[Et3NH][HSO4] catalyzed efficient synthesis of 5-arylidene-rhodanine conjugates and their antitubercular activity

Subhedar, Dnyaneshwar D.; Shaikh, Mubarak H.; Nawale, Laxman; Yeware, Amar; Sarkar, Dhiman; Shingate, Bapurao B.

doi:10.1007/s11164-016-2484-0

Cited by 24 publications

(9 citation statements)

References 73 publications

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“…Yield 78%; R f = 0.58; Mp = 280 °C (lit. [ 35 ] 284–286 °C); 1 H-NMR (300 MHz, ppm, DMSO- d 6 ): 3.04 (s, 6H, 2CH 3 ), 6.80-6.83 (d, J = 8.67 Hz, 2H, arom. ), 7.40-7.43 (d, J = 9.04 Hz, 2H, arom), 7.51 (s, 1H, =CH), 13.55 (s, 1H, NH); 13 C-NMR (DMSO- d 6 ) δ (ppm): 195.49, 169.95, 152.22, 133.69, 133.35, 120.26, 117.87, 112.64, 40.00; MS: m / z : 263.10 (M−) (264.37).…”

Section: Methodsmentioning

confidence: 99%

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Environmentally Friendly Approach to Knoevenagel Condensation of Rhodanine in Choline Chloride: Urea Deep Eutectic Solvent and QSAR Studies on Their Antioxidant Activity

et al. 2018

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A series of rhodanine derivatives was synthesized in the Knoevenagel condensation of rhodanine and different aldehydes using choline chloride:urea (1:2) deep eutectic solvent. This environmentally friendly and catalyst free approach was very effective in the condensation of rhodanine with commercially available aldehydes, as well as the ones synthesized in our laboratory. All rhodanine derivatives were subjected to 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) scavenging activity investigation and quantitative structure-activity relationship (QSAR) studies were performed to elucidate their structure-activity relationship. The best multiple linear QSAR model demonstrate a stability in the internal validation and Y-randomization (R2 = 0.81; F = 24.225; Q2loo = 0.72; R2Yscr = 0.148). Sphericity of the molecule, ratio of symmetric atoms enhanced atomic mass along the principle axes in regard to total number of atoms in molecule, and 3D distribution of the atoms higher electronegativity (O, N, and S) in molecules are important characteristic for antioxidant ability of rhodanine derivatives. Molecular docking studies were carried out in order to explain in silico antioxidant studies, a specific protein tyrosine kinase (2HCK). The binding interactions of the most active compound have shown strong hydrogen bonding and van der Waals interactions with the target protein.

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Section: Methodsmentioning

confidence: 99%

“…Yield 26%; R f = 0.67; Mp = 199 °C (lit. 202–203 °C [ 35 , 36 , 37 , 38 ]; 1 H-NMR (300 MHz, ppm, DMSO- d 6 ): 7.49–7.61 (m, 5H, arom. ), 7.65 (s, 1H, =CH), 13.74 (s. 1H, NH); 13 C-NMR (DMSO- d 6 ) δ (ppm): 196.01, 170.19, 133.44, 132.06, 131.19, 130.93, 129.91; MS: m/z : 220.00 (M−) (221.30).…”

Section: Methodsmentioning

confidence: 99%

Environmentally Friendly Approach to Knoevenagel Condensation of Rhodanine in Choline Chloride: Urea Deep Eutectic Solvent and QSAR Studies on Their Antioxidant Activity

et al. 2018

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Section: Figure 1 Examples Of Rhodanine Derivatives With Biological Activitiesmentioning

confidence: 99%

“…Although many protocols have been reported to synthesize rhodanines, most of them are focused on the Knoevenagel condensation of rhodanine moiety with aldehydes for 5-arylidene rhodanines (Scheme 1). [41][42][43][44] Actually, the synthesis method of rhodanine skeleton, the key building block, is awfully limited. Classical way is the one-pot three component strategy whth carbon disulfide or thiophosgene generally involved, which the experimental procedures suffer from the use of toxic and corrosive reagent (Scheme 2, a).…”

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A New Synthesis Strategy for Rhodanine and Its Derivatives

Pan¹,

An²,

Wu³

et al. 2021

Synlett

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Rhodanine and its derivatives have been known as privileged structures in pharmacological research because of their wide spectrum of biological activities, but the synthesis method of rhodanine skeleton is limited. In this paper, not only rhodanine skeleton, but also N-aryl rhodanines can be directly prepared via the reaction of thioureas and thioglycolic acid in one step catalyzed by protic acid, which provides a new approach of the synthesis of rhodanine and its derivatives. The developed strategy is straightforward, efficient, atom economical and convenient in good yields.

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“…[ 40 ] Indeed, it is appreciable to explore the cheap and readily available ionic liquid in organic synthesis. The ionic liquid [Et 3 NH][HSO 4 ] has been used extensively in various organic transformations, for the synthesis of thiazolidine and oxazolidine derivatives, [ 41 ] quinolone derivatives, [ 42 ] α‐aminophosphonates, [ 43 ] 5‐arylidine‐rohdanine conjugates, [ 44 ] synthesis of coumarin, [ 45 ] and biscoumarins. [ 46 ]…”

Section: Introductionmentioning

confidence: 99%

[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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[Et3NH][HSO4] catalyzed efficient synthesis of 5-arylidene-rhodanine conjugates and their antitubercular activity

Cited by 24 publications

References 73 publications

Environmentally Friendly Approach to Knoevenagel Condensation of Rhodanine in Choline Chloride: Urea Deep Eutectic Solvent and QSAR Studies on Their Antioxidant Activity

Environmentally Friendly Approach to Knoevenagel Condensation of Rhodanine in Choline Chloride: Urea Deep Eutectic Solvent and QSAR Studies on Their Antioxidant Activity

A New Synthesis Strategy for Rhodanine and Its Derivatives

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

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[Et3NH][HSO4] catalyzed efficient synthesis of 5-arylidene-rhodanine conjugates and their antitubercular activity

Cited by 24 publications

References 73 publications

Environmentally Friendly Approach to Knoevenagel Condensation of Rhodanine in Choline Chloride: Urea Deep Eutectic Solvent and QSAR Studies on Their Antioxidant Activity

Environmentally Friendly Approach to Knoevenagel Condensation of Rhodanine in Choline Chloride: Urea Deep Eutectic Solvent and QSAR Studies on Their Antioxidant Activity

A New Synthesis Strategy for Rhodanine and Its Derivatives

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

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