Multi-component one-pot synthesis and antimicrobial activities of 3-methyl-1,4-diphenyl-7-thioxo-4,6,8,9-tetrahydropyrazolo[ 5,4-b]pyrimidino[5,4- e]pyridine-5-one and related derivatives

Molecules

Volumn 17, Issue 12, 2012, Pages 14464-14483

  El Emary, Talaat I ^a   El Mohsen, Shawkat A Abd ^a  

^a Assiut University   (Egypt)

Author keywords

Anti microbial activity; One pot reactions; Pyrazolo 5,4 b pyrimidino 5,4 e pyridines; Synthesis

Indexed keywords

3 METHYL 1,4 DIPHENYL 7 THIOXO 4,6,8,9 TETRAHYDRO PYRAZOLO(5,4 B)PYRIMIDINO(5,4 E)PYRIDINE 5 ONE; 3-METHYL-1,4-DIPHENYL-7-THIOXO-4,6,8,9-TETRAHYDRO-PYRAZOLO(5,4-B)PYRIMIDINO(5,4-E)PYRIDINE-5-ONE; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; PYRAZOLE DERIVATIVE; PYRIDINE DERIVATIVE; PYRIDONE DERIVATIVE; PYRIMIDINE DERIVATIVE;

ALKYLATION; ARTICLE; BACTERIUM; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; FUNGUS; SYNTHESIS;

ALKYLATION; ANTI-INFECTIVE AGENTS; ANTIFUNGAL AGENTS; BACTERIA; FUNGI; MOLECULAR STRUCTURE; PYRAZOLES; PYRIDINES; PYRIDONES; PYRIMIDINES;

EID: 84871553493     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules171214464     Document Type: Article

References (47)

1. Ganem, B. Strategies for innovation in multicomponent reaction design. Acc. Chem. 2009, 42, 463-472.
2. Padwa, A. Domino reactions of rhodium (II) carbenoids for alkaloid synthesis. Chem. Soc. Rev. 2009, 38, 3072-3081.
3. Ali, R.; Amir, T.M.; Morteza, R.; Aram, R. Novel three-component reaction of a secondary amine and a 2-hydroxybenzaldehyde derivative with an isocyanide in the presence of silica gel: An efficient one-pot synthesis of benzo[b]furan derivatives. Tetrahedron Lett. 2009, 50, 5625-5627.
4. Zeinab, Z.; Mehdi, K.; Ali, R.; Alireza, F.; Ali, S.; Katarzyna, Ś.; Tadeusz Lis, A.S. Synthesis of functionalized furo[3,2-c]coumarins via a one-pot oxidative pseudo three-component reaction in poly(ethylene glycol. Tetrahedron 2012, 68, 6721-6726.
5. Domling, A. Multicomponent reactions. Chem. Rev. 2006, 106, 17-89.
6. D'Souza, D.M.; Muller, T.J. Multi-component syntheses of heterocycles by transition-metal catalysis. J. Chem. Soc. Rev. 2007, 36, 1095-1108.
7. Ali, R.; Ali, S. Iminophosphorane-mediated one-pot synthesis of 1,3,4-oxadiazole Derivatives. ARKIVOC 2008, xvi, 235-242.
8. Ali, S.; Ali, R.; Nouri, B.; Richard, W. The reaction of (N-isocyanimino)triphenylphosphorane with dialkyl acetylenedicarboxylates in the presence of 1,3-diphenyl-1,3-propanedione: A novel three-component reaction for the stereoselective synthesis of dialkyl (Z)-2-(5,7-diphenyl-1,3,4-oxadiazepin- 2-yl)-2-butenedioates. Tetrahedron Lett. 2007, 48, 2617-2620.
9. Ali, S.; Ali, R. The reaction of (N-isocyanimino)triphenylphosphorane with benzoic acid derivatives: A novel synthesis of 2-aryl-1,3,4-oxadiazole derivatives. Tetrahedron Lett. 2007, 48, 1549-1551.
10. Shore, G.; Yoo, W.J.; Li, C.J.; Organ, M. Propargyl amine synthesis catalysed by gold and copper thin films using microwave assistant, continuous flow organic synthesis. Chem. Eur. J. 2010, 16, 126-133.
11. Hardy, C.R. The chemistry of pyrazolopyridine. Adv. Heterocyl. Chem. 1984, 36, 343-409.
12. Elnagdi, M.H.; Elgemeie, G.H.; El-Moghayar, R.M.H. Chemistry of pyrazolopyrimidines. Adv. Heterocycl. Chem. 1987, 41, 319-376.
13. Jiaro, Q.; Jaime, P.; Silva, C.; Rodrigo, A.; Braulio, I.; Manuel, N.; Justo, C.; Mike, H. Solvent free synthesis of fused pyrazolo [1,5-a]pyrimidines by reaction of 5-amino-1-H-pyrazoles and ß-triketones. Open Org. Chem. J. 2008, 2, 92-99.
14. Jiaro, Q.; Jaime, P.;Rodrigo, A.; Manuel, N.; Justo, C.; Mike, H. Regioselective synthesis of novel substituted pyrazolo[1,5-a]pyrimidines under solvent-free conditions. Tetrahedron Lett. 2008, 49, 6254-6256.
15. Jiaro, Q.; Jaime, P.; Hugo, S.; Rodrigo, A.; Braulio, I.; Manuel, N.; Justo, C. Regioselective synthesis of fused benzopyrazolo[3,4-b]quinolines under solvent-free conditions. Tetrahedron Lett. 2007, 48, 1987-1990.
16. Aly, M.F.; El-Naggar, G.M.; El-Emary, T.I.; Girgg, R.; Metwally, S.A.; Sivagnanam, S. X=Y-ZH Compounds as potential 1,3-Dipoles part 41. Azomethine Ylide Formation from the reaction of-Amino acids and esters wth Alloxan (Strecker Degradation) and with 1-phenyl-3-methyl pyrazoline 4,5-dione. Tetrahedron 1994, 50, 895-906.
17. Selleri, S.; Burni, F.; Castanzo, A.; Gueririni, G.; Malmbeg-Aiello, P.; lavarone, G.; Martini, C. Synthesis and preliminary evaluation of pyrazolo[1,5-a]pyrido[3,4-e]pyrimidin-6-(7H)-ones and related comounds as benzodiazepine receptor ligands and anticonvulsant agents. Eur. J. Med. Chem. 1992, 27, 985-990.
18. Poreba, K.; Wietrzyk, J.; Opolski, A. Synthesis and antiproliferative activity in vitro of new 2,3 or 4 substituted pyrido[2',3':3,4]pyrazolo[1,5-a] pyrimidines. Acta Pol. Pharm. 2006, 63, 189-194.
19. Ismail, M.M.F.; Ammar, Y.A.; El-Zahaby, H.S.A.; Eisa, S.I.; Barakat, S.E. Synthesis of Novel-1-pyrazolylpyridinopyrimidin2-ones as potential Anti-inflammatory and Analgesic Agent. Arch. Pharm. Chem. Life Sci. 2007, 340, 476-481.
20. Bi, Y.; Stoy, P.; He, B.; Adam, L.; Krupinski, J.; Normandin, D.; Pongrac, R.; Seliger, L.; Waston, A.; Macor, J.E. The discovery of novel, potent and selective PDE inhibitors. Bioorg. Med. Chem. Lett. 2001, 11, 2461-2464.
21. Ahluwalia, V.K.; Dahiya, A.; Garg, V. Reaction of 5-amino-4-formyl-3- methyl(or phenyl)-1-phenyl-1H-pyrazoles with active methylene compounds: Synthesis of fused heterocyclic rings. Indian J. Chem. 1997, 36B, 88-90 and references sited therein.
22. Metwally, S.A.; El-Naggar, G.M.; El-Emary, T.I. Reactions of 4-(Dicyanomethylene)-3-methyl-1-phenyl-2-pyrazolin-5-one towards methylene comoponds. Liebgs Ann. Chem. 1991, 62, 961-962.
23. Metwally, S.A.; El-Naggar, G.M.; Younis, M.I.; Elnagdi, M.H.; El-Emary, T.I. Reactions of 4-(Dicyanomethylene)-3-methyl-1-phenyl-2-pyrazolin-5-one towards Amines and Phenols. Liebgs Ann. Chem. 1989, 40, 1037-1040.
24. El-Emary, T.I.; El-Dean, A.M.; El-Kashef, H.S. Facile synthesis of some new pyrazolo [3,4-b] pyrazines and their antifungal activity. II Farmaco 1998, 53, 383-388.
25. El-Kashef, H.S.; El-Emary, T.I.; Gasquet, M.; Timon-David, M.J.; Vanele, P. New pyrazolo [3,4-b] pyrazines: Synthesis and biological activity. Pharmazie 2000, 55, 572-577.
26. El-Emary, T.I.; El-kashef, H.S.; Hussein, A.M. New Polycyclic Azines Derived from Pyrazolo [3,4-b] pyridine. Pharmazie 2000, 55, 356-358.
27. Hussein, A.M.; El-Emary, T.I. Polycyclic Pyrazoles: Routes to New Pyrazoloazines. J. Chem. Res. 1998, 228-236.
28. El-Emary, T.I.; Bakhite, E.A. Synthesis and biological screening of new 1,3-diphenylpyrazoles with different moieties at position-4. Pharmazie 1999, 2, 106-111.
29. El-Emary, T.I.; Abdel-Mohsen, Sh.A. Synthesis and antimicrobial activity of some new 1,3-diphenyl pyrazoles bearing pyrimidine, pyrimidinethione, thiazolopyrimidine, triazolopyrimidine, thio and alkyl-thiotriazolpyrimidinone moieties at 4-position. Phosphorous Sulfur Silicon 2006, 181, 2459-2474.
30. El-Emary, T.I.; Khalil, A.; Ali, G.A.; El-Adasy, A.A. A facile synthesis of some new Thiazolo[3,2-a]pyridines containing pyrazolyl moiety and their antimicrobial activity. Phosphorous Sulfur Silicon 2005, 180, 19-30.
31. El-Emary, T.I. Synthesis of newly substituted pyrazoles and substituted pyrazolo[3,4-b]pyridines based on 5-amino-3-methyl-1-phenylpyrazole. J. Chin. Chem. Soc. 2007, 54, 507-518.
32. El-Emary, T.I. Synthesis, reactions and biological activity of some new pyrazolo [3,4-b] pyrazines. J. Chin. Chem. Soc. 2006, 53, 391-401.
33. El-Emary, T.I. Synthesis of some newly condensed and uncondensed pyrazolo[3,4-b]pyridines. Assiut Univ. J. Chem. 2006, 35, 45-63.
34. Jairo, Q.; Diana, M.; Braulio, I.; Ridrigo, A.; Manuel, N.; Adolfo, S.; Justo, C.; John, N. Regioselective synthesis of 4,7,8,9-tetrahydro-2H- pyrazolo[3,4-b]quinolin-5(6H)-ones. Mechanism and structural analysis. Tetrahedron 2001, 57, 6947-6953.
35. Bazgir, A; Khanaposhanti, M.; Sooki, A. One-pot synthesis and antibacterial activities of pyrazolo[4′,3′:5,6]pyrido[2,3-d] pyrimidine-dione derivatives. Bioorg. Med. Chem. Lett. 2008, 18, 5800-5803.
36. Chebanov, V.A.; Sakhno, Y.I.; Desenk, S.M.; Chernenko, V.N.; Musatov, V.I.; Shishkina, S.V.; Shishkin, O.V.; Kappe, O. Cyclocondensation reactions of 5-aminopyrazoles, pyruvic acids and aldehydes. Multicomponent approaches to pyrazolopyridines and related products. Tetrahedron 2007, 1229-1242.
37. Shaabani, A.; Seyyedhamez, M.; Maleki, A.; Behnan, M.; Rezazdeh, F. Synthesis of fully substituted pyrazolo[3,4-b]pyridine-5-carboxamide derivatives via a one-pot four-component reaction. Tetrahedron Lett. 2009, 50, 2911-2913.
38. Balamurugan, K.; Perumal, S.; Menedez, J.C. New four-component reaction in water: A convergent approach to the metal-free synthesis of spiro[indoline/ acenaphthylene-3,4'-pyrazolo[3,4-b]pyridine derivatives. Tetrahedron 2011, 67, 3201-3208.
39. Shawali, A.S.; Elghandour, A.H.; Sayed, A.R.A novel one-pot synthesis of 3-arylazo[1,2,4]triazolo[4,3-a]pyrimidin-5-(1H)-ones. Synth. Commun. 2001, 31, 731-740.
40. Bedford, G.R.; Taylor, P.J.; Webb, G.A. 15N-NMR studies of guanidines. II-The fused-in guanidine unit of some oxoheterocycles: A combined 15N-NMR, 13C-NMR and IR study. Magn. Res. Chem. 1995, 33, 389-394.
41. Elguero, J.; Goya, P.; Martinez, A.; Rozas, I. On the Tautomerism of 2-Phenacyl-4-pyrimidinones and Related Compounds. Chem. Ber. 1989, 122, 919-924.
42. Greenhill, J.V.; Ismail, M.J.; Bedford, G.R.; Edwards, P.N.; Taylor, P.J. Conformational and tautmeric studies of acyl guanidines Part 2. Vibrations and C-13 nuclear magnetic resonance spectroscopy. J. Chem. Soc. Perkin Trans. 1985, 2, 1265-1274.
43. Reiter, J.; Bongo, L.; Dyortsok, P. On triazoles XI. structure elucidation of isomeric 1,2,4-triazolopyrimidinones. Tetrahedron 1987, 43, 2497-2504.
44. Rami, V.J. One-Pot Synthesis of Mono-and Dinitro-1,2,4-triazino[3,2-b] benzothiazoles. Liebigs Ann. Chem. 1988, 11, 1089-1090.
45. Heinisch, G.; Holzer, W. Pyrazoles 3. N-1 Protected 4-Substituted Pyrazoles-Synthesis and Nmr Investigation. Heterocycles 1988, 27, 2443-2457.
46. Khalil, Z.H.; Geies, A.A. Synthesis and reactions of some thieno[2,3-d]pyrimidine derivatives. Phosphorus Sulfur Silicon 1991, 60, 223-231.
47. Kwon-Chung, K.J.; Bennett, J.W. Principles of antifungal and antibacterial therapy. Med. Mycol. Lea Febiger. Philadel. 1992, 81-102.