Novel Polyazaheterocyclic Systems: Synthesis, Antitumor, and Antimicrobial Activities

다국어 초록 (Multilingual Abstract)

A series of new polyazaheterocyclic ring systems was synthesized via the reaction of enaminone 5 with active methylene compounds, hydrazine hydrate, hydroxylamine, and heterocyclic amines. The structures of the newly synthesized compounds were substantiated on the basis of spectral data and elemental analyses. The antitumor activity of the enaminone 5 against the human breast cell line MCF-7, the liver carcinoma cell line HEPG2-1, and HELA cells was determined. In addition, the antimicrobial activity of some selected products was evaluated.

참고문헌 (Reference)

1 Farghaly, T. A, "Synthesis, anti-HCV, antioxidant,and peroxynitrite inhibitory activity of fused benzosuberone derivatives" 45 : 492-500, 2010

2 Baraldi, P. G, "Synthesis of new pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines and related heterocycles" 60 : 5093-5104, 2004

3 Anderson, J. D, "Synthesis of certain pyrazolo[3,4-d]pyrimidin-3-one nucleosides" 27 : 439-453, 1990

4 Dawood, K. M, "Synthesis of Spiro-pyrazole-3,3'-thiopyrano [2,3-b]pyridines and azolo[a] pyrido[2',3':5,6]thiopyrano [3,4-d]pyrimidines as new ring systems with antifungal and antibacterial activities" 42 : 221-225, 2005

5 Shawali, A. S, "Synthesis and tautomeric structure of 6-arylhydrazono 1H-pyrazolo[3',4':4,5]pyrimido [1,6-b][1,2,4]triazepines" 65 : 644-647, 2009

6 Rezessy, B, "Synthesis and structure elucidation of new thiazolotriazepines" 55 : 5909-5922, 1999

7 Ahmed, M. S. M, "Synthesis and reactions of 3-hydrazino-2,7,8,9-tetrahydro-1H-benzo[6',7']cyclohepta[1',2':4,5]pyrido[2,3-d]pyrimidin-1-one" xiii : 31-41, 2009

8 Abdallah, S. O, "Synthesis and chemical reactivity of 3-oxo-2-arylhydrazono-propanenitriles" 42 : 781-786, 2005

9 Gomtsyan, A, "Synthesis and biological evaluation of pteridine and pyrazolopyrimidine based adenosine kinase inhibitors" 14 : 4165-4168, 2004

10 Rashad, A. E, "Synthesis and antiviral evaluation of some new pyrazole and fused pyrazolopyrimidine derivatives" 16 : 7102-7106, 2008

11 Shawali, A. S, "Synthesis and antitumor activity of novel pyrazolylenaminone and bis(pyrazolyl)ketones via hydrazonoyl halides" 46 : 548-551, 2009

12 Hassanien, A. Z. A, "Studies with functionally substituted methylbenzotriazoles:novel synthesis of functionally substituted pyrazolo[5,1-c]-1,2,4-triazines benzotriazol-1-yl, 1-pyrazol-4-yl, benzotriazoles and 1-isoxazol-4yl benzotriazoles" 51 : 575-579, 2004

13 Hassanien, A. Z. A, "Studies with functionally substituted methylbenzotriazoles:novel synthesis of functionally substituted pyrazolo[5,1-c]-1,2,4-triazines benzotriazol-1-yl, 1-pyrazol-4-yl, benzotriazoles and 1-isoxazol-4yl benzotriazoles" 51 : 575-579, 2004

14 Ducrocq, C, "Structure-activity relationship in a series of newly synthesized 1-amino-substituted ellipticine derivatives" 23 : 1212-1216, 1980

15 Bennett, P, "Stereochemistry of cyclopropyl ketones from the reaction of dimethylsulphoxonium methylide with 3-benzylidenechroman-4-ones" I : 1554-1556, 1972

16 Essassi, E. M, "Recherches en serie triazepine-1,2,4: I - Determination de la structure de la triazolotriazepinone obtenue par action de l'acetylacetate d'ethyle sur le diamino-3,4 triazole-1,2,4" 12 : 661-663, 1975

17 Anderson, D. J, "Rearrangements of 5-azidoisoxazoles" 32 : 1189-1196, 1995

18 Romano, C, "Reactions of 1,2-diaminobenzimidazoles with β-dicarbonyl compounds" 44 : 7185-7192, 1988

19 Baraldi, P. G, "Pyrazolo[4,3-e]1,2,4-triazolo [1,5-c]pyrimidine derivatives as highly potent and selective human A3 adenosine receptor antagonists: Influence of the chain at N8 pyrazole nitrogen" 43 : 4768-4780, 2000

20 Baraldi, P. G, "Pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine derivatives as highly potent and selective human A3 adenosine receptor antagonists" 42 : 4473-4478, 1999

21 Grothaus, C. E, "On the reactions of certain methylene hydrogen derivatives containing cyanide, thiocyanate or sulfinate radicals" 58 : 1334-1336, 1936

22 Peat, A. J, "Novel pyrazolopyrimidine derivatives as GSK-3 inhibitors" 14 : 2121-2125, 2004

23 Mosselhi, A. N. M, "Novel pentaheterocycles. First general synthesis entry to functionalized derivatives of pyrido[2,3-f:5,6-f']di[1,2,4]triazolo[4,3-a]pyrimidine-5(1H)-ones" 135 : 211-222, 2004

24 Ballell, L, "New thiopyrazolo[3,4-d]pyrimidine derivatives as antimycobacterial agents" 17 : 1736-1740, 2007

25 Baraldi, P. G, "New potent and selective human adenosine A3 receptor antagonists" 21 : 456-459, 2000

26 Skehan, P, "New colorimetric cytotoxicity assay for anticancer-drug screening" 82 : 1107-1112, 1990

27 Farghaly, T. A, "Microwave assisted synthesis of annelated benzosuberone as new penta-heterocyclic ring systems" x : 54-63, 2009

28 Lamsabhi, M, "Gas-phase basicity of 2,7-dimethyl-[1,2,4]-triazepine thio derivatives" 106 : 7383-7389, 2002

29 Al-Saleh, B, "Enaminones as building blocks in heterocyclic synthesis. Synthesis of polyfunctionally substituted 3-azolylpyridines and azolylazoloazines by thermal and microwave heating" 8 : 575-577, 2004

30 Riyadh, S. M, "Enamines as precursors to polyfunctional heteroaromatic compounds; a decade of development" 75 : 1849-1905, 2008

31 Dominguez, E, "Convenient one-pot preparative method for 4,5-diarylisoxazoles involving amine exchange reactions" 61 : 5435-5439, 1996

32 Irobi, O. N, "Antimicrobial activity of bark extracts of Bridelia ferruginea (Euphorbiaceae)" 43 : 185-190, 1994

33 Grayer, R. J, "A survey of antifungal compounds from higher plants" 37 : 19-42, 1994

34 Shawali, A. S, "A facile synthesis of some pyrazolo analogues of tricyclic purine derivatives via hydrazonoyl halides" 6 (6): 140-149, 1994