Fluorescence Properties of Donor Acceptor Chromophores on Newly Synthesized Pyridine-3-Carbonitriles

Toche, Raghunath B.; Kazi, Muddassar A.; Ghotekar, Bhausaheb K.; Bagul, Sandeep M.; Tantak, Chanda D.; Jachak, Madhukar N.

doi:10.1007/s10895-009-0511-x

Cited by 9 publications

(2 citation statements)

References 13 publications

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“…Thus, the condensation reaction of bis‐benzylidene 2 with hydroxylamine hydrochloride in aqueous sodium hydroxide in ethanol afforded the isoxazoledioxolane 3 . The reaction was performed via Micheal addition reaction, where the (OH) group of hydroxylamine attack on β‐carbon in benzylidene 2 , then followed by condensation of the amino group with carbonyl carbon of benzylidene 2 [36, 37] (Scheme 1). The structure of isoxazole 3 was elucidated by elemental analyses and spectral data.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and evaluation of a new series of spiro aryl dioxolane compounds: A new scaffold as potential poly(ADP‐ribose)polymerase‐1 (PARP‐1) inhibitors

Maigali

El-Shanawany

El‐Sayed

et al. 2022

Journal of Heterocyclic Chem

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A new series of spiro aryl dioxolane derivatives were synthesized and evaluated to find a new scaffold as potential poly(ADP-ribose)polymerases-1 (PARP-1) inhibitors. This key starting compound, 2,6-bis(methoxybenzylidene)cyclohexanone, was functionalized with different nucleophilic reagents via cyclocondensation reactions to obtain new benzylidene scaffolds containing diverse aryl groups such as spiroindazoleorquinazoline [1,3]dioxolane compounds. Furthermore, the Michael addition reaction of bis-benzylidene with some active methylene compounds afforded spirochromene-or naphthalene-[1,3]dioxolane compounds. All the synthesized compounds revealed promising inhibition with IC 50 values in the nanomolar range (0.997-2.698 nM), not significantly different from that of Olaparib (IC 50 = 0.861 nM). Compounds 5b and 15 (IC 50 = 1.009 and 0.997 nM) showed the highest potency among all the prepared compounds and accordingly their ability to inhibit the growth of BRCA1 mutated breast cancer cell line MDA-MB-436 was tested, where compound 5b (IC 50 = 0.67 μM) showed a potency ten folds higher than that of Olaparib but compound 15 (IC 50 = 7.47 μM) exerted lower activity but still comparable to that of Olaparib (IC 50 = 6.84 μM). Both resulted in the arrest of cell cycle at S phase and caused cell apoptosis. In silico studies including absorption, distribution, metabolism, excretion (ADME) properties, drug-likeness, and molecular docking were carried out to support the above-mentioned findings. This work presents compounds 5b and 15 as promising scaffolds as PARP-1 inhibitors. | INTRODUCTIONPoly(ADP-ribose) polymerases (PARPs) comprise a family of adenosine diphosphate ribosyltransferases (ADPribosyltransferases) found in all six major eukaryotic supergroups, as well as several species of prokaryotes and dsDNA virus. This family comprises 18 members that are implicated in different processes on the cellular level such as controlling genome integrity and checkpoints for the cell cycle and also have a role in the signaling pathways of DNA repair, transcription, and apoptosis. PARP proteins transfer ADP-ribose moieties to arginine, glutamate, aspartate, cysteine, lysine, and serine acceptor sites [1][2][3][4].The most abundant and well-known member is PARP-1, due to its important role in DNA damage

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Section: Resultsmentioning

confidence: 99%

Synthesis and evaluation of a new series of spiro aryl dioxolane compounds: A new scaffold as potential poly(ADP‐ribose)polymerase‐1 (PARP‐1) inhibitors

Maigali

El-Shanawany

El‐Sayed

et al. 2022

Journal of Heterocyclic Chem

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“…Electric hindrance is the build-up and rejections of electric positive charges in a step/stage of a reaction involving isomers [31]. Electric hindrances are mostly responsible for the significant differences observed in an isomeric product during organic synthesis.…”

Section: Electric Hindrance and Percentage Yield In Isomersmentioning

confidence: 99%

Syntheses, Complexation and Biological Activity of Aminopyridines: A Mini-Review

Orie¹,

Duru²,

Ngochindo³

2021

AJHC

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Aminopyridines are among the classes of heterocyclic compounds that have been extensively studied in the last few decades owing to their interesting biological activities. They exist in three isomeric forms: 2-aminopyridine, 3-aminopyridine and 4-aminopyridine. The diversity in their pharmacological activities has attracted the attention of many researchers to explore the reasons for their wide potential. This study examines recent advances related to the efficient procedure for synthesizing different types of aminopyridine derivatives, its coordination site with metals and biological activities using systematic literature review and content analysis. Other important concepts of aminopyridines discussed are basicity, electric hindrance as related to percentage yield of isomeric forms and spectra updates on the characterization of aminopyridines. The findings from this study also reveal the array of solvents used for purification processes; ideas on isomers that have not been used in the synthesis of aminopyridine derivatives and their respective biological activities. The significance of this study is on the various synthetic methods revealed, which may be helpful to the development of newer compounds with aminopyridines moieties that could offer high bioactivity and lesser toxicity.

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Synthesis of Quinolone Substituted Pyrazoles, Isoxazoles and Pyridines as a Potential Blue Luminophors

Toche¹,

Kazi²,

Patil³

et al. 2010

J Fluoresc

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Series of quinolone C(3)-substituted pyrazolines, isoxazolines, pyridines and pyrimidines were synthesized in good yields by the cyclocondensation reactions of 1, 2-unsaturated ketones and hydrazines, hydroxylamine hydrochloride and dimedone respectively. The quinolone derivatives (3, 5 and 7) were synthesized and further studied for their photophysical properties. High absorption and quantum yield are found for N(1)-phenyl and C(3,4)-dimethoxy substituents on phenyl ring (3h). Energy optimization by PM6 methods showed high stability required for selection of suitable candidates to be use as future blue emitters.

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Fluorescence Properties of Donor Acceptor Chromophores on Newly Synthesized Pyridine-3-Carbonitriles

Cited by 9 publications

References 13 publications

Synthesis and evaluation of a new series of spiro aryl dioxolane compounds: A new scaffold as potential poly(ADP‐ribose)polymerase‐1 (PARP‐1) inhibitors

Synthesis and evaluation of a new series of spiro aryl dioxolane compounds: A new scaffold as potential poly(ADP‐ribose)polymerase‐1 (PARP‐1) inhibitors

Syntheses, Complexation and Biological Activity of Aminopyridines: A Mini-Review

Synthesis of Quinolone Substituted Pyrazoles, Isoxazoles and Pyridines as a Potential Blue Luminophors

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