Eco-friendly and sustainable synthetic approaches to biologically significant fused N-heterocycles

Gupta, Shiv Shankar; Kumari, Surekha; Kumar, Inder; Sharma, Upendra

doi:10.1007/s10593-020-02678-5

Cited by 26 publications

(5 citation statements)

References 8 publications

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“…A recent review on multicomponent green synthesis of N-containing heterocycles using mixed oxides as heterogeneous catalysts is also reported [30]. A group of workers had recently published review on "Eco-friendly and sustainable synthetic approaches to biologically significant fused N-heterocycles" [31]. Other groups had also presented well-documented work on the synthesis of heterocyclic compounds using greener methods [32][33][34].…”

Section: Microwave Irradiationmentioning

confidence: 99%

Greener Approach towards the Synthesis of Nitrogen Based Heterocycles

Dinodia

2023

Strategies for the Synthesis of Heterocycles and Their Applications

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The preferable application of green chemistry in research is to utilize environment benign, mild, non toxic, reproducible catalyst and efficient solvents in synthesis of molecules. Use of green chemistry techniques had enabled in dramatically reducing chemical waste and reaction times as has recently been reported in several organic syntheses reactions. Greener routes are required in the synthesis of N-heterocycles, due to the remarkable importance of these compounds in medicinal chemistry. This chapter is dedicated to the synthesis of N containing heterocyclic compounds using eco-friendly solvent like water and bio-derived solvents (glycerol, ethyl lactate, and gluconic acid aqueous solution). Water and bio-based solvents for the synthesis of aromatic nitrogen heterocycles was chosen due to the negligible toxicity associated with these solvents. Apart from being eco-friendly, water also has the potential to become a universally acceptable solvent due to its abundance and low cost. Work on microwave synthesis is also reported as it is an eco-friendly and faster process for the synthesis of these N-based heterocyclic compounds. Due to its rapid action to produce products with greater purity and yield, it is now being used worldwide.

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Section: Microwave Irradiationmentioning

confidence: 99%

Greener Approach towards the Synthesis of Nitrogen Based Heterocycles

Dinodia

2023

Strategies for the Synthesis of Heterocycles and Their Applications

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“…Nitrogen-containing heteroarenes are widely found in synthetic and naturally occurring molecules with significant biological potential. [1][2] These N-heteroarenes are prevalent among drug candidates, making up around 75% of the drug molecules authorized by the USFDA. 3 N-heteroaryl structures are essential components of DNA, RNA, and vitamins like pyridoxine and niacin.…”

Section: Introductionmentioning

confidence: 99%

Photocatalytic Synthesis of unsymmetrical Bis-N-Heterocycles

Gupta,

Rav,

Chandra

et al. 2024

Preprint

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In this study, a sustainable approach has been revealed for the synthesis of bis-N-heteroaryl motifs comprising an indole and an isoquinoline/quinoline moieties. A novel photolabile phthalimide reagent based on indole was specifically designed to facilitate its coupling with medicinally valuable quinoline and isoquinoline motifs in the Minisci-type reaction. Indomethacin and ibuprofen-based reagents were also coupled with isoquinolines to generate a unique chemical space for further exploration in drug discovery research. Detailed experimental and theoretical studies were conducted to understand the mechanism of the developed protocol. This protocol can be a green tool for integrating drug molecules to discover new therapeutic leads.

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“…Heterocycles such as oxadiazoles [4,10,11], quinoxalines [12], triazoles [10,13], pyrazoles [14], quinoxaline-sulfonamides [15], lamivudine [16], thiadiazoles [17,18], furans Heterocycles such as oxadiazoles [4,10,11], quinoxalines [12], triazoles [10,13], pyrazoles [14], quinoxaline-sulfonamides [15], lamivudine [16], thiadiazoles [17,18], furans [4,10,11], and ciprofloxacin oxadiazole [19], etc., display a wide array of biological activities against different diseases, especially tyrosinase inhibitory activities [4,20]. Piperazine-based heterocyclic molecules [21][22][23] demonstrate a broad spectrum of biological and pharmacological chemotherapeutic potential [24], for instance, antimicrobial [25,26], antifungal [27], insecticidal [28], anti-oxidant [29], and anti-inflammatory [30,31], and they are currently also employed as anti-cancer agents [32]. The structures of some of the FDA-approved piperazine-based drugs are given in Figure 3.…”

Section: Introductionmentioning

confidence: 99%

“…iomedicines 2023, 11, x FOR PEER REVIEW 3 of 20 [4,10,11], and ciprofloxacin oxadiazole [19], etc., display a wide array of biological activities against different diseases, especially tyrosinase inhibitory activities [4,20]. Piperazine-based heterocyclic molecules [21][22][23] demonstrate a broad spectrum of biological and pharmacological chemotherapeutic potential [24], for instance, antimicrobial [25,26], antifungal [27], insecticidal [28], anti-oxidant [29], and anti-inflammatory [30,31], and they are currently also employed as anti-cancer agents [32]. The structures of some of the FDA-approved piperazine-based drugs are given in Figure 3.…”

Section: Introductionmentioning

confidence: 99%

Bacterial Tyrosinase Inhibition, Hemolytic and Thrombolytic Screening, and In Silico Modeling of Rationally Designed Tosyl Piperazine-Engrafted Dithiocarbamate Derivatives

Zahoor,

Hafeez,

Mansha

et al. 2023

Biomedicines

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Piperazine is a privileged moiety that is a structural part of many clinical drugs. Piperazine-based scaffolds have attracted the attention of pharmaceutical and medicinal scientists to develop novel, efficient therapeutic agents owing to their significant and promising biological profile. In the current study, an ecofriendly ultrasonic-assisted synthetic approach was applied to achieve a novel series of 1-tosyl piperazine dithiocarbamate acetamide hybrids 4a–4j, which was evaluated for in vitro tyrosinase inhibition and thrombolytic and hemolytic cytotoxic activities. Among all the piperazine-based dithiocarbamate acetamide target molecules 4a–4j, the structural analogs 4d displayed excellent tyrosinase inhibition efficacy (IC50 = 6.88 ± 0.11 µM) which was better than the reference standard drugs kojic acid (30.34 ± 0.75 µM) and ascorbic acid (11.5 ± 1.00 µM), respectively, which was further confirmed by in silico induced-fit docking (IFD) simulation Good tyrosinase activities were exhibited by 4g (IC50 = 7.24 ± 0.15 µM), 4b (IC50 = 8.01 ± 0.11 µM) and 4c (IC50 = 8.1 ± 0.30 µM) dithiocarbamate acetamides, which were also better tyrosinase inhibitors than the reference drugs but were less active than the 4d structural hybrid. All the derivatives are less toxic, having values in the 0.29 ± 0.01% to 15.6 ± 0.5% range. The scaffold 4b demonstrated better hemolytic potential (0.29 ± 0.01%), while a remarkably high thrombolytic chemotherapeutic potential was displayed by analog 4e (67.3 ± 0.2%).

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Eco-friendly and sustainable synthetic approaches to biologically significant fused N-heterocycles

Cited by 26 publications

References 8 publications

Greener Approach towards the Synthesis of Nitrogen Based Heterocycles

Greener Approach towards the Synthesis of Nitrogen Based Heterocycles

Photocatalytic Synthesis of unsymmetrical Bis-N-Heterocycles

Bacterial Tyrosinase Inhibition, Hemolytic and Thrombolytic Screening, and In Silico Modeling of Rationally Designed Tosyl Piperazine-Engrafted Dithiocarbamate Derivatives

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