Carbene-catalyzed kinetic resolution of bispirooxindoles: selective lactam amidation and access to challenging chiral scaffolds

Pu, Yiru; Zuo, Yi Y.; Liu, Jie; Li, Meimei; Huang, Hui; Yang, Joey; Deng, Yun; Wang, Maolin; Lü, Jun

doi:10.1039/d2qo01724e

Cited by 3 publications

(2 citation statements)

References 38 publications

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“…Nano-delivery and structural modification are currently the primary approaches and strategies to break through the bottleneck of active monomer components in the clinic [128][129][130]. Various nanotechnology platforms in the field of biomedicine, spanning both diagnostics and therapy, have received significant attention in recent years, presenting greater prospects for the therapeutic application of PPT.…”

Section: Challenges and Future Perspectivesmentioning

confidence: 99%

Advances in nanoscale carrier-based approaches to reduce toxicity and enhance efficacy of podophyllotoxin

Zhang,

Zuo,

Zhang

et al. 2023

Acta Materia Medica

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Podophyllotoxin (PPT), an aryltetralin-type lignan isolated from Podophyllum species, exhibits a wide range of biologic and pharmacologic activities, and mainly serves as an antiviral agent or antitumor drug in clinical applications. However, the therapeutic potential of PPT has been hindered due to its detrimental systemic toxicity, poor solubility, and bioavailability. Nanoparticles, which preferentially accumulate in tumors through enhanced permeability and retention effects, have become useful tools for targeted drug delivery, thus securing a niche in cancer therapies. The nano-based drug delivery platform has been introduced to PPT delivery for the purpose of improved solubility, enhanced efficacy, and reduced toxicity. For decades, extensive efforts have been dedicated to designing and developing various PPT delivery systems to mitigate undesirable toxicity and expand clinical applicability. Herein, we briefly review the latest achievements in PPT delivery patterns and pharmacodynamic concerns with the expectation of shedding light on future research and potential applications of PPT.

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Section: Challenges and Future Perspectivesmentioning

confidence: 99%

Advances in nanoscale carrier-based approaches to reduce toxicity and enhance efficacy of podophyllotoxin

Zhang,

Zuo,

Zhang

et al. 2023

Acta Materia Medica

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“…Enantioselective C–C bond formation has become well-established. The asymmetric induction of primary or secondary alcohol, phenol, , sulfoximine, and amide counterparts utilizing chiral acyl azolium has also been developed recently. Compared to that of secondary alcohols, the KR of tertiary alcohols using NHC catalysis is a more challenging task.…”

mentioning

confidence: 99%

Kinetic Resolution of Acyclic Tertiary Propargylic Alcohols by NHC-Catalyzed Enantioselective Acylation

An,

Liu,

Wang

et al. 2024

Org. Lett.

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We report herein an efficient NHC-catalyzed kinetic resolution of acyclic tertiary propargylic alcohols that provides them in high to excellent enantioselectivity. This is the first example of kinetic resolution realized by enantioselective acylation. The recovered enantioenriched alcohols can be facilely converted into other valuable compounds such as densely functionalized tertiary alcohols and carbmates in high yields and excellent stereopurity. Density functional theory calculations were performed to determine the reaction mechanism and to understand the origin of enantiodiscrimination.

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Novel sulfonyl-substituted tetrandrine derivatives for colon cancer treatment by inducing mitochondrial apoptosis and inhibiting PI3K/AKT/mTOR pathway

Ling,

Li,

Wang

et al. 2024

Bioorganic Chemistry

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Carbene-catalyzed kinetic resolution of bispirooxindoles: selective lactam amidation and access to challenging chiral scaffolds

Abstract: Despite kinetic resolution (KR) via N-heterocyclic carbene (NHC)-catalyzed acylation minimizing any competitive racemic background reactions, NHC-activated lactam amidation of KR is mostly unexplored. Enantioenriched bispirooxindoles bearing multichiral quaternary stereocenters are...

Cited by 3 publications

References 38 publications

Advances in nanoscale carrier-based approaches to reduce toxicity and enhance efficacy of podophyllotoxin

Advances in nanoscale carrier-based approaches to reduce toxicity and enhance efficacy of podophyllotoxin

Kinetic Resolution of Acyclic Tertiary Propargylic Alcohols by NHC-Catalyzed Enantioselective Acylation

Novel sulfonyl-substituted tetrandrine derivatives for colon cancer treatment by inducing mitochondrial apoptosis and inhibiting PI3K/AKT/mTOR pathway

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