Synthesis and antimicrobial activity of new adamantane derivatives II

Abstract

A series of new derivatives of adamantane was synthesised. The new compound 4-(adamant-1-ylethylenoxycarbonyl)phthalanhydride obtained from 1-adamantaneethanol and trimellitic anhydride chloride, as well as 4-(adamant-1-ylmethylenoxycarbonyl)phthalanhydride, appeared very useful for preparation of a number of N-substituted phthalimides. Antimicrobial activity of newly obtained derivatives such as, for example, 4-(adamant-1-ylethylenoxycarbonyl)-N-(L-phenylalanyl)phthalimide or 4-(adamant-1-ylmethylenoxycarbonyl)-N-(L-leucyl)-phthalimide was tested against Staphylococcus aureus, Bacillus sp., Micrococcus flavus and Enterococcus faecium. The minimal inhibitory concentrations for these compounds against Bacillus cereus were 15 and 8 microg/ml, respectively.

4-Thiazolidinone derivatives as potent antimicrobial agents: microwave-assisted synthesis, biological evaluation and docking studies

“…Thiazolidin-4-ones are known to possess a wide range of biological activities, such as antibacterial, [29][30][31][32][33] antifungal, 29-33 antiviral, [34][35][36] anti-inammatory, 32 antitubercular, [37][38][39] etc. Furthermore, adamantane is an interesting moiety in medicinal chemistry known for its antiviral, [40][41][42][43] antimicrobial, [44][45][46] anti-inammatory 16,47 and anti-Alzheimer's 48 activities.…”

The use of tri-O-acetyl-d-glucal and -d-galactal in the synthesis of ω-aminoalkyl 2-deoxy- and 2,3-dideoxy-d-hexopyranosides

“…[22][23][24][25][26][27][28] The appropriate products of Ferrier's rearrangement, 4,6-di-O-acetyl-2,3-dideoxyhexenopyranosides 6a-e, were achieved in satisfactory yield (Scheme 2). The NMR data indicated the formation of a-anomers exclusively (Table 1, entries [7][8][9][10][11]. In order to confirm the a-configuration of the adducts obtained, a representative molecule 6b was hydrogenated at atmospheric pressure in the presence of Pd/C catalyst.…”

The Crystal and Molecular Structure of 2-[(3,4-dimethoxybenzylidene)amino]adamantane

“…It has been reported in literature that different adamantane derivatives show antitumor (MONFORTE et al, 1981;DA SETTIMO et al, 1995) and antimicrobial activities (FERLE-VIDOVIÇ et al, 1983;KOLOCOURIS et al, 1994). Recently, additional to antiviral activitiy, it has been determined that several adamantane derivatives also possess antibacterial and antifungal activity as well (ORZESZKO et al, 2000). In the course of ongoing work on synthesis and structural characterization studies of some new compounds containing adamantane ligands (ÇALIS et al, 2002), the title compound was synthesized and we report here its crystal structure.…”