Natural product-based synthesis of novel anti-infective isothiocyanate- and isoselenocyanate-functionalized amphilectane diterpenes

Bioorganic & Medicinal Chemistry Letters
2016.0

Abstract

The marine natural product (-)-8,15-diisocyano-11(20)-amphilectene (1), isolated from the Caribbean sponge Svenzea flava, was used as scaffold to synthetize five new products, all of which were tested against laboratory strains of Plasmodium falciparum and Mycobacterium tuberculosis H37Rv. The scaffold contains two isocyanide units that are amenable to chemical manipulation, enabling them to be elaborated into a small library of sulfur and selenium compounds. Although most of the analogs prepared were less potent than the parent compound, 5 was nearly equipotent showing IC50 values of 0.0066 μM and 0.0025 μM, respectively, against two strains (Dd2 and 3D7) of the malaria parasite. On the other hand, when assayed against the tuberculosis bacterium, analogs 5 and 6 were found to be more potent than 1.

Knowledge Graph

Similar Paper

Natural product-based synthesis of novel anti-infective isothiocyanate- and isoselenocyanate-functionalized amphilectane diterpenes
Bioorganic & Medicinal Chemistry Letters 2016.0
Bifunctionalized Amphilectane Diterpenes from the Sponge <i>Stylissa</i> cf. <i>massa</i>
Journal of Natural Products 2012.0
Antimalarial Isocyano and Isothiocyanato Sesquiterpenes with Tri- and Bicyclic Skeletons from the Nudibranch <i>Phyllidia ocellata</i>
Journal of Natural Products 2015.0
Antimalarial Isocyano and Isothiocyanato Sesquiterpenes with Tri- and Bicyclic Skeletons from the Nudibranch <i>Phyllidia ocellata</i>
Journal of Natural Products 2015.0
Terpene Isocyanides, Isocyanates, and Isothiocyanates from the Okinawan Marine Sponge <i>Stylissa</i> sp.
Journal of Natural Products 2004.0
Terpene Isocyanides, Isocyanates, and Isothiocyanates from the Okinawan Marine Sponge <i>Stylissa</i> sp.
Journal of Natural Products 2004.0
Antimalarial Activity of Sesquiterpenes from the Marine Sponge Acanthella klethra
Journal of Natural Products 1992.0
Novel thiolactone–isatin hybrids as potential antimalarial and antitubercular agents
Bioorganic &amp; Medicinal Chemistry Letters 2011.0
Antimalarial Activity:  The Search for Marine-Derived Natural Products with Selective Antimalarial Activity
Journal of Natural Products 1996.0
Synthesis of antimalarial amide analogues based on the plant serrulatane diterpenoid 3,7,8-trihydroxyserrulat-14-en-19-oic acid
Bioorganic &amp; Medicinal Chemistry Letters 2017.0