Different Strategies to the Synthesis of Indazole and its Derivatives: A Review

Raut, Santosh; Atul, Tidke; Dhotre, Bharat K.; Arif, Pathan Mohd

doi:10.2174/1570193x16666190430160324

Cited by 19 publications

(7 citation statements)

References 119 publications

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“…Heterocyclic compounds with gold metal complexes, [35] platinum metal complexes [36] used as anticancer agents, series of Au(I) and Ag(I) complexes of imidazole also used for cancer treatment [37] . The compounds of other heterocycles similar to indole are indazole, it showing various bioactivities similar to indole [38,39] . The compounds of tetrakis linked with phosphorus and heterocycles are also showing various bioactivities [40] …”

Section: Introductionmentioning

confidence: 99%

“…[37] The compounds of other heterocycles similar to indole are indazole, it showing various bioactivities similar to indole. [38,39] The compounds of tetrakis linked with phosphorus and heterocycles are also showing various bioactivities. [40] In the view of above mentioned synthetic and biological importance of indole and oxadiazole compounds, we have decided to synthesis a single compound having both the nucleus.…”

Section: Introductionmentioning

confidence: 99%

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Design, Synthesis of 3‐(5‐Substituted Phenyl‐[1,3,4]oxadiazol‐2‐yl)‐1H‐indole and Its Microbial Activity

Suryawanshi¹,

Suryawanshi²,

Mhaske³

et al. 2023

Chemistry & Biodiversity

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Fischer indole synthesis of indole by using phenyl-hydrazine and acetaldehyde resulted 1H-Indole while phenyl-hydrazine reacted with malonaldehyde gives 1H-Indole-3-carbaldehyde. Also Vilsmeier-Haack formylation of 1H-Indole gives 1H-Indole-3-carbaldehyde. 1H-Indole-3-carbaldehyde were oxidized to form 1H-Indole-3carboxylic acid. 1H-Indole reacted with excess of BuLi at À 78 °C using dry ice also gives 1H-Indole-3-carboxylic acid. Obtained 1H-Indole-3-carboxylic acid was converted to ester and ester in to acid hydrazide. Finally 1H-Indole-3-carboxylic acid hydrazide reacted with substituted carboxylic acid gives microbial active indole substituted oxadiazoles. Synthesized compounds 9a -j showing promising in vitro anti microbial activities against S. aureus bacteria compared with Streptomycin. Compound 9a, 9f and 9g showing activities against E. coli compared with standards. Compound 9a and 9f are found potent active against B. subtilis compared with reference standard while compound 9a, 9c and 9j active against S. typhi.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Design, Synthesis of 3‐(5‐Substituted Phenyl‐[1,3,4]oxadiazol‐2‐yl)‐1H‐indole and Its Microbial Activity

Suryawanshi¹,

Suryawanshi²,

Mhaske³

et al. 2023

Chemistry & Biodiversity

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“…[23][24][25][26] It has a range of functions, including antiarrhythmic, antitumor, antibacterial, antifungal, antimicrobial, anti-HIV, anti-inflammatory, anti-hypertensive, and serotonin 5-HT 3 receptor antagonist activities. [27][28][29][30][31][32] There is a list of miscellaneous compounds that contain indazole nuclei loaded with different functional groups showing major pharmacological properties in drug molecules and serving as a structural moiety. For instance, Niraparib (marketed preparation bearing indazole nucleus) has been commonly used as an anticancer medication to treat recurrent epithelial ovarian, breast, primary peritoneal or fallopian tube, and prostate cancer.…”

Section: Introductionmentioning

confidence: 99%

Exploration of N‐(6‐Indazolyl) benzenesulfonamide Derivatives as Potential Antioxidants and Antimicrobial Agents: Integrating Synthesis, In Silico Docking, and Bioactivity Profiling

Yadav,

Rao,

Kumar

et al. 2023

ChemistrySelect

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A new series of N‐(1‐(2‐chloropyrimidin‐4‐yl)‐1H‐indazol‐5‐yl) benzenesulfonamide derivatives (4 a–i) and N‐(1‐(2‐chloropyrimidin‐4‐yl)‐6‐ethoxy‐1H‐indazol‐5‐yl) benzenesulfonamide derivatives (5 a–i) was synthesized via reduction of 1‐(2‐halopyrimidin‐4‐yl)‐5‐nitro‐1H‐indazole (3) with SnCl2 followed by reaction with various aryl sulphonyl chlorides in pyridine. The structures were confirmed using IR, 1H‐NMR, 13C‐NMR, and mass spectral methods. Compounds 4 a–i and 5 a–i were evaluated for antifungal and antibacterial activities against Gram‐negative and Gram‐positive bacteria. They also exhibited antioxidant potential in DPPH (IC50=0.094‐0.467 μmol/ml) and ABTS assays (IC50=0.101–0.496 μmol/ml). Remarkably, N‐(1‐(2‐chloropyrimidin‐4‐yl)‐1H‐indazol‐5‐yl)‐2‐nitrobenzenesulfonamide displayed the highest antibacterial activity, while N‐(1‐(2‐chloropyrimidin‐4‐yl)‐1H‐indazol‐5‐yl)‐4‐methoxybenzenesulfonamide showed excellent antifungal potential. Compound N‐(1‐(2‐chloropyrimidin‐4‐yl)‐1H‐indazol‐5‐yl)‐2‐nitrobenzenesulfonamide exhibited the most significant antioxidant activity. In this study, molecular dynamics simulations were utilized to rigorously examine the stability of ligand‐protein complexes, demonstrating a consistent and robust binding of the most potent compound within the target proteins′ binding sites. Computational assessments were further employed to predict the drug‐likeness and ADMET properties of the synthesized compounds. The results unequivocally confirmed the remarkable antioxidant and antimicrobial potential of all derivatives, a finding substantiated by comprehensive molecular docking analyses that revealed intricate interactions involving hydrogen bonds, electrostatic forces, and hydrophobic contacts. These findings collectively provide invaluable insights into the complex molecular structure and receptor target site dynamics, laying a strong foundation for the development of novel active antioxidant and antimicrobial agents with promising pharmaceutical implications.

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“…Compounds with multi‐heterocyclic nucleus show dynamic biological activities are most widely studied in the last decade. Heterocyclic compounds are key building blocks of potential pharmaceutical candidates [1,2]. Extensive literature survey on heterocyclic compounds reveals that the hydrophilic and lipophilic character of hetero atoms rendered great importance to heterocycles in the pharmaceutical sector.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and microbial screening of 8‐(benzyloxy)‐5‐(2‐[1,3‐diphenyl‐1H‐pyrazol‐4‐yl]thiazol‐4‐yl)quinolin‐2(1H)‐one derivatives

Choudhare¹,

Wagare

Kadam³

et al. 2021

Journal of Heterocyclic Chem

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The present investigation describe the synthesis of 8‐(benzyloxy)‐5‐(2‐[1,3‐diphenyl‐1H‐pyrazol‐4‐yl]thiazol‐4‐yl)quinolin‐2(1H)‐one derivatives. Quinolin‐8‐ol was transformed by five step synthetic procedures into 8‐Benzyloxy‐5‐(2‐bromo‐acetyl)‐1H‐quinolin‐2‐one. Subsequently, 8‐Benzyloxy‐5‐(2‐bromo‐acetyl)‐1H‐quinolin‐2‐one condensed with 1,3‐Diphenyl‐1H‐pyrazole‐4‐carbothioic acid amide in the presence of acetonitrile to afford 8‐(benzyloxy)‐5‐(2‐[1,3‐diphenyl‐1H‐pyrazol‐4‐yl]thiazol‐4‐yl)quinolin‐2(1H)‐one derivatives. Synthesized compounds were screened for their antimicrobial activity against gram‐positive and gram‐negative bacteria. Most of the synthesized compounds are found to be active against tested bacterial strains and fungal strain.

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Different Strategies to the Synthesis of Indazole and its Derivatives: A Review

Cited by 19 publications

References 119 publications

Design, Synthesis of 3‐(5‐Substituted Phenyl‐[1,3,4]oxadiazol‐2‐yl)‐1H‐indole and Its Microbial Activity

Design, Synthesis of 3‐(5‐Substituted Phenyl‐[1,3,4]oxadiazol‐2‐yl)‐1H‐indole and Its Microbial Activity

Exploration of N‐(6‐Indazolyl) benzenesulfonamide Derivatives as Potential Antioxidants and Antimicrobial Agents: Integrating Synthesis, In Silico Docking, and Bioactivity Profiling

Synthesis and microbial screening of 8‐(benzyloxy)‐5‐(2‐[1,3‐diphenyl‐1H‐pyrazol‐4‐yl]thiazol‐4‐yl)quinolin‐2(1H)‐one derivatives

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