N-(1-Adamantylcarbamothioyl)benzamides: Synthesis, Biological Evaluation and Adme Predictions

Abstract

This paper presents the synthesis of five novel benzamide derivatives containing adamantane moiety. The compounds structure was proven through elemental analysis, FT-IR, 1 H-NMR and 13 C-NMR spectroscopy. Their therapeutic potential was evaluated by the in vitro testing of the antimicrobial activity. Two different parameters of the antimicrobial activity were determined: minimum inhibitory concentration (MIC) and minimal biofilm eradication concentration (MBEC). Also, an in vitro cytotoxicity study was carried out on Hep-2 cell line. An in silico study of the compounds determined their ADME profile. The study reports the preliminary biological screening of five novel benzamides with adamantane scaffold, that evidenced a good toxicological and ADME profile, thus representing favourable candidates for further studies. RezumatÎn această lucrare este prezentată sinteza a cinci noi derivați ai benzamidei care conțin fragmentul adamantan. Structura compușilor a fost dovedită prin analiză elementală, spectroscopie FT-IR, 1 H-RMN și 13 C-RMN. Potențialul lor terapeutic a fost evaluat prin testarea in vitro a activității antimicrobiene. S-au determinat doi parametri diferiți ai activității antimicrobiene, respectiv: concentrația minimă inhibitorie (MIC) și concentrația minimă de eradicare a biofilmului (MBEC). De asemenea, a fost efectuat un studiu de citotoxicitate in vitro, pe linia celulară HEp-2. Un studiu in silico al compușilor a determinat profilul lor ADME. Studiul raportează screening-ul biologic preliminar a cinci noi benzamide cu fragment de adamantan, care prezintă profil toxicologic și ADME favorabil, prezentând astfel un potențial promițător pentru studii ulterioare.

A very promising antibiofilm activity against Candida albicans from an in vitro screening for antimicrobial, antibiofilm and antiproliferative activity of new synthesized 4-cinnamamido- and 2-phenoxyacedamido-1H-pyrazol-5-yl)benzamides.

“…Acetamidobenzamides are well represented in literature as antimicrobial, antibio lm and antiproliferative agents. Fusaribenzamide A 1 [1], fusarithioamide B 2 [2], and N-(1-Adamantylcarbamothioyl)benzamides 3 [3] are examples of antimicrobial acetamidobenzamides (Fig. 1).…”

Concomitant HPLC Analysis of Adapalene and Nadifloxacin in the Presence of Glycolic Acid

“…The three components are individually used or in combination with benzoyl peroxide as active pharmaceutical ingredients in topical anti-acne products. Extensive clinical trials recommend the use of fixed combination gels to benefit from the synergistic effect of a topical antibiotic with a retinoid and a superficial peeling agent, as acne is a multifactorial pathology involving abnormal bacterial proliferation, inflammation of the skin with consequent change in its permeability [9]. GA is used in cosmetic products for acne treatment in concentrations over 3% therefore it can interfere when active compounds as NDX or ADP have to be analysed by analytical methodologies with low specificity.…”