Abstract
In this work the multi-component reactions of either of the arylhydrazocyclohexan-1,3-dione derivatives 3a-c with either of benzaldehyde (4a), 4-chlorobenzaldehyde (4b) or 4-methoxybenzaldehyde (4c) and either malononitrile (5a) or ethyl cyanoacetate (5b) giving the 5,6,7,8-tetrahydro-4H-chromene derivatives 6a-r, respectively, are presented. The reaction of two equivalents of cyclohexan-1,3-dione with benzaldehyde gave the hexahydro-1H-xanthene-1,8(2H)-dione derivative 7. On the other hand, the multi-component reactions of compound 1 with dimedone and benzaldehyde gave 13. Both of 7 and 13 underwent heterocyclization reactions to produce fused thiophene, pyran and thiazole derivatives. Selected compounds among the synthesized compounds were tested against six cancer cell lines where most of them gave high inhibitions; especially compounds 3b, 3c, 6b, 6c, 6d, 6f, 6i, 6m, 6n, 8b, 14a, 15 and 16 being the most cytotoxic compounds. Further tests against the five tyrosine kinases c-Kit, Flt-3, VEGFR-2, EGFR, and PDGFR and Pim-1 kinase showed that compounds 3c, 6c, 6d, 6f, 6n, 14a and 15 were the most potent of the tested compounds toward the five tyrosine kinases and compounds 3c, 6c, 6d, 6n and 15 displayed the highest inhibitions toward Pim-1 kinase.
Highlights
Pyran derivatives are known as important class of compounds that exist in nature and have many applications[1] especially fused pyrans are important core units comprising many natural products
The arylhydrazone derivatives 3a–c were obtained through the coupling reaction between cyclohexane-1,3-dione (1) and either benzenediazonium chloride (2a), 4-methylbenzenediazonium chloride (2b) or 4-chlorobenzenediazonium chloride (2c) in ethanol solution containing the appropriate amount of sodium acetate
4-methoxybenzaldehyde (4c) and either malononitrile (5a) or ethyl cyanoacetate (5b) in 1,4-dioxane solution containing a catalytic amount of triethylamine gave the 5,6,7,8-tetrahydro-4H-chromene derivatives 6a–r, respectively (Scheme 1)
Summary
Pyran derivatives are known as important class of compounds that exist in nature and have many applications[1] especially fused pyrans are important core units comprising many natural products. Due to their various kinds of biological activities pyrans and their fused derivatives attracted the attention within the last few years. Pyranochalcones have many applications like antimutagenic, antimicrobial, antiulcer, and antitumor activities.[6,7,8] Pyrans and their fused derivatives showed different kinds of biological activities. Such high importance of pyrans and their derivatives together with the ease of their synthesis with high yields direct many works through their synthesis
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