title: Synthesis and in vitro evaluation of (R), (S) and (R/S)-2-hexyne-1,4-diol, a natural product produced by fungus Clitocybe catinus, and related analogs as potential anticancer agents.
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.
authors.affiliation: Departamento de Química Fundamental, Universidade Federal de Pernambuco, Recife, PE, Brazil; Departamento de Antibióticos, Universidade Federal de Pernambuco, Recife, PE, Brazil.
authors.forename: Iza Mirela R G
authors.initials: IMRG
authors.lastname: Princival
authors.affiliation: Departamento de Química Fundamental, Universidade Federal de Pernambuco, Recife, PE, Brazil.
authors.forename: Jeiely G
authors.initials: JG
authors.lastname: Ferreira
authors.affiliation: Departamento de Antibióticos, Universidade Federal de Pernambuco, Recife, PE, Brazil.
authors.forename: Teresinha G
authors.initials: TG
authors.lastname: Silva
authors.affiliation: Departamento de Antibióticos, Universidade Federal de Pernambuco, Recife, PE, Brazil.
authors.forename: Jaciana S
authors.initials: JS
authors.lastname: Aguiar
authors.affiliation: Departamento de Química Fundamental, Universidade Federal de Pernambuco, Recife, PE, Brazil.
authors.forename: Jefferson L
authors.initials: JL
authors.lastname: Princival
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001487:Basidiomycota / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D000480:Alkynes; D000970:Antineoplastic Agents; D001688:Biological Products
keywords: Bioactive; Enantiomers; Propargylic; Synthesis; Tumor