ABSTRACT
The search for natural products and related analogs as potential anticancer agents has seen a significant growth worldwide. Since small sized propargylic diols can be found in nature and chemically synthesized, their evaluation against cancer cells has been of great interest, being a topic of relevance to be investigated. For this purpose, a scalable approach aiming at the synthesis of several propargylic diols and their bioactivity against seven tumor cell lines were evaluated. Interestingly, when the compound 1a, a natural product produced by fungus Clitocybe catinus, was tested in its racemic mixture a more effective activity was observed if compared when enantiopure R-1a or S-1a were tested separately.
Subject(s)
Alkynes/pharmacology , Antineoplastic Agents/pharmacology , Basidiomycota/chemistry , Biological Products/pharmacology , Alkynes/chemical synthesis , Alkynes/chemistry , Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/chemistry , Biological Products/chemical synthesis , Biological Products/chemistry , Cell Line, Tumor , Cell Proliferation/drug effects , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , Humans , Molecular Structure , Structure-Activity RelationshipABSTRACT
Internal bis-substituted propargylic diols were subjected to enzymatic kinetic resolution promoted by CAL-B. Employing a two round sequence EKR, mono- and bis-acetoxy propargylic products were obtained in a high enantiomeric ratio (E > 200). The efficiently resolved chiral 8b was applied in a concise synthesis of (S)-1b, an optically active natural product produced by fungi Clitocybe catinus.
