title: Expanding Synthesizable Space of Disubstituted 1,2,4-Oxadiazoles.
abstract: One-pot synthesis of 3,5-disubstituted 1,2,4-oxadiazoles from carboxylic acids and nitriles was optimized to parallel chemistry. The method was validated on a 141 member library; the desired products were recovered with a high success rate and in moderate yields. Practical application of the approach was demonstrated in the synthesis of bioactive compound pifexole and agonists of free fatty acid receptor 1. A library of 4 948 100 synthesizable drug-like 3,5-disubstituted 1,2,4-oxadiazoles was enumerated based on the method and available validated reagents.
authors.affiliation: Enamine Ltd. , 78 Chervonotkatska Street, Kyiv, 02094, Ukraine.|ChemBioCenter, Kyiv National Taras Shevchenko University , 61 Chervonotkatska Street, Kyiv, 02094, Ukraine.
authors.forename: Andrey
authors.initials: A
authors.lastname: Tolmachev
authors.affiliation: Enamine Ltd. , 78 Chervonotkatska Street, Kyiv, 02094, Ukraine.
authors.forename: Andrey V
authors.initials: AV
authors.lastname: Bogolubsky
authors.affiliation: ChemBioCenter, Kyiv National Taras Shevchenko University , 61 Chervonotkatska Street, Kyiv, 02094, Ukraine.|UkrOrgSyntez Ltd. (UORSY) , 29 Schorsa Street, Kyiv, 01133, Ukraine.
authors.forename: Sergey E
authors.initials: SE
authors.lastname: Pipko
authors.affiliation: Enamine Ltd. , 78 Chervonotkatska Street, Kyiv, 02094, Ukraine.
authors.forename: Alexander V
authors.initials: AV
authors.lastname: Grishchenko
authors.affiliation: Enamine Ltd. , 78 Chervonotkatska Street, Kyiv, 02094, Ukraine.
authors.forename: Dmytro V
authors.initials: DV
authors.lastname: Ushakov
authors.affiliation: Enamine Ltd. , 78 Chervonotkatska Street, Kyiv, 02094, Ukraine.
authors.forename: Anton V
authors.initials: AV
authors.lastname: Zhemera
authors.affiliation: UkrOrgSyntez Ltd. (UORSY) , 29 Schorsa Street, Kyiv, 01133, Ukraine.
authors.forename: Oleksandr O
authors.initials: OO
authors.lastname: Viniychuk
authors.affiliation: Enamine Ltd. , 78 Chervonotkatska Street, Kyiv, 02094, Ukraine.|The Institute of High Technologies, Kyiv National Taras Shevchenko University , 4 Glushkov Street, Building 5, Kyiv, 03187, Ukraine.
authors.forename: Anzhelika I
authors.initials: AI
authors.lastname: Konovets
authors.affiliation: Department of Chemistry, Kyiv National Taras Shevchenko University , 64 Volodymyrska Street, Kyiv, 01601, Ukraine.
authors.forename: Olga A
authors.initials: OA
authors.lastname: Zaporozhets
authors.affiliation: Enamine Ltd. , 78 Chervonotkatska Street, Kyiv, 02094, Ukraine.|Department of Chemistry, Kyiv National Taras Shevchenko University , 64 Volodymyrska Street, Kyiv, 01601, Ukraine.
authors.forename: Pavel K
authors.initials: PK
authors.lastname: Mykhailiuk
authors.affiliation: ChemBioCenter, Kyiv National Taras Shevchenko University , 61 Chervonotkatska Street, Kyiv, 02094, Ukraine.
authors.forename: Yurii S
authors.initials: YS
authors.lastname: Moroz
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry*; D006801:Humans; D009570:Nitriles / Q000737:chemistry*; D010069:Oxadiazoles / Q000737:chemistry*; D010091:Oximes / Q000138:chemical synthesis; D043562:Receptors, G-Protein-Coupled / Q000819:agonists; D013329:Structure-Activity Relationship
chemical_list: D002264:Carboxylic Acids; D009570:Nitriles; D010069:Oxadiazoles; D010091:Oximes; D043562:Receptors, G-Protein-Coupled; C000608634:amidoxime; C003259:pifexole
keywords: 1,2,4-oxadiazoles; carboxylic acids; nitriles; one-pot parallel synthesis; readily accessible (REAL) arrays