- Design, synthesis, and preliminary biological evaluation of 2,3-dihydro-3-hydroxymethyl-1,4-benzoxazine derivatives
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We synthesized a series of novel small molecules, 2,3-dihydro-3-hydroxymethyl-1,4-benzoxazine derivatives, by tandem reduction-oxirane opening of 2-nitroaroxymethyloxiranes in moderate or excellent yields. We investigated the effects of all of the compounds on HUVEC apoptosis and A549 cell growth. The results showed that 6,8-dichloro-2,3-dihydro-3-hydroxymethyl-1,4-benzoxazine was the most effective small molecule in promoting HUVEC apoptosis and inhibiting A549 cell proliferation, but 6-amino-2,3-dihydro-3-hydroxymethyl-1,4-benzoxazine could remarkably inhibit HUVEC apoptosis and might induce the formation of microvessel.
- Jiao, Pei-Fu,Zhao, Bao-Xiang,Wang, Wei-Wei,He, Qiu-Xia,Wan, Mao-Sheng,Shin, Dong-Soo,Miao, Jun-Ying
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Read Online
- Glycerol Valorization towards a Benzoxazine Derivative through a Milling and Microwave Sequential Strategy
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Glycerol and aminophenol intermolecular condensation has been investigated through a milling and microwave-assisted sequential strategy, towards the synthesis of a benzoxaxine derivative. Mechanochemical activation prior to the microwave-assisted process could improve the probability of contact between the reagents, and greatly favors the higher conversion of aminophenol. At the same time, following a mechanochemical–microwave sequential approach could tune the selectivity towards the formation of a benzoxazine derivative, which could find application in a wide range of biomedical areas.
- Espro, Claudia,Luque, Rafael,Osman, Sameh M.,Perosa, Alvise,Reyes, Antonio A. Romero,Rodríguez-Padrón, Daily,Selva, Maurizio,Torres-Pastor, Miguel ángel
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supporting information
(2022/01/26)
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- Transition-Metal Acetate-Promoted Intramolecular Nitrene Insertion to Vinylogous Carbonates for Divergent Synthesis of Azirinobenzoxazoles and Benzoxazines
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Synthesis and isolation of highly unstable azirinobenzoxazole and benzoxazines in a chemodivergent fashion from aryl azido vinylogous carbonates by simple change in transition metal acetate is described. Thermal or rhodium(II) acetate-mediated decompositi
- Gharpure, Santosh J.,Naveen, Sudi,Samala, Ganesh,Vishwakarma, Dharmendra S.
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p. 1456 - 1460
(2019/01/04)
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- 2,6-Difluorobenzamide Inhibitors of Bacterial Cell Division Protein FtsZ: Design, Synthesis, and Structure–Activity Relationships
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A wide variety of drug-resistant microorganisms are continuously emerging, restricting the therapeutic options for common bacterial infections. Antimicrobial agents that were originally potent are now no longer helpful, due to their weak or null activity toward these antibiotic-resistant bacteria. In addition, none of the recently approved antibiotics affect innovative targets, resulting in a need for novel drugs with innovative antibacterial mechanisms of action. The essential cell division protein filamentous temperature-sensitive Z (FtsZ) has emerged as a possible target, thanks to its ubiquitous expression and its homology to eukaryotic β-tubulin. In the latest years, several compounds were shown to interact with this prokaryotic protein and selectively inhibit bacterial cell division. Recently, our research group developed interesting derivatives displaying good antibacterial activities against methicillin-resistant Staphylococcus aureus, as well as vancomycin-resistant Enterococcus faecalis and Mycobacterium tuberculosis. The aim of the present study was to summarize the structure–activity relationships of differently substituted heterocycles, linked by a methylenoxy bridge to the 2,6-difluorobenzamide, and to validate FtsZ as the real target of this class of antimicrobials.
- Straniero, Valentina,Zanotto, Carlo,Straniero, Letizia,Casiraghi, Andrea,Duga, Stefano,Radaelli, Antonia,De Giuli Morghen, Carlo,Valoti, Ermanno
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p. 1303 - 1318
(2017/09/01)
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- First use of HEH in oxazine synthesis: Hydroxy-substituted 2 H-1,4-benzoxazine derivatives
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The synthesis of 2H-1,4-benzoxazine derivatives from 1,2-epoxy-3-(2- nitroaryloxy)propanes in the presence of Hantzsch 1,4-dihydropyridine (HEH) and Pd/C as a catalyst was achieved. The nitro group was reduced before the epoxide functionality, leading to attack of the amino group on the epoxide moiety in a 6-exo-fashion. By introducing a methyl group at the 1-position, the 7-endo ring-closed product could also be formed. Georg Thieme Verlag Stuttgart - New York.
- Meng, Qing-Yuan,Liu, Qiang,Li, Jing,Xing, Rui-Guang,Shen, Xiao-Xia,Zhou, Bo
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experimental part
p. 3283 - 3286
(2010/03/04)
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