Solvent-free, green and efficient synthesis of pyrano[4, 3-b]pyrans by grinding and their biological evaluation as antitumor and antioxidant agents
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A facile, green, and efficient method has been developed for the synthesis of pyrano[4, 3-b]pyrans via a one-pot reaction of aromatic aldehydes, malononitrile, and 4-hydroxy-6-methyl-pyran-2-one in the presence of ammonium acetate under solvent-free conditions using grinding method. The experimental simplicity, short reaction time, easy work-up, avoidance of organic solvents, and utilization of an inexpensive and readily available catalyst make this new methodology practical and economically attractive. The antitumor activity of the compounds was tested against human breast cancer cell line MCF-7. Compounds 4l, 4o, and 4p showed good cytotoxic activity comparable with standard drug Doxorubicin. On the other hand, compounds 4q and 4r exhibited potent growth inhibitory activity. Furthermore, the synthesized compounds were screened for in vitro antioxidant activity by DPPH assay. All the compounds assayed showed moderate to good free radical scavenging activity.
KeywordsPyrano[4, 3-b]pyrans Green chemistry One-pot synthesis Grinding Solvent-free Cytotoxicity Antioxidant activity
The authors are thankful to the authorities of Deshpande Laboratories Pvt. Ltd., Bhopal (M.P.), India and Pinnacle Biomedical Research Institute, Bhopal (M.P.), India for the studies of biological activities. The authors also thank The Director, SAIF, Panjab University, Chandigarh for NMR and MS spectral data.
- Da-Qing S, Li-Hui N, Qi-Ya Z (2008) One-pot three-component synthesis of pyrano[3,2-c]pyran-5-one derivatives in aqueous medium. Chin J Org Chem 28:1633Google Scholar
- Fan X, Feng D, Qu Y, Zhang X, Wang J, Loiseau PM, Andrei G, Snoeck R, De-Clercq E (2010) Practical and efficient synthesis of pyrano[3,2-c]pyridone, pyrano[4,3-b]pyran and their hybrids with nucleoside as potential antiviral and antileishmanial agents. Bioorg Med Chem Lett 20:809CrossRefPubMedGoogle Scholar
- Pochet L, Doucet C, Schynts M, Thierry N, Boggetto N, Pirotte B, Jiang KY, Masereel B, de Tullio P, Delarge J, Reboud-Ravaux M (1996) Esters and amides of 6-(chloromethyl)-2-oxo-2H-1-benzopyran-3-carboxylic acid as inhibitors of α-chymotrypsin: significance of the “aromatic” nature of the novel ester-type coumarin for strong inhibitory activity. J Med Chem 39:2579CrossRefPubMedGoogle Scholar
- Shirini F, Marjani K, Nahzomi HT (2007) Silica triflate as an efficient catalyst for the solvent-free synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Arkivoc 1:51Google Scholar
- Thirunarayanan G, Vanangamudi G (2006) Synthesis of some 4-bromo-1-naphthyl chalcones using silica-sulfuric acid reagent under solvent free conditions. Arkivoc 12:58Google Scholar
- Uher M, Konecny V, Rajniakove O (1994) Synthesis of 5-hydroxy-2-hydroxymethyl-4H-pyran-4-one derivatives with pesticide activity. Chem Pap 48:282Google Scholar
- Wang XS, Zhou JX, Zeng ZS, Li YL, Da-Qing S, Tu SJ (2006) One-pot synthesis of pyrano[3,2-c]pyran derivatives catalyzed by KF/Al2O3. Arkivoc 11:107Google Scholar