Search

A number of new octahydro-2H-chromene acetamide derivatives based on the monoterpenoid (−)-isopulegol were synthesized using a one-pot three-component Prins—Ritter reaction. The structure of the target compounds was determined using 1H and 13C NMR spectroscopy, high resolution mass spectrometry, and X-ray diffraction analysis. Most of the products exhibited high analgesic activity in in vivo tests. The highest analgesic activity was found for spirocyclic compound (4S)-2d, the effect of which is apparently mediated through the dopamine system. It was shown that compound (4S)-2d has a low acute toxicity. [ABSTRACT FROM AUTHOR]

A number of new derivatives of octahydro-2H-chromene based on monoterpenoid (–)-isopulegol has been synthesized. The composition and structure of the products have been established using NMR spectroscopy, high-resolution mass spectrometry, and X-ray diffraction analysis. It has been shown that the majority of obtained compounds show high analgesic activity in vivo. (4S)‑Diastereomers of morpholinoacetamide derivatives of octahydro-2H-chromene showed the highest efficiency in both tests (acetic acid-induced writhing test and hot plate test). [ABSTRACT FROM AUTHOR]

A series of new compounds with hydrogenated 2H-chromene framework was synthesized starting from aliphatic aldehydes and available p-menthane monoterpenoid (−)-isopulegol in the presence of montmorillonite K10. These compounds were formed as a pair of diastereoisomers, which were isolated individually using column chromatography. Some of the compounds obtained were found to exhibit high analgesic activity in in vivo tests. [ABSTRACT FROM AUTHOR]

Tyrosyl-DNA phosphodiesterase 1 (Tdp1) is one of the important DNA repair enzymes responsible for the repair of DNA damage caused by anticancer drugs, such as topotecan. In this regard, enzyme activity is one of the possible causes of tumor resistance to chemotherapy, and the use of inhibitors of this enzyme is considered as a promising adjuvant therapy. We have obtained a number of new isomeric naphthyl derivatives of thiophenyl octahydro-2H-chromene, the structure of one of which is confirmed by X-ray structural analysis. Based on molecular modeling data, the structure of the ligand-Tdp1 complex has been proposed. All compounds obtained inhibit Tdp1 at a concentration of about 2 μM. Low toxicity of three compounds was shown, which makes them promising candidates for the development of accompanying cancer therapy. [ABSTRACT FROM AUTHOR]

A series of compounds with a hydrogenated 2H-chromene skeleton was synthesized by the reaction of ketones and available para-menthane monoterpenoid (—)-isopulegol. A condensation product of (—)-isopulegol with the monoterpene ketone l-menthone was synthesized for the first time. The synthesized heterocycles were tested for analgesic activity and compounds with high analgesic activity in the in vivo tests were identified. [ABSTRACT FROM AUTHOR]

Six imines including four new ones were synthesized via the reaction of monoterpenoid aldehydes with aminoadamantanes. The inhibitory activities of the synthesized compounds against purified human recombinant DNA repair enzyme tyrosyl-DNA phosphodiesterase 1 (Tdp1) fell in the range IC50 = 5.5-7.1 μM. [ABSTRACT FROM AUTHOR]

Hexahydro-2H-chromenes with thiophene fragments were synthesized via reactions of a p-menthane monoterpenoid diol with several thiophenecarboxaldehydes. Most of the synthesized compounds with an additional thiophene fragment displayed analgesic activity in vivo tests at a dose of 10 mg/kg. It was found that the activity in either an acetate-writhing test or a hot-plate test depended on the type and location of substituent in the heteroaromatic ring. [ABSTRACT FROM AUTHOR]

A number of compounds with a substituted hexahydro-2 H-4,6-(epoxymethano)chromen8(5 H)-one framework was synthesized starting from monoterpenoid (-)-verbenone and aromatic aldehydes containing methoxy and hydroxy groups. Cytotoxic activity of these compounds on human tumor cell lines was studied for the first time. Compounds containing three methoxy groups in each aromatic ring were found to be the most promising for further studies. [ABSTRACT FROM AUTHOR]