Microwave-assisted Cu-catalyzed C–C bond formation: one-pot synthesis of fully substituted 1,2,3-triazoles using nonsymmetrical iodoalkynes and their biological evaluation

Narsimha, Sirassu; Battula, Kumara Swamy; Reddy, Y. V. R.; Nagavelli, Vasudeva Reddy

doi:10.1007/s10593-019-02408-6

Cited by 35 publications

(14 citation statements)

References 51 publications

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“…Additionally, the activity of 1,2,3-triazole-containing dibenzo [b, e][1,4]diazepin-11-one hybrid 83 (IC 50 : 0.71 μm, MTT assay) against A549 cells is much higher than that of 5fluorouracil (IC 50 : 3.47 μm), and this hybrid could induce the G2/M phase of cell cycle arrest and apoptosis, indicating that hybrid 83 could be used for further studies as anti-lung cancer candidates (Praveen Kumar et al, 2016). Some other compounds which are combined by 1,2,3-triazole and benzodiazepine/benzoxepine/dithiocarbamate/ deoxysalinomycin/myrrhanone B /phenanthrene/pyrano(2,3-c) phenazine/paeonol/naphthalimide/sesquiterpene/sulfonate ester/sapinofuranone/triterpene/thiourea/benzothiazinone/ benzoxazinone/furan/nimesulide (Kuntala et al, 2015;Poornima et al, 2015;Sudhapriya et al, 2015;Chandrashekhar et al, 2016;Reddy et al, 2016;Shaikh et al, 2016;Abdallah et al, 2017;Battula et al, 2017;Kumar et al, 2017;Lu et al, 2017;Mareddy et al, 2017;Mo et al, 2017;Nguyen et al, 2017;Narsimha et al, 2018;Ou et al, 2019;Yang et al, 2019;Jiang et al, 2020;Kanabar et al, 2020;Madasu et al, 2020;Qi et al, 2020;) also possess certain activity against lung cancer cell lines, but their activities are generally far inferior to those of the references. Hence, these derivatives still need further structural modifications.…”

Section: Miscellaneous 123-triazole-containing Compoundsmentioning

confidence: 99%

1,2,3-Triazole-Containing Compounds as Anti–Lung Cancer Agents: Current Developments, Mechanisms of Action, and Structure–Activity Relationship

Liang

Sun

et al. 2021

Front. Pharmacol.

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Lung cancer is the most common malignancy and leads to around one-quarter of all cancer deaths. Great advances have been achieved in the treatment of lung cancer with novel anticancer agents and improved technology. However, morbidity and mortality rates remain extremely high, calling for an urgent need to develop novel anti–lung cancer agents. 1,2,3-Triazole could be readily interact with diverse enzymes and receptors in organisms through weak interaction. 1,2,3-Triazole can not only be acted as a linker to tether different pharmacophores but also serve as a pharmacophore. This review aims to summarize the recent advances in 1,2,3-triazole–containing compounds with anti–lung cancer potential, and their structure–activity relationship (SAR) together with mechanisms of action is also discussed to pave the way for the further rational development of novel anti–lung cancer candidates.

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Section: Miscellaneous 123-triazole-containing Compoundsmentioning

confidence: 99%

1,2,3-Triazole-Containing Compounds as Anti–Lung Cancer Agents: Current Developments, Mechanisms of Action, and Structure–Activity Relationship

Liang

Sun

et al. 2021

Front. Pharmacol.

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“…In vitro cytotoxic assays were performed on the A549, MCF-7, IMR-32, and HeLa human cancer cell lines to determine the efficacy of each compound. Among them, high activity was observed for both 39b and 39c against the MCF-7 and A-549 cell lines …”

Section: Synthesis Of Cu-catalyzed Heterocyclic Moieties Via Microwav...mentioning

confidence: 99%

“…Among them, high activity was observed for both 39b and 39c against the MCF-7 and A-549 cell lines. 17 The 6). 17 In the year 2020, our group demonstrated the synthesis of 1,4disubstituted 1,2,3-triazoles 43 using ionic liquid supported Cu(II) catalyst 42 under microwaves.…”

Section: Synthesis Of Cu-catalyzed Heterocyclic Moieties Via Microwav...mentioning

confidence: 99%

Copper Catalyzed Synthesis of Heterocyclic Molecules via C–N and C–O Bond Formation under Microwaves: A Mini-Review

Jena

Chanda

2023

ACS Omega

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Heterocyclic moieties play a significant role in the field of drug discovery. C−N and C−O bond formation reactions are the primary synthetic sequence for the generation of heterocyclic molecules. The generation of C−N and C−O bonds involves the use of mostly Pd or Cu catalysts although other transition metal catalyst's are also involved. However, in C−N and C−O bond formation reactions, several problems were faced such as catalytic systems containing costly ligands, lack of substrate scope, lots of waste generation, and high temperature conditions. So it is imperative to uncover new eco-friendly synthetic strategies. In view of enormous drawbacks, it is important to develop an alternate microwave-assisted synthesis of heterocycles via C−N and C−O bond formation, which provides a short reaction time, tolerance for functional groups, and less waste production. Numerous chemical reactions have been accelerated using microwave irradiation which provides a cleaner reaction profile, lower energy consumption, and higher yields. This review article highlights a comprehensive overview on the potential application of microwave assisted synthetic routes for the synthesis of diverse heterocycles via mechanistic pathways covering the year ranges from 2014 to 2023, along with possible biological interests.

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“…In view of the (i) significant roles of fused 1,2,3-triazoles, 1,3-thiazine, and imidazo[2,1-b] [1,3]thiazines in the development of several antibacterial compounds (Figure 1), (ii) green chemistry applications of CÀ N bond coupling to access potent biologically active compounds, (iii) application of molecular hybridization approaches [24] to access potent biologically active compounds, and (iv) in continuation of research work on the synthesis and biological evaluation of 1,2,3-traizole-based compounds. [25][26][27][28][29][30][31][32][33] Herein, we planned to synthesize some new fused imidazo[2,1-b][1,2,3]triazolo [4,5-d] [1,3]thiazine hybrids in onepot using inexpensive Cu-catalyzed sequential 1,3-dipolar cycloaddtion followed by intramolecular CÀ N bond formation (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Fused Imidazo[2,1‐b][1,2,3]triazolo[4,5‐d][1,3]thiazines: One‐Pot Synthesis, Antibiofilim, Bactericidal Effects, and in silico Studies

Ramu¹,

Krishna²,

Nasipireddy³

et al. 2023

ChemistrySelect

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strated the most promising Minimum Inhibitory Concentration values comparing to others. The MIC values were ranged from 1.56 μg to 12.5 μg, especially compounds 5 c, 5 d, and 5 e displayed superior activity against tested strains compared to the standards. We also documented the results of anti-biofilm profiles for the compounds 5 c, 5 d, 5 e, 5 h, 5 m and 5 n. Based on the result, we noted that, the active derivatives 5 c, 5 d, and 5 e were strongly inhibited the biofilm of MSSA and MRSA biofilm growth with BFIC values ranging from 3.34 � 0.05 to 8.32 � 0.32 μg/mL. In accordance to the results of antibiofilm property, the compounds 5 c, 5 d and 5 e were further evaluated for bactericidal effect against selected Staphylococcus aureus mutant strains. In concern to the results, we confirmed that, the bactericidal effect was found significant with compound 5 d and followed by 5 c and 5 e. In silico docking simulation studies were performed to evaluate the molecular interactions of 5 c, 5 d, 5 e, 5 h, 5 m and 5 n compounds with the S.aureus (MRSA), Penicillin-binding protein (PDB ID: 1MWT, co-crystallised ligand inhibitor Pencillin G). Finally, the in silico pharmacokinetic profile was predicted for potent compounds using SWISS/ADME and pkCSM.

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Microwave-assisted Cu-catalyzed C–C bond formation: one-pot synthesis of fully substituted 1,2,3-triazoles using nonsymmetrical iodoalkynes and their biological evaluation

Cited by 35 publications

References 51 publications

1,2,3-Triazole-Containing Compounds as Anti–Lung Cancer Agents: Current Developments, Mechanisms of Action, and Structure–Activity Relationship

1,2,3-Triazole-Containing Compounds as Anti–Lung Cancer Agents: Current Developments, Mechanisms of Action, and Structure–Activity Relationship

Copper Catalyzed Synthesis of Heterocyclic Molecules via C–N and C–O Bond Formation under Microwaves: A Mini-Review

Fused Imidazo[2,1‐b][1,2,3]triazolo[4,5‐d][1,3]thiazines: One‐Pot Synthesis, Antibiofilim, Bactericidal Effects, and in silico Studies

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