodanine. Tetrahedron Lett. 2000, 41, 5729.
7. Arcadi, A.; Attanasi, O. A.; Giorgi, G.; Filippone, P.; Rossi, E.; Santeusanio, S. Pyrido[3,4-c]thiazoles through combined palladium-catalysed coupling of 2-substituted-5-acetyl-4-thiazolyltriflates with alkynes/annulation reactions. Tetrahedron Lett. 2003, 44, 8391.
8. Fahmy, Y. T. H.; Bekhit, A. A. Synthesis of some new bis-thiazoles as possible anticancer agents. Pharmazie, 2002, 57, 800.
9. Shih, M.-H.; Ke, F.-Y. J. Syntheses and evaluation of antioxidant activity of sydnonyl substituted thiazolidinone and thiazoline derivatives. Bioorg. Med. Chem. 2004, 12, 4633.
10. Manaka, A.; Ishii, T.; Takahashi, K.; Sato, M. 2-Acylimino-3-alkyl-3H- thiazoline derivatives: one-pot, three-component condensation synthesis of novel β-turn mimics. Tetrahedron Lett. 2005, 46, 419.
11. Sanemitsu, Y.; Kawamura, S.; Satoh, J.; Katayama, T.; Hashimoto, S., Synthesis and herbicidal activity of 2-acylimino-3-phenyl-1,3-thiazolines - A new family of bleaching herbicides. J. Pestic. Sci. 2006, 31(3), 305.
12. Bae, S.; Hahnand, H.-G.; Nam, K. D. Solid-Phase synthesis of fungitoxic 2-Imino-1,3-thiazolines. J. Comb. Chem. 2005, 7, 7.
13. Bolos, C. A.; Papazisis, K. T.; Kortsaris, A. H.; Voyatzi, S.; Zambouli, D.; Kyziakidis, D. A. Antiproliferative activity of mixed-ligand dien-Cu(II) complexes with thiazole, thiazoline and imidazole derivatives. J. Inorg. Biochem. 2002, 88, 25;
14. Barros-Garcia, F. J.; Bernalte-Garcia, A.; Higes-Rolando, F. J.; Luna-Giles, F.; Maldonado-Rogado, M. A. Vinuelas-Zahínos E., synthesis, crystal structure, spectroscopic and magnetic properties of copper(II) complexes with 2-(2-pyridyl)imino-N-(2-thiazolin-2-yl)thiazolidine (PyTT). J. Inorg. Chim. Acta 2004, 357, 3574.
15. Chen, Y.; Zhao, Y. J. Synthesis and characterization of polyacrylonitrile-2-amino-2-thiazoline resin and its sorption behavior for noble metal ions. React. Funct. Poly. 2003, 55, 89.
16. Bouchekara, M.; Djafri, A.; Vanthyne, N.; Roussel, C. Atropisomerism in some N,N′-diaryl-2-iminothiazoline derivatives: chiral separation and configurational stability, Arkivoc, 2002, 72.
17. Barros-Garcia, F. J.; Bernalte-Garcia, A.; Lozano-Vila, A. M.; Luna-Giles, F.; Vinuelas-Zahinos, E. Pseudotetrahedral cobalt(II) complexes with thiazoline and thiazine derivative ligands: Synthesis and characterization. Polyhedron, 2005, 24, 129.
18. Zhu, X.; Yu, Q.; Cutler, R. G.; Culmsee, C. W.; Holloway, H. W. Novel p53 inactivators with neuroprotective action: Syntheses and pharmacological evaluation of 2-Imino-2,3,4,5,6,7-hexahydrobenzothiazole and 2-Imino-2,3,4,5,6,7-hexahydrobenzoxazole derivatives. J. Med. Chem. 2002, 45, 5090.
19. A.; Dono, R.; Lingor, P.; Planchamp, V.; Lamballe, F.; Bahr, M.; Kraus, J-L.; Maina, F. Imino-tetrahydrobenzothiazole derivatives as p53 inhibitors: Discovery of a highly potent in vivo inhibitor and its action mechanism. J. Med. Chem. 2006, 49, 3645.
20. Sondhi, S. M.; Bhattacharjee, G.; Jameel, R. K.; Shukla, R.; Raghubir, R.; Lozach, O.; Meijer, L. Antiinflammatory, analgesic and kinase inhibition activities of some acridine derivatives. Cent. Eur. J. Chem. 2004, 2, 1.
21. Kimpe, N. D.; Cock, W.; Keppens, M.; Smaele, D. D.; Meszaroz, A., Synthesis of 2-Imino-4-thiazolines, 2-Imino-4-alkoxythiazolidines, Thiazoles and 4-Imidazolin-2-ones from a-Halomethyl ketimines. J. Heterocyclic Chem. 1996, 33, 1179.
22. D'hooghe, M.; Waterinekx, A.; Kimpe, N. D. A novel entry toward 2-Imino-1,3-thiazolidines and 2-Imino-1,3-thiazolines by ring transformation of 2-(Thiocyanomethyl) aziridines. J. Org. Chem. 2005, 70, 227.
23. Saeed, A.; Parvez, M. The crystal structure of 1-(4-chlorophenyl)-3-(4- methylbenzoyl)thiourea. Cent. Eur. J. Chem. 2005, 3, 780.
24. Blessing, R. H. An empirical correction for absorption anisotropy. Acta Cryst. 1995, A51, 33-38.
25. Spek, A. L. Single crystal structure validation with the program PLATON. J. Appl. Cryst. 2003, 36, 7.
26. Sheldrick, G. M. Acta Cryst. 1990, A46, 467-473.
27. Sheldrick, G. M. SHELXL-97: Phase annealing in SHELX90: direct methods for larger structures, program for the refinement of crystal structures. University of Gottingen, Germany, 1997.