Solvent-free synthesis of nitrilotriacetamide and diketopiperazines from nitrilotriacetic acid under microwave irradiation and their antimicrobial activity

Synthetic Communications

Volumn 37, Issue 22, 2007, Pages 3981-3988

  Öztürk, Gülşen ^a   Gümgüm, Bahattin ^a   Kizil, Murat ^a   Emen, Sevil ^a  

^a DICLE UNIVERSITY   (Turkey)

Author keywords

Amide; Antimicrobial activity; Diketopiperazine; Microwave irradiation; Solvent free synthesis

Indexed keywords

2,2',2' NITRILO TRIS(N BENZYL ACETAMIDE); N BUTHYL 2 (4 BUTHYL 3,5 DIOXOPIPERAZINE 1 YL)ACETAMIDE; N DIBENZYL 2 (4 DIBENZYL 3,5 DIOXOPIPERAZINE 1 YL)ACETAMIDE; N HEXZYL 2 (4 HEXZYL 3,5 DIOXOPIPERAZINE 1 YL)ACETAMIDE; NITRILOTRIACETAMIDE; NITRILOTRIACETIC ACID; PIPERAZINEDIONE; SOLVENT; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG SENSITIVITY; DRUG SYNTHESIS; HEATING; MICROWAVE IRRADIATION; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 36348947330     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701572795     Document Type: Article

References (30)

1. Perreux, L.; Loupy, A.; Volatron, F. Tetrahedron. 2002, 58, 2155-2162.
2. Edith, G.; Smeets, L.; Leo, A. J. M.; van Steen, B. J.; Sliedregt, G.; Kruse, C.; Orru, R.; Leurs, V. A. Tetrahedron Lett. 2005, 46, 3751-3754.
3. Smith, D. A.; Cramer, S.; Sucheck, S.; Jankun, E. S. Tetrahedron Lett. 1992, 33, 7765-7768.
4. Smith, D. A.; Sucheck, S.; Cramer, S.; Baker, D. Synth. Commun. 1995, 25 (24), 4123-4132.
5. Dinsmore, C. J.; Beshore, D. C. Tetrahedron. 2002, 58, 3297-3312.
6. Chase, B. H.; Downes, A. M. J. Chem. Soc. 1953, 3874.
7. Viscontini, M.; Bally, J.; Meier. J. Helv. Chim. Acta 1952, 35, 451.
8. Witiak, D. T.; Wei, Y. J. Org. Chem. 1991, 56, 5408.
9. Yuste, F.; Pallás, Y.; Barrios, H. J. Heterocycl. Chem. 1986, 23, 189.
10. Li, Q.; Shao, H. W.; Jiang, H. L.; Xie, Y. Y. Pharmazie. 1995, 50, 447.
11. Abdel-Hamide, S. G. J. Indian Chem. Soc. 1997, 74, 613.
12. Lucietto, F. R.; Milne, P. J; Kilian, G.; Frost, C. L.; Van de Venterv, M. Peptides. 2006, 27, 2706-2714.
13. Prakash, K. R. C.; Tang, Y.; Kozikowski, A. P.; Flippen-Anderson, J. L.; Knoblach, S. M.; Faden, A. I. Bioorg. Med. Chem. 2002, 10, 3043-3048.
14. Tomassini, J. E.; Davies, M. E.; Hastings, J. C.; Lingham, R.; Mojena, M.; Raghoobar, S. L.; Sing, S. B.; Tkacz, J. S.; Goetz, M. A. Antimicrobial agents Chemother. 1996, 1189-1193.
15. Trischman, J. A.; Oeffner, R. E.; Luna, M. G.; Kazaoka, M. Mar. Biotechnol. 2004, 6, 215-220.
16. Ugi, I. K.; Ebert, B.; Hörl, W. Chemosphere 2001, 43, 75-81.
17. Wang, D. X.; Liang, M. T.; Tian, G. J.; Lin, H.; Liu, H. Q. Tetrahedron lett. 2002, 43, 865-867.
18. Jain, R.; Sundram, A.; Lopez, S.; Neckermann, G.; Wu, C.; Hackbarth, C.; Chen, D.; Wang, W.; Ryder, N. S.; Weidmann, B.; Patel, D.; Trias, J.; White, R.; Yuan, Z. Bioorg. Med. Chem. Lett. 2003, 13, 4223-4228.
19. Wang, Y.; Mueller, U. G. J. Chem. Ecology 1999, 25, 935-941.
20. Santagada, V.; Fiorino, F.; Perissutti, E.; Severino, B.; Terracciano, S.; Cirino, G.; Caliendo, G. Tetrahedron Lett. 2003, 44, 1145-1148.
21. Gümgüm, B.; Öztürk, G. Chem. Speciation Bioavailability 2001, 13 (1), 25-29.
22. Öztürk, G.; Gümgüm, B.; Akba, O. Catal. Lett. 2002, 3-4 (82), 233-235.
23. Öztürk, G.; Gümgüm, B. React. Kinet. Catal. Lett. 2004, 2 (82), 395-399.
24. FR Patent 1459810. 1966, US Patent 3326974, 1967.
25. Appelbaum, P. C.; Clark, C. L.; Jacobs, M. R. J. Clin. Microbial. 1998, 36, 3579-3584.
26. Patterson, T. F.; Kirkpatrick, W. R.; Turner, T. M.; Fothergill, A. W.; McCarthy, D. I.; Redding, S. W.; Rinaldi, M. G. J. Clin. Microbial. 1998, 25, 3429-3432.
27. Tang, Y.; Thang, K. Z.; Zhang, J.; Su, C. Y.; Liu, W. S.; Liu, S. W.; Tan, M. Y. Inorg. Chem. Commun. 2005, 8, 1018-1021.
28. Wang, Y.; Mueller, U. G.; Clardy, J. J. Chem. Ecol. 1999, 25, 935-941.
29. Tomassini, J. E.; Davies, M. E.; Hastings, J. C.; Lingham, R.; Mojena, M.; Raghoobar, S. L.; Singh, S. B.; Tkacz, J. S.; Goetz, M. A. Antimicrobial agents chemother 1996, 40, 1189-1193.
30. Trischman, A. J.; Oeffner, R. E.; de Luna, M. G.; Kazaoka, M. Marine Biotechnol. 2004, 6, 215-220.