One-pot synthesis of novel 1,2,3-triazole-pyrimido[4,5-c]isoquinoline hybrids and evaluation of their antioxidant activity

Narsimha, Sirassu; Battula, Kumara Swamy; Nagavelli, Vasudeva Reddy

doi:10.1080/00397911.2018.1440315

Cited by 28 publications

(10 citation statements)

References 36 publications

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“…A series of newly functionalised 1,2,3-triazole-pyrimido[4,5-c]isoquinolines were synthesised for antioxidant screening. 153 In vitro antioxidant activity analysis (by 2,2-diphenyl-1-picrylhydrazyl (DPPH) method) revealed that compound 126 (Fig. 19) exhibited stronger antioxidant potency with an IC 50 value 6.02 µM than the positive control drug Trolox did (1.94-fold higher activity than the positive control drug Trolox).…”

Section: Antioxidant Activitymentioning

confidence: 99%

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Bozorov

Zhao

Aisa

2019

Bioorganic & Medicinal Chemistry

618

289

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A B S T R A C TThe 1,2,3-triazole ring is a major pharmacophore system among nitrogen-containing heterocycles. These fivemembered heterocyclic motifs with three nitrogen heteroatoms can be prepared easily using 'click' chemistry with copper-or ruthenium-catalysed azide-alkyne cycloaddition reactions. Recently, the 'linker' property of 1,2,3-triazoles was demonstrated, and a novel class of 1,2,3-triazole-containing hybrids and conjugates was synthesised and evaluated as lead compounds for diverse biological targets. These lead compounds have been demonstrated as anticancer, antimicrobial, anti-tubercular, antiviral, antidiabetic, antimalarial, anti-leishmanial, and neuroprotective agents. The present review summarises advances in lead compounds of 1,2,3-triazolecontaining hybrids, conjugates, and their related heterocycles in medicinal chemistry published in 2018. This review will be useful to scientists in research fields of organic synthesis, medicinal chemistry, phytochemistry, and pharmacology. Chemistry: synthesis and properties of the 1,2,3-triazolesThe general synthetic route of 1,2,3-triazoles using click chemistry is described in Scheme 1A. The most popular route to 1,2,3-triazoles is Cu(I)-catalysed Huisgen 1,3-dipolar cycloaddition, which is the https://doi.

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Section: Antioxidant Activitymentioning

confidence: 99%

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Bozorov

Zhao

Aisa

2019

Bioorganic & Medicinal Chemistry

618

289

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“…Owing to the remarkable pharmacological properties of phenothiazine and 1,2,3-triazole derivatives, we aimed to design a moiety that embodied both the active pharmacophores in a single molecular framework and to evaluate their biological activities especially anti-proliferative activity (Figure 1). Therefore, in the present study and in continuation of our work on1,2,3-triazole containing heterocycles (Narsimha et al, 2014(Narsimha et al, , 2018Reddy et al, 2016Kumar et al, 2017;Swamy et al, 2016Swamy et al, , 2017Swamy et al, , 2017a, we report the synthesis of novel1,2,3-triazole-phenothiazine along with alipophilic spacer and evaluation of their antiproliferative and antibacterial activity.…”

Section: Introductionmentioning

confidence: 56%

Synthesis, antiproliferative and antibacterial activity of novel Phenothiazine-[1, 2, 3] triazole hybrids

Narsimha¹,

Reddy²,

Nagavelli³

2019

Asian J Pharm Pharmacol

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Objective: Twenty five 1,2,3-triazole derivatives of phenothiazines (5a-5k, 6a-6g, and 7a-7g) were synthesized in order to evaluate their anti-proliferative and antibacterial activities. Material and methods: The newly synthesized 1 13 compounds were characterized by spectroscopic (FTIR, H NMR, C NMR and Mass) analysis after synthesis. All compounds were screened for their in vitro anticancer activity against MCF-7 (breast), HeLa (cervical) and A-549 (alveolar) cell lines. The minimum inhibitory concentrations (MIC) of the synthesized compounds (5a-5k, 6a-6g and 7a-7g) were tested against the gram-positive organisms B. subtilis, S. aureus and S. epidermidis and the gram-negative organisms E. coli, P. aeruginosa, and K. pneumoniae. Results: The in vitro cytotoxic examination results revealed that compounds 7a and 7b exhibited good anti-proliferative activity against three cancer cell lines, MCF-7, HeLa and A-549 with IC values ranging from 09.11 ± 0.3 µM to 20.11 ± 1.0 µM respectively. Antibacterial activity revealed that 50 the compounds 5d, 6d, and 7d against B. subtilis and S. aureus, compound 5i against P. aeruginosa and compound 5j against E. coli and P. aeruginosa have shown equipotent activity on comparing with the standard drugs penicillin and streptomycin. Conclusion: We succeeded in guiding the change of substituents in the triazole ring together with the phenothiazine-5,5-dioxide group, which played a crucial role in the development of a promising anticancer activity and also shown equipotent antibacterial activity against gram-positive and gram-negative organisms. By making a simple modification of the structure, a new potent analog having the desired anticancer and antibacterial activity can be produced with good efficiency. 4 concentrated under reduced pressure to afford crude 1 compound 4. White solid (Yield 72%), mp 125-127°C. H NMR (400 MHz, CDCl ) δ: 8.01-7.95 (m, 2H), 7.77-7.70 3 (m, 2H), 7.60-7.57 (m, 2H), 7.40-7.36 (m, 2H), 4.77 (s, 2H, N-CH ), 2.36 (s, 1H, -CH); ESI-MS m/z: 270 [M+H]. 2General procedure for the preparation of (5a-k, 6a-g and 7a-g)To a solution of alkyne (1.5 mmol) and aryl azide (2.0 mmol) in THF (15 mL) was added copper iodide (10 mol %) and the reaction mixture was stirred at room temperature for

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“…Based on the above successful synthesis of fused 1,2,3triazole derivatives via intramolecular C-H arylation of in situ generated 1,4-disubstituted 1,2,3-triazoles and previous therapeutic properties of triazoles and quinolines, as well as continuation of our research on 1,2,3-triazoles (Narsimha et al, 2014(Narsimha et al, , 2018aRanjithet al, 2017;Swamy et al, 2016Swamy et al, , 2017Swamy et al, , 2017aVasudeva Reedy et al, 2016a, we report an efficient method for the synthesis of fused hetrocyclic derivatives having triazole and quinoline…”

Section: Introductionmentioning

confidence: 81%

Microwave-assisted one pot synthesis of fused [1,2,3]triazolo-pyrano[3,2-h]quinolines and their biological evaluation

Babu¹,

Ravinder²,

Narsimha³

2019

Asian J Pharm Pharmacol

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Objectives: Microwave-assisted one-pot synthesis of fused [1,2,3]triazolyl [4',5':4,5]pyrano [3,2-h]quinolines and evaluation of their anticancer activity. Materials and Methods: The newly synthesized compoundswere characterized 1 13by spectroscopic (FTIR, H NMR, C NMR and Mass) analysis after synthesis. All compounds were screened for theirin vitro cytotoxic activity against MCF-7, A-549, and HeLa tumor cell lines using MTT analysis. Results: The results of cytotoxic activity revealedthat compound 3jhas shown potent activity against MCF-7 and HeLa with IC 50 values 16.88 ± 0.5 & 11.42 ± 0.6 μM, which are comparable to the standard drug, doxorubicin. Conclusions: We have developed a new method for the synthesis of fused 1,2 3-triazole derivatives and the protocol involves a Cu-catalyzed one pot [3+2] cycloaddition followed by C-C bond coupling reaction under microwave condition. Most of the analogues showed strong activity against HeLa and moderate activity against MCF-7 and A-549. The results indicate that these compounds have the potential to develop as leads, and their additional simple structural modifications in the title compounds can produce promising anti-cancer agents for the human cervical cancer HeLa cell line.

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One-pot synthesis of novel 1,2,3-triazole-pyrimido[4,5-c]isoquinoline hybrids and evaluation of their antioxidant activity

Cited by 28 publications

References 36 publications

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Synthesis, antiproliferative and antibacterial activity of novel Phenothiazine-[1, 2, 3] triazole hybrids

Microwave-assisted one pot synthesis of fused [1,2,3]triazolo-pyrano[3,2-h]quinolines and their biological evaluation

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