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Emergence of 2-Pyrone and Its Derivatives, from Synthesis to Biological Perspective: An Overview and Current Status

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Abstract

Pyrone moieties are present in natural products and can be synthesized by a diverse range of synthetic methods, resulting in the formation of various derivatives through chemical modifications. Many pyrone-based derivatives are commercially available and are biocompatible. They are building blocks of various intermediates in organic synthesis. They possess remarkable biological properties including antimicrobial, antiviral, cytotoxic, and antitumor activity. These characteristics have made them valuable for the development of drugs. We have summarized recent developments in the synthesis of 2-pyrone and its derivatives and their potential applications. With regard to synthetic approaches, the focus has been on metal-free and transition metal-catalyzed reactions.

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Abbreviations

AcOH:

Acetic acid

Anti-TB:

Antituberculosis

HIV:

Human immunodeficiency virus

AIDS:

Acquired immunodeficiency syndrome

ATPase:

Adenosine triphosphatase

Au:

Gold

BINAP:

2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl

Bn:

Benzyl

Bz:

Benzoyl

Boc:

tert-Butoxycarbonyl

Bu:

Butyl

COD:

1,5-Cyclooctadiene

Cp*:

Pentamethylcyclopentadienyl

Cu:

Copper

Cy:

Cyclohexyl

DCM:

Dichloromethane

DCE:

1,2-Dichloroethane

DHPB:

3,4-Dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine

DIPEA:

N,N-Diisopropylethylamine

DMF:

N,N-Dimethylformamide

DMSO:

Dimethylsulfoxide

dppe:

1,4-Bis(diphenylphosphino)ethane

equiv:

Equivalent

EDG:

Electron-donating group

E:

Electrophile

EWG:

Electron-withdrawing group

GPI:

Glycosylphosphatidylinositol

GTPase:

Guanosine triphosphatase

Hex:

Hexyl

HFIP:

Hexafluoroisopropanol

IC50 :

Half-maximal inhibitory concentration

IEDDA:

Inverse electron demand Diels–Alder

KPF6 :

Potassium hexafluorophosphate

LHMDS:

Lithium bis(trimethylsilyl)amide

MIC:

Minimum inhibitory concentration

MTB:

Mycobacterium tuberculosis

NBS:

N-Bromosuccinimide

NHC:

N-Heterocyclic carbenes

Ni:

Nickel

NIS:

N-Iodosuccinimide

N:

Nucleophile

PCC:

Pyridinium chlorochromate

Pcy3:

Tricyclohexylphosphine

Pd:

Palladium

Pent:

Pentyl

Ph:

Phenyl

PPh3:

Triphenylphosphine

Ras MAPK:

Ras/Mitogen-activated protein kinase

rt:

Room temperature

TBDMS:

tert-Butyldimethylsilyl chloride

TEA:

Triethylamine

TFAA:

Trifluoroacetic anhydride

THF:

Tetrahydrofuran

TES:

Triethylsilyl (SiEt3)

TMS:

Trimethylsilyl (SiMe3)

Rh:

Rhodium

Ru:

Ruthenium

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, People’s Republic of China

    Tanveer Ahmad

  2. Interdisciplinary Research Center for Advanced Materials, King Fahd University of Petroleum and Minerals, Dhahran, 31261, Saudi Arabia

    Tahir Rasheed

  3. Department of Chemistry, University of Science and Technology of China, Hefei, 230026, Anhui, People’s Republic of China

    Majid Hussain

  4. Department of Chemistry, University of Sahiwal, Sahiwal, 57000, Pakistan

    Komal Rizwan

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  1. Tanveer Ahmad
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Ahmad, T., Rasheed, T., Hussain, M. et al. Emergence of 2-Pyrone and Its Derivatives, from Synthesis to Biological Perspective: An Overview and Current Status. Top Curr Chem (Z) 379, 38 (2021). https://doi.org/10.1007/s41061-021-00350-w

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