A rapid and simple method was developed for the synthesis of diarylmethyl thioethers a DABCO-catalyzed 1,6-conjugate addition reaction of -quinone methides (-QMs) with organosulfur reagents. A series of diarylmethyl thioethers were synthesized at 13-85% yields by this method. After that, the antibacterial activities of synthesized diarylmethyl thioethers and their derivatives were evaluated. The MIC range (μg mL) against ATCC 25923 and clinically isolated methicillin-resistant was 8-128 and 64-128, respectively.
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http://dx.doi.org/10.1039/d3ra01815f | DOI Listing |
Org Biomol Chem
September 2023
Medicinal & Process Chemistry Division CSIR-Central Drug Research Institute, Sector 10, Jankipuram Extension, Lucknow 226031, India.
A simple, efficient, and transition metal-free approach was developed for accessing 4-thio-substituted chroman and diarylmethyl thioethers from sulfonyl hydrazones. This protocol provides straightforward access to a class of diarylmethane derivatives with good to excellent yields. This operationally simple protocol exhibited good tolerance for labile functional groups, providing biologically relevant chemical libraries.
View Article and Find Full Text PDFOrg Lett
July 2023
Natural Product and Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Jammu 180001, India.
Herein, we present the BF/BF mediated activation of diphenyl phosphite for the formation of thionium ions from aldehydes and thiophenols. These reactive species subsequently undergo reaction with generated phenol, resulting in the synthesis of diarylmethyl thioethers. It was demonstrated that the addition of external phenol in the reaction produced unsymmetrical -diarylmethyl thioethers in good yields.
View Article and Find Full Text PDFRSC Adv
April 2023
State Key Laboratory of Functions and Applications of Medicinal Plants, School of Pharmacy, and Engineering Research Center for the Development and Application of Ethnic Medicine and TCM (Ministry of Education), Guizhou Medical University Guiyang 550004 People's Republic of China
A rapid and simple method was developed for the synthesis of diarylmethyl thioethers a DABCO-catalyzed 1,6-conjugate addition reaction of -quinone methides (-QMs) with organosulfur reagents. A series of diarylmethyl thioethers were synthesized at 13-85% yields by this method. After that, the antibacterial activities of synthesized diarylmethyl thioethers and their derivatives were evaluated.
View Article and Find Full Text PDFOrg Biomol Chem
August 2020
Institut de Chimie des Substances Naturelles CNRS, Univ. Paris-Saclay, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France.
The combined Lewis acid catalytic system, generated from molecular iodine and tritylium tetrafluoroborate effectively catalyzed the Friedel-Crafts (FC) arylation of diarylmethyl sulfides providing an efficient access to various unsymmetrical triarylmethanes. The addition of tritylium and iodine created a more active catalytic system to promote the cleavage of sulfidic C-S bonds.
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