Graphite catalyzed solvent free synthesis of dihydropyrimidin-2(1H)-ones/thiones and their antidiabetic activity.
A solvent free three component condensation reaction between an aldehyde, ethyl acetoacetate and urea catalyzed by graphite, a green catalyst is described for the synthesis of dihydropyrimidin-2(1H)-ones. This protocol is scalable and the catalyst is reusable. This method is also applied for the synthesis of dihydropyrimidin-2(1H)-thiones. α-Amylase, a key enzyme in carbohydrate metabolism is generally targeted for management of type 2 diabetes. The therapeutic potential of the dihydropyrimidinones and dihydropyrimidinthiones to inhibit α-amylase activity was evaluated by in vitro assay. Of the synthesized compounds 3,4-dihydropyrimidin-2(1H)-thione (1k) demonstrated highest inhibition of α-amylase activity.
Department of Chemistry, Goa University, Taleigao Plateau, Goa 403206, India.
Kashinath L
KL
Dhumaskar
Department of Biotechnology, Goa University, Taleigao Plateau, Goa 403206, India.
Surya Nandan
SN
Meena
Department of Biotechnology, Goa University, Taleigao Plateau, Goa 403206, India. Electronic address: saga@unigoa.ac.in.
Sanjeev C
SC
Ghadi
Department of Chemistry, Goa University, Taleigao Plateau, Goa 403206, India. Electronic address: stilve@unigoa.ac.in.
Santosh G
SG
Tilve
D002384:Catalysis; D003924:Diabetes Mellitus, Type 2 / Q000188:drug therapy* / Q000201:enzymology / Q000378:metabolism; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006108:Graphite / Q000737:chemistry*; D006801:Humans; D007004:Hypoglycemic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D011743:Pyrimidines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013871:Thiones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000516:alpha-Amylases / Q000037:antagonists & inhibitors* / Q000378:metabolism
D004791:Enzyme Inhibitors; D007004:Hypoglycemic Agents; D011743:Pyrimidines; D013871:Thiones; C000595184:ethyl 6-methyl-4-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate; D006108:Graphite; D000516:alpha-Amylases
Antidiabetic; Biginelli reaction; Dihydropyrimidinones; Graphite catalysis; Multicomponent reaction; Solvent less; α-Amylase inhibition