- Design and microwave-assisted synthesis of dimers of 1,5-benzodiazepine-1,2,3-triazole hybrids bearing alkyl/aryl spacers and their biological assessment
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Large series of novel N-bis-1,2,3-triazolo-linked-1,5-benzodiazepin-2-ones (BZD) have been synthesized under microwave irradiation through a Cu(I)-catalyzed double 1,3-dipolar alkyne-azide coupling reaction. This process is of considerable synthetic advantages in terms of time saving and remarkable yields. The chemical structures of the isolated compounds have been elucidated on the basis of extensive spectroscopic methods including 1D & 2D NMR, IR and HRMS. All the synthesized compounds have been evaluated for their antimicrobial and antioxidant activities. In vitro antimicrobial environment, almost all of compounds have shown an interesting activity. Among the dimers of 1,5-benzodiazepine-1,2,3-triazole compounds tested, the results revealed that the potent antibacterial was recorded to compounds 3g,l for Gram-positive (within MIC = 31.25 and 125 μg/mL), and 3h,k for Gram-negative (within MIC = 31.25 and 125 μg/mL). Besides, the results demonstrate that compounds 3h,k have demonstrated the strongest potential against all the tested fungus (within MIC = 62.5 and 125 μg/mL). The antioxidant evaluation indicated that most compounds exhibited a moderate to good biological activity.
- Jaafar, Zouhour,Chniti, Sami,Ben Sassi, Ahlem,Dziri, Hayet,Marque, Sylvain,Lecouvey, Marc,Gharbi, Rafik,Msaddek, Moncef
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- Highly diastereoselective synthesis of rigid 3-enamino-1, 5-benzodiazepines
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A variety of new (3-Z)-3-((alkyl/aryl)aminomethylene)-4-(2-hydroxyphenyl)-1, 3-dihydro-2H-1, 5-benzodiazepin-2-ones were synthesized via addition of primary amines on the benzopyrano[4, 3-c]-1H-1, 5-benzodizepin-2-one. High yields with excellent diastereoselectivity were obtained. The structure of cis-?-enamino-1, 5-benzodiazepine derivatives was characterized by 1D and 2D NMR and confirmed by an X-Ray diffraction analysis. All prepared compounds were evaluated for their in vitro antibacterial activities and promising results were given.
- Chniti, Sami,Nsira, Asma,Khouaja, Sadok,Mechria, Ali,Gharbi, Rafik,Msaddek, Moncef,Lecouvey, Marc
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- 1,5-Benzodiazepin-2-ones: Investigation of a Family of Photoluminescent Materials
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Photoluminescent materials, that are now ubiquitous in our everyday life, have particularly attracted the attention of the scientific community these past few years due to potential important applications such as in bioimaging, sensing, or optoelectronics
- Mtiraoui, Hasan,Gharbi, Rafik,Msaddek, Moncef,Bretonnière, Yann,Andraud, Chantal,Sabot, Cyrille,Renard, Pierre-Yves
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p. 4720 - 4727
(2016/07/06)
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- Solution and solid-state fluorescence of 2-(2′-hydroxyphenyl)-1,5-benzodiazepin-2-one (HBD) borate complexes
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A new family of fluorescent 1,5-benzodiazepin-2-one (HBD) borate complexes was prepared in good yields, and fully characterized by means of MS, NMR and IR spectroscopy, as well as X-ray crystal structure analysis for compound 13. Unlike their uncomplexed congeners, most of these cyclic boranils were emissive both in solution and the solid state, with maxima in the range of 426-596 nm. A systematic study of substituent effects revealed that the presence of a halogen atom specifically at position 8 of the fused-aromatic ring system led to an increase in fluorescence intensity in solution while electron rich substituents tended to extinguish the photoluminescence. Finally, a proof-of-concept study highlighted that the amide moiety of the benzodiazepinone framework could be functionalized with a chemical handle useful for subsequent specific modifications.
- Mtiraoui, Hasan,Gharbi, Rafik,Msaddek, Moncef,Bretonnière, Yann,Andraud, Chantal,Renard, Pierre-Yves,Sabot, Cyrille
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p. 86352 - 86360
(2016/10/19)
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- INHIBITORS OF THE SHIGA TOXINS TRAFFICKING THROUGH THE RETROGRADE PATHWAY
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The present invention relates to the use of compounds of general formula (I) and (II) for the preparation of a drug for preventing and/or treating disorders caused by Shiga toxins and related toxins.
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- Aroyl[bis(4-hydroxycoumarin-3-yl)]methanes in reactions with 1,2-diaminobenzenes
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The reaction of aroyl[bis(4-hydroxycoumarin-3-yl)]methanes with 1,2-phenylenediamines in PriOH is accompanied by the recyclization to 8-R-or 7-R-4-(2-hydroxyphenyl)-1,5-benzodiazepin-2-ones, whereas the reaction with o-phenylenediamine and its
- Kolos,Gozalishvili,Yaremenko,Shishkin,Shishkina,Konovalova
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p. 2277 - 2283
(2008/09/20)
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- Synthesis of some new biologically active coumarin derivatives
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The reaction of 4-hydroxycoumarin in toluene with a variety of aromatic binucleophilic compounds has been studied. 3-(Dimethylaminomethylene)chromane-2, 4-dione was used as a key intermediate for the preparation of bis[N-(4-oxocoumarinylmethylene)]-1,4-di
- Hamdi,Lidrissi,Saoud,Romerosa Nievas,Zarrouk
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p. 320 - 325
(2008/02/03)
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- New method of synthesis of 1,5-benzodiazepin-2-ones from 4-hydroxycoumarin
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A new method of synthesis of 1,5-benzodiazepine-2-ones, from 4-hydroxycoumarin and substituted 1,2-phenylenediamines by heating in xylene or acetic acid-ethanol, is reported.
- Hamdi,Grech,Sakellariou,Speziale
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p. 509 - 511
(2007/10/02)
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