Indazole scaffold: a generalist for marketed and clinical drugs

Cao, Yaquan; Luo, Chunying; Pu, Yang; Li, Pan; Wu, Chunli

doi:10.1007/s00044-020-02665-7

Cited by 26 publications

(16 citation statements)

References 169 publications

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“…There are many commercially available indazole-based drugs such as axitinib, niraparib, linifanib. [44] From the last few years, several indazole [45] containing antifungal agents, anticancer agents and kinase inhibitors have been developed by various methods [5] among which Cadogan cyclization is found to be an easy way for indazole synthesis. Villar and colleagues prepared a series of 2-phenyl-2H-indazole derivatives 83 through Cadogan cyclization by a one-pot procedure including the use of ultrasound (Scheme 19) and investigated their anti-protozoal activities [46] against E. histolytica, G. intestinalis, and T. vaginalis.…”

Section: Formation Of Indazole Moietymentioning

confidence: 99%

“…Indazole moiety is found to be an important pharmacophore for drug discovery. There are many commercially available indazole‐based drugs such as axitinib, niraparib, linifanib [44] . From the last few years, several indazole [45] containing antifungal agents, anticancer agents and kinase inhibitors have been developed by various methods [5] among which Cadogan cyclization is found to be an easy way for indazole synthesis.…”

Section: Synthesis Of Chemical Frameworkmentioning

confidence: 99%

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A Minireview on the Scope of Cadogan Cyclization Reactions Leading to Diverse Azaheterocycles

Kaur

Kumar

2022

Asian J Org Chem

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From the last two decades, Cadogan cyclization reaction is considered as one of the best routes for the preparation of various azaheterocycles comprising carbazoles, indoles, coumarins, carbolines, pyrazoloquinoxalines, S,N‐heterotetracenes from the nitro‐based substrates by using a variety of tetravalent phosphorus‐based reagents. To date the majority of Cadogan reactions are found to be intramolecular reactions, however, interestingly, a case of intermolecular Cadogan reaction is also reported, resulting in the widening of the reaction scope for futuristic perspectives. We report the Cadogan cyclization reactions for the synthesis of azaheterocycles from 2018 to present according to multiple classes of chemical frameworks including its scope (FDA approved drugs), along with the possibilities and mechanistic developments for unexpected products.

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Section: Formation Of Indazole Moietymentioning

confidence: 99%

Section: Synthesis Of Chemical Frameworkmentioning

confidence: 99%

A Minireview on the Scope of Cadogan Cyclization Reactions Leading to Diverse Azaheterocycles

Kaur

Kumar

2022

Asian J Org Chem

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“…Indole, imidazole, triazole, thiadiazole, pyrrole, benzimidazole, benzotriazole, and pyridine are some of the selected nitrogen-containing examples in the literature. [4][5][6][7] In recent years, triazoles have been increasingly utilized in drugs. Triazoles have been tested on various diseases and extensive literature is available in this context.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, anti‐TB activities, and molecular docking studies of 4‐(1,2,3‐triazoyl)arylmethanone derivatives

Turkmen

Erdemir

Mayda

et al. 2022

J Biochem & Molecular Tox

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Infectious diseases such as tuberculosis (TB) are leading causes of human death.Antibiotics are effective molecules to combat bacterial infections by affecting the processes required for bacterial cell growth and proliferation. The development of new antibiotics has become an important issue as overdosed or incorrect use of antibiotic lead to the development of antibiotic resistance. In this study, a new series of 4-(1,2,3-triazoyl)arylmethanone derivatives has been synthesized using the one-pot Copper-Catalyzed Oxidative Cross-Dehydrogenative Coupling/Oxidative Cycloaddition strategy to overcome the aforementioned problems. New compounds were characterized by using spectroscopic techniques ( 1 H, 13 C-APT-NMR, FT-IR, and HRMS-TOF). In vitro antimycobacterial activities of the arylmethanone derivatives against the Mycobacterium tuberculosis H 37 Rv standard strain were examined using the resazurin microplate method in the presence of streptomycin and rifampycin as standard medicines. Bioactive assays demonstrated promising results that some of the synthesized 4-(1,2,3-triazoyl) arylmethanone derivatives exhibited good anti-TB activities. Notably, compounds 6b, 6f, and 6g gave the most potent efficiency with minimum inhibitory concentration values of 4 μg/ml (12.8, 11.7, and 12.8 μΜ, respectively). Among the synthesized compounds, the cytotoxicity measurements of the 6b, 6f, 6g, 6d, and 6v derivatives were screened and it was found that the 6f derivative did not show any cytotoxicity. Molecular docking analyses are utilized to identify the binding mode and the key interactions between target compounds and the ligand-binding site of M. tuberculosis enoyl-acyl carrier protein reductase enzyme (MtInhA, EC 1.3.1.9). The docking results were in agreement with the in vitro results, which confirm the synthesized ligands bind to MtInha with moderate to low affinity.

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“…Some of these molecules are drugs already commercially available and many more are being developed. [12][13][14][15][16][17][18][19][20][21] These diverse biological activities are observed in indazole derivatives functionalized at different positions of the indazole ring, especially at the pyrazole ring positions. Among them, 1Hindazole regioisomers have been the most important compounds.…”

Section: Introductionmentioning

confidence: 99%

“…Many of those synthesized C-3 indazole derivatives have pharmaceutical interest in different therapeutical areas, and led to some marketed drugs. [7,20] Therefore, the synthesis of indazole regioisomers still remains a very demanding goal. Recently, indazole derivatives have gained attention in other areas, such as materials chemistry, due to their solvatochromism, electronic and photophysical properties, with potential applications as dyes, fluorescent probes and imaging agents.…”

Section: Introductionmentioning

confidence: 99%

New C‐3 Substituted 1H‐ and 2H‐Indazolephosphonic Acid Regioisomers: Synthesis, Spectroscopic Characterization and X‐Ray Diffraction Studies

et al. 2021

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Indazole is known as an important structural motif in medicinal chemistry and, recently, has also gained attention in other areas, such as materials chemistry, with many studies showing different potential applications for their regioisomers. Phosphonates are also a class of compounds with diverse applications, ranging from medicinal to material applications. Here we present the synthesis of 1H‐ and 2H‐indazolephosphonic acid derivatives substituted at C‐3, involving mono‐ or bisphosphonic acids, from their corresponding carboxylic acid and esters. These compounds were fully characterized, and their spectroscopic data were evaluated to identify and distinguish the structural scaffold of each phosphonic acid. Crystallization of [hydroxy(1‐methyl‐1H‐indazol‐3‐yl)methanediyl]bis(phosphonic acid) 7 afforded crystals suitable for single crystal X‐ray diffraction studies and its crystal structure details are also discussed.

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Indazole scaffold: a generalist for marketed and clinical drugs

Cited by 26 publications

References 169 publications

A Minireview on the Scope of Cadogan Cyclization Reactions Leading to Diverse Azaheterocycles

A Minireview on the Scope of Cadogan Cyclization Reactions Leading to Diverse Azaheterocycles

Synthesis, anti‐TB activities, and molecular docking studies of 4‐(1,2,3‐triazoyl)arylmethanone derivatives

New C‐3 Substituted 1H‐ and 2H‐Indazolephosphonic Acid Regioisomers: Synthesis, Spectroscopic Characterization and X‐Ray Diffraction Studies

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