Iodine-Promoted C–H Bond Amination Reaction for the Synthesis of Fused Tricyclic Heteroarenes DOI Creative Commons

Rachel E. Crittell,

Rehema Nakiwala,

Margaux J. Lavenue

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 13, 2024

Fused heterocyclic scaffolds, such as benzimidazoles or larger ring systems containing a benzimidazole fragment, are frequently encountered in pharmaceutical compounds and other biologically active molecules. While there many examples of N9- and/or C3-substituted 9H-benzo[4,5]imidazo[2,1-c][1,2,4]triazoles, current the regioselective preparation N1-substituted 1H-benzo[4,5]imidazo[2,1-c][1,2,4]triazoles limited to N1-aryl substituted compounds, which also contain C3-substituent. Here, we report an iodine-promoted C–H bond amination reaction that allows selective with variety aryl alkyl N1-substituents. Not only do these cyclization reactions allow access new substitution pattern on benzo[4,5]imidazo[2,1-c][1,2,4]triazole scaffold, but they tolerant toward wide range functional groups, including esters, amides, alcohols, alkynes, alkenes. Our findings expand synthetic toolbox for nitrogen fused heteroarenes.

Language: Английский

In vitro α-amylase and α-glucosidase inhibition study of dihydropyrimidinones synthesized via one-pot Biginelli reaction in the presence of a green catalyst DOI
Vinuta Kamat, Delicia A. Barretto, Boja Poojary

et al.

Bioorganic Chemistry, Journal Year: 2024, Volume and Issue: 143, P. 107085 - 107085

Published: Jan. 3, 2024

Language: Английский

Citations

14
Fluorescent imidazole derived sensor for selective in vitro and in vivo Fe2+ detection and bioimaging in zebrafish with DFT studies DOI
Aravind R. Nesaragi, Jahir Ahmed, Mabkhoot Alsaiari

et al.

Optical Materials, Journal Year: 2024, Volume and Issue: 148, P. 114850 - 114850

Published: Jan. 13, 2024

Language: Английский

Citations

12
Imidazole-centred cupric ions sensor: Experimental validation, theoretical understanding, and zebrafish bioimaging DOI

Keshav Kumar Harish,

Aravind R. Nesaragi, Naveen Kumar Kalagatur

et al.

Journal of Photochemistry and Photobiology A Chemistry, Journal Year: 2024, Volume and Issue: 452, P. 115565 - 115565

Published: March 6, 2024

Language: Английский

Citations

10
Imidazole‐Centred Oxadiazole Sensor for Detecting Al3+ and Fe3+ Cations in Living Cells: A Zebrafish Bioimaging Approach DOI
Aravind R. Nesaragi,

Bi Bi Ayisha Mulla,

Sharanappa Chapi

et al.

Applied Organometallic Chemistry, Journal Year: 2025, Volume and Issue: 39(4)

Published: March 9, 2025

ABSTRACT This study introduces a novel organic fluorescent chemosensor, designated as imidazole 4‐(1‐(4‐(5‐(4‐( tert ‐butyl)phenyl)‐1,3,4‐oxadiazol‐2‐yl)phenyl)‐1 H ‐phenanthro[9,10‐ d ]imidazol‐2‐yl)‐N,N‐diphenylaniline ( TIMTB ). Engineered specifically for detecting aluminium (Al 3+ ) and iron (Fe ions, demonstrates exceptional selectivity, rapid response times, efficacy in complex matrices such biological fluids environmental samples. Comprehensive evaluations through UV absorption, fluorescence spectroscopy, pH‐dependent studies confirm 's high sensitivity selectivity towards Al Fe . Further, the was supported by Density Functional Theory (DFT) studies. , synthesized with an imidazole‐oxadiazole core, exhibited significantly low cytotoxicity (14 ± 0.15 μM). In aqueous ethanol medium, probe achieved notably detection limits of 2 nM 2.19 μM Minimal observed both in‐vitro (MDA‐MB‐231 cells) in‐vivo (zebrafish, Danio rerio studies, paving way its application tracing intracellular ions zebrafish embryos. robust performance underscores potential invaluable tool monitoring biomedical applications.

Language: Английский

Citations

1
Selective Al3+ and Fe3+ detection using imidazole–oxadiazole sensors: bioimaging evidence from zebrafish DOI
Aravind R. Nesaragi, Praveen Naik,

Bi Bi Ayisha Mulla

et al.

New Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This study presents TIMF, a novel chemosensor for Al 3+ and Fe detection. TIMF displays high selectivity, rapid response, low cytotoxicity. Spectroscopic DFT studies confirm its sensitivity, with successful in vitro vivo applications.

Language: Английский

Citations

1
Imidazole-Thiazole Based Dual Chemosensor for Cu2+ and Co2+ Ions with Identical Excitation Wavelength and Colorimetric TFA Sensing, Theoretical Validation DOI
Aravind R. Nesaragi,

Jyoti Nagalik,

T. M. Sharanakumar

et al.

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: unknown, P. 140816 - 140816

Published: Nov. 1, 2024

Language: Английский

Citations

3
Triphenylamine‐Based Dual Chemosensor for Cu2+ and Co2+ Ions and Volatile Acid Vapour Sensor, DFT Calculations DOI Open Access
Aravind R. Nesaragi,

Jyoti Nagalik,

Mounesh

et al.

Applied Organometallic Chemistry, Journal Year: 2025, Volume and Issue: 39(4)

Published: March 16, 2025

ABSTRACT In this work, a novel fluorescent chemosensor 3‐(2‐(2‐(4‐(diphenylamino)phenyl)‐4,5‐diphenyl‐1 H ‐imidazol‐1‐yl)thiazol‐4‐yl)‐2 ‐chromen‐2‐one ( TCCM ) was effectively synthesized and characterized through NMR Mass spectrum. An approach towards the recognition of Cu 2+ Co ions using turn‐off fluorescence technique developed. The also exhibited colorimetric fluorometric sensing behaviour with visible response to trifluoroacetic acid (TFA). Upon addition TFA , new peak formation at 500 nm in absorption spectra along colour change from colourless brown. addition, it exhibits high selectivity limit detection 4.2 3.9 μM, respectively. It discovered that sensor quite selective for had lot competing ions. Further, studies were supported by DFT analysis NBO studies.

Language: Английский

Citations

0
WELPSA: A Green Catalyst Mediated Microwave Assisted Efficient Synthesis of Novel 5‐Aminopyrazole‐4‐Carbonitrile Derivatives as Anticancer Agents (MCF‐7, A‐549) and In Silico Studies DOI
Aravind R. Nesaragi, Vinuta Kamat, Sharanappa Chapi

et al.

Archiv der Pharmazie, Journal Year: 2025, Volume and Issue: 358(4)

Published: April 1, 2025

ABSTRACT Malononitrile, modified hydrazine, and quinoline aldehyde were combined in a one‐pot reaction under microwave irradiation to create the medicinally significant family of heterocyclic scaffolds, quinoline, coumarin, thiazole, pyrazole 4‐carbonitrile derivatives with help green solvent as water. WELPSA (water extract lemon peel‐soaked ash) is used speed up solvent‐free environment, according more environmentally friendly protocols. This methodology offers several advantages like short duration, synthesis, high yield, no need for chromatographic techniques, catalyst recyclability five cycles, so on. Synthesized evaluated anticancer potential against lung (A549) breast cancer cell lines. Among tested compounds, 4i 4j exhibited remarkable activities. Further investigations using Annexin V staining flow cytometry revealed that both compounds effectively induced apoptosis A549 cells. Compound was subjected molecular docking dynamic studies understand basis their activity, which demonstrated strong interaction target protein 1m17, providing insights into its mechanism action. These findings highlight promising candidates drug development.

Language: Английский

Citations

0
B(C6F5)3‐Catalysed Alkylation of Imidazo[1,2‐a]pyridines Using α,β‐Unsaturated Ketones DOI Creative Commons
Nusaybah Alotaibi, Rasool Babaahmadi, Milan Pramanik

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(12)

Published: Feb. 3, 2024

Abstract Fluorinated triarylboranes have shown a breadth of reactivity as catalysts for organic transformations, particularly in carbon‐carbon bond forming reactions. Herein we report facile, metal‐free synthetic route the addition 2‐phenylimidazo[1,2‐ ]pyridines to α , β ‐unsaturated ketones using B(C 6 F 5 ) 3 catalyst. 25 examples reactions leading products up 97 % yield are reported. DFT studies show role and hydrogen shuttling mechanism this Michael alkylation.

Language: Английский

Citations

1
Synthetic Approaches Toward Imidazo‐Fused Heterocycles: A Comprehensive Review DOI
Pragati Kushwaha,

Rashi,

Ayush Bhardwaj

et al.

Journal of Heterocyclic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 24, 2024

ABSTRACT Imidazole moiety when fused with other heterocyclic system form numerous compounds different types of pharmacological and biological activities. In this review, we discussed a comprehensive analysis the synthetic methodologies reaction mechanisms for imidazo‐fused molecules. These molecules represent crucial class due to their significant applications versatile chemical reactivity. This article meticulously examined various routes construction heterocycles, ranging from traditional methods modern approaches such as microwave‐assisted reactions, NPs‐catalyzed light‐mediated synthesis, electrochemical transition metal‐free synthesis routes. By consolidating current knowledge highlighting future directions, review aims serve treasure research community in fields organic chemistry, medicinal material science.

Language: Английский

Citations

1