Synthesis of quinoline coupled [1,2,3]-triazoles as a promising class of anti-tuberculosis agents

Kumar, K. Krishna; Subbiah, Seenivasan; Kumar, Vanaja; Das, Thangamuthu Mohan

doi:10.1016/j.carres.2011.06.028

Cited by 90 publications

(24 citation statements)

References 32 publications

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“…However, introduction of small hydrophilic substituent such as hydroxyl linked to the C‐4 of triazole via methylene showed dramatic loss in potent inhibition against MTB . Pentoses or hexoses in the chair conformation with 3,4 ‐trans diacetyl orientation such as quinoline glycoconjugate of D‐galactose ( 34 ) (3 S ,4 R ) were generally more potent inhibitor than those with corresponding 3,4‐ cis‐ diacetyl orientation (3S,4S) among the saccharide‐coupled compounds . Boechat and coworkers carried out the synthesis of N ‐phenyl‐1,2,3‐triazole‐isonicotinoyl hydrazide derivatives and were evaluated for anti‐TB against MTB H 37 Rv .…”

Section: 23‐triazole Derivatives For Treatment Of Tuberculosismentioning

confidence: 99%

Triazole: A Promising Antitubercular Agent

et al. 2015

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Tuberculosis is a contagious disease with comparatively high mortality worldwide. The statistics shows that around three million people throughout the world die annually from tuberculosis and there are around eight million new cases each year, of which developing countries showed major share. Therefore, the discovery and development of effective antituberculosis drugs with novel mechanism of action have become an insistent task for infectious diseases research programs. The literature reveals that, heterocyclic moieties have drawn attention of the chemists, pharmacologists, microbiologists, and other researchers owing to its indomitable biological potential as anti-infective agents. Among heterocyclic compounds, triazole (1,2,3-triazole/1,2,4-triazole) nucleus is one of the most important and well-known heterocycles, which is a common and integral feature of a variety of natural products and medicinal agents. Triazole core is considered as a privileged structure in medicinal chemistry and is widely used as 'parental' compounds to synthesize molecules with medical benefits, especially with infection-related activities. In the present review, we have collated published reports on this versatile core to provide an insight so that its complete therapeutic potential can be utilized for the treatment of tuberculosis. This review also explores triazole as a potential targeted core moiety against tuberculosis and various research ongoing worldwide. It is hoped that this review will be helpful for new thoughts in the quest for rational designs of more active and less toxic triazole-based antituberculosis drugs.

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Section: 23‐triazole Derivatives For Treatment Of Tuberculosismentioning

confidence: 99%

Triazole: A Promising Antitubercular Agent

et al. 2015

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“…Homogenous Cu(I) catalysis may lead to a product that is considerably contaminated with residual copper 23 . Heterogenous catalysts are known to afford cleaner products.…”

Section: Resultsmentioning

confidence: 99%

“…138 mg (99%) of beige solid was obtained; mp: 160 °C (lit. 23 160–162 °C); 1 H NMR (400 MHz; DMSO-d 6 ; TMS): δ 8.74 (s, 1H, Ar), 8.42 (d, J = 8.5 Hz, 1H, Ar), 8.00 (dd, J = 8.5 Hz, 4.1 Hz, 2H, Ar), 7.88 (d, J = 7.7 Hz, 2H, Ar), 7.79 (appt, J = 7.8 Hz, 1H, Ar), 7.63 (appt, J = 7.5 Hz, 1H, Ar), 7.45 (appt, J = 7.7 Hz, 3H, Ar), 7.34 (appt, J = 7.4 Hz, 1H, Ar), 5.97 (2H, s, ArCH 2 N); 13 C NMR (101 MHz; DMSO-d 6 ; TMS): δ 154.7, 148.4, 147.7, 137.8, 130.5, 130.3, 129.2, 128.8, 128.2, 127.8, 127.6, 127.2, 125.7, 120.2, 119.7, 56.5.…”

Section: Methodsmentioning

confidence: 99%

Electrolytic copper as cheap and effective catalyst for one-pot triazole synthesis

Mularski

Czaplińska

Cieślik

et al. 2018

Sci Rep

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Electrolytic copper is a well-known form of pure, oxygen free copper that is used for industrial applications. In this work, the catalytic potential of this relatively cheap material was studied. The addition of less than 0.015 mol equivalent of copper powder effectively catalysed the one-pot synthesis of triazoles from a diverse range of organic halides and alkynes. Quantitative conversions in aqueous solvents can be achieved within minutes. The heterogenous nature of the catalyst afforded a low level of copper contamination in the products, thus meeting the rigorous criteria of the pharmaceutical industry.

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“…Our research group is focused on developing one-pot synthetic transformations for complex molecules [29][30][31]. Two individual research groups have reported the multistep pathway to access the cinnamyl-1H-1,2,3-triazole derivatives IX from acetates of MBH adducts (Scheme 2) [32,33].…”

Section: Methodsmentioning

confidence: 99%

Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts

Soundararajan

Shobana

Subimol

et al. 2020

Beilstein J. Org. Chem.

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The direct transformation of Morita–Baylis–Hillman (MBH) adducts into molecules of interest is a crucial process wherein allylic hydroxy-protected or halogenated MBH adducts are commonly preferred. Herein, we report an azidophosphonium salt (AzPS)-catalysed straight forward protocol for synthesising structurally demanding (E)/(Z)-cinnamyl-1H-1,2,3-triazoles and halomethylcoumarins from MBH adducts. The novel methodology, efficient catalyst, and direct utilization of MBH adducts under mild reaction conditions qualify the reported procedures as powerful synthetic tools.

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Synthesis of quinoline coupled [1,2,3]-triazoles as a promising class of anti-tuberculosis agents

Cited by 90 publications

References 32 publications

Triazole: A Promising Antitubercular Agent

Triazole: A Promising Antitubercular Agent

Electrolytic copper as cheap and effective catalyst for one-pot triazole synthesis

Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts

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