Synthesis, Antitumor and Cytotoxic Activity of New Adamantyl O‐Acylamidoximes and 3‐Aryl‐5‐Adamantane‐1,2,4‐Oxadiazole Derivatives

Abstract

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 1H and 13C 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.

Synthesis and antibacterial activity of novel Schiff bases of thiosemicarbazone derivatives with adamantane moiety

“…Adamantane compounds have shown relatively good antivirus, antitumor, and anti-Parkinson's syndrome activities [16][17][18][19][20][21]. The introduction of adamantyl groups into the molecular structure of other compounds often enhances the biological activity of the compound.…”

Synthesis and Bioactivity of Hydrazide-Hydrazones with the 1-Adamantyl-Carbonyl Moiety

“…A number of studies were conducted, focusing on such derivatives with the hope to find new compounds and biological activities. As a result, many adamantane derivatives were discovered with numerous biological activities, such as antiviral [15][16][17][18][19][20], antimicrobial [18,[20][21][22][23][24][25][26][27][28][29][30], anticancer [23,27,[31][32][33][34][35], angiogenesis inhibition [36], anti-inflammation [37], 11β hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibition [38][39][40], and tyrosinase inhibition [41] activities. Among them, nine compounds were approved for use in clinics, including amantadine, memantine, rimantadine, tromantadine, adapalene, vildagliptine, saxagliptine, bromanatane, and adapromine.…”

Synthesis and Bioactivity of Thiosemicarbazones Containing Adamantane Skeletons

“…Since the first adamantane derivative, amantadine, was found to have antiviral [21][22][23] activity, the synthesis and biological activities of adamantane derivatives, which became an interesting topic, were pursued by a lot of researchers. Therefore, many adamantane derivatives were discovered with various biological activities, i.e., antiviral [24][25][26][27][28][29], antimicrobial [27,[29][30][31][32][33][34][35][36][37][38][39], anticancer [32,36,[40][41][42][43][44] activities.…”