An eco-friendly synthesis and antimicrobial activities of dihydro-2 H-benzo- and naphtho-1,3-oxazine derivatives (original) (raw)
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Synthesis, antimicrobial and cytotoxicity study of 1,3-disubstituted-1H-naphtho[1,2-e][1,3]oxazines
European Journal of Medicinal Chemistry, 2012
A series of new 1,3-disubstituted-1H-naphtho[1,2-e][1,3]oxazines (3 and 7) was synthesized in good yields and the structure was determined with the help of NMR, 2D-NMR, HRMS studies and X-ray crystallography. These compounds were tested in vitro for their antibacterial activity against Grampositive and Gram-negative bacteria and as well as for antifungal activity. The compounds 3c, 3e, 7a, 7d and 7k showed significant antibacterial activity and 7l showed moderate antifungal activity. The cytotoxicity of 1,3-disubstituted-1H-naphtho[1,2-e][1,3]oxazines showed that 3e and 7e are more effective against breast, lung and colon cell proliferation.
European Journal of …, 2012
A series of new 1,3-disubstituted-1H-naphtho[1,2-e][1,3]oxazines (3 and 7) was synthesized in good yields and the structure was determined with the help of NMR, 2D-NMR, HRMS studies and X-ray crystallography. These compounds were tested in vitro for their antibacterial activity against Grampositive and Gram-negative bacteria and as well as for antifungal activity. The compounds 3c, 3e, 7a, 7d and 7k showed significant antibacterial activity and 7l showed moderate antifungal activity. The cytotoxicity of 1,3-disubstituted-1H-naphtho[1,2-e][1,3]oxazines showed that 3e and 7e are more effective against breast, lung and colon cell proliferation.
Synthesis and Characterization of New 3,4-Dihydro-2H-benzo- and Naphtho-1,3-oxazine Derivatives
Asian Journal of Chemistry, 2016
The synthesis of benzoxazine compounds dates back over 70 years [1-4] but their potential was only realized recently [5]. Among all benzoxazine compounds, 1,3-benzoxazine have received greater attention as they are used in the production of polymeric materials [6-8] and are also of significant interest in pharmacological fields [9]. 1,3-Benzoxazines as monomers are used in the synthesis of a new type of phenolic resins called polybenzoxazines through thermally activated ring-opening polymerization [10,11]. These polybenzoxazines possesses not only the properties of traditional phenolic resins but other unique properties such as low water absorption, high modulus, high strength, high glass transition temperatures, high char yield and low volumetric shrinkage upon curing [12-15]. Furthermore, 1,3-benzoxazines are known for their wide range of biological activities and hence used as fungicides, bactericide, anti-inflammatory, antidepressants and antitumor agents [16,17]. Numerous approaches are used for the synthesis of 1,3benzoxazine compounds using different solvents [18-20]. Among the approaches is the step-wise procedure which has recently gained considerable interest and more importantly tolerates various functional groups [21]. For this reason, the
Synthesis and Characterizations of New 1, 3-Oxazine Derivatives
2011
In this study, Betti's classical procedure, a Mannich-type aminoalkylation reaction of 2-naphthol with various aldehydes was applied in the presence of ammonia and then 1,3disubstituted-2,3-dihydro-1H-naphtoxazines were synthesized. The structures of the obtained new compounds have been clarified by spectroscopic methods and confirmed with elemental analysis results. From the synthesized compounds, 1,3-Di(2-naphthyl)-2,3-dihydro-1H-naphto[1,2-e][1,3]oxazine was investigation of the effects of solvent and concentration with UV-Visible Spectrophotometer. Additionally, this compound was analyzed the mutagenic and anti-mutagenic properties.
Bioorganic & medicinal chemistry letters, 2017
A new series of functionalized (Z)-3-(2-oxo-2-substituted ethylidene)-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-ones 23-26, incorporating pharmaceutically privileged substructures such as cyclopropyl, naphthyl, biphenyl and cyclohexylphenyl were synthesized in excellent yields. All the synthesized compounds were screened for their in vitro antibacterial activity against gram-(+)ve and gram-(-)ve bacterial species i.e. S. griseus, S. aureus, B. subtillis and E. coli as well as in vitro antifungal activity against fungal species i.e. F. oxysporium, A. niger, P. funiculosum and T. reesei, respectively. In this study, compounds containing cyclopropyl and cyclohexylphenyl substructures were identified as promising antimicrobial agents than standard drugs, ampicillin and chloramphenicol as well as ketoconazole. SAR study illustrates that electron-withdrawing groups increases the antibacterial as well as antifungal activity of 2-oxo-benzo[1,4]oxazines and vice versa. Compounds 23e and 26e, the ...
3,4–dihydro–2H–1,3–benzoxazines and their oxo–derivatives chemistry and bioactivities
3,4–Dihydro–2H–1,3–benzoxazines derivatives are a significant class of heterocycles with a particular awareness due to their remarkable biological activities in humans, plant as well as in animals and also, they are naturally occurrence. Because of alteration in the benzoxazines skeleton, beside their comparative chemical simplicity and accessibility, make these compounds to be suitable sources of other bioactive compounds. Resulting in the discovery of a wide set of these compounds that have a broad biological activity such as antifungal, antibacterial, anti-HIV, anticancer, anticonvulsant, anti-inflammatory and so on. Subsequently, this review herein gives a brief overview of derivatives of 3,4–dihydro–2H–1,3–benzoxazines monomers and their oxo– derivatives chemistry and bioactivities.
Asian Journal of Chemistry, 2013
Many important medicines, dyes, insecticides, etc., are found in the series of heterocyclic compounds, called oxazines 1 and thiazines 2. They are found mainly in the polycyclic divisions in which other rings, such as the benzene ring, are fused to the oxazines or thiazine ring. A considerable number of reports concerning 1,3-oxazine 3-5 derivatives which have undergone their greatest development in the last few years came in to the notice. This is due to partially the fact that these compounds show interesting pharmacological activity 6-11 and wide range of biological activity with uses as herbicides and agricultural microbiocides, as well as bactericide, fungicide, antidepressive, antiinflammatory and antitumor agents 12-15. Moreover 1,3-oxazine monomers were recently used to develop a new type of phenolic resin namely polybenzoxazines, by the ring openining polymerization on thermal curing 16,17. EXPERIMENTAL Salicyldehyde (spectrochem), sodium borohydride (spectrochem), aniline (CDH), 4-methyl aniline (Thomas Baker), 4-chloro aniline (CDH), 4-bromo aniline (spectrochem), 2-aminopyridine (spectrochem), 3-aminopyridine (spectrochem), 5bromo-salicyldehyde (spectrochem) were used as received. Solvents were purified by standard procedures. All reactions and workup were conducted under air, except when noted otherwise. TLC was performed on MERCK TLC Silica gel 60 F254 plates and visualized by iodine. Yields refer
Novel one -pot synthesis of a series of 6-chloro-2,4-diphenyl-3,4-dihydro-2H-1,3-benzoxazine derivatives [2a -2j] from the reaction of P-Chlorophenol and substituted aromatic aldehyde in methanolic ammonia solution. All synthesized compounds were characterized on the basis of IR,NMR spectroscopic data and Elemental Analysis. Anti-bacterial and Anti-fungal activities were evaluated and compared with the standard drugs, some compounds of the series exhibited promising anti-bacterial and anti-fungal activity compared to standard drugs.