59256-46-1Relevant academic research and scientific papers
General synthetic approach towards annelated 3a,6-epoxyisoindoles by tandem acylation/IMDAF reaction of furylazaheterocycles. Scope and limitations
Zubkov, Fedor I.,Nikitina, Eugenia V.,Galeev, Timur R.,Zaytsev, Vladimir P.,Khrustalev, Victor N.,Novikov, Roman A.,Orlova, Daria N.,Varlamov, Alexey V.
, p. 1659 - 1690 (2014/02/14)
An efficient and versatile one-pot synthesis of 3,6a-epoxyisoindoles annelated with oxazine, oxazole, thiazine, thiazole, pyrimidine fragments and with their benzoannelated analogues is presented. The method is based on tandem N-acylation/intramolecular cycloaddition (the intramolecular Diels-Alder reaction of furan, IMDAF) reaction between α,β-unsaturated acid anhydrides and α-furyl substituted azaheterocycles. The latter can be easily prepared by condensation of diverse furfurals and 1,2- or 1,3-N,X-binucleophiles (aminoalcohols, aminothiols, diamines). The observed IMDAF reaction is stereoselective: exo-adducts are formed exclusively with large prevalence of one of the diastereoisomers. In most cases, the condensation/N-acylation/IMDAF reaction sequence may be carried out via a one-pot domino protocol. The scope and limitations of the proposed approach are thoroughly investigated. The obtained Diels-Alder adducts are attractive and useful substrates for further transformations. Fused isoindoles can be prepared from them in one-step by aromatization of the 7-oxabicyclo[2.2.1]heptene ring. Other transformations, including halogenation, ring cleavage, and Wagner-Meerwein skeletal rearrangement, are also demonstrated. The spatial structures of the obtained compounds have been established by X-ray diffraction analyses.
Synthesis and antifungal activity of N-(alkyl/aryl)-2-(3-oxo-1,4- benzothiazin-2-yl)acetamide
Gupta,Wagh
, p. 697 - 702 (2007/10/03)
A series of N-(alkyl/aryl)-2-(3-oxo-1,4-benzothiazin-2-yl)acetamide have been synthesized by condensation of substituted amines with maleic anhydride (MA) followed by cyclization with o-aminothiophenol (o-ATP). All the compounds have been screened for their antifungal activity against Tricophyton rubrum, Epidermophyton floccosum and Malassazia furfur. In the primary screening, some of the compounds exhibited appreciable activity. The structures of the synthesized compounds 7a-z have been established on the basis of elemental analysis and spectral data.
Reversible and irreversible inhibitory activity of succinic and maleic acid derivatives on acetylcholinesterase
Trujillo-Ferrara,Vazquez, Ivan,Espinosa, Judith,Santillan, Rosa,Farfan, Norberto,Hoepfl, Herbert
, p. 313 - 322 (2007/10/03)
Aryl succinic and maleic acid derivatives are potent inhibitors of bovine acetylcholinesterase in vitro. Succinic acid aminophenol derivatives 1b-e and 2b-d act as reversible inhibitors of acetylcholinesterase, while maleic acid aminophenol derivatives 3b-d and 4c-e act as choline subsite-directed irreversible inhibitors, detected by dialysis in the presence of edrophonium. Linear relationships between the logarithm of the velocity of hydrolysis of acetylcholine plotted against the time of incubation at several different inhibitor concentrations were determined. The Ki for reversible competitive inhibitors was determined. For irreversible inhibitors the Ki for the dissociation constant of the enzyme-inhibitor complex at the beginning of the recognition process was also determined as well as the inactivation constant of the enzyme-inhibitor adduct formation k+2 and the bimolecular inhibition constant ki for the inhibition of acetylcholinesterase by aminophenol derivatives 3b-d and 4c-e. The conclusions of this study can be summarized as follows for both families: (a) the aromatic moiety played a critical role in the recognition of the active site; (b) in case of the reversible inhibitor, when the ester function took the place of the hydroxyl fragment, there was an important increase in the affinity; and (c) the distance between phenolic hydroxyl and nitrogen was critical because the inhibition is ortho?metapara.
Synthesis and antimicrobial activities of N-substituted imides
Zentz, Frederic,Valla, Alain,Le Guillou, Regis,Labia, Roger,Mathot, Anne-Gabrielle,Sirot, Danielle
, p. 421 - 426 (2007/10/03)
In the field of our research programs concerning novel antimicrobial agents, a series of N-substituted imides was synthesized. These compounds were obtained by cyclization of amido-acids in acetic anhydride/sodium acetate or hexamethyldisilazane/zinc bromide for the hydroxy-aromatic derivatives. The hydroxy-alkyl maleimides were directly prepared by condensation of the corresponding amino-alcohol with maleic anhydride in boiling toluene. Most of N-substituted maleimides showed an interesting antimicrobial activity towards bacteria from the ATCC collection (Staphylococcus aureus ATCC 25923, Enterococcus faecalis ATCC 29212, Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853) but the MIC values for P. aeruginosa were always high (128 μg/ml). The imides with alkyl substituents showed higher activities than aromatic analogues with MIC values in the range of 8-32 μg/ml. Comparatively, succinimides were practically inactive.
1H and 13C NMR spectra for a series of arylmaleamic acids, arylmaleimides, arylsuccinamic acids and arylsuccinimides
Trujillo-Ferrara, Jose,Santillan, Rosa,Beltran, Hiram I.,Farfan, Norberto,Hoepfl, Herbert
, p. 682 - 686 (2007/10/03)
The 1H and 13C NMR spectra of 17 succinic anhydride derivatives and 25 maleic anhydride derivatives were completely assigned using one- and two-dimensional NMR techniques. Copyright
A Simple Synthesis of 2,2'-Bisbenzimidazolylethylen And Its Analogues
Dash, Bhabagrahi,Dora, Essilidi K.,Panda, Chandra S.
, p. 697 - 698 (2007/10/02)
o-Aminomaleanilic acid (IIa) has been conveniently prepared and employed as a novel synthon for one-step synthesis of 2,2'-bisbenzimidazolylethylene (IIIa) in polyphosphoric acid medium.Analogous compounds (IIIb-f)have also been synthesized from o-hydroxy- and o-mercaptomaleanilic acids (IIb and IIc) following a similar procedure.
