One‐Pot Synthesis of Chiral Succinate Dehydrogenase Inhibitors and Antifungal Activity Studies DOI Creative Commons
Donghua Du, Yu Chen, Chao Yang

et al.

Advanced Science, Journal Year: 2025, Volume and Issue: unknown

Published: May 19, 2025

Abstract In this work, a series of novel chiral succinate dehydrogenase inhibitors (SDHIs) are synthesized through one‐pot Rh‐catalyzed asymmetric hydrogenation‐condensation strategy. This method exhibits high efficiency (up to 1000 Ton, 94% yield over two steps), stereoselectivity 99% ee), and broad substrate scope (68 examples in total), providing superior pathway for the synthesis such fungicides. Mechanistic studies indicate that amino group at 2‐position phenyl ring acts as an activating group, enhancing reactivity control reaction. Furthermore, these molecules exhibit broad‐spectrum highly effective antifungal biological activity. Notably, enantiomers show significant differences both vitro vivo fungi‐inhibiting experiments. Especially, ( S )‐ 5f showcases activity against Botrytis cinerea (EC 50 = 0.48 µ m ) is much higher than its R enantiomer 36.7 ). Molecular docking calculations, molecular dynamic simulation, enzyme assays, ligand‐target interaction experiments demonstrate (ΔG MM‐PBSA −18.86 kcal mol −1 , K D 6.04 inhibits more effectively −13.01 8.5 Moreover, have significantly different effects on spore germination destruction fungal phenotype.

Language: Английский

Asymmetric hydrogenation of α-pyrrolyl terminal alkenes: an easy access to enantioenriched pyrroles bearing a C2 Me-substituted stereogenic center DOI Creative Commons

Ao Zhou,

Nianxin Rong,

Han Zhuang

et al.

Green Synthesis and Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: April 1, 2025

Language: Английский

Citations

0
Insights into the role of transition metal M (M = Mo, Fe, Ru, Cu, Pt) in acetone hydrogenation on M@Ni(111) single-atom surface alloys: A DFT study DOI

G. Liu,

Qinwei Zhang, Zixuan Zhao

et al.

Molecular Catalysis, Journal Year: 2025, Volume and Issue: 580, P. 115111 - 115111

Published: April 11, 2025

Language: Английский

Citations

0
Stereoselective Nickel-Catalyzed Iterative 1,2-Reduction of Trisubstituted Enones to Cycloalkanols Bearing Two Contiguous Stereocenters DOI
Yue Liu, Chaoxin Yang,

Linhong Zuo

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 14, 2025

Herein we first report a nickel-catalyzed asymmetric iterative 1,2-reduction of trisubstituted enones to cycloalkanols with two contiguous stereocenters in high yields excellent diastereo- and enantioselectivities (36 examples, up 98.5:1.5 er, >20:1 dr, TON = 500). The combined experimental computational mechanistic studies suggested energy changes during consecutive reduction processes provided range unique rationales that have not been disclosed hydrogenation-related studies.

Language: Английский

Citations

0
One‐Pot Synthesis of Chiral Succinate Dehydrogenase Inhibitors and Antifungal Activity Studies DOI Creative Commons
Donghua Du, Yu Chen, Chao Yang

et al.

Advanced Science, Journal Year: 2025, Volume and Issue: unknown

Published: May 19, 2025

Abstract In this work, a series of novel chiral succinate dehydrogenase inhibitors (SDHIs) are synthesized through one‐pot Rh‐catalyzed asymmetric hydrogenation‐condensation strategy. This method exhibits high efficiency (up to 1000 Ton, 94% yield over two steps), stereoselectivity 99% ee), and broad substrate scope (68 examples in total), providing superior pathway for the synthesis such fungicides. Mechanistic studies indicate that amino group at 2‐position phenyl ring acts as an activating group, enhancing reactivity control reaction. Furthermore, these molecules exhibit broad‐spectrum highly effective antifungal biological activity. Notably, enantiomers show significant differences both vitro vivo fungi‐inhibiting experiments. Especially, ( S )‐ 5f showcases activity against Botrytis cinerea (EC 50 = 0.48 µ m ) is much higher than its R enantiomer 36.7 ). Molecular docking calculations, molecular dynamic simulation, enzyme assays, ligand‐target interaction experiments demonstrate (ΔG MM‐PBSA −18.86 kcal mol −1 , K D 6.04 inhibits more effectively −13.01 8.5 Moreover, have significantly different effects on spore germination destruction fungal phenotype.

Language: Английский

Citations

0