Synthesis and antidiabetic activity of 2,4-thiazolidindione, imidazolidinedione and 2-thioxo-imidazolidine-4-one derivatives bearing 6-methyl chromonyl pharmacophore

Ceylan–Ünlüsoy, Meltem; Kazak, Canan; Bayro, Ornela; Verspohl, Eugen J.; Ertan, Rahmiye; Dündar, Oya Bozdağ

doi:10.3109/14756366.2012.723207

Cited by 19 publications

(7 citation statements)

References 18 publications

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“…In medicinal chemistry, Knoevenagel products show pharmacological actions such as antiviral, antitubercular, anti-Parkinson's, anti-diabetic, anti-oxidant, and anti-cancer activity. The cytotoxic capacity of some Knoevenagel products is due to the inhibition of multiple enzyme targets and the induction of cellular events (18)(19)(20)(21)(22)(23)(24)(25)(26)(27).…”

Section: Introductionmentioning

confidence: 99%

The Knoevenagel reaction: a review of the unfinished treasure map to forming carbon–carbon bonds

Beurden

Koning

Molendijk

et al. 2020

Green Chemistry Letters and Reviews

125

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The formation of carbon-carbon bonds is a quest that has required a lot of research throughout the last 125 years of history of chemistry. The creation of these bonds is key to producing a wide variety of advanced products with great societal importance. In the past, the Knoevenagel reaction entailed a big part of these reactions. All the Knoevenagel reactions are performed with nitrogen-based catalysts, categorized as tertiary amines, secondary amines, primary amines, and ammonium salts. These catalysts operate through different reaction paths, with very deviant intermediates concerning each category. Subsequently, these intermediates create new research opportunities considering their catalytic activity. Some remarks are made in the context of green chemistry, with quantitative analysis using e-factor calculations. In this perspective, the importance of Knoevenagel chemistry exemplified, which is repeatedly overlooked throughout history.

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Section: Introductionmentioning

confidence: 99%

The Knoevenagel reaction: a review of the unfinished treasure map to forming carbon–carbon bonds

Beurden

Koning

Molendijk

et al. 2020

Green Chemistry Letters and Reviews

125

View full text Add to dashboard Cite

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“…In the past few decades, various developments were achieved utilising different catalytic conditions, such as Lewis acid‐catalysed, nanocatalysts, organocatalysts and ionic liquids [27–29] . The Knoevenagel condensed products reached a stage of excellence in the field of medicinal chemistry, owing to their pharmacological properties such as antiviral, anti‐tubercular, anti‐Parkinson's, antidiabetic, antioxidant and anticancer activities [30–41] . Natural products like ajmalicine ( 1 , antihypertensive alkaloid) and pharmaceuticals like AMG 837 ( 2 , type II diabetes) and clinical agents such as atorvastatin ( 3 , cardiovascular disease), lumefantrine ( 4 , malaria) and sunitinib ( 5 , gastrointestinal stromal tumor) are the representatives prepared by utilising Knoevenagel reaction (Figure 1).…”

Section: Pharmaceutical Significance Of the Knoevenagel Reactionmentioning

confidence: 99%

“…[27][28][29] The Knoevenagel condensed products reached a stage of excellence in the field of medicinal chemistry, owing to their pharmacological properties such as antiviral, anti-tubercular, anti-Parkinson's, antidiabetic, antioxidant and anticancer activities. [30][31][32][33][34][35][36][37][38][39][40][41] Natural products like ajmalicine (1, antihypertensive alkaloid) and pharmaceuticals like AMG 837 (2, type II diabetes) and clinical agents such as atorvastatin (3, cardiovascular disease), lumefantrine (4, malaria) and sunitinib (5, gastrointestinal stromal tumor) are the representatives prepared by utilising Knoevenagel reaction (Figure 1). [17,[42][43][44] Dr. Ramya Tokala was born in Vijayawada, Andhra Pradesh, India, in 1991.…”

Section: Pharmaceutical Significance Of the Knoevenagel Reactionmentioning

confidence: 99%

Contribution of Knoevenagel Condensation Products toward the Development of Anticancer Agents: An Updated Review

2022

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Knoevenagel condensation is an entrenched, prevailing, prominent arsenal following greener principles in the generation of α, β-unsaturated ketones/carboxylic acids by involving carbonyl functionalities and active methylenes. This reaction has proved to be a major driving force in many multicomponent reactions indicating the prolific utility toward the development of biologically fascinating molecules. This eminent reaction was acclimatised on different pharmacophoric aldehydes (benzimidazole, β-carboline, phenanthrene, indole, imidazothiadiazole, pyrazole etc.) and active methylenes (oxindole, barbituric acid, Meldrum's acid, thiazolidinedione etc.) to generate the library of chemical compounds. Their potential was also explicit to understand the significance of functionalities involved, which thereby evoke further developments in drug discovery. Furthermore, most of these reaction products exhibited remarkable anticancer activity in nanomolar to micromolar ranges by targeting different cancer targets like DNA, microtubules, Topo-I/II, and kinases (PIM, PARP, NMP, p300/CBP) etc. This review underscores the efficiency of the Knoevenagel condensation explored in the past six-year to generate molecules of pharmacological interest, predominantly toward cancer. The present review also provides the aspects of structure-activity relationships, mode of action and docking study with possible interaction with the target protein.

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“…Most procedures for the preparation of 3-substituted 5-alkyl/arylidene hydantoins involve a Knoevenagel-type condensation (as already described above) preceded or followed by a substitution reaction at the N- 3 nitrogen of the hydantoin by alkylation with a halogeno derivative or by Mitsunobu reaction with an alcohol (Scheme ). − This protocol enabled notably pyren-1-ylidene hydantoins, 5-arylidene-3-(4-substituted benzyl)sulfonylhydantoins, 3-phenethyl-5-furfurylmethylidene hydantoin, chromophore-containing arylidene hydantoins, 3-methoxyphenyl-5-(3-bromo-4-hydroxy)-benzylidene hydantoin, and other 3-acetamide-5-arylidene hydantoin derivatives to be prepared (Figure ). ,− …”

Section: Alkylidene Hydantoinsmentioning

confidence: 99%

Recent Advances in the Synthesis of Hydantoins: The State of the Art of a Valuable Scaffold

et al. 2017

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The review highlights the hydantoin syntheses presented from the point of view of the preparation methods. Novel synthetic routes to various hydantoin structures, the advances brought to the classical methods in the aim of producing more sustainable and environmentally friendly procedures for the preparation of these biomolecules, and a critical comparison of the different synthetic approaches developed in the last twelve years are also described. The review is composed of 95 schemes, 8 figures and 528 references for the last 12 years and includes the description of the hydantoin-based marketed drugs and clinical candidates.

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Synthesis and antidiabetic activity of 2,4-thiazolidindione, imidazolidinedione and 2-thioxo-imidazolidine-4-one derivatives bearing 6-methyl chromonyl pharmacophore

Cited by 19 publications

References 18 publications

The Knoevenagel reaction: a review of the unfinished treasure map to forming carbon–carbon bonds

The Knoevenagel reaction: a review of the unfinished treasure map to forming carbon–carbon bonds

Contribution of Knoevenagel Condensation Products toward the Development of Anticancer Agents: An Updated Review

Recent Advances in the Synthesis of Hydantoins: The State of the Art of a Valuable Scaffold

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