69610-40-8Relevant articles and documents
A new class of fluorinated 5-pyrrolidinylsulfonyl isatin caspase inhibitors for PET imaging of apoptosis
Krause-Heuer, Anwen M.,Howell, Nicholas R.,Matesic, Lidia,Dhand, Geetanjali,Young, Emma L.,Burgess, Leena,Jiang, Cathy D.,Lengkeek, Nigel A.,Fookes, Christopher J. R.,Pham, Tien Q.,Sobrio, Franck,Greguric, Ivan,Fraser, Benjamin H.
, p. 347 - 352 (2013)
Thirteen compounds in a new class of fluorinated 5-pyrrolidinylsulfonyl isatin derivatives were synthesised that have potent and selective inhibitory activity against effector caspases-3 and -7. With in vivo animal PET imaging studies of cerebral ischemia being planned, N-benzylation with selected para-substituted benzylic halides allowed systematic variation of lipophilicity (logP 1.94-3.31) without decreasing inhibition potency (IC50). From this series the p-methoxybenzyl analogue was selected for initial 'proof-of-concept' [18F]-fluoride radiolabelling which proceeded in good yield and purity with no need for a protection/deprotection strategy. The Royal Society of Chemistry.
l -Proline as a Valuable Scaffold for the Synthesis of Novel Enantiopure Neonicotinoids Analogs
Bonilla-Landa, Israel,Cuapio-Mu?oz, Ulises,Luna-Hernández, Axel,Reyes-Luna, Alfonso,Rodríguez-Hernández, Alfredo,Ibarra-Juarez, Arturo,Suarez-Mendez, Gabriel,Barrera-Méndez, Felipe,Caram-Salas, Nadia,Enríquez-Medrano, J. Francisco,Díaz De León, Ramón E.,Olivares-Romero, José Luis
, p. 1455 - 1465 (2021/02/16)
In this research, six neonicotinoid analogs derived from l-proline were synthesized, characterized, and evaluated as insecticides against Xyleborus affinis. Most of the target compounds showed good to excellent insecticidal activity. To the best of our knowledge, this is the first report dealing with the use of enantiopure l-proline to get neonicotinoids. These results highlighted the compound 9 as an excellent candidate used as the lead chiral insecticide for future development. Additionally, molecular docking with the receptor and compound 9 was carried out to gain insight into its high activity when compared to dinotefuran. Finally, the neurotoxic evaluation of compound 9 showed lower toxicity than the classic neonicotinoid dinotefuran.
Larger scale Stahl oxidation with instant Cu removal in convenient synthesis of chiral bidentate N–heterocyclic carbene precursor
Grudzień, Krzysztof,Noga?, Wojciech,Szczepaniak, Grzegorz,Grela, Karol
supporting information, (2021/02/26)
Commercially available N-Boc protected L-proline can be efficiently converted into a chiral, bidentate, aminoalkyl N-heterocyclic carbene ligand precursor in high yield (50% total after 4 steps) without column chromatography purification at any moment. The developed synthetic path includes: (1) redox step leading to an aldehyde, (2) imine condensation and in situ reduction to 1,2-diamine; (3) heterocyclization; (3) removal of the protecting group. Instant separation of Cu traces after the key Stahl oxidation at gram-scale was facilitated by the use of bis(isocyanide) scavenger, SnatchCat, forming insoluble, easy to remove RNC:→[Cu] complexes that allowed usto obtain crude intermediate suitably pure for next steps without tedious purification.
