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One Pot Synthesis of Novel Cyanopyridones as an Intermediate of Bioactive Pyrido[2,3-d]Pyrimidines
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 Title & Authors
One Pot Synthesis of Novel Cyanopyridones as an Intermediate of Bioactive Pyrido[2,3-d]Pyrimidines
Khatri, Taslimahemad T.; Shah, Viresh H.;
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Synthesis, structural characterization, and biological activity studies of novel pyrido[2,3-d]pyrimidines (10a-h, 11a-h) are described. Cyclization of cynoacetamides (4, 5) with malonitrile (7) and aldehyde (6a-h) via Hantzsch pyridine synthesis afforded cyanopyridones (8a-h, 9a-h), which on cyclization with formic acid under microwave conditions led to the final product. All the reactions are significantly faster and the isolated yields are remarkably higher in microwave conditions compared to the conventionally heated reactions. The compounds were tested in vitro for their antibacterial activity against Escherichia coli, Pseudomonas aeruginosa, Bacillus subtillus, Staphylococcus aureus, and Micrococcus luteus and antifungal activity against Trichphyton longifusus, Candida albicans, Microsporum canis, Fusarium solani. Compounds 10b, 10e, 11b and 11e exhibited good antibacterial and antifungal activities compared with standards.
Microwave-assisted synthesis;2-Cyano-N-phenylacetamides;Pyrido[2,3-d]pyrimidines;Antibacterial activity;Antifungal activity;
 Cited by
Zbancioc, G.; et al. Microwave Assisted Reactions of Some Azaheterocylic Compounds. Molecule. 2009, 14(1), 403. crossref(new window)

Bardagi, J. I.; Rossi, R. A. Short Access to 6-Substituted Pyrimidine Derivatives by the S (RN) Mechanism. Synthesis of 6-Substituted Uracils Through a One-pot Procedure. J Org Chem. 2010, 75(15), 5271. crossref(new window)

Youssef, M. M.; Amin, M. A. Microwave Assisted Synthesis of Some New Thiazolopyrimidine, Thiazolodipyrimidine and Thiazolopyrimidothiazolopyrimidine Derivatives with Potential Antioxidant and Antimicrobial Activity. Molecules. 2012, 17(8), 9652. crossref(new window)

Kanagarajan, V.; et al. A Facile Microwave Assisted Green Chemical Synthesis of Novel Piperidino 2-Thioxoimidazolidin- 4-ones and Their in Vitro Microbiological Evaluation. J. Enzyme. Inhib. Med. Chem. 2011, 26(1), 67. crossref(new window)

Gitto, R.; et al. Synthesis and Evaluation of Pharmacological Profile of 1-Aryl-6,7-dimethoxy-3,4-dihydroisoquinoline- 2(1H)-sulfonamides. Bioorg. Med. Chem. 2009, 17(10), 3659. crossref(new window)

Rodriguez, H.; et al. Eco-friendly Methodology to Prepare N-Heterocycles Related to Dihydropyridines: Microwaveassisted Synthesis of Alkyl 4-Arylsubstituted-6-chloro-5- formyl-2-methyl-1,4-dihydropyridine-3-carboxylate and 4- Arylsubstituted-4,7-dihydrofuro[3,4-b]pyridine-2,5(1H, 3H)- dione. Molecules 2011, 16(11), 9620. crossref(new window)

Martinez, J.; et al. Green Approach & # 8212; Multicomponent Production of Boron & # 8212; Containing Hantzsch and Biginelli Esters. Int. J. Mol. Sci. 2013, 14(2), 2903. crossref(new window)

Balatsos, N. A.; et al. Inhibition of Human Poly(A)-specific Ribonuclease (PARN) by Purine Nucleotides: Kinetic Analysis. J. Enzyme. Inhib. Med. Chem. 2009, 24(2), 516. crossref(new window)

Raboisson, P.; et al. Design, Synthesis and Structure-activity Relationships of a Series of 9-Substituted Adenine Derivatives as Selective Phosphodiesterase Type-4 Inhibitors. Eur. J. Med. Chem. 2003, 38(2), 199. crossref(new window)

Manikowski, A.; et al. Inhibition of Herpes Simplex Virus Thymidine Kinases by 2-Phenylamino-6-oxopurines and Related Compounds: Structure-activity Relationships and Antiherpetic Activity in Vivo. J. Med. Chem. 2005, 48(11), 3919. crossref(new window)

Pandey, A.; et al. Identification of Orally Active, Potent, and Selective 4-Piperazinylquinazolines as Antagonists of the Platelet-derived Growth Factor Receptor Tyrosine Kinase Family. J. Med. Chem. 2002, 45(17), 3772. crossref(new window)

Antonello, A.; et al. Design, Synthesis, and Biological Evaluation of Prazosin-related Derivatives as Multipotent Compounds. J. Med. Chem. 2005, 48(1), 28. crossref(new window)

Bathini, Y.; et al. 2-Aminoquinazoline Inhibitors of Cyclindependent Kinases. Bioorg. Med. Chem. Lett. 2005, 15(17), 3881. crossref(new window)

Matulenko, M. A.; et al. 5-(3-Bromophenyl)-7-(6-morpholin- 4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-ylamine: Structure-activity Relationships of 7-substituted Heteroaryl Analogs as Non-nucleoside Adenosine Kinase Inhibitors. Bioorg. Med. Chem. 2005, 13(11), 3705. crossref(new window)

Wu, Z.; et al. Development of Pyridopyrimidines as Potent Akt1/2 Inhibitors. Bioorg. Med. Chem. Lett. 2008, 18(4), 1274. crossref(new window)

Ribble, W.; et al. Discovery and Analysis of 4H-pyridopy- Rimidines, a Class of Selective Bacterial Protein Synthesis Inhibitors. Antimicrob Agents Chemother. 2010, 54(11), 4648. crossref(new window)

Guiles, J. W.; et al. Development of 4H-Pyridopyrimidines: A Class of Selective Bacterial Protein Synthesis Inhibitors. Org. Med. Chem. Lett. 2012, 2(1), 5. crossref(new window)

Kovacs, J. A.; et al. Potent Antipneumocystis and Antitoxoplasma Activities of Piritrexim, a Lipid-soluble Antifolate. Antimicrob Agents Chemother. 1988, 32(4), 430. crossref(new window)

Gangjee, A.; et al. Pneumocystis Carinii and Toxoplasma Gondii Dihydrofolate Reductase Inhibitors and Antitumor Agents: Synthesis and Biological Activities of 2,4-Diamino- 5-methyl-6-[(monosubstituted anilino)methyl] pyrido[2,3- d]pyrimidines. J. Med. Chem. 1999, 42(13), 2447. crossref(new window)

Gangjee, A.; et al. Synthesis and Biological Evaluation of 2,4-Diamino-6-(arylaminomethyl)pyrido[2,3-d]pyrimidines as Inhibitors of Pneumocystis Carinii and Toxoplasma Gondii Dihydrofolate Reductase and as Antiopportunistic Infection and Antitumor Agents. J. Med. Chem. 2003, 46(23), 5074. crossref(new window)

Lee, C. H.; et al. Discovery of 4-Amino-5-(3-bromophenyl)- 7-(6-morpholino-pyridin-3-yl)pyrido[2,3-d] pyrimidine, an Orally Active, Non-nucleoside Adenosine Kinase Inhibitor. J. Med. Chem. 2001, 44(13), 2133. crossref(new window)

Trumpp-Kallmeyer, S.; et al. Development of a Binding Model to Protein Tyrosine Kinases for Substituted Pyrido[ 2,3-d]pyrimidine Inhibitors. J. Med. Chem. 1998, 41(11), 1752. crossref(new window)

El-Gazzar, A. R.; Hafez, H. N. Synthesis of 4-Substituted pyrido[2,3-d]pyrimidin-4(1H)-one as Analgesic and Antiinflammatory Agents. Bioorg. Med. Chem. Lett. 2009, 19(13), 3392. crossref(new window)

Kamlesh, K.; Taslimahemad, K.; Praful, P. One Pot Synthesis of Bioactive Novel Cyanopyridones. J. Korean Chem. Soc. 2013, 57(4), 476. crossref(new window)

Al-Sehemi, A. G. A Convenient Synthesis and Characterization of 1,2-Dihydrpyridine-2-one, Pyrido[2,3-d]pyrimidine and Thieno [3,4-c]pyridine derivatives. Der. Pharma. Chemica. 2010, 2(2), 336.

Mont, N.; et al. A Diversity Oriented, Microwave Assisted Synthesis of N-Substituted 2-Hydro-4-amino-pyrido[2,3- d]pyrimidin-7(8H)-ones. Mol. Divers. 2009, 13(1), 39. crossref(new window)

Wang, K.; et al. Cyanoacetamide Multicomponent Reaction (I): Parallel Synthesis of Cyanoacetamides. J. Comb. Chem. 2009, 11(5), 920. crossref(new window)

Linday, E. M. Practical Introduction to Microbiology; E & FN spon Ltd: London, U.K., 1962; p 177.

Collins, C. H. Microbiological Methods; Butterworths: London, U.K., 1967; p 364.