Synergistic Catalysis of Ag(I) and Organo‐<i>N</i>‐heterocyclic Carbenes: One‐Pot Synthesis of New Anticancer Spirooxindole‐1,4‐dihydropyridines

Balaboina, Ramesh; Thirukovela, Narasimha Swamy; Kankala, Shravankumar; Sridhar, Balasubramanian; Bathula, Surendar Reddy; Vadde, Ramakrishna; Jonnalagadda, Sreekantha B.; Vasam, Chandra Sekhar

doi:10.1002/slct.201803507

Cited by 17 publications

(6 citation statements)

References 158 publications

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“…Ag(I)‐NHCs are air‐stable and exhibit an equilibrium between neutral and ionic structures in solution. This methodology allowed the researchers to develop a methodology with good reaction scopes (15 examples), short reaction times under mild reaction conditions, affording the spirooxindole‐1,4‐dihydropyridines in good yields [174] . In summary, the authors suggested that there is condensation of the cyclic ketone with ammonium acetate to form an enamine that undergoes Michael reaction with the isatylidene malononitrile derivatives (the Knoevenagel condensed product) to form an adduct that after heterocyclization and subsequent tautomerism affords the desired spirooxindole derivatives (Scheme 91).…”

Section: Spirooxindole Derivativesmentioning

confidence: 99%

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Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Brandão

Marques

Carreiro

et al. 2021

The Chemical Record

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Multicomponent reactions (MCRs) are a valuable tool in diversity‐oriented synthesis. Its application to privileged structures is gaining relevance in the fields of organic and medicinal chemistry. Isatin, due to its unique reactivity, can undergo different MCRs, affording multiple interesting scaffolds, namely oxindole‐derivatives (including spirooxindoles, bis‐oxindoles and 3,3‐disubstituted oxindoles) and even, under certain conditions, ring‐opening reactions occur that leads to other heterocyclic compounds. Over the past few years, new methodologies have been described for the application of this important and easily available starting material in MCRs. In this review, we explore these novelties, displaying them according to the structure of the final products obtained.

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Section: Spirooxindole Derivativesmentioning

confidence: 99%

“…Dinuclear Zn [45] CuI/DBU [51] CuSO 4 .5H 2 O [54] , [55] , [59] chiral guanidine/CuI [191] Ag(I)‐NHC complex [174] …”

Section: Spirooxindole Derivativesmentioning

confidence: 99%

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Brandão

Marques

Carreiro

et al. 2021

The Chemical Record

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“…Balaboina and his colleagues (Balaboina et al, 2019) have prepared spiro oxindole-hydroquinolines (90), which paves a contemporary pathway for the drugs against cancer cells employing a single-pot method aside from Ag(I) and organo-N-heterocyclic carbenes used as a catalyst. This new catalyst was a progeny from labile Ag(I)-NHC in ethanol; therefore, it accommodates acidic Ag(I) alongside a basic NHC.…”

Section: Miscellaneous Catalystsmentioning

confidence: 99%

“…Such properties include calcium channel blocking, anti-mycobacterial, antioxidant, anti-dyslipidemic, Alzheimer's disease, and antidiabetic activities (Kumar et al, 2010;Sirisha et al, 2011;Niaz et al, 2015;Schaller et al, 2018;Malek et al, 2019). Because of the growing reputation of dihydropyridines in the pharmaceutical field, numerous MCRs have been designed to synthesise 1,4-dihydropyridine scaffolds by utilising various heterogeneous catalysts (da Costa Cabrera et al, 2019;Rajesh et al, 2013;Mahinpour et al, 2018;Heydari et al, 2016;Bhaskaruni et al, 2017;Balaboina et al, 2019). Thus, the new MCRs with green protocols have drawn considerable interest, mainly in organic synthesis, drug development, and material science areas with green approaches using effective recyclable heterogeneous catalysts, sustainable procedures with remarkable atom, and carbon efficiency as added benefits.…”

Section: Introductionmentioning

confidence: 99%

Recent Progresses in the Multicomponent Synthesis of Dihydropyridines by Applying Sustainable Catalysts Under Green Conditions

et al. 2021

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The synthesis of dihydropyridines, valuable molecules with diverse therapeutic properties, using eco-friendly heterogeneous catalysts as a green alternative received significant consideration. By selecting appropriate precursors, these compounds can be readily modified to induce the desired properties in the target product. This review focused on synthesising diverse dihydropyridine derivatives in single-pot reactions using magnetic, silica, and zirconium-based heterogeneous catalytic systems. The monograph describes preparation techniques for various catalyst materials in detail. It covers facile and benign magnetic, silica, zirconium-based, and ionic liquid catalysts, exhibiting significant efficacy and consistently facilitating excellent yields in short reaction times and in a cost-effective way. Most of the designated protocols employ Hantzsch reactions involving substituted aldehydes, active methylene compounds, and ammonium acetate. These reactions presumably follow Knoevenagel condensation followed by Michael addition and intra-molecular cyclisation. The multicomponent one-pot protocols using green catalysts and solvents have admirably increased the product selectivity and yields while minimising the reaction time. These sustainable catalyst materials retain their viability for several cycles reducing the expenditure are eco-friendly.

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“…Dihydropyridines are well known for their calcium channel blocking activity [10] . However, off‐lately, anticancer properties of 1,4‐DHP derivatives have attracted a great deal of interest among medicinal chemists [11–15] . There are very few articles reported that discuss their anticancer activity.…”

Section: Introductionmentioning

confidence: 99%

Microwave‐Assisted Synthesis of 4‐Aryl‐1,4‐dihydropyridines as Potent Anticancer Agent and Their In‐Silico Studies

et al. 2022

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In our effort directed toward the discovery of novel potent anticancer agents, a large library of novel 4‐aryl‐1,4‐dihydropyridines (23‐58) with heterocyclic ring at 4, position of aryl group has been synthesized through Hantzsch synthesis. These synthesized hybrids have been well characterized and evaluated for their cytotoxic activities against a panel of human cancer cell lines viz. EAC, HEK, and MCF cell lines by MTT assay. The cytotoxic activity has been revealed by the effects of various types of substituent present on the dihydropyridine ring. All the synthetics (23‐58) have shown good potency against EAC cell line. However, compounds 36, 40, 42, and 54 have displayed significant inhibitory potential against both EAC and MCF‐7 cell lines. In addition, these promising analogues have been selected for their molecular docking studies against 5TVQ protein to know the binding affinity which was identified to be a plausible target site. Compound 42 has exerted the highest inhibition effect on cancerous cells and more potency than the reference drug, doxorubicin even at low concentration (1μg/ml) and showed non‐toxicity to human normal cells suggesting high safety to normal cells. Compound 42 has also shown the highest docking score and inhibition constant which could be regarded as convincing lead for further clinical pursuit.

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Synergistic Catalysis of Ag(I) and Organo‐N‐heterocyclic Carbenes: One‐Pot Synthesis of New Anticancer Spirooxindole‐1,4‐dihydropyridines

Cited by 17 publications

References 158 publications

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Recent Progresses in the Multicomponent Synthesis of Dihydropyridines by Applying Sustainable Catalysts Under Green Conditions

Microwave‐Assisted Synthesis of 4‐Aryl‐1,4‐dihydropyridines as Potent Anticancer Agent and Their In‐Silico Studies

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