The acid-catalysed synthesis of 7-azaindoles from 3-alkynyl-2-aminopyridines and their antimicrobial activity.

doi:10.1039/c3ob41798k

Paper

DOI: 10.1039/c3ob41798k

The acid-catalysed synthesis of 7-azaindoles from 3-alkynyl-2-aminopyridines and their antimicrobial activity.

Published Jan 14, 2014 · Tlabo C. Leboho, S. V. van Vuuren, J. Michael

Organic & biomolecular chemistry

Q2 SJR score

Citations

Influential Citations

Open Access PDF Full text Semantic Scholar

Abstract

The synthesis of 7-azaindoles from 3-alkynyl-2-aminopyridines using acidic conditions, namely, a mixture of trifluoroacetic acid (TFA) and trifluoroacetic anhydride (TFAA), is described. This methodology resulted in the synthesis of fifteen 7-azaindoles, with most containing substituents at the 2- and 5-positions. The majority of these were tested for antimicrobial activity against a range of bacteria and yeasts. The 7-azaindoles displayed the best activity against the yeasts, particularly against Cryptococcus neoformans, where activities as low as 3.9 μg ml(-1) were observed.

Study Snapshot

7-azaindoles synthesized using acidic conditions show promising antimicrobial activity against bacteria and yeasts, particularly Cryptococcus neoformans.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Full text analysis coming soon...

References

DOI: 10.1007/s40265-013-0037-z

Cryptococcal Infections: Changing Epidemiology and Implications for Therapy

Cryptococcal infections continue to cause significant morbidity and mortality, with advances in diagnostic tools and pre-emptive treatment in resource-limited settings.

2013·56citations·R. L. La Hoz et al.·Drugs

Drugs

DOI: 10.3760/cma.j.issn.0366-6999.20121945

Epidemiology of opportunistic invasive fungal infections in China: review of literature.

Opportunistic invasive fungal infections in China are increasing in incidence and impact public health, with high morbidity and mortality rates and higher care costs.

2013·34citations·Yong Liao et al.·Chinese medical journal

Chinese medical journal

DOI: 10.1128/AAC.00426-12

In Vitro Antiviral Characteristics of HIV-1 Attachment Inhibitor BMS-626529, the Active Component of the Prodrug BMS-663068

BMS-626529, the active component of the prodrug BMS-663068, shows promising in vitro antiviral activity against most HIV-1 viruses and shows potential for synergistic interactions with various antiretroviral drugs.

2012·127citations·B. Nowicka-Sans et al.·Antimicrobial Agents and Chemotherapy

Antimicrobial Agents and Chemotherapy

DOI: 10.1016/J.TET.2010.06.083

Microwave-assisted synthesis of indole- and azaindole-derivatives in water via cycloisomerization of 2-alkynylanilines and alkynylpyridinamines promoted by amines or catalytic amounts of neutral or basic salts

Microwave-assisted cycloisomerization in water efficiently prepares differently substituted indoles and azaindoles without added metal catalyst, achieving good to high yields without added metal catalyst.

2010·49citations·A. Carpita et al.·Tetrahedron

Tetrahedron

DOI: 10.1021/cc100029y

Library of 1,4-disubstituted 1,2,3-triazole analogs of oxazolidinone RNA-binding agents.

This study has developed a library of 1,4-disubstituted 1,2,3-triazole analogs, which show potential as RNA binding agents for antibacterial therapy.

2010·37citations·G. Acquaah-Harrison et al.·Journal of combinatorial chemistry

Journal of combinatorial chemistry

DOI: 10.1016/J.TETLET.2009.09.135

Microwave-assisted synthesis of indole-derivatives via cycloisomerization of 2-alkynylanilines in water without added catalysts, acids, or bases

Microwave-assisted cycloisomerization of 2-alkynylaniline derivatives in water allows for the preparation of differently substituted indoles without added catalysts, acids, or bases.

2009·21citations·A. Carpita et al.·Tetrahedron Letters

Tetrahedron Letters

DOI: 10.1016/j.bmcl.2009.07.091

The synthesis of 2- and 3-aryl indoles and 1,3,4,5-tetrahydropyrano[4,3-b]indoles and their antibacterial and antifungal activity.

Synthesis of 2- and 3-aryl indoles and 1,3,4,5-tetrahydropyrano[4,3-b]indoles resulted in compounds with significant antibacterial and antifungal activity.

2009·84citations·Tlabo C. Leboho et al.·Bioorganic & medicinal chemistry letters

Bioorganic & medicinal chemistry letters

DOI: 10.1021/cr900032s

Variolins and related alkaloids.

Variolins and related alkaloids show potential as pharmacological inhibitors of protein kinases, potentially benefiting human health by regulating metabolism and functions.

2009·201citations·S. Walker et al.·Chemical reviews

Chemical reviews

Citations

DOI: 10.1016/j.mcat.2024.113835

Catalytic transfer hydrogenation of substituted nitro-aromatics through in-situ generated Co(0) nanoparticle from Co(II) complexes supported by pentadentate ligands

This study presents a sustainable, environmentally friendly, and affordable method for transfer hydrogenation of nitroarenes to amines using Co(0) nanoparticles, which can be applied to the synthesis of clinically significant compounds like benzocaine, butamben, dapsone, and paracetamol.

2024·5citations·Anshu Singh et al.·Molecular Catalysis

Molecular Catalysis

DOI: 10.1002/cbdv.202200692

A New 7‐Azaindole Structure Analog: Molecular Docking, Synthesis and Preliminary Biological Activity in Vitro for Anticancer

Compound P1, a new 7-azaindole analog, shows promising anticancer activity in vitro, with higher cytotoxicity to HOS cells and lower toxicity to normal L929 cells.

2022·1citation·Yifeng Zhan et al.·Chemistry & Biodiversity

Chemistry & Biodiversity

DOI: 10.1080/17518253.2021.2006319

Water extract of pomegranate ash–I2 as sustainable system for external oxidant/metal/catalyst-free oxidative iodination of (hetero)arenes

This study presents a sustainable method for synthesis of aryl iodides using molecular iodine in water extract of pomegranate ash, offering a sustainable solution for waste management and chemical transformations.

2021·17citations·Rama Moorthy Appa et al.·Green Chemistry Letters and Reviews

Green Chemistry Letters and Reviews

DOI: 10.1016/j.bioorg.2020.104502

Synthesis, biological properties and structural study of new halogenated azolo[4,5-b]pyridines as inhibitors of CK2 kinase.

New halogenated azolo[4,5-b]pyridines show potential as CK2 kinase inhibitors, with the most active compounds showing potential in treating cancer cells.

2020·12citations·K. Chojnacki et al.·Bioorganic chemistry

Bioorganic chemistry

DOI: 10.48402/IMIST.PRSM/JASAB-V2I1.21121

2D-QSAR study of the anti-obesity activity for the compounds based on 2-anilino, 4-aryl pyrimidines and 2,4-diaryl 7-azaindoles using statistical methods

The study developed a two-dimensional QSAR model to explore the links between obesity and CAMKK2 inhibitors, identifying 32 compounds with potential anti-obesity activity.

2020·4citations·H. Hajji et al.

DOI: 10.3390/molecules23102673

Metal-Catalyzed Cross-Coupling Reactions on Azaindole Synthesis and Functionalization

Metal-catalyzed reactions offer diverse synthetic methods for obtaining rare azaindoles and their functionalization, which are attractive for drug discovery programs.

2018·27citations·A. Santos et al.·Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry

Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry

DOI: 10.1002/chem.201801632

Substituted 1H-1,2,3-Triazol-4-yl-1H-pyrrolo[2,3-b]pyridines by De Novo One-Pot Ring-Forming Coupling/Cyclization/Desilylation Cu Alkyne/Azide Cycloaddition (AAC) Sequence.

This one-pot ring-forming method efficiently prepares substituted 1H-1,2,3-triazol-4-yl-pyrrolo[2,3-b]pyridines with a novel sequential Pd/Cu-catalyzed process using tri(iso-propyl)silyl

2018·5citations·T. Lessing et al.·Chemistry

Chemistry

DOI: 10.1002/EJOC.201800129

Hypervalent Fluoroiodane‐Triggered Synthesis of Fluoro‐Azabenzoxazepines and Azaindoles

Hypervalent Fluoroiodane-triggered reactions enable the synthesis of novel fluorinated scaffolds and enable their conversion into azaindoles in a one-pot, three-step reaction sequence.

2018·19citations·C. Brunner et al.·European Journal of Organic Chemistry

European Journal of Organic Chemistry

DOI: 10.4236/MRC.2017.63009

Palladium-Catalyzed Sonogashira Coupling Reaction of 2-Amino-3-Bromopyridines with Terminal Alkynes

Palladium-catalyzed Sonogashira coupling reaction efficiently produces 2-amino-3-alkynylpyridines with moderate to excellent yields (72%-96%) under optimized conditions.

2017·4citations·Qing Zhu et al.