Subscribe

Subscribe to our Newsletter and get informed about new publication regulary and special discounts for subscribers!

ILCPA > Volume 74 > Synthesis and Biological Evaluation of some Novel...
Synthesis and Biological Evaluation of some Novel Pyrano[2,3-<i>d</i>]Pyrimidine Derivatives
< Back to Volume

Synthesis and Biological Evaluation of some Novel Pyrano[2,3-d]Pyrimidine Derivatives

Full Text PDF

Abstract:

The synthesis of novel Pyrano[2,3-d]pyrimidine derivatives, had been synthesized by three component domino Knoevenagel hetero Diels-Alder reaction. The products were assayed for their in vitro biological assay antibacterial activity against with two Gram-positive bacteria Staphylococcus aureus MTCC-96, Streptococcus pyogenes MTCC 443, two Gram-negative bacteria Escherichia coli MTCC 442, Pseudomonas aeruginosa MTCC 441 and three fungal strains Candida albicans MTCC 227, Aspergillus Niger MTCC 282, Aspergillus clavatus MTCC 1323 taking ampicillin, chloramphenicol, ciprofloxacin, norfloxacin, nystatin, and griseofulvin as standard drugs. Among the various synthesized heterocyclic compounds, 1b, 1c and 1g are display broad spectrum antibacterial and antifungal activities against both gram-positive and gram-negative bacteria as compared with standard drugs.

Info:

Periodical:
International Letters of Chemistry, Physics and Astronomy (Volume 74)
Pages:
9-14
DOI:
https://doi.org/10.18052/www.scipress.com/ILCPA.74.9
Citation:
P. K. Talpara et al., "Synthesis and Biological Evaluation of some Novel Pyrano[2,3-d]Pyrimidine Derivatives", International Letters of Chemistry, Physics and Astronomy, Vol. 74, pp. 9-14, 2017
Online since:
June 2017
Authors:
Pratik K. Talpara, Guarang G. Dubal, Viresh H. Shah
Keywords:
Antimicrobial Activity, Domino Knoevenagel Hetero Diels-Alder Reaction, Pyrano[2,3-d]Pyrimidine
Export:
RIS, BibTeX, Text
Distribution:
Open Access

Creative Commons License
This work is licensed under a
Creative Commons Attribution 4.0 International License

References:

[1] L.F. Tietze, Domino reactions in organic chemistry, Wiley-VCH, Weinheim. 20 (2006) 208–330.

[2] J.K. Gallos, A.E. Koumbis, Domino Knoevenagel hetero Diels-Alder reactions of sugar derived δ, ε-unsaturated aldehydes, Arkivoc. 6 (2003) 135–144.

DOI: https://doi.org/10.3998/ark.5550190.0004.616

[3] L.F. Tietze, U. Beifuss, Sequential transformations in organic chemistry: A synthetic strategy with a future, Angewandte Chemie International Edition in English. 32(2) (1993) 131–163.

DOI: https://doi.org/10.1002/anie.199301313

[4] M.E. Fox, I.C. Lennon, G. Meek, A novel synthesis of 5-hydroxy-2, 2-dimethyl-10-propyl-2H-pyrano [2, 3-f] chromen-8-one, Tetrahedron Letters. 43(16) (2002) 2899–2902.

DOI: https://doi.org/10.1016/s0040-4039(02)00428-8

[5] G.L. Anderson, J.L. Shim, A.D. Broom, Pyrido [2, 3-d] pyrimidines. IV. Synthetic studies leading to various oxopyrido [2, 3-d] pyrimidines, The Journal of Organic Chemistry. 41(7) (1976) 1095–1099.

DOI: https://doi.org/10.1002/chin.197630249

[6] E.M. Grivsky et al., Synthesis and antitumor activity of 2, 4-diamino-6-(2, 5-dimethoxybenzyl)-5-methylpyrido [2, 3-d] pyrimidine, J. Med. Chem. 23 (1980) 327–329.

[7] D. Heber, C. Heers, U. Ravens, Positive inotropic activity of 5-amino-6-cyano-1, 3-dimethyl-1, 2, 3, 4-tetrahydropyrido [2, 3-d] pyrim idine-2, 4-dione in cardiac muscle from guinea-pig and man. Part 6: Compounds with positive inotropic activity, Die Pharmazie. 48(7) (1993).

DOI: https://doi.org/10.1002/ardp.19903230911

[8] Y. Sakuma et al., Fused pyrimidine derivative, process for preparation of same and pharmaceutical preparation comprising same as active ingredient, U.S. Patent 5, 378, 700, (1995).

[9] L.R. Bennett et al., Antihypertensive activity of 6-arylpyrido [2, 3-d] pyrimidin-7-amine derivatives, J. Med. Chem. 24(4) (1981) 382–389.

[10] J. Davoll, J. Clarke, F.E. Eislager, Antimalarial substances. 26. Folate antagonists. 4. Antimalarial and antimetabolite effects of 2, 4-diamino-6-[(benzyl) amino] pyrido [2, 3-d] pyrimidines, J. Med. Chem. 15(8) (1972) 837–839.

DOI: https://doi.org/10.1021/jm00278a009

[11] B. Baruah, P.J. Bhuyan, Tertiary amine effect: synthesis of some novel spirosubstituted pyrido [2, 3-d] pyrimidines, Tetrahedron Letters. 50(2) (2009) 243–245.

DOI: https://doi.org/10.1016/j.tetlet.2008.10.125

[12] A.H. Shamroukh et al., Synthesis, isomerization, and antimicrobial evaluation of some pyrazolopyranotriazolopyrimidine derivatives, Archiv der Pharmazie. 340(7) (2007) 345–351.

[13] A.H. Shamroukh et al., Synthesis of pyrazolo [4', 3': 5, 6] pyrano [2, 3‐d] pyrimidine derivatives for antiviral evaluation, Archiv der Pharmazie. 340(5) (2007) 236–243.

[14] C. Musstazza et al., Synthesis of pyrazolo [1, 5-a]-, 1, 2, 4-triazolo [1, 5-a]-and imidazo [1, 2-a] pyrimidines related to zaleplon, a new drug for the treatment of insomni, J. Heterocycl. Chem. 38 (2001) 1119–1130.

[15] Y. Gao et al., Effective synthesis of 7‐amino‐6‐cyano‐5‐aryl‐5 H‐pyrano [2, 3‐d] pyrimidine‐2, 4 (1 H, 3 H)‐diones under microwave irradiation, Synthetic communications. 34(7) (2004) 1295–1299.

DOI: https://doi.org/10.1081/scc-120030318

[16] I. Devi, Kumar, P.J. Bhuyan, A novel three-component one-pot synthesis of pyrano [2, 3-d] pyrimidines and pyrido [2, 3-d] pyrimidines using microwave heating in the solid state, Tetrahedron Letters. 44(45) (2003) 8307–8310.

DOI: https://doi.org/10.1016/j.tetlet.2003.09.063

[17] T.S. Jin et al., A clean one-pot synthesis of 7-amino-5-aryl-6-cyano-1, 5-dihydro-2H-pyrano [2, 3-d] pyrimidine-2, 4 (3H)-diones in aqueous media under ultrasonic irradiation, J. Chem. Res. 3 (2005) 162–163.

DOI: https://doi.org/10.3184/0308234054213672

[18] H.R. Safaei et al., Glycerol as a biodegradable and reusable promoting medium for the catalyst-free one-pot three component synthesis of 4H-pyrans, Green Chem. 14(6) (2012) 1696–1704.

DOI: https://doi.org/10.1039/c2gc35135h

[19] Vogel's Textbook of practical organic chemistry, Fifth Edition, ELBS, Longman Scientific and Technical: England, 1989, Reprinted, (1994).

[20] National Committee for Clinical and Laboratory Standards, Method for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically Approved Standard, fourth ed. NCCLS, Villanova, Italy, Document M 100-S7. (1997) S100–S157.

Show More Hide