Pesimquinolones produced by Penicillium simplicissimum and their inhibitory activity on nitric oxide production

Dai, Chong; Chen, Chunmei; Guan, Danyingzi; Chen, Hailun; Wang, Fuxin; Wang, Wenjing; Zang, Yi; Li, Qin; Wei, Mengsha; Li, Xiaoxin; Zhang, Xiaotian; Wang, Jianping; Zhou, Qun; Zhu, Hucheng; Zhang, Yonghui

doi:10.1016/j.phytochem.2020.112327

Cited by 8 publications

(1 citation statement)

References 11 publications

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“…Quinolones play a pivotal role in drug development as one of the key pharmacophore in modern drug design 4 – 6 . The 3,4-dioxygenated 5-hydroxy-4-aryl-quinolin-2(1 H )-one alkaloids 7 constitute a relatively new and steadily growing family of natural products with diverse biological properties, including cytotoxic 8 – 10 , antiviral 11 , 12 , antioxidant 13 , antifouling 14 , and anti-inflammatory 15 activities. The structures of few representatives including aniduquinolones A ( 1 ) and B ( 2 ) 16 , yaequinolone F ( 3 ) 17 , 18 , aflaquinolones A–D ( 4 – 7 ) 14 , 19 , (+)-22- O -( N -Me-L-valyl)-aflaquinolone B ( 8 ) and (+)-22- O -( N -Me-L-valyl)-21- epi -aflaquinolone B ( 9 ) 11 are depicted in Fig.…”

Section: Introductionmentioning

confidence: 99%

Scalable total synthesis of (+)-aniduquinolone A and its acid-catalyzed rearrangement to aflaquinolones

Guo

Mou

et al. 2022

Commun Chem

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The strong antibacterial, antiviral and anticancer activities demonstrated by quinolones make them promising lead structures and important synthetic targets for drug discovery. Here, we report, to the best of our knowledge, the first scalable total synthesis of antiviral (+)-aniduquinolone A, possessing a 3,4-dioxygenated 5-hydroxy-4-aryl-quinolin-2(1H)-one skeleton. This synthetic strategy explores E-stereoselective Horner–Wadsworth–Emmons (HWE) olefination as the key step to assemble isopropenyl substituted tetrahydrofuran onto the 3,4-dioxygenated 5-hydroxy-4-aryl-quinolin-2(1H)-one core, which is built by highly diastereoselective intramolecular aldol reaction. Moreover, two sets of stereoisomers of aniduquinolone A with substantially overlapping NMR data were synthesized completely and assigned unambiguously by comprehensive analysis of both their spectroscopic and X-ray diffraction data. Unexpectedly, aflaquinolones A, C, and D that feature different 2,4-dimethyl cyclohexanone moieties were transformed successfully from (+)-aniduquinolone A by treating with TFA. The methodology delineated herein can be applied broadly to the synthesis of natural alkaloids containing the core structure of 3,4-dioxygenated 5-hydroxy-4-aryl-quinolin-2(1H)-one.

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