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Synthesis, Antitumor and Cytotoxic Activity of New Adamantyl O ‐Acylamidoximes and 3‐Aryl‐5‐Adamantane‐1,2,4‐Oxadiazole Derivatives
Author(s) -
Aguiar Deivson Ferreira,
Dutra Luana Letícia Alves,
Dantas Willyenne Marília,
Camelo de Carvalho Guilherme Graziany,
Gonçalves Lemes Romélia Pinheiro,
do Ó Pessoa Claudia,
Koscky Paier Carlos Roberto,
Barros Araujo Patricia Lopes,
Araujo Elmo Silvano,
Pena Lindomar José,
de Oliveira Ronaldo Nascimento
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201901285
Subject(s) - adamantane , chemistry , aryl , substituent , stereochemistry , medicinal chemistry , organic chemistry , alkyl
O ‐Acylamidoxime and 1,2,4‐oxadiazole derivatives were synthesized from adamantanecarbonyl chloride 1 and a diversity of arylamidoximes 2 a‐k . First, O ‐acylamidoximes intermediates 3 a‐k were synthesized and subsequent cyclization under microwave irradiation afforded 1,2,4‐oxadiazol derivatives 4 a‐k . Molar Heat of Reaction Calorimetry studies performed from O ‐acylamidoximes revealed influence of the substituent groups. A one‐pot two‐step methodology was also developed proving to be a viable protocol. Compounds were characterized by 1 H and 13 C Nuclear Magnetic Resonance (NMR) Spectroscopy, Elemental Analysis or High Resolution Mass Spectral Analysis, and subjected to cytotoxic studies in non‐tumoral Vero cells and antiproliferative activity tests in six malignant cell lines. Our findings suggest that compounds 3 derivatives presented a concentration‐dependent profile for chronic myeloid leukemia (K562) and acute promyelocytic leukemia (HL‐60) cell.