Synthesis of Pyrano[2,3‐d]pyrimidine‐2,4‐diones and Pyridino[2,3‐d]pyrimidine‐2,4,6,8‐tetraones: Evaluation Antitumor Activity

Abstract

A series of some novel pyrano [2,3-d]pyrimidine 4-10 with 75-95% yields and pyridino[2,3-d]pyrimidine derivatives 11-16 with 75-92% yields is reported. The building structures have been achieved by reaction of 5-arylidene barbituric acid 2 and active nucleophile carbon or nitrogen as examples barbituric acid and acetyl acetone or refluxing of bispyrimidine-2,4,6-trione derivative 3 with cyclizing reagents such as phosphorous pentoxide, hydrazine hydrate and aminothiazole. The newly synthesized structures have been elucidated on the basis of their spectral analysis. Some selected members were screened for antitumor activity. Among the screened compounds 9, 16, 7, 10 and 8 exhibited high antitumor activity.

Insights into the recent progress in the medicinal chemistry of pyranopyrimidine analogs

“…Thus, compounds 162a and 162e seem to be reliable for further cancer drug design. 101 Haggam et al 102 designed a series of bicyclic pyranopyrimidines 164-167 from the readily available arylidene barbituric acid 163. Subsequently, the reactions of compound 163 with each acetylacetone, 2-cyanoacetamide, malononitrile, and ethyl cyanoacetate yielded the desired bicyclic pyranopyrimidines 164-167, respectively (Scheme 37).…”

Recent advancements in the multicomponent synthesis of heterocycles integrated with a pyrano[2,3-d]pyrimidine core

“…1). Alternatively, pyranopyrimidine heterocycles have signicant and condential biological and physiological potency since this class of compounds demonstrated antibacterial, antitumor, [1][2][3] antimicrobial, [4][5][6][7] anti-inammatory, 8,9 antioxidant, antidiabetic, 10,11 tyrosine phosphatase inhibitors, 12 antitubercular, 13 Hh signaling inhibitors in NIH3T3 cells, 14 antihypertensive, 15 antimalarial, 16 antiviral, 17 anticancer, 18,19 and cardiotonic agents. 20,21 In another route, pyranopyrimidines act as sirtuin inhibitors, for instance, the inhibition activity of SIRT1 was formerly reported by Rotili et al 22 as shown in Fig.…”

Synthesis and Biological Evaluation of New Chromenes and Chromeno[2,3-d] pyrimidines

“…These motifs are wellestablished in the literature as important biologically effective heterocyclic compounds. 1,2,3,4,5 These compounds are the subject of many research studies due to their large potential for pharmacological activities. These activities include antitumoral, 6 antibacterial, 7 anti-fungicidal, analgesic, 8 anti-allergic, 9 cardiotonic, hepatoprotective, 10 antihypertensive, 11 activity.…”