An alternative approach: a highly selective dual responding fluoride sensor having active methylene group as binding site

2012 ◽  
Vol 10 (11) ◽  
pp. 2263 ◽  
Author(s):  
Priyadip Das ◽  
Manoj K. Kesharwani ◽  
Amal K. Mandal ◽  
Eringathodi Suresh ◽  
Bishwajit Ganguly ◽  
...  
Keyword(s):  
Binding Site ◽  
Alternative Approach ◽  
Fluoride Sensor ◽  
Active Methylene ◽  
Methylene Group

A New Reactive Ketenaminal: Synthesis, Coupling Reaction, Tautomeric Study, Docking and Antimicrobial Evaluation of the Products

2020 ◽  
Vol 16 (6) ◽  
pp. 761-773
Author(s):  
Huda K. Mahmoud ◽  
Hanadi A. Katouah ◽  
Marwa F. Harras ◽  
Thoraya A. Farghaly
Keyword(s):  
Binding Site ◽  
Antimicrobial Agents ◽  
Coupling Reaction ◽  
Docking Study ◽  
Binding Mode ◽  
Binding Energies ◽  
Simple Method ◽  
Antimicrobial Evaluation ◽  
New Compounds ◽  
Active Methylene

Background: One of the most successful reagents used in the synthesis of the reactive enaminone is DMF-DMA, but it is very expensive with harmful effects on the human health and reacts with special compounds to generate the enaminone such as active methylene centers. Aim: In this article, we synthesized a new ketenaminal by simple method with inexpensive reagents (through desulfurization in diphenylether). Methods: Thus, a novel reactive ketenaminal (enaminone) was synthesized from the desulfurization of 2-((2-(4-chlorophenyl)-2-oxoethyl)thio)-5,7-bis(4-methoxyphenyl)pyrido[2,3-d]pyrimidin- 4(3H)-one with diphenylether. The starting keteneaminal was coupled with diazotized anilines via the known coupling conditions to give a new series of 2-(4-chlorophenyl)-1-(2-(arylhydrazono)-2- oxoethyl)-5,7-bis(4-methoxy-phenyl)pyrido[2,3-d]pyrimidin-4(1H)-ones. Results: The structures of the new compounds were elucidated based on their IR, 1H-NMR, 13CNMR, and Mass spectra. Moreover, the potency of these compounds as antimicrobial agents has been evaluated. The results showed that some of the products have high activity nearly equal to that of the used standard antibiotic. Additionally, the docking study was done to get the binding mode of the synthesized compounds with the binding site of the DHFR enzyme. The results of molecular docking of the synthesized arylhydrazono compounds are able to fit in DHFR binding site with binding energies ranging from -4.989 to -8.178 Kcal/mol. Conclusion: Our goal was achieved in this context by the synthesis of new ketenaminal from inexpensive reagents, which was utilized in the preparation of bioactive arylhydrazone derivatives.

Synthesis and Transformations of Ethyl 3-Formyl-1H-indole-2-carboxylate. Preparation of Aplysinopsin and β-Carboline Thiohydantoin Analogues

2006 ◽  
Vol 61 (4) ◽  
pp. 413-419 ◽  
Author(s):  
Renata Jakše ◽  
David Bevk ◽  
Amalija Golobič ◽  
Jurij Svete ◽  
Branko Stanovnik
Keyword(s):  
Thiobarbituric Acid ◽  
Active Methylene ◽  
Methylene Group

Various aplysinopsin and β -carboline thiohydantoin analogues were prepared starting from ethyl 3-formyl-1H-indole-2-carboxylate by condensation with the active methylene group of 2-thiohydantoin, rhodanine, or thiobarbituric acid derivatives

THIAZOLIDINEDIONES: REACTIVITY OF THE ACTIVE METHYLENE GROUP

1997 ◽  
Vol 3 (4) ◽  
Author(s):  
V.L.M. GUARDA ◽  
M. PERRISSIN ◽  
I.R. PITTA ◽  
S.L. GALDINO ◽  
C. LUU DUC
Keyword(s):  
Active Methylene ◽  
Methylene Group

Heterocyclization of thioamides containing an active methylene group (review)

2008 ◽  
Vol 44 (12) ◽  
pp. 1429-1459 ◽  
Author(s):  
V. N. Britsun ◽  
A. N. Esipenko ◽  
M. O. Lozinskii
Keyword(s):  
Active Methylene ◽  
Methylene Group

Chemistry and Tautomerism of Coupling Products of Diazotised Sulfamethoxazole with some Compounds Containing an Active Methylene Group

2002 ◽  
Vol 2002 (2) ◽  
pp. 64-65 ◽  
Author(s):  
Saber M. Hassan ◽  
Hussein A. Emam ◽  
Mohamed A. Habib
Keyword(s):  
Azo Compounds ◽  
Active Methylene ◽  
Methylene Group

Azo compounds (2–5) bearing a sulfamethoxazole moiety were prepared. The action of hydrazinecarbodithioate derivatives on (2–4) afforded pyrazoledithiocarboxylates (8–10).

scholarly journals [1,5]-Hydride Shift-Cyclization versus C(sp2)-H Functionalization in the Knoevenagel-Cyclization Domino Reactions of 1,4- and 1,5-Benzoxazepines

Molecules ◽  
2020 ◽  
Vol 25 (6) ◽  
pp. 1265 ◽  
Author(s):  
Dóra Szalóki Vargáné ◽  
László Tóth ◽  
Balázs Buglyó ◽  
Attila Kiss-Szikszai ◽  
Attila Mándi ◽  
...  
Keyword(s):  
Density Functional ◽  
Time Dependent ◽  
Chiral Hplc ◽  
Cyclization Reactions ◽  
Substitution Pattern ◽  
Functional Theory ◽  
Hydride Shift ◽  
Ic50 Value ◽  
Active Methylene ◽  
Methylene Group

Domino cyclization reactions of N-aryl-1,4- and 1,5-benzoxazepine derivatives involving [1,5]-hydride shift or C(sp2)-H functionalization were investigated. Neuroprotective and acetylcholinesterase activities of the products were studied. Domino Knoevenagel-[1,5]-hydride shift-cyclization reaction of N-aryl-1,4-benzoxazepine derivatives with 1,3-dicarbonyl reagents having active methylene group afforded the 1,2,8,9-tetrahydro-7bH-quinolino [1,2-d][1,4]benzoxazepine scaffold with different substitution pattern. The C(sp3)-H activation step of the tertiary amine moiety occurred with complete regioselectivity and the 6-endo cyclization took place in a complete diastereoselective manner. In two cases, the enantiomers of the chiral condensed new 1,4-benzoxazepine systems were separated by chiral HPLC, HPLC-ECD spectra were recorded, and absolute configurations were determined by time-dependent density functional theory- electronic circular dichroism (TDDFT-ECD) calculations. In contrast, the analogue reaction of the regioisomeric N-aryl-1,5-benzoxazepine derivative did not follow the above mechanism but instead the Knoevenagel intermediate reacted in an SEAr reaction [C(sp2)-H functionalization] resulting in a condensed acridane derivative. The AChE inhibitory assays of the new derivatives revealed that the acridane derivative had a 6.98 μM IC50 value.

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