Synthesis of 1-Aryl-3-phenethylamino-1-propanone hydrochlorides as possible potent cytotoxic agents

Molecules

Volumn 12, Issue 12, 2007, Pages 2579-2588

  Mete, Ebru ^a   Gul, Halise Inci ^a   Kazaz, Cavit ^a  

^a ATATÜRK UNIVERSITY   (Turkey)

Author keywords

Acetophenone; Mono Mannich base; Prodrug; Spectral analyses; Synthesis

Indexed keywords

CYTOTOXIN; MANNICH BASE;

ARTICLE; CHEMISTRY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY;

CYTOTOXINS; MAGNETIC RESONANCE SPECTROSCOPY; MANNICH BASES; MASS SPECTROMETRY; SPECTROPHOTOMETRY, INFRARED; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 38149106523     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/12122579     Document Type: Article

References (29)

1. Dimmock, J. R.; Kumar, P. Anticancer and cytotoxic properties of Mannich bases. Curr. Med. Chem. 1997, 4, 1-22.
2. Erciyas, E.; Erkaleli, H. I.; Cosar, G. Antimicrobial evaluation of some styryl ketone derivatives and related thiol adducts. J. Pharm. Sci. 1994, 83, 545-548.
3. Manavathu, E. K.; Vashishtha, S. C.; Alangaden, G. J.; Dimmock, J. R. In vitro antifungal activity of some Mannich bases of conjugated styryl ketones. Can. J. Microbiol. 1998, 44, 74-79.
4. Gul, H. I.; Denizci, A. A.; Erciyas, E. Antimicrobial evaluation of some Mannich bases of acetophenones and their representative quaternary derivatives. Arzneimittel-Forsch. 2002, 52, 773-777.
5. Gul, H. I.; Ojanen, T.; Hanninen, O. Antifungal evaluation of some bis Mannich bases derived from acetophenone and their corresponding piperidinols and stability studies. Biol. Pharm. Bull. 2002, 25, 1307-1310.
6. Gul, H. I.; Ojanen, T.; Vepsalainen, J.; Gul, M.; Erciyas, E.; Hanninen, O. Antifungal activity of some mono, bis and quaternary Mannich bases derived from acetophenone. Arzneimittel-Forsch. 2001, 51, 72-75.
7. Gul, H. I.; Sahin, F.; Gul, M.; Ozturk, S.; Yerdelen, K. O. Evaluation of antimicrobial activities of several Mannich bases and their derivatives. Arch. Pharm. (Weinheim) 2005, 338, 335-338.
8. Gul, H. I.; Vepsalainen, J.; Gul, M.; Erciyas, E.; Hanninen, O. Cytotoxic activities of mono and bis Mannich bases derived from acetophenone against Renca and Jurkat cells. Pharm. Acta Helv. 2000, 74, 393-398.
9. Gul, M.; Gul, H. I.; Vepsalainen, J.; Erciyas, E.; Hanninen, O. Effect of acetophenone derived Mannich bases on cellular glutathione level in Jurkat cells: a possible mechanism of action. Arzneimittel-Forsch. 2001, 51, 679-682.
10. Gul, H. I.; Gul, M.; Erciyas, E. Syntheses and stability studies of some Mannich bases of acetophenones and evaluation of their cytotoxicity against Jurkat cells. Arzneimittel-Forsch. 2002, 52, 628-635.
11. Gul, H. I.; Gul, M.; Hänninen, O. Cytotoxic activities of some mono and bis Mannich bases derived from acetophenone in brine shrimp bioassay. Arzneimittel-Forsch. 2002, 52, 840-843.
12. Gul, H. I.; Gul, M.; Vepsalainen, J.; Erciyas, E.; Hanninen, O. Cytotoxicity of some azines of acetophenone derived mono-Mannich bases against Jurkat cells. Biol. Pharm. Bull. 2003, 26, 631-637.
13. Gul, M.; Gul, H. I.; Das, U.; Hanninen, O. Biological evaluation and structure-activity relationships of bis-(3-aryl-3-oxo-propyl)-methylamine hydrochlorides and 4-aryl-3-arylcarbonyl-1-methyl-4-piperidinol hydrochlorides as potential cytotoxic agents and their alkylating ability towards cellular glutathione in human leukemic T cells. Arzneimittel-Forsch. 2005, 55, 332-337.
14. Gul, M.; Atalay, M.; Gul, H. I.; Nakao, C.; Lappalainen, J.; Hanninen, O. The effects of some Mannich bases on heat shock proteins HSC70 and GRP75, and thioredoxin and glutaredoxin levels in Jurkat cells. Toxicol. In Vitro 2005, 19, 573-580.
15. Suleyman, H.; Gul, H. I.; Gul, M.; Alkan, M.; Gocer, F. Anti-inflammatory activity of bis(3-aryl-3-oxo-propyl)methylamine hydrochloride in rat. Biol. Pharm. Bull. 2007, 30, 63-67.
16. Atwal, M. S.; Bauer, l.; Dixit, S. N.; Gearien, J. E.; Megahy, M.; Morris, R.; Pokorny, C. Analgetics. II. Relationship between structure and activity of some beta-aminoketones. J. Med. Chem. 1969, 12, 994-997.
17. Chen, H.; Ji, Z.; Wong, L. K.; Siuda, J. F.; Narayanan, V. L. Synthesis, antiinflammatory, and cytotoxic activities of 2-alkyl and 2-benzyl-2- dimethylaminomethyl-5-(E)-arylidene cyclopentanone hydrochlorides. Pharm. Res. 1996, 13, 1482-1487.
18. Suleyman, H.; Gul, H. I.; Asoglu, M. Antiinflammatory activity of 3-benzoyl-1-methyl-4-phenyl-4-piperidinol hydrochloride. Pharmacol. Res. 2003, 47, 471-475.
19. Koechel, D. A.; Rankin, G. O. Diuretic activity of Mannich base derivatives of ethacrynic acid and certain ethacrynic acid analogues. J. Med. Chem. 1978, 21, 764-769.
20. Lee, C. M.; Plattner, J. J.; Ours, C. W.; Horrom, B. W.; Smital, J. R.; Pernet, A. G.; Bunnell, P. R.; El-Masry, S. E.; Dodge, P. W. [[(Aminomethyl)aryl]oxy]acetic acid esters. A new class of high-ceiling diuretics. 1. Effects of nitrogen and aromatic nuclear substitution. J. Med. Chem. 1984, 27, 1579-1587.
21. Borenstein, M. R.; Doukas, P. H. Anticonvulsant activity of indanylspirosuccinimide Mannich bases. J. Pharm. Sci. 1987, 76, 300-302.
22. Dimmock, J. R.; Jonnalagadda, S. S.; Phillips, O. A.; Erciyas, E.; Shyam, K.; Semple, H. A. Anticonvulsant properties of some Mannich bases of conjugated arylidene ketones. J. Pharm. Sci. 1992, 81, 436-440.
23. Gursoy, A.; Karali, N.; Buyuktimkin, S.; Demirayak, S.; Ekinci, A. C.; Ozer, H. Some 3-hydrazono-2-indolinones and N-Mannich bases as potential anticonvulsants. Farmaco 1996, 51, 437-442.
24. Gul, H. I.; Calis, U.; Vepsalainen, J. Synthesis and evaluation of anticonvulsant activities of some bis-Mannich bases and corresponding piperidinols. Arzneimittel-Forsch. 2002, 52, 863-869.
25. Gul, H. I.; Calis, U.; Vepsalainen, J. Synthesis of some mono-Mannich bases and corresponding azine derivatives and evaluation of their anticonvulsant activity. Arzneimittel-Forsch. 2004, 54, 359-364.
26. Gul, M.; Gul, H. I.; Hanninen, O. Effects of Mannich bases on cellular glutathione and related enzymes of Jurkat cells in culture conditions. Toxicol. In Vitro 2002, 16, 107-112.
27. Roth, H. J.; Schwarz, D.; Hundeshagen, G. Photoreactions of phthalimide Mannich bases in methanol. Arch. Pharm. (Weinheim) 1976, 309, 48-52.
28. Collino, F.; de-Nardo, M. Mannich ketobases with narcotic antagonist activity. Boll. Chim. Farm. 1983, 122, 393-404.
29. Prost, M., Urbain, M., Charlier, R. 3-Amino-4'-Hydroxybutyrophenones. Belg. Chim. Therapeut. 1970, 5, 303-311.