Enhancing the Potential of Miniature-Scale DNA-Compatible Radical Reactions via an Electron Donor–Acceptor Complex and a Reversible Adsorption to Solid Support Strategy DOI
Bizhen Lin, Weiwei Lu, Zhen‐Yu Chen

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(19), P. 7381 - 7385

Published: Sept. 21, 2021

DNA-encoded library (DEL) technology is a powerful tool in the discovery of bioactive probe molecules and drug leads. Mostly, success DEL stems from molecular diversity chemical libraries. However, construction DELs has been restricted by idiosyncratic needs required low concentration (∼1 mM or less) intermediate. Here, we report visible-light-promoted on-DNA radical coupling reactions via an electron donor–acceptor (EDA) complex reversible adsorption to solid support (RASS) strategy. This protocol provides unique solution challenges increasing reactivity highly diluted DNA substrates reducing residues heavy metals photocatalysts. A series indole sulfone selenide derivatives were obtained with good quantitative conversions. It anticipated that these mild-condition will significantly improve find widespread utility construction.

Language: Английский

Transition-Metal-Catalyzed C–S, C–Se, and C–Te Bond Formations via Cross-Coupling and Atom-Economic Addition Reactions. Achievements and Challenges DOI
I. P. Beletskaya, Valentine P. Ananikov

Chemical Reviews, Journal Year: 2022, Volume and Issue: 122(21), P. 16110 - 16293

Published: Sept. 16, 2022

In the present review, we discuss recent progress in field of C–Z bond formation reactions (Z = S, Se, Te) catalyzed by transition metals. Two complementary methodologies are considered─catalytic cross-coupling and catalytic addition reactions. The development advanced systems is aimed at improved catalyst efficiency, reduced loading, better cost environmental concerns, higher selectivity yields. important rise research efforts sustainability green chemistry areas critically assessed. paramount role mechanistic studies a new generation addressed, key achievements, problems, challenges summarized for this field.

Language: Английский

Citations

207
Incorporating Selenium into Heterocycles and Natural Products─From Chemical Properties to Pharmacological Activities DOI
Wei Hou, Hongtao Xu

Journal of Medicinal Chemistry, Journal Year: 2022, Volume and Issue: 65(6), P. 4436 - 4456

Published: March 4, 2022

Selenium (Se)-containing compounds have emerged as potential therapeutic agents for the treatment of a range diseases. Through tremendous effort, considerable knowledge has been acquired to understand complex chemical properties and biological activities selenium, especially after its incorporation into bioactive molecules. From this perspective, we compiled extensive literature evidence summarize critically discuss relationship between pharmacological selenium strategic organic molecules, heterocycles natural products. We also provide perspectives regarding challenges in selenium-based medicinal chemistry future research directions.

Language: Английский

Citations

185
DNA-encoded libraries (DELs): a review of on-DNA chemistries and their output DOI Creative Commons
Ying Shi,

Yanran Wu,

Jianqiang Yu

et al.

RSC Advances, Journal Year: 2021, Volume and Issue: 11(4), P. 2359 - 2376

Published: Jan. 1, 2021

A DNA-encoded library is a collection of small molecules covalently linked to DNA that has unique information about the identity and structure each member. chemical (DEL) broadly adopted by major pharmaceutical companies used in numerous drug discovery programs. The application DEL technology advantageous at initial period because reduced cost, time, storage space for identification target compounds. key points construction DELs comprise development selection encoding methods, transfer routine reaction from off-DNA on-DNA, exploration new reactions on DNA. limitations diversity were gradually using novel DNA-compatible based formation cleavage various bonds. Here, we summarized series chemistry building blocks analysed druggability screened hit via past five years.

Language: Английский

Citations

88
Chitosan-selenium nanoparticles (Cs–Se NPs) modulate the photosynthesis parameters, antioxidant enzymes activities and essential oils in Dracocephalum moldavica L. under cadmium toxicity stress DOI
Fatemeh Azimi, Mehdi Oraei, Gholamreza Gohari

et al.

Plant Physiology and Biochemistry, Journal Year: 2021, Volume and Issue: 167, P. 257 - 268

Published: Aug. 10, 2021

Language: Английский

Citations

87
The expanding reaction toolkit for DNA-encoded libraries DOI Creative Commons

Richard J. Fair,

Ryan T. Walsh,

Christopher D. Hupp

et al.

Bioorganic & Medicinal Chemistry Letters, Journal Year: 2021, Volume and Issue: 51, P. 128339 - 128339

Published: Aug. 31, 2021

Over the past decade, DNA-encoded libraries (DELs) have emerged as a leading platform for small molecule drug discovery among pharmaceutical companies, biotech companies and academic hunters alike. This revolutionary technology has tremendous potential that is yet to be fully realized, exploration of therapeutically relevant chemical space fueled by ever-expanding repertoire DNA-compatible reactions used construct libraries. Advances in direct coupling reactions, like photo-catalytic cross couplings, unique cyclizations such formation 1,2,4-oxadiazoles, new functional group transformations are valuable contributions DEL reaction toolkit, indicate where future development efforts should focus order maximize productivity DELs.

Language: Английский

Citations

75
gem ‐Difluoromethylene Alkyne‐Enabled Diverse C−H Functionalization and Application to the on‐DNA Synthesis of Difluorinated Isocoumarins DOI
Hui Gao, Shuang Lin, Shuning Zhang

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 60(4), P. 1959 - 1966

Published: Oct. 6, 2020

Using gem-difluoromethylene alkynes as effectors, unprecedented diverse C-H activation/[4+2] annulations of simple benzoic acids are reported. The chemodivergent reaction outcomes well-tuned by Rh/Ir-catalyzed system; in the RhIII catalysis, 3-alkenyl-1H-isochromen-1-one and 3,4-dialkylideneisochroman-1-one skeletons afforded a solvent-dependent manner whereas difluoromethylene-substituted 1H-isochromen-1-ones generated under IrIII -catalyzed system. Mechanistic studies revealed that unusually double β-F eliminations fluorine effect-induced regioselective reductive elimination independently involved to enable distinct modes for divergent product formations. Besides, synthetic application both derivatization obtained diene products on-DNA synthesis DNA-tagged difluorinated isocoumarin have been demonstrated, which manifested great potential utility developed protocols.

Language: Английский

Citations

72
Selenium as an emerging versatile player in heterocycles and natural products modification DOI
Wei Hou,

Hewei Dong,

Xiang Zhang

et al.

Drug Discovery Today, Journal Year: 2022, Volume and Issue: 27(8), P. 2268 - 2277

Published: April 4, 2022

Language: Английский

Citations

65
Evolution of chemistry and selection technology for DNA-encoded library DOI Creative Commons
Peixiang Ma, Shuning Zhang, Qianping Huang

et al.

Acta Pharmaceutica Sinica B, Journal Year: 2023, Volume and Issue: 14(2), P. 492 - 516

Published: Oct. 11, 2023

DNA-encoded chemical library (DEL) links the power of amplifiable genetics and non-self-replicating phenotypes, generating a diverse world. In analogy with biological world, DEL world can evolve by using central dogma, wherein DNA replicates PCR reactions to amplify genetic codes, sequencing transcripts information, DNA-compatible synthesis translates into phenotypes. Importantly, is key expanding space. Besides, evolution-driven selection system pushes chemicals under selective pressure, i.e., desired strategies. this perspective, we summarized recent advances in synthetic toolbox panning strategies, which will shed light on drug discovery harnessing vitro evolution via DEL.

Language: Английский

Citations

29
Mechanochemical synthesis of organoselenium compounds DOI Creative Commons
Shanshan Chen,

Chunying Fan,

Zijian Xu

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Jan. 26, 2024

We disclose herein a strategy for the rapid synthesis of versatile organoselenium compounds under mild conditions. In this work, magnesium-based selenium nucleophiles are formed in situ from easily available organic halides, magnesium metal, and elemental via mechanical stimulation. This process occurs liquid-assisted grinding (LAG) conditions, requires no complicated pre-activation procedures, operates broadly across diverse range aryl, heteroaryl, alkyl substrates. symmetrical diselenides efficiently obtained after work-up air, while one-pot nucleophilic addition reactions with various electrophiles allow comprehensive unsymmetrical monoselenides high functional group tolerance. Notably, method is applied to regioselective selenylation diiodoarenes polyaromatic aryl halides that difficult operate solution approaches. Besides selenium, sulfur tellurium also competent process, which showcases potential methodology facile organochalcogen compounds.

Language: Английский

Citations

14
Rh(III)-Catalyzed Atroposelective C–H Selenylation of 1-Aryl Isoquinolines DOI

Dong‐Song Zheng,

Pei‐Pei Xie,

Fangnuo Zhao

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(8), P. 6009 - 6015

Published: April 5, 2024

Rhodium(III)-catalyzed atroposelective C–H selenylation of 1-aryl isoquinolines has been achieved. The direct reaction between and 2-(phenylselanyl)isoindoline-1,3-dione in the presence chiral SCpRh(III) complex afforded a series axially isoquinoline selenides up to 95% yield 96% ee. features mild conditions broad substrate scope. DFT calculations revealed that C–Se bond formation step proceeds through formal SN2 pathway.

Language: Английский

Citations

14