The construction of fluorophoric thiazolo-[2,3-b]quinazolinone derivatives: a multicomponent domino synthetic approach

Mohanta, Prajna Parimita; Pati, Hari N.; Behera, Ajaya Kumar

doi:10.1039/d0ra01066a

Cited by 14 publications

(12 citation statements)

References 40 publications

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“…Taking our previously reported results into consideration, 22 we attempted analogous one pot three component cascade reaction of equimolar mixture of 2-amino thiazole 1, aryl aldehydes 2a-h and cyclic-1,3-dicarbonyls 3a-b under acid mediated microwave heating at 150 °C in a microwave synthesizer. Here also, unexpected formation of a series of compound 5 was achieved in spite of compound 4 ( Scheme 1 ).…”

Section: Resultsmentioning

confidence: 99%

“…1 ) was also synthesized by previously reported procedure. 22 Fluorescence spectra of benzothiazoloquinazolinone (II) were then measured upon addition of 5 equivalents various metal ions. From the fluorescence spectra, it was observed that no such significant change in emission intensities at 395 nm was occurred after addition of the metal ions (see Fig.…”

Section: Resultsmentioning

confidence: 99%

“…In continuation of our interest in exploring the synthesis and study of fluorogenic properties of unique thiazolo[2,3- b ]quinazolinones via one-pot cascade reaction under microwave irradiation technique, 22 in this context, we expanded the range of accessible angular –OH functionalized thiazolo[2,3- b ]quinazolinone analogues using 2-amino thiazole precursor. Accumulating evidences towards the formation of thiazolo[2,3- b ]quinazolinones having unique structural arrangement and interesting fluorescence properties, we have investigated the selectivity and sensitivity of HSO 4 − and Hg 2+ ions in aqueous (H 2 O : MeOH, 20 : 80 v/v) medium using this novel receptor.…”

Section: Introductionmentioning

confidence: 99%

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A new class of fluorogenic thiazolo[2,3-b]quinazolinone receptor: selective detection towards mercury and hydrogen bisulfate ions in aqueous medium

et al. 2021

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A new class of fluorogenic thiazolo[2,3-b]quinazolinone receptor: selective detection towards mercury and hydrogen bisulfate ions in aqueous medium

et al. 2021

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“…cooling then poured in ice-water with stirring followed by filtration of the solid product and watching thoroughly with cold water many times to remove the excess of acids , drying then recrystallized from water (Table 1) Method B ( Mohanta, Pati & Behera, 2020): Equimolar (0.001 mole) of thioamide , dimidone and substituted benzaldehyde were mixed and irradiated under microwave oven at power (700 watt) for (1 min) in presence of (2 % mole)boric acid and (2 drops ) glacial acetic acid. Cooling followed by adding (10ml) of acetone to separate the boric acid then filtration and reduce the filtrate volume to a half by evaporation followed by adding of ice-water with stirring to afford the solid product which then filtrated off, dry followed by recrystallized form water.…”

Section: Methodsmentioning

confidence: 99%

Green and efficient protocol for synthesis a new series of fused pyrimidine derivatives incorporating thioamide moiety

Abdullah

Younis

2022

ijhs

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In the recent decades, heterocyclic compounds six membered ring occupied a great deals of attention due to its wide and varied applications in medical, pharmaceutical, agricultural and industrial fields. Herein in this work fused pyrimidine as active type of the mentioning above have been successfully prepared by using supreme green chemistry techniques represented by solid phase one-pot muticomponent reaction (Biginille reaction) and microwave irradiation via mixing equimolar of thioamide (phenyl thiourea)-dimedone and substituted Benzaldehyde in presence of (2% mole) of boric acid and few drops of glacial acetic acid as selective acid catalyst at power (700 watt) for (1 min) to afford 7,7, dimethyl-1-phenyl-4-aryl-3,4,6,7,8–5H-quinazolin-2-thione-5-one (1-7) as pure products with high persentage.

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“…A series of thirty-four fluorophoric thiazolo- [2, 3-b] quinazolinone derivatives (5aa, 5ab, …., 5bq) ( Fig. S6 ) was synthesized and characterized by Mohanta et al, (2020) (21). All the ligands were drawn in Chemdraw Ultra 8.0 and were converted into 3D MDL Mol format by using chem3D Ultra 8.0.…”

Section: Modeling Of Fluorophoric Thiazolo-[23-b] Quinazolinone Derimentioning

confidence: 99%

Molecular Modeling of Novel Fluorophoric Thiazolo- [2, 3-B] Quinazolinones to Study Epidermal Growth Factor Receptor Tyrosine Kinase Inhibition Potency

Mir¹,

Dash²,

Chopdar³

et al. 2021

Preprint

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Epidermal growth factor receptor tyrosine kinase (EGFR-TK) is one of the key regulators that exhibit pivotal role in proliferation of cancer cell. Quinazolinones are studiedly widely as effective EGFR-TK inhibitor because of their higher affinity to bind with adenosine triphosphate (ATP) binding site of receptor tyrosine kinases. However, their toxicity due to non-specific binding to tyrosine kinase in non-cancerous normally dividing cells of the body limits its applicability as a cancer therapeutics. In the present investigation a series of thirty-four novel synthesized thiazolo- [2, 3-b] quinazolinones were studied in silico as EGFR-TK inhibitors. All the thirty-four compounds were screened against EGFR-TK domain using multiple software’s (AutoDock Vina, Argus Lab, YASARA, and MOE). The interactions of the ligands with amino acid residues, namely, Lys721, Met769 and Asp831 of the active site were through the functional groups on aryl substituents at position 3 and 5 of the thiazolo- [2, 3-b] quinazolinone scaffold. The methyl substituents at position 8 of the ligands had prominent hydrophobic interactions in the active site cavity of EGFR-TK domain. The compounds 5ab, 5aq, and 5bq were predicted to be non-toxic and drug-like by in silico ADMET investigations. These compounds were considered for further investigation due to their non-toxicity and higher docking score ranking in different docking methods. The molecular dynamics (MD) simulation for 100 ns of docked complexes revealed the stability of these compounds. The binding free energy determined using Molecular Mechanics Generalized Born Model and Solvent Accessibility (MM-GBSA) method indicate that thiazolo- [2, 3-b] quinazolinone has high inhibitory efficacy similar to the standard drug, erlotinib (5ab - 22.45, 5aq -22.23, 5bq -20.76, and erlotinib -24.11 kcal/mol). In silico studies and MD simulations indicated that compounds (5ab, 5aq and 5bq) could be potential EGFR-TK inhibitors and require further validation as cancer therapeutics using carcinoma cell lines.

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The construction of fluorophoric thiazolo-[2,3-b]quinazolinone derivatives: a multicomponent domino synthetic approach

Abstract: A library of unique fluorophoric thiazolo[2,3-b]quinazolinones were synthesized under acid catalyzed one pot microwave irradiation technique.

Cited by 14 publications

References 40 publications

A new class of fluorogenic thiazolo[2,3-b]quinazolinone receptor: selective detection towards mercury and hydrogen bisulfate ions in aqueous medium

A new class of fluorogenic thiazolo[2,3-b]quinazolinone receptor: selective detection towards mercury and hydrogen bisulfate ions in aqueous medium

Green and efficient protocol for synthesis a new series of fused pyrimidine derivatives incorporating thioamide moiety

Molecular Modeling of Novel Fluorophoric Thiazolo- [2, 3-B] Quinazolinones to Study Epidermal Growth Factor Receptor Tyrosine Kinase Inhibition Potency

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