Synthesis and biological evaluation of novel triazole-biscoumarin conjugates as potential antitubercular and anti-oxidant agents

Danne, Ashruba B.; Choudhari, Amit; Sarkar, Dhiman; Sangshetti, Jaiprakash N.; Khedkar, Vijay M.; Shingate, Bapurao B.

doi:10.1007/s11164-018-3490-1

Cited by 20 publications

(9 citation statements)

References 68 publications

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“…The methine proton became visible as a singlet near to δ 4.24-6.36 ppm. Moreover, in the 13 C NMR spectra, the signals at δ 163.88-169.81 and δ 32.93-37.89 ppm corresponded to carbonyl and methine carbon atoms.…”

Section: Resultsmentioning

confidence: 97%

“…Further, the structures of all the synthesized compounds (5a-i) were validated by 1 H NMR, 13 C NMR and mass spectrometry. Moreover, the resonating signal at δ 10.09-11.91 ppm corresponded to the OH proton in 1 H NMR spectra.…”

Section: Scheme 1 Synthesis Of Biscoumarins and Bisdimedones Using C-so 3 H As An Acid Catalyst Under Green Conditionsmentioning

confidence: 99%

“…Biscoumarin, a bridged dimer of 4-hydroxycoumarin, has been reviewed [6] and reported with its vast pharmaceutical activities such as anticancer [7][8][9][10], anticoagulant [11], antioxidant [12,13], urease inhibitory activity [14], Zika virus inhibitor [15], antiviral [16], inhibition of α-glucosidase [17], antimicrobial activity [18][19][20][21][22], antilipoxygenase activity [23], inhibition of snake venom [24], inhibition of HIV integrase [25] and proliferation inhibition of K-562 [26]. Despite its pharmacological applications, they are also employed in industrial applications as fluorescent and colorimetric sensors [27], ligands [28], semiconductors [29], photoluminescent [30] and designing of WLED [31].…”

Section: Introductionmentioning

confidence: 99%

“…2H), 7.94 (dd, J = 8.0 Hz, 1.5 Hz, 2H), 8.64 (br, 3H, OH);13 C NMR (125 MHz, DMSO-d 6 ) δ 165.57, 164.77, 152.03, 146.24, 145.74, 132.62, 131.99, 123.86, 123.13, 117.47, 117.16, 116.29, 114.18, 112.17, 104.38, 90.94, 54.83, 35.17; ESI-MS (m/z): 458.10 [M +].…”

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confidence: 99%

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Black yet green: A heterogenous carbon-based acid catalyst for the synthesis of biscyclic derivatives under eco-friendly conditions

Teli¹,

Sethiya²,

Agarwal³

2021

Res Chem Intermed

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In this study, a simple, cost-efficient and green protocol has been described for the synthesis of biscoumarin and bisdimedone derivatives via one-pot Knoevenagel-Michael reaction of aromatic aldehydes with 4-hydroxycoumarin and dimedone, respectively. This approach has defined a new way of synthesizing products (4a-i and 5a-i) in high yields using carbon sulfonic acid as a heterogeneous solid acid catalyst. All the reactions have been executed in a greener medium in short reaction times with high-to-excellent yields. This organic synthesis adheres to the principles of green chemistry as the catalyst is cheap, gentle toward environment, easy to handle and reusable up to six cycles, easily separable through filtration, green reaction media and high yield of derivatives in short reaction time. The structure of the synthesized compounds was established by spectral analysis.

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Section: Resultsmentioning

confidence: 97%

Section: Scheme 1 Synthesis Of Biscoumarins and Bisdimedones Using C-so 3 H As An Acid Catalyst Under Green Conditionsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Black yet green: A heterogenous carbon-based acid catalyst for the synthesis of biscyclic derivatives under eco-friendly conditions

Teli¹,

Sethiya²,

Agarwal³

2021

Res Chem Intermed

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“…Danne et al . have designed variety of triazole biscoumarins ( Table ) and assessed in vitro anti‐oxidant and anti‐tubercular activity via DPPH radical scavenging and Mtb H37Ra.…”

Section: Biological Activity Of Biscoumarinmentioning

confidence: 99%

An Insight View on Synthetic Protocol, Mechanistic and Biological Aspects of Biscoumarin Derivatives

2019

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Biscoumarin has emerged as one of the most unique and valuable moiety in the field of synthetic as well as in medicinal chemistry. This moiety has been examined for the designing of potent derivatives and hybrids with other moieties and substituents exhibiting a myriad of medicinal properties. These far‐flung characteristics enthralled the researchers to discover various methods for the synthesis of biscoumarin nucleus and its derivatives from 4‐hydroxycoumarin and varieties of aldehydes using different types of catalysts to improve the selectivity, purity and yield of the products. Moreover, liberal scope is available for this structural unit which needs to be explored by chemists for the advancement of new potential drug candidates. This article summarizes the current eco‐benign pathways for the synthetic strategies of biscoumarins under various reaction conditions viz. solid supported catalyst, ionic liquid, nanoparticles, Lewis acid, heteropolyacids, nanocomposites etc.

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[Et₃NH][HSO₄] catalyzed solvent‐free synthesis of new 1,2,3‐triazolidene‐indolinone derivatives

Siddiqui

Nagargoje

Raza

et al. 2022

Journal of Heterocyclic Chem

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A series of new 1,2,3‐triazolidene‐indolinone derivatives (17a‐j) were designed and synthesized via [Et3NH] [HSO4] catalyzed solvent‐free approach. The synthesis strongly relied on Knoevenagel condensation of 1,4‐disubstituted 1,2,3‐triazolyl aldehydes (15a‐j) and oxindole (5). The solvent‐free approach and Brønsted acidity of [Et3NH] [HSO4] ionic liquid increased the rate of reaction and provided the corresponding 1,2,3‐triazolidene‐indolinone derivatives (17a‐j) in excellent yields. The reusability of ionic liquid is also established with persistent effective yields up to four cycles. These novel 1,2,3‐triazolidene‐indolinone derivatives may exhibit potential biological response due to the presence of potent moieties and presence of triazolidene‐exocyclic double bond.

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Synthesis and biological evaluation of novel triazole-biscoumarin conjugates as potential antitubercular and anti-oxidant agents

Cited by 20 publications

References 68 publications

Black yet green: A heterogenous carbon-based acid catalyst for the synthesis of biscyclic derivatives under eco-friendly conditions

Black yet green: A heterogenous carbon-based acid catalyst for the synthesis of biscyclic derivatives under eco-friendly conditions

An Insight View on Synthetic Protocol, Mechanistic and Biological Aspects of Biscoumarin Derivatives

[Et₃NH][HSO₄] catalyzed solvent‐free synthesis of new 1,2,3‐triazolidene‐indolinone derivatives

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Synthesis and biological evaluation of novel triazole-biscoumarin conjugates as potential antitubercular and anti-oxidant agents

Cited by 20 publications

References 68 publications

Black yet green: A heterogenous carbon-based acid catalyst for the synthesis of biscyclic derivatives under eco-friendly conditions

Black yet green: A heterogenous carbon-based acid catalyst for the synthesis of biscyclic derivatives under eco-friendly conditions

An Insight View on Synthetic Protocol, Mechanistic and Biological Aspects of Biscoumarin Derivatives

[Et3NH][HSO4] catalyzed solvent‐free synthesis of new 1,2,3‐triazolidene‐indolinone derivatives

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Product

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[Et₃NH][HSO₄] catalyzed solvent‐free synthesis of new 1,2,3‐triazolidene‐indolinone derivatives