A Facile Synthesis and Discovery of Highly Functionalized Tetrahydro-pyridines and Pyridines as Antimycobacterial Agents

Kumar, Raju Suresh; Rajesh, Stephen Michael; Perumal, Subbu; Banerjee, D.; Yogeeswari, Perumal; Sriram, Dharmarajan

doi:10.1248/cpb.58.602

Cited by 11 publications

(4 citation statements)

References 43 publications

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“…As shown in previous reports, the heterocyclic scaffold of a crop protection agent positively drives uptake and bioavailability, in most cases delivering better biological efficacy 13,14 . Pyridine‐based compounds have been playing a crucial role as agrochemicals including fungicides, insecticides/acaricides and herbicides 15,16 . In our continuing efforts to develop new fungicidal agents, we explored a hybrid scaffold combining the structures of heterocyclic or pyridine motif and gefitinib 17 .…”

Section: Introductionmentioning

confidence: 95%

“…13,14 Pyridine-based compounds have been playing a crucial role as agrochemicals including fungicides, insecticides/ acaricides and herbicides. 15,16 In our continuing efforts to develop new fungicidal agents, we explored a hybrid scaffold combining the structures of heterocyclic or pyridine motif and gefitinib. 17 This new series of simplified quinazolin-6-ylcarboxylates contain the N-(3-chloro-4-fluorophenyl)quinazolin-4-amine moiety, which represents the binding group of ATP-binding site of gefitinib, 18 combined with heterocyclic or pyridine motif through ester bond.…”

Section: Introductionmentioning

confidence: 99%

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Fungicidal activity of novel quinazolin‐6‐ylcarboxylates and mode of action on Botrytis cinerea

Yan

Chen

et al. 2023

Pest Management Science

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BACKGROUND Fungal diseases remain important causes of crop failure and economic losses. As the resistance toward current selective fungicides becomes increasingly problematic, it is necessary to develop efficient fungicides with novel chemotypes. RESULTS A series of novel quinazolin‐6‐ylcarboxylates which combined the structures of pyridine or heterocyclic motif and the N‐(3‐chloro‐4‐fluorophenyl)quinazolin‐4‐amine moiety, a binding group of ATP‐binding site of gefitinib, were evaluated for their fungicidal activity on different phytopathogenic fungi. Most of these compounds showed excellent fungicidal activities against Botrytis cinerea and Exserohilum rostratum, especially compound F17 displayed the highest activity with EC50 values as 3.79 μg mL−1 against B. cinerea and 2.90 μg mL−1 against E. rostratum, which was similar to or even better than those of the commercial fungicides, such as pyraclostrobin (EC50, 3.68, 17.38 μg mL−1) and hymexazol (EC50, 4.56, 2.13 μg mL−1). Moreover, compound F17 significantly arrested the lesion expansion of B. cinerea infection on tomato detached leaves and strongly suppressed grey mold disease on tomato seedlings in greenhouse. The abilities of compound F17 to induce cell apoptosis of the non‐germinated spores, to limit oxalic acid production, to reduce malate dehydrogenase (MDH) expression, and to block the active pocket of MDH protein were demonstrated in B. cinerea. CONCLUSION The novel quinazolin‐6‐ylcarboxylates containing ATP‐binding site‐directed moiety, especially compound F17, could be developed as a potential fungicidal candidate for further study. © 2023 Society of Chemical Industry.

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Section: Introductionmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

Fungicidal activity of novel quinazolin‐6‐ylcarboxylates and mode of action on Botrytis cinerea

Yan

Chen

et al. 2023

Pest Management Science

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“…THP derivatives were also converted into pyridine derivatives that exhibited relatively higher activity. 33 Another multicomponent reaction of aromatic aldehydes, arylamines, and β -ketoester in the presence of bismuth nitrate was carried out by Yankin et al 34 It resulted in the formation of alkyl 4-arylamino-1,2,6-triaryl-1,2,5,6-THPs-3-carboxylates. Compounds 12, 13, 14, and 15 were found to be weakly active antibacterial agents (MIC = 250 µ g/mL against E. coli and S. aureus) as compared to standard antibiotics.…”

Section: Thps As Antibacterial Agentsmentioning

confidence: 99%

Tetrahydropyridine: a promising heterocycle for pharmacologically active molecules

Mohsin¹,

Ahmad²

2018

Turk J Chem

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The tetrahydropyridine (THP) ring system has received considerable focus due to its excellent ability to act as a pharmacophore. It is recognized as a major constituent in natural alkaloids. THP derivatives have been reported for a diverse range of biological activities. Recent synthetic works contain syntheses of monosubstituted, disubstituted, trisubstituted, highly functionalized, and condensed structures. In this review, we summarize the recent literature dealing with the bioactive nature of this important heterocycle.

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“…The product comprising three diastereomeric enols, 113-115 were extracted with ether and separated by column chromatography (Scheme 23). 47 These THPD esters was further dehydrogenated with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) to generate functionalized pyridines in excellent yields. These novel heterocycles was observed to possess good to excellent in vitro activity against Mycobacterium tuberculosis H37Rv.…”

Section: Using Ammonium Acetate As Amino Sourcementioning

confidence: 99%

Recent developments in multicomponent synthesis of structurally diversified tetrahydropyridines

2016

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A Facile Synthesis and Discovery of Highly Functionalized Tetrahydro-pyridines and Pyridines as Antimycobacterial Agents

Cited by 11 publications

References 43 publications

Fungicidal activity of novel quinazolin‐6‐ylcarboxylates and mode of action on Botrytis cinerea

Fungicidal activity of novel quinazolin‐6‐ylcarboxylates and mode of action on Botrytis cinerea

Tetrahydropyridine: a promising heterocycle for pharmacologically active molecules

Recent developments in multicomponent synthesis of structurally diversified tetrahydropyridines

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