Isolation, synthesis and absolute configuration of 4,5-dihydroxypiperines improving behavioral disorder in AlCl3-induced dementia

Luo, Jia; Xiang, Jia-Yao; Yuan, Hao-Yang; Wu, Junqi; Li, Haizhou; Shen, Yuehai; Xu, Min

doi:10.1016/j.bmcl.2021.128057

Cited by 4 publications

(3 citation statements)

References 17 publications

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“…However, it has been discovered that 4,5-dihydroxypiperines, which are obtained from P. retrofractum , are effective against aluminum trichloride-induced dementia. Keeping in view the pharmacological aspects of 4,5-dihydroxypiperines, Luo et al [ 136 ] in 2021 devised the total synthesis of their stereoisomers. For this purpose, piperine 351 was subjected to AD-mix-α and AD-mix-β one by one, thus producing 352 and 353 in 44.5% yields.…”

Section: Review Of the Literaturementioning

confidence: 99%

Sharpless Asymmetric Dihydroxylation: An Impressive Gadget for the Synthesis of Natural Products: A Review

et al. 2023

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Sharpless asymmetric dihydroxylation is an important reaction in the enantioselective synthesis of chiral vicinal diols that involves the treatment of alkene with osmium tetroxide along with optically active quinine ligand. Sharpless introduced this methodology after considering the importance of enantioselectivity in the total synthesis of medicinally important compounds. Vicinal diols, produced as a result of this reaction, act as intermediates in the synthesis of different naturally occurring compounds. Hence, Sharpless asymmetric dihydroxylation plays an important role in synthetic organic chemistry due to its undeniable contribution to the synthesis of biologically active organic compounds. This review emphasizes the significance of Sharpless asymmetric dihydroxylation in the total synthesis of various natural products, published since 2020.

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Section: Review Of the Literaturementioning

confidence: 99%

Sharpless Asymmetric Dihydroxylation: An Impressive Gadget for the Synthesis of Natural Products: A Review

et al. 2023

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“…As illustrated in Scheme 5 , Luo et al synthesized four piperine derivates 35 (4R,5R), 36 (4S,5S), 37 (4S,5R), and 38 (4R,5S), which were established by NMR, optical rotation, and CD spectra [ 62 ]. As demonstrated in Scheme 6 , the sample amine groups were introduced at the aliphatic olefin chain of piperine through a trisulfur-radical-anion-triggered C(sp 2 )-H amination of α,β-unsaturated carbonyl to obtain derivate 39 [ 63 ].…”

Section: Structural Modifications Of Piperine and Its Derivativesmentioning

confidence: 99%

“…LC 50 (mg/mL) 1 14.20 [29] 23e 0.16 [29] 23f 0.12 [29] 23u 0.18 [29] 23v 0.16 [29] 25f 0.14 [28] 25l 0.16 [28] 25u 0.19 [28] 25v 0.13 [28] spirodiclofen a 0.12 [29] a Spirodiclofen: a commercial acaricide. As illustrated in Scheme 5, Luo et al synthesized four piperine derivates 35 (4R,5R), 36 (4S,5S), 37 (4S,5R), and 38 (4R,5S), which were established by NMR, optical rotation, and CD spectra [62]. As demonstrated in Scheme 6, the sample amine groups were introduced at the aliphatic olefin chain of piperine through a trisulfur-radical-anion-triggered C(sp 2 )-H amination of α,β-unsaturated carbonyl to obtain derivate 39 [63].…”

Section: Compoundmentioning

confidence: 99%

Piperine: Chemistry and Biology

Han,

Zhang,

et al. 2023

Toxins

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Piperine is a plant-derived promising piperamide candidate isolated from the black pepper (Piper nigrum L.). In the last few years, this natural botanical product and its derivatives have aroused much attention for their comprehensive biological activities, including not only medical but also agricultural bioactivities. In order to achieve sustainable development and improve survival conditions, looking for environmentally friendly pesticides with low toxicity and residue is an extremely urgent challenge. Fortunately, plant-derived pesticides are rising like a shining star, guiding us in the direction of development in pesticidal research. In the present review, the recent progress in the biological activities, mechanisms of action, and structural modifications of piperine and its derivatives from 2020 to 2023 are summarized. The structure-activity relationships were analyzed in order to pave the way for future development and utilization of piperine and its derivatives as potent drugs and pesticides for improving the local economic development.

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