Synthesis and antifungal evaluation of imines derived from 3-Amino-2-isopropyl-3H-quinazolin-4-one

Organic Communications

Volumn 6, Issue 4, 2013, Pages 139-147

  Karakaya, Idris ^a,b   Karabuga, Semistan ^c   Ulukanli, Zeynep ^a   Ulukanli, Sabri ^a  

^a OSMANIYE KORKUT ATA UNIVERSITY   (Turkey)

^b ATATÜRK UNIVERSITY   (Turkey)

^c KAHRAMANMARAS SUTCU IMAM UNIVERSITY   (Turkey)

Author keywords

Antifungal; Antimicrobial; Imines; Quinazolinone; Schiff bases

Indexed keywords

EID: 84894080238     PISSN: None     EISSN: 13076175     Source Type: Journal    
DOI: None     Document Type: Article

References (50)

1. Abdel-Jalil, R. J.; Aldoqum, H. M.; Ayoub, M. T.; Voelter, W. Synthesis and antitumor activity of 2-aryl-7-fluoro-6-(4-methyl-1-piperazinyl)-4(3H)-quinazolinones. Heterocycles 2005, 65, 2061-2070.
2. El-Sherbeny, M. A. Synthesis, antitumor activity, and anti-HIV-1 testing of certain heterocyclic systems containing an adamantane nucleus. Arch. Pharm., 2000, 333, 323-328.
3. El-Azab, A. S.; ElTahir, K. E. H. Design and synthesis of novel 7-aminoquinazoline derivatives: Antitumor and anticonvulsant activities. Bioorg. Med. Chem. Lett., 2012, 22, 1879-1885.
4. Raffa, D.; Edler, M. C.; Daidone, G.; Maggio, B.; Merickech, M. et al. Synthesis, cytotoxicity, and inhibitory effects on tubulin polymerization of a new 3-heterocyclo substituted 2-styrylquinazolinones. Eur. J. Med. Chem., 2004, 39, 299-304.
5. Maggio, B.; Daidone, G.; Raffa, D.; Plescia, S.; Mantione, L. et al. Synthesis and pharmacological study of ethyl 1-methyl-5-(substituted 3,4-dihydro-4-oxoquinazolin-3-yl)-1H-pyrazole-4-acetates. Eur. J. Med. Chem., 2001, 36, 737-742.
6. Yesilada, A.; Koyunoglu, S.; Saygili, N.; Kupeli, E.; Yesilada, E. et al. Synthesis, anti-inflammatory and analgesic activity screening of some new 4(3H)-quinazolinone derivatives. Arch. Pharm., 2004, 337, 96-104.
7. Farag, A. A.; Khalifa, E. M.; Sadik, N. A.; Abbas, S. Y.; Al-Sehemi, A. G. et al. Synthesis, characterization, and evaluation of some novel 4(3H)-quinazolinone derivatives as anti-inflammatory and analgesic agents. Med. Chem. Res., 2013, 22, 440-452.
8. Bajaj, K.; Srivastava, V. K.; Kumar, A. Newer substituted benzoxazepinyl-quinazolinones as potent antipsychotic and anticonvulsant agents. Arzneimittel-Forsch., 2003, 53, 480-485.
9. Amir, M.; Ali, I.; Hassan, M. Z. Design and synthesis of some new quinazolin-4-(3H)-ones as anticonvulsant and antidepressant agents. Arch. Pharm. Res., 2013, 36, 61-68.
10. Ossman, A. R. E.; Barakat, S. E. Synthesis and Anticonvulsant Activity of Some New 3-(PSulfamoylphenyl)-4(3h)-Quinazolinones. Arzneimittel-Forsch., 1994, 44-2, 915-919.
11. Elfeky, S. A. H.; Elsamii, Z. K. A. Synthesis and Anticonvulsant Properties of Some Novel Quinazolinone Thiosemicarbazone and 4-Thiazolidone Derivatives. J. Chem. Tech. Biot., 1991, 51, 61-66.
12. Daidone, G.; Raffa, D.; Maggio, B.; Plescia, F.; Cutuli, V. M. C. et al. Synthesis and pharmacological activities of novel 3-(isoxazol-3-yl)-quinazolin-4(3H)-one derivatives. Arch. Pharm., 1999, 332, 50-54.
13. Gursoy, A.; Karali, N. Synthesis and primary cytotoxicity evaluation of 3-[[(3-phenyl-4(3H)quinazolinone-2-yl)mercaptoacetyl] hydrazono]-1H-2-indolinones. Eur. J. Med. Chem., 2003, 38, 633-643.
14. Dinakaran, M.; Selvam, P.; DeClercq, E.; Sridhar, S. K. Synthesis, antiviral and cytotoxic activity of 6-bromo-2,3-disubstituted-4(3H)-quinazolinones. Biol. Pharm Bull., 2003, 26, 1278-1282.
15. De Clercq, E. New developments in anti-HIV chemotherapy. Curr. Med. Chem., 2001, 8, 1543-1572.
16. Jolivet-Fouchet, S.; Fabis, F.; Bovy, P.; Ochsenbein, P.; Rault, S. Novel rearrangement of pyrrolo[2,1-c] [1,4]benzodiazepines into pyrrolo[2,1-b]quinazolinones, analogous of alkaloid, vasicinone. Heterocycles., 1999, 51, 1257.
17. Lee, E. S.; Park, J. G.; Jahng, Y. A facile synthesis of simple alkaloids-synthesis of 2,3-polymethylene-4(3H)-quinazolinones and related alkaloids. Tetrahedron Letters, 2003, 44, 1883-1886.
18. Kamal, A.; Ramana, K. V.; Ankati, H. B.; Ramana, A. V. Mild and efficient reduction of azides to amines: synthesis of fused [2,1-b]quinazolinones. Tetrahedron Letters, 2002, 43, 6861-6863.
19. Kamal, A.; Ramana, K. V.; Rao, M. V. Chemoenzymatic synthesis of pyrrolo[2,1-b]quinazolinones: Lipase-catalyzed resolution of vasicinone. J. Org. Chem., 2001, 66, 997-1001.
20. Snider, B. B.; Zeng, H. B. Total syntheses of (-)-fumiquinazolines A, B, and I. Org. Lett., 2000, 2, 4103-4106.
21. Snider, B. B.; Zeng, H. B. Total syntheses of (-)-fumiquinazolines C, E, and H. Org. Lett., 2002, 4, 1087-1090.
22. Snider, B. B.; Zeng, H. B. Total synthesis of (-)-fumiquinazolines A, B, C, E, H, and I. Approaches to the synthesis of fiscalin A. J. Org. Chem., 2003, 68, 545-563.
23. Numata, A.; Takahashi, C.; Matsushita, T.; Miyamoto, T.; Kawai, K. et al. Fumiquinazolines, Novel Metabolites of a Fungus Isolated from a Saltfish. Tetrahedron Letters, 1992, 33, 1621-1624.
24. Takahashi, C.; Matsushita, T.; Doi, M.; Minoura, K.; Shingu, T. et al. Fumiquinazolines a-G, Novel Metabolites of a Fungus Separated from a Pseudolabrus Marine Fish. J. Chem. Soc. Perk. Trans.1, 1995, 2345-2353.
25. Connolly, D. J.; Cusack, D.; O'Sullivan, T. P.; Guiry, P. J. Synthesis of quinazolinones and quinazolines. Tetrahedron, 2005, 61, 10153-10202.
26. Liu, J. F.; Kaselj, M.; Isome, Y.; Chapnick, J.; Zhang, B. L. et al. Microwave-assisted concise total syntheses of quinazolinobenzodiazepine alkaloids. J. Org. Chem., 2005, 70, 10488-10493.
27. Avendano, C.; Menendez, J. C. Chemistry of pyrazino[2,1-b]quinazoline-3,6-diones. Curr. Org. Chem., 2003, 7, 149-173.
28. Mohanta, P. K.; Kim, K. New synthetic route to tetracyclic quinazolin-4(3H)-one ring system. Heterocycles, 2002, 57, 1471-1485.
29. He, F.; Foxman, B. M.; Snider, B. B. Total syntheses of (-)-asperlicin and (-)-asperlicin C. J. Am. Chem. Soc., 1998, 120, 6417-6418.
30. Witt, A.; Gustavsson, A.; Bergman, J. Studies towards the synthesis of the benzodiazepine alkaloid auranthine. Synthesis of an acetylated derivative. J. Heterocyclic Chem., 2003, 40, 29-35.
31. Liu, J. F.; Lee, J. Y.; Dalton, A. M.; Bi, G.; Yu, L. B. et al. Microwave-assisted one-pot synthesis of 2,3-disubstituted 3H-quinazolin-4-ones. Tetrahedron Letters, 2005, 46, 1241-1244.
32. Dabiri, M.; Salehi, P.; Khajavi, M. S.; Mohammadi, A. A. Microwave-assisted one-pot three component synthesis of some new 4(3H)-quinazolinone derivatives. Heterocycles, 2004, 63, 1417-1421.
33. Sun, Q.; Zhou, X. M.; Kyle, D. J. Solid-phase synthesis of 3,4-dihydro-2(1H)-quinazolinones and 3,4-dihydro-1H-quinazolin-2-thiones. Tetrahedron Letters, 2001, 42, 4119-4121.
34. Song, A. M.; Marik, J.; Lam, K. S. Solid-phase synthesis of 3-alkyl-2-arylamino-3,4-dihydroquinazolines. Tetrahedron Letters, 2004, 45, 2727-2730.
35. Weber, C.; Bielik, A.; Szendrei, G. I.; Greiner, I. Novel solid-phase synthesis of 2,6-disubstituted 4(3H)-quinazolinones for combinatorial library generation. Tetrahedron Letters, 2002, 43, 2971-2974.
36. Weber, C.; Demeter, A.; Szendrei, G. I.; Greiner, I. Solid-phase synthesis of 2,6-and 2,7-diamino-4(3H)-quinazolinones via palladium-catalyzed amination. Tetrahedron Letters, 2003, 44, 7533-7536.
37. Jeon, M. K.; Kim, D. S.; La, H. J.; Ha, D. C.; Gong, Y. D. Solid-phase synthesis of 2-cyanoquinazolin-4(3H)-one and 2,3-dihydrooxazolo[2,3-b]quinazolin-5-one derivatives utilizing resin-bound anthranilic acid derivatives. Tetrahedron Letters, 2005, 46, 7477-7481.
38. Makino, S. Solid-phase synthesis of quinazoline-2,4-diones and their analogues from resin-bound compounds with primary amines. Mini-Rev. Med. Chem., 2006, 6, 625-632.
39. Gursoy, A.; Unal, B.; Karali, N.; Otuk, G. Synthesis, characterization and primary antimicrobial activity evaluation of 3-phenyl-6-methyl-4(3H)-quinazolinone-2-yl-mercaptoacetic acid arylidenehydrazides. Turk. J. Chem., 2005, 29, 233-245.
40. Eid, A. I.; Aboulenein, M. N.; Eldifrawy, S.; Bibers, M.; Elhawary, S. Synthesis and Antibacterial Activity of Some 4 (Quinazolinones-H-3. Eur. J. Med. Chem., 1979, 14, 463-466.
41. Buyuktimkin, S.; Ekinci, A. C.; Buyuktimkin, N.; Otuk, G. Pharmacological Studies on Quaternized 4(3h)-Quinazolinones. J. Pharm. Sci., 1992, 81, 1092-1094.
42. Reddy, P. S.; Reddy, P. P.; Vasantha, T. A review on 2-heteryl and heteroalkyl-4(3H)-quinazolinones. Heterocycles, 2003, 60, 183-226.
43. Pandeya, S. N.; Sriram, D.; Nath, G.; DeClercq, E. Synthesis, antibacterial, antifungal and anti-HIV activities of Schiff and Mannich bases derived from isatin derivatives and N-[4-(4 '-chlorophenyl)thiazol-2-yl] thiosemicarbazide. Eur. J. Med. Chem., 1999, 9, 25-31.
44. Panda, J.; Srinivas, S. V.; Rao, M. E. B.; Panda, C. S. Synthesis and antimicrobial activity of some pyrazoline derivatives of 4(3H)-quinazolinones. J. Indian Chem. Soc., 2002, 79, 770-771.
45. El-Hiti, G. A.; Abdel-Megeed, M. F.; Mahmoud, Y. A. G. Synthesis and antimicrobial activities of novel sugar (2-phenylquinazolin-4-yl)hydrazones and their osazones. Indian J. Chem. B., 2000, 39, 368-376.
46. Fahmy, A. F. M.; Elhashash, M. A.; Habashy, M. M.; Elwannise, S. A. Some Reactions of 2-Isopropyl-[4h]-3,1-Benzoxazin-4-One. Rev Roum Chim., 1978, 23, 1567-1573.
47. Barker, E. The stereochemical consequences of N-N-chiral axes in 3-acylaminoquinazolinones. (PhD Thesis) Leicester University, Leicester/UK 1995.
48. Bhalla, M.; Srivastava, V. K.; Bhalla, T. N.; Shanker, K. Antiinflammatory and Analgesic Activity of Indolyl Quinazolones and Their Congeners. Arzneimittel-Forsch., 1993, 43-1, 595-600.
49. Srivastava, V. K.; Singh, S.; Gulati, A.; Shanker, K. Antiparkinsonian Agents from Quinazolinylthiazolidinones and Azetidinones. Indian J. Chem. B, 1987, 26, 652-656.
50. Quiroga, E. N.; Sampietro, A. R.;Vattuone, M. A. Screening antifungal activities of selected medicinal plants. Jour. of Ethnopharm., 2001, 74, 89-96.