Synthesis, antimicrobial and nematicidal evaluation of a new class of triazolo[4,3-c]quinazolinylthiazolidinones

Reddy, Cherkupally Sanjeeva; Kumar, G. Rajesh; Sunitha, B. U.

doi:10.1007/s00044-016-1538-6

Cited by 9 publications

(4 citation statements)

References 25 publications

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“…Cacchi et al [20] have also developed an alternative method for the synthesis of the 7-aminoindole derivatives, which involves the Buchwald-Hartwig C–N bond formation of the intermediate 7-bromoindoles with primary and secondary amines. The 2-aryl-4-chloroquinazolines compounds, 3a and 3b , used as coupling partners, were prepared by treatment of the known 2-arylquinazolin-4(3 H )-ones with phosphoryl chloride under reflux, following the literature procedure [21]. Amination of the electrophilic 4-chloroquinazoline derivatives, 3a (X = H) and 3b (X = 4-F), with 7-aminoindoles, 2a – d , in the presence of 5% HCl in tetrahydrofuran-isopropanol (THF-iPrOH) mixture under reflux afforded the corresponding indole-aminoquinazoline hybrids, 4a – h .…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, Biological Evaluation and Molecular Docking of Novel Indole-Aminoquinazoline Hybrids for Anticancer Properties

Mphahlele

Mmonwa

Aro

et al. 2018

IJMS

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A series of indole-aminoquinazolines was prepared via amination of the 2-aryl-4-chloroquinazolines with the 7-amino-2-aryl-5-bromoindoles. It was then evaluated for cytotoxicity in vitro against human lung cancer (A549), epithelial colorectal adenocarcinoma (Caco-2), hepatocellular carcinoma (C3A), breast adenocarcinoma (MCF-7), and cervical cancer (HeLa) cells. A combination on the quinazoline and indole moieties of a 2-phenyl and 2-(4-fluorophenyl) rings in compound 4b; 2-(4-fluorophenyl) and 3-chlorophenyl rings in compound 4f; or the two 2-(4-fluorophenyl) rings in compound 4g, resulted in significant and moderate activity against the Caco-2 and C3A cell lines. The indole-aminoquinazoline hybrids compounds 4f and 4g induced apoptosis in Caco-2 and C3A cells, and were also found to exhibit moderate (IC50 = 52.5 nM) and significant (IC50 = 40.7 nM) inhibitory activity towards epidermal growth factor receptor (EGFR) against gefitinib (IC50 = 38.9 nM). Molecular docking suggests that 4a–h could bind to the ATP region of EGFR like erlotinib.

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Section: Resultsmentioning

confidence: 99%

“…124−126 °C (Lit. [21] 123−125 °C); 1 H-NMR (DMSO- d 6 ) 7.56 (4H, m, ArH), 7.90 (1H, t, J = 6.9 Hz, ArH), 8.04 (4H, m, ArH).…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Biological Evaluation and Molecular Docking of Novel Indole-Aminoquinazoline Hybrids for Anticancer Properties

Mphahlele

Mmonwa

Aro

et al. 2018

IJMS

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“…with thiosemicarbazide using ethanol. The starting compound was anthranilamide which undergoes oxidative cyclocondensation with benzaldehyde to afford 55 which was further refluxed with SOCl 2 in the presence of DMF to give intermediate 56 [54]. In 2016, Dhongade-Desai et al described a multicomponent reaction between substituted quinazolinone 59a-f, hydrazine hydrate, and aromatic aldehydes under catalyst-free and microwave irradiation conditions to get derivatives 62a-f [27].…”

Section: Synthesis From 4-hydrazinoquinazolinesmentioning

confidence: 99%

Triazoloquinazoline: Synthetic Strategies and Medicinal Importance

Jabeen,

Aslam,

Ahmad

et al. 2023

Recent Advances on Quinazoline

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Triazoloquinazoline is a fused heterocyclic nucleus, formed by the fusion of two fundamental heterocyclic moieties; triazole and quinazoline. This class of compound is known for its potential as a therapeutic agent and is endowed with several pharmacological applications. Triazoloquinazoline and its derivatives have shown a variety of biological applications such as anticancer, anti-inflammatory, antimicrobial, antiviral, antihypertensive, anticonvulsant, antidiabetic, antioxidant, adenosine receptor antagonist, and significant cytotoxic activities. Hence, this privileged scaffold could act as an important candidate in the field of drug development. Many synthetic protocols have been developed to efficiently synthesize this fused heterocycle and its derivatives. Triazole and quinazoline rings fused at different positions which occurs in various isomeric forms such as, 1,2,4-triazolo[1,5-c]quinazoline, 1,2,4-triazolo[1,5-a]quinazoline, 1,2,4-triazolo[4,3-c]quinazoline, 1,2,4-triazolo[4,3-a]quinazoline, etc. This book chapter covers the synthesis of various isomeric forms of triazoloquinazoline as well as their biological activities.

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“…1,3‐Thiazines were used in diverse organic synthesis and transformations as reaction intermediates. [ 3 ] 1,3‐Thiazine derivatives showed various biological activities such as antimicrobial, [ 4 ] anti‐inflammatories, [ 5 ] anti‐cancer, [ 6 ] anti‐diabetic, [ 7 ] analgesics, [ 8 ] sedative‐hypnotic, [ 9 ] herbicidal, [ 10 ] anti‐oxidant, [ 11 ] calcium‐channel modulators. [ 12 ] Also, 1,3‐thiazine nucleus moieties represent notable prospective of anti‐radiation agents [ 3b ] and employed as an anabolic agent in medicine [ 13 ] .…”

Section: Introductionmentioning

confidence: 99%

Trifluoroborane catalyzed chemoselective synthesis of highly functionalized 1,3‐thiazin‐2‐ylidenes

Luo

Bhavanarushi

Avula

et al. 2020

Journal of Heterocyclic Chem

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Synthesis, antimicrobial and nematicidal evaluation of a new class of triazolo[4,3-c]quinazolinylthiazolidinones

Cited by 9 publications

References 25 publications

Synthesis, Biological Evaluation and Molecular Docking of Novel Indole-Aminoquinazoline Hybrids for Anticancer Properties

Synthesis, Biological Evaluation and Molecular Docking of Novel Indole-Aminoquinazoline Hybrids for Anticancer Properties

Triazoloquinazoline: Synthetic Strategies and Medicinal Importance

Trifluoroborane catalyzed chemoselective synthesis of highly functionalized 1,3‐thiazin‐2‐ylidenes

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