Design, parallel synthesis of Biginelli 1,4-dihydropyrimidines using PTSA as a catalyst, evaluation of anticancer activity and structure activity relationships via 3D QSAR studies

Faizan, Syed; Kumar, B. R. Prashantha; Naishima, Namburu Lalitha; Ashok, Tara Devi S.; Justin, Antony; Kumar, Mukesh; Chandrashekarappa, Revanasiddappa Bistuvalli; Raghavendra, Narasimha; Kabadi, Pradeep; Adhikary, Laxmi

doi:10.1016/j.bioorg.2021.105462

Cited by 10 publications

(4 citation statements)

References 35 publications

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“…CoMSIA investigations were also carried out to derive the structure–activity relationship in a 3D grid space by graphing experimental versus projected cytotoxic activities. [ 84 ] According to Nishimura et al, an effective synthesis procedure for the brand‐new 2‐oxo/thioxo‐1,2,3,4‐tetrahydropyrimidines was created. These techniques were extremely useful for synthesizing 4,4‐disubstituted 2‐oxo/thioxo‐1,2,3,4‐tetrahydropyrimidines, which are not synthesized by standard techniques.…”

Section: Biological Applicationsmentioning

confidence: 99%

Catalytic role in Biginelli reaction: Synthesis and biological property studies of 2‐oxo/thioxo‐1,2,3,4‐tetrahydropyrimidines

Kamat

Reddy

Kumar

2023

Archiv der Pharmazie

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The Biginelli reaction has received significant consideration in recent years due to its easily accessible aldehyde, urea/thiourea, and active methylene compounds. When it comes to pharmacological applications, the Biginelli reaction end‐products, the 2‐oxo‐1,2,3,4‐tetrahydropyrimidines, are vital in pharmacological applications. Due to the ease of carrying out the Biginelli reaction, it offers a number of exciting prospects in various fields. Catalysts, however, play an essential role in Biginelli's reaction. In the absence of a catalyst, it is difficult to form products with a good yield. Many catalysts have been used in search of efficientmethodologies, including biocatalysts, Brønsted/Lewis acids, heterogeneous catalysts, organocatalysts, and so on. Nanocatalysts are currently being applied in the Biginelli reaction to improve the environmental profile as well as speed up the reaction process. This review describes the catalytic role in the Biginelli reaction and pharmacological application of 2‐oxo/thioxo‐1,2,3,4‐tetrahydropyrimidines. This study provides information that will facilitate the development of newer catalytic methods for the Biginelli reaction, by academics as well as industrialists. It also offers a broad scope for drug design strategies, which may enable the development of novel and highly effective bioactive molecules.

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Section: Biological Applicationsmentioning

confidence: 99%

Catalytic role in Biginelli reaction: Synthesis and biological property studies of 2‐oxo/thioxo‐1,2,3,4‐tetrahydropyrimidines

Kamat

Reddy

Kumar

2023

Archiv der Pharmazie

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“…Recently, the parallel synthesis of new Biginelli 1,4-dihydropyrimidines 71 was reported by Faizan et al [99]. The desired compounds were synthesized via parallel synthesis by multicomponent-cyclisation reaction between aliphatic, aryl, heteroaryl aldehydes, o-methyl acetoacetanilide 70, and excess of urea or thiourea 1 in absolute ethanol and using p-toluen sulfonic acid as catalyst (Scheme 32).…”

Section: Beta-ketoamides and Beta-ketosulfonamidesmentioning

confidence: 99%

Synthesis of 3,4-Dihydropyrimidin(thio)one Containing Scaffold: Biginelli-like Reactions

et al. 2022

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The interest in 3,4-dihydropyrimidine-2(1H)-(thio)ones is increasing every day, mainly due to their paramount biological relevance. The Biginelli reaction is the classical approach to reaching these scaffolds, although the product diversity suffers from some limitations. In order to overcome these restrictions, two main approaches have been devised. The first one involves the modification of the conventional components of the Biginelli reaction and the second one refers to the postmodification of the Biginelli products. Both strategies have been extensively revised in this manuscript. Regarding the first one, initially, the modification of one of the components was covered. Although examples of modifications of the three of them were described, by far the modification of the keto ester counterpart was the most popular approach, and a wide variety of different enolizable carbonylic compounds were used; moreover, changes in two or the three components were also described, broadening the substitution of the final dihydropyrimidines. Together with these modifications, the use of Biginelli adducts as a starting point for further modification was also a very useful strategy to decorate the final heterocyclic structure.

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“…It involves the design, synthesis, and optimization of molecules to target specific biological mechanisms or disease processes. 1 Diverse methods are employed to comprehend the molecular basis of disease, to identify drug targets, and to design molecules that interact with these drug targets with therapeutic advantages. 2,3 Studies of structure–activity relationships (SARs) advise the modification of lead compounds to increase their therapeutic efficacy and decrease their toxicity.…”

Section: Introductionmentioning

confidence: 99%

Anticancer potential of novel symmetrical and asymmetrical dihydropyridines against breast cancer via EGFR inhibition: molecular design, synthesis, analysis and screening

Faizan,

Talath,

Wali

et al. 2024

RSC Adv.

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Design, parallel synthesis of Biginelli 1,4-dihydropyrimidines using PTSA as a catalyst, evaluation of anticancer activity and structure activity relationships via 3D QSAR studies

Cited by 10 publications

References 35 publications

Catalytic role in Biginelli reaction: Synthesis and biological property studies of 2‐oxo/thioxo‐1,2,3,4‐tetrahydropyrimidines

Catalytic role in Biginelli reaction: Synthesis and biological property studies of 2‐oxo/thioxo‐1,2,3,4‐tetrahydropyrimidines

Synthesis of 3,4-Dihydropyrimidin(thio)one Containing Scaffold: Biginelli-like Reactions

Anticancer potential of novel symmetrical and asymmetrical dihydropyridines against breast cancer via EGFR inhibition: molecular design, synthesis, analysis and screening

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