Synthesis and preliminary biological evaluation of 1,3,5-triazine amino acid derivatives to study their MAO inhibitors

Molecules

Volumn 20, Issue 9, 2015, Pages 15976-15988

  Khattab, Sherine N ^a   Khalil, Hosam H ^a   Bekhit, Adnan A ^b   El Rahman, Mohamed Mokbel Abd ^a   El Faham, Ayman ^a,c   Albericio, Fernando ^c,d,e,f  

^a Alexandria University Faculty Of Science   (Egypt)

^b Alexandria University Faculty of Pharmacy   (Egypt)

^c KING SAUD UNIVERSITY   (Saudi Arabia)

^d UNIVERSITY OF KWAZULU NATAL   (South Africa)

^e INSTITUTE FOR RESEARCH IN BIOMEDICINE   (Spain)

^f UNIVERSITY OF BARCELONA   (Spain)

Author keywords

1,3,5 triazine derivatives; Amino acids; Monoamine oxidase; Morpholine; Piperidine

Indexed keywords

AMINO ACID; CLORGYLINE; MONOAMINE OXIDASE INHIBITOR; MORPHOLINE DERIVATIVE; PIPERIDINE; PIPERIDINE DERIVATIVE; TRIAZINE DERIVATIVE;

CHEMISTRY; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AMINO ACIDS; CLORGYLINE; MONOAMINE OXIDASE INHIBITORS; MORPHOLINES; PIPERIDINES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZINES;

EID: 84947931377     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules200915976     Document Type: Article

References (36)

1. Kalgutkar, A.S., Dalvie, D.K., Castagnoli, N., Taylor, T. Interactions of Nitrogen-Containing Xenobiotics with Monoamine Oxidase (MAO) Isozymes A and B: SAR Studies on MAO Substrates and Inhibitors. Chem. Res. Toxicol. 2001, 14, 1139-1162.
2. Legoabe, L.J., Petzer, A., Petzer, J.P. Selected C7-substituted chromone derivatives as monoamine oxidase inhibitors. Bioorg. Chem. 2012, 45, 1-11.
3. Youdim, M.B.H., Bakhle, Y.S. Monoamine oxidase: Isoforms and inhibitors in Parkinson?s disease and depressive illness. Br. J. Pharmacol. 2006, 147, S287-S296.
4. Anderson, M.C., Hasan, F., McCrodden, J.M. Monoamine oxidase inhibitors and the cheese effect. Neurochem. Res. 1993, 18, 1145-1149.
5. Tetrud, J.W., Koller, W.C. A novel formulation of selegiline for the treatment of Parkinson?s disease. Neurology 2004, 63, S2-S6.
6. Riederer, P., Danielczyk, W., Grunblatt, E. Monoamine-oxidase-B inhibition in Alzheimer?s disease. Neurotoxicology 2004, 25, 271-277.
7. Hassan, S.Y., Khattab, S.N., Bekhit, A.A., Amer, A. Synthesis of 3-benzyl-2-substituted quinoxalines as novel monoamine oxidase A inhibitors. Bioorg. Med. Chem. Lett. 2006, 16, 1753-1756.
8. Khattab, S.N., Hassan, S.Y., Bekhit, A.A., El-Massry, A., Langer, V., Amer, A. Synthesis of new series of quinoxaline based MAO-inhibitors and docking studies. Eur. J. Med. Chem. 2010, 45, 4479-4489.
9. Khattab, S.N., Bekhit, A.A., El-Faham, A., El-Massry, A., Amer, A. Synthesis of Some Pyridazinyl acetic Acid Derivatives as a Novel Class of Monoamine Oxidase-A Inhibitors. Chem. Pharm. Bull. 2008, 56, 1717-1721.
10. El-Faham, A., Al Marhoon, Z., Abdel-Megeed, A., Khattab, S.N., Bekhit, A., Albericio, F. α-Ketoamino acid ester derivatives as promising MAO inhibitors. Biol. Org. Med. Chem. Lett. 2015, 25, 70-74.
11. Foster, B.J., Harding, B.J., Leyland-Jones, B., Hoth, D. Hexamethylmelamine: A critical review of an active drug. Cancer Treat. Rev. 1986, 38, 197-217.
12. Tranchand, B., Catimel, G., Lucas, C., Sarkany, M., Bastian, G., Evene, E., Guastalla, J.P., Negrier, S., Rebattu, P., Dumortier, A., et al. Phase-I clinicalandpharmacokinetic study of S9788, anew multidrug-resistance reversal agent given alone and in combination with Doxorubicin to patients with advanced solid tumers. Cancer Chemother. Pharmacol. 1998, 41, 281-291.
13. Ono, M., Kawahara, N., Goto, D., Wakabayashi, Y., Ushiro, S., Yoshida, S., Izumi, H., Kuwano, M., Sato, Y. Inhibition of tumor growth and neovascularization by an anti-gastric ulcer agent, irsogladine. Cancer Res. 1996, 56, 1512-1516.
14. Maeda, M., Iigo, M., Tsuda, H., Fujita, H., Yonemura, Y., Nakagawa, K., Endo, Y., Sasaki, T. Antimetastatic and antitumor effects of 2, 4-diamino-6-(pyridine-4-yl)-1, 3, 5-Driazine(4PyDAT) on the high lung metastatic colon 26 tumor in mice. Anti-Cancer Drug Des. 2000, 15, 217-223.
15. Menicagli, R., Samaritani, S., Signore, G., Vaglini, F., Via, L.D. In vitro cytotoxic activities of 2-Alkyl-4, 6-diheteroalkyl-1, 3, 5-Driazines: New molecules in anticancer research. J. Med. Chem. 2004, 47, 4649-4652.
16. Baindur, N., Chadha, N., Brandt, B.M., Asgari, D., Patch, R.J., Schalk-Hihi, C., Carver, T.E., Petrounia, I.P., Baumann, C.A., Ott, H., et al. 2-Hydroxy-4, 6-diamino-[1, 3, 5]triazines: A Novel Class of VEGF-R2 (KDR) Tyrosine Kinase Inhibitors. J. Med. Chem. 2005, 48, 1717-1720.
17. Pandey, V.K., Tusi, S., Tusi, Z., Joshi, M., Bajpai, S. Synthesis and biological activity of substituted 2, 4, 6-s-Driazines. Acta Pharm. 2004, 54, 1-12.
18. Porter, J.R., Archibald, S.C., Brown, J.A., Childs, K., Critchley, D., Head, J.C., Hutchinson, B., Parton, T.A.H., Robinson, M.K., Shock, A., et al. Discovery and evaluation of N-(triazin-1, 3, 5-yl) phenylalanine derivatives as VLA-4 integrin antagonists. Bioorg. Med. Chem. Lett. 2002, 12, 1591-1594.
19. Mylari, B.L., Withbroe, G.J., Beebe, D.A., Brackett, N.S., Conn, E.L., Coutcher, J.B., Oates, P.J., Zembrowski, W.J. Design and synthesis of a novel family of triazine-based inhibitors of sorbitol dehydrogenase with oral activity: 1-{4-[3R, 5S-dimethyl-4-(4-methyl-[1, 3, 5]triazin-2-yl)-piperazin-1-yl]-[1, 3, 5]triazin-2-yl}-(R) ethanol. Bioorg. Med. Chem. 2003, 11, 4179-4188.
20. Henke, B.R., Consler, T.G., Go, N., Hale, R.L., Hohman, D.R., Jones, S.A., Lu, A.T., Moore, L.B., Moore, J.T., Orband-Miller, L.A., et al. A New Series of Estrogen Receptor Modulators That Display Selectivity for Estrogen Receptor β. J. Med. Chem. 2002, 45, 5492-5505.
21. Klenke, B., Stewart, M., Barrett, M.P., Brun, R., Gilbert, I.H. Synthesis and Biological Evaluation of s-Driazine Substituted Polyamines as Potential New Anti-Drypanosomal Drugs. J. Med. Chem. 2001, 44, 3440-3452.
22. Jensen, N.P., Ager, A.L., Bliss, R.A., Canfield, C.J., Kotecka, B.M., Rieckmann, K.H., Terpinski, J., Jacobus, D.P. Phenoxypropoxybiguanides, prodrugs of DHFR-inhibiting diaminotriazine antimalarials. J. Med. Chem. 2001, 44, 3925-3931.
23. Agarwal, A., Srivastava, K., Puri, S.K., Chauhan, P.M.S. Syntheses of 2, 4, 6-Drisubstituted triazines as antimalarial agents. Bioorg. Med. Chem. Lett. 2005, 15, 531-533.
24. Srinivas, K., Srinivas, U., Harakishore, K., Jayathirha, R.V., Bhanuprakash, K., Murthy, U.S.N. Synthesis and antibacterial activity of 2, 4, 6-Dri substituted s-Driazines. Bioorg. Med. Chem. Lett. 2005, 15, 1121-1123.
25. McKay, G.A., Reddy, R., Arhin, F., Belley, A., Lehoux, D., Moeck, G., Sarmiento, I., Parr, T.R., Gros, P., Pelletier, J., et al. Triaminotriazine DNA helicase inhibitors with antibacterial activity. Bioorg. Med. Chem. Lett. 2006, 16, 1286-1290.
26. Ghaib, A., Menager, S., Verite, P., Lafont, O. Synthesis of variously 9, 9-dialkylated octahydropyrimido [3, 4-A]-s-Driazines with potential antifungal activity. IL Farmaco 2002, 57, 109-116.
27. Lubbers, T., Angehrn, P., Gmunder, H., Herzig, S., Kulhanek, J. Design, synthesis, and structure-Activity relationship studies of ATP analogues as DNA gyrase inhibitors. Bioorg. Med. Chem. Lett. 2000, 10, 821-826.
28. Lebreton, S., Newcombe, N., Bradley, M. Antibacterial single-bead screening. Tetrahedron 2003, 59, 10213-10222.
29. Sunduru, N., Sharma, M., Srivastava, K., Rajakumar, S., Puri, S.K., Saxena, J.K., Chauhan, P.M.S. Synthesis of oxalamide and triazine derivatives as a novel class of hybrid 4-Aminoquinoline with potent antiplasmodial activity. Bioorg. Med. Chem. 2009, 17, 6451-6462.
30. D?Atri, G., Gomarasca, P., Resnati, G., Tronconi, G., Scolastico, C., Sirtori, C.R. Novel pyrimidine and 1, 3, 5-Driazine hypolipemic agents. J. Med. Chem. 1984, 27, 1621-1629.
31. Silen, J.L., Lu, A.T., Solas, D.W., Gore, M.A., Maclean, D., Shah, N.H., Coffin, L.M., Bhinderwala, N.S., Wang, Y., Tsutsui, K.L., et al. Screening for novel antimicrobials from encoded combinatorial libraries by using a two-dimensional agar format. Antimicrob. Agents Chemother. 1998, 42, 1447-1453.
32. Zhou, C., Min, J., Liu, Z., Young, A., Deshazer, H., Gao, T., Chang, Y., Kallenbach, N.R. Synthesis and biological evaluation of novel 1, 3, 5-Driazine derivatives as antimicrobial agents. Bioorg. Med. Chem. Lett. 2008, 18, 1308-1311.
33. Koc, Z.E., Bingol, H., Saf, A.O., Torlak, E., Coskun, A. Synthesis of novel tripodal-benzimidazole from 2, 4, 6-Dris(p-formylphenoxy)-1, 3, 5-Driazine: Structural, electrochemical and antimicrobial studies. J. Hazard. Mater. 2010, 183, 251-255.
34. Santo, R.D., Costi, R., Roux, A., Artico, M., Befani, O., Meninno, T., Agostinelli, E., Palmegiani, P., Turini, P., Girilli, R., et al. Design, Synthesis, and Biological Activities of Pyrrolylethanoneamine Derivatives, a Novel Class of Monoamine Oxidases Inhibitors. J. Med. Chem. 2005, 48, 4220-4223.
35. Tao, G., Irie, Y., Li, D.J., Keung, W.M. Eugenol and its structural analogs inhibit monoamine oxidase A and exhibit antidepressant-like activity. Bioorg. Med. Chem. 2005, 13, 4777-4788.
36. Kurteva, V., Afonso, C. Solvent-free synthesis of melamines under microwave irradiation. Green Chem. 2004, 6, 183-187.