Abstract
The target compounds 1-(4-(1H-indol-3-yl)-6-(4-methoxyphenyl)pyrimidin-2-yl)hydrazine (5) was synthesized by reacting 6-(1H-Indol-3-yl)-4-(4-methoxyphenyl)pyrimidine-2(1H)-thione 4 with hydrazine hydrate. Compound 5 was used as a precursor for the synthesis of new pyrazolo pyrimidine derivatives 6-9. Moreover, the 5-amino-1H-pyrazole-4-carbonitrile derivative 6 was then converted into another set of novel compounds 10-14. On the other hand a series of transformations were carried out using the newly synthesized 1-(4-(1H-indol-3-yl)-6-(4-methoxyphenyl) pyrimidin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one (11) to afford the pyrazolo pyrimidine derivatives 15-18. Antiproliferatve activities for some of the newly synthesized compounds were evaluated.
Highlights
Chalcones are characterized by their easy synthesis by Claisen-Schmidt condensation in good yields and the presence of the α,β unsaturated carbonyl system linked to two aromatic rings which encourage the chalcones cyclization through Michael addition to give interesting heterocyclic compounds which exhibit antitumor [6,7], antimitotic [8], antimutagenic [9] antibacterial [10], antiviral [11], antiinflammatory [12], antiulcerative [13] and hepatoprotective [14]
Through several years of research and cross referencing other related journals on the preparation of chalcones and their derivatives, chalcone compound 3 and thiopyrimidinone 4 were prepared as reported in literature [1]
The hydrazino-pyrimidine derivative 5 was synthesized by reacting the thiopyrimidinone 4 with hydrazine hydrate in refluxing alcohol, the structure of compound 5 was confirmed by IR, 1H NMR, MS spectra and elemental analysis, where its IR revealed the absorption bands at νmax=3212 for the NH2 and 3184, 3109 cm-1 for the two NH groups, 1H NMR spectrum gave the signals at δ=8.93-8.95 as a broad singlet for NH2, hydrazine NH and at 11.65 ppm., for the indole NH respectively
Summary
Chalcones constitute an important group of natural products and are the precursors of flavonoids, isoflavonoids and many synthetic heterocycles of different biological activities including pyrimidines, pyrazolines, pyrazolopyrimidines and diazepines [1,2,3,4,5].Chemically, chalcones are characterized by their easy synthesis by Claisen-Schmidt condensation in good yields and the presence of the α,β unsaturated carbonyl system linked to two aromatic rings which encourage the chalcones cyclization through Michael addition to give interesting heterocyclic compounds which exhibit antitumor [6,7], antimitotic [8], antimutagenic [9] antibacterial [10], antiviral [11], antiinflammatory [12], antiulcerative [13] and hepatoprotective [14]. The formed precipitate was filtered and recrystallized from ethanol to give pale brown crystals of compound 6 mp 174-6°C, yield 76% IR: νmax/cm-1 3356 (NH2), 3164 (NH), 2224 (C≡N).1H NMR (DMSO-d6): δ 3.49 (s, 3H, OCH3), 7.01-7.27 (m, 4H, Ar H’s), 7.46 (d, 2H, J=8.6 Hz, Ar-H), 7.87 (s, 1H, pyrazole), 8.28 (s, 1H, indole), 8.30 (d, 2H, J=8.6 Hz, ArH's), 8.56 (s, 1H, pyrimidin), 8.85 (s, 2H, D2O Exch., NH2), 11.66 (s, 1H, D2O Exch., indole NH).
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