title: Antifungal activity of enynediesters and acetylenic compounds obtained by synthesis and in silico prediction pattern.
abstract: OBJECTIVE
  In this paper, we describe the preparation and synthesis of several enynediesters, conjugated diynes and acetylenic compounds from starting materials comprising one hydroxyl and one acetylenyl group and their antifungal activity.
  
  
  METHODS
  For synthesis of the compounds, a combined solution of N,N'-dicyclohexylcarbodiimide and 4-dimethylaminopyridin in CH2Cl2 was added to a solution of compound containing one hydroxyl group and propiolic acid at 0°C over a period of 1 hour. As the reaction occurs under very mild conditions this procedure offers easy access to 1,3-diynes in a very short reaction time. Some of the compounds are commercially available. The antifungal activity of these compounds against Candida albicans, Aspergillus niger and Saccharomyces cerevisiae was investigated.
  
  
  RESULTS
  Among the compounds tested, some showed potent activity.
  
  
  CONCLUSIONS
  The results of synthesis showed that the direct coupling of two acetylenes is suitable for the preparation of diynes. The in silico study used here was able to predict if the compound with triple bond can posses the antifungal activity with a reasonable prediction. The result of investigations at both in silico and in vitro levels confirmed that the position of the triple bond is important for antifungal activity.
authors.affiliation: Drug Design and Bioinformatics Unit, Medical Biotechnology Department, Biotechnology Research Center, Pasteur Institute, #69 Pasteur Avenue, P.O Box 13164 Tehran, Iran.
authors.forename: P
authors.initials: P
authors.lastname: Azerang
authors.forename: S
authors.initials: S
authors.lastname: Sardari
mesh_terms: D000480:Alkynes / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001234:Aspergillus niger / Q000187:drug effects*; D002176:Candida albicans / Q000187:drug effects*; D003198:Computer Simulation; D053280:Diynes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D004353:Drug Evaluation, Preclinical; D004952:Esters / Q000138:chemical synthesis / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D008956:Models, Chemical; D015394:Molecular Structure; D012441:Saccharomyces cerevisiae / Q000187:drug effects*
chemical_list: D000480:Alkynes; D000935:Antifungal Agents; D053280:Diynes; D004952:Esters