Der Pharma Chemica
Journal for Medicinal Chemistry, Pharmaceutical Chemistry and Computational Chemistry

Abstract

Synthesis of novel 1,6-naphthyridines, pyrano[3,2-c]pyridines and pyrido[4,3-d]pyrimidines derived from 2,2,6,6-tetramethylpiperidin-4-one for in vitro anticancer and antioxidant evaluation

Author(s): Hanan A. Solimana, Mahmoud N. M. Yousifa, Makarem M. Saidb, Nasser A. Hassana,Mamdouh M. Alic, Hanem M. Awadd, Farouk M. E. Abdel-Megeida

Reaction of 2,2,6,6-tetramethylpiperidin-4-one (1) with different aromatic aldehydes afforded the diarylidenes 2a-f. Compound 1 reacted in one-pot reaction with aromatic aldehydes and malononitrile in ammonium acetate, and also with arylidene malononitrile in ammonium acetate to give the corresponding 1,6-naphthyridine-3-carbonitriles 3a-f and 4a-f, respectively. Compounds 3b, 4b were acetylated using acetic anhydride to give the mono- and triacetylated products 5a,b; 6a,b, respectively. Compound 1 was reacted with cyanoacetamide and aromatic aldehydes in ammonium acetate or ethyl cyanoactate and aromatic aldehydes in ammonium acetate to give 1,6-naphthyridine- 3-carboxamides 7a-c or 1,6-naphthyridine-3-carboxylates 8a-c, respectively. On the other hand, reaction of compound 1 with aromatic aldehydes and malononitrile in triethylamine afforded the pyrano[3,2-c]pyridine-3- carbonitriles 9a-c. Also, compound 9c was acetylated with acetic anhydride to give the tri-acetylated product 10. Pyrido[4,3-d]pyrimidine-2-thione derivatives 11a-c were obtained by reaction of compound 1 with aromatic aldehydes and thiourea. Compounds 11a-c were reacted further with chloroacetic acid to give the corresponding 9- arylidene-pyrido[4,3-d]thiazolidino[3,2-a]pyrimidin-3-one derivatives 12a-c which in turn reacted with aromatic aldehydes to give the corresponding 2,9-diarylidenes 13a-c. Multi-component reaction of compound 1 with 4- chlorobenzaldehyde and 6-amino-S-methylthiouracil in DMF afforded the corresponding pyrimido[4,5- b][1,6]naphthyridine derivatives 14 which reacted with hydrazine hydrate to give the corresponding 2-hydrazinyl derivative 15. Antioxidant and anticancer results of the products are reported.


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