Synthesis of some new thienopyridine and pyridothienopyrimidine derivatives with expected antitumor activity

International Journal of Medical Science

© 2016 by SSRG - IJMS Journal

Volume 3 Issue 9

Year of Publication : 2016

Authors : Mona S. Kadah

10.14445/23939117/IJMS-V3I9P102

How to Cite?

Mona S. Kadah, "Synthesis of some new thienopyridine and pyridothienopyrimidine derivatives with expected antitumor activity," SSRG International Journal of Medical Science, vol. 3,  no. 9, pp. 5-10, 2016. Crossref, https://doi.org/10.14445/23939117/IJMS-V3I9P102

Abstract:

The thioxopyridine derivative (2) on treatment with ethyl chloroacetate gave the corresponding ethyl 3-aminothieno [2,3-b]pyridin-2- carboxylate (3). Condensation of 3 with Ac2O gave the corresponding 4-H-pyrido[3',2':4,5]thieno[3,2-d] [1,3]oxazine derivative (4). Reaction of 4 with bifunctional groups gave 3,4- dihydropyrido[3',2':4,5]thieno[3,2-d]pyrimidines (5a,b) and 2-carbamoyl-3-acetamidothieno[2,3-b]pyridine derivative (6). Intramolecular cyclization of 6 by Ac2O/AcOH gave (7). Reaction of 5b with different electrophilic reagents were studied. Also, 5a upon treatment with ethyl chloroacetate and/or methyl iodide (K2CO3) furnished the corresponding Nethylacetate (13) and N-methyl derivative (16) respectively. Hydrazinolysis of 13 gave the corresponding acetohydrazide (14) which on treatment with benzaldehyde furnished the corresponding 1H-pyrazol-4-yl derivative (15). The IR, 1H NMR and MS spectra of newly derivatives were discussed. The antitumor activity against the liver tumor cell line HepG2 of the prepared compounds were tested. Compounds 8a, 14 were more potent (IC50 = 2.75 and 2.12 g/ml) than the standard drug (IC50 = 4.60 g/ml).

Keywords:

  Cyanothioxapyridine, Thienopyridine, Pyridothieno pyrimidine and antitumor, HepG2.

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