213672-92-5Relevant articles and documents
Modification of the Enantioselectivity of Biocatalytic meso-Desymmetrization for Synthesis of Both Enantiomers of cis-1,2-Disubstituted Cyclohexane by Amidase Engineering
Hu, Hui-Juan,Wang, Qi-Qiang,Wang, De-Xian,Ao, Yu-Fei
, p. 4538 - 4543 (2021/08/09)
Both enantiomers of cis-1,2-disubstituted cyclohexane have been obtained enantioselectively through engineered amidase-catalyzed desymmetrization of meso carbocyclic 1,2-dicarboxamides under mild condition. Based on the enzyme-substrate binding model sugg
Alicyclic β- And γ-amino acids: Useful scaffolds for the stereocontrolled access to amino acid-based carbocyclic nucleoside analogs
Remete, Attila Márió,Kiss, Loránd
, (2019/01/21)
Stereocontrolled synthesis of some amino acid-based carbocyclic nucleoside analogs containing ring C=C bond has been performed on β- and γ-lactam basis. Key steps were N-arylation of readily available β- or γ-lactam-derived amino ester isomers and amino a
Cyclohexene-fused 1,3-oxazines with selective antibacterial and antiparasitic action and low cytotoxic effects
de Brito, Maria R.M.,Peláez, Walter J.,Faillace, Martín S.,Milit?o, Gardenia C.G.,Almeida, Jackson R.G.S.,Argüello, Gustavo A.,Szakonyi, Zsolt,Fül?p, Ferenc,Salvadori, Maria C.,Teixeira, Fernanda S.,Freitas, Rivelilson M.,Pinto, Pedro L.S.,Mengarda, Ana C.,Silva, Marcos P.N.,Da Silva Filho, Ademar A.,de Moraes, Josué
, p. 273 - 279 (2017/08/04)
Oxazine derivatives, a class of heterocyclic compounds, exhibit a variety of biological properties, such as anticonvulsant and antitumor activities. In this study, we evaluated the effect of two cyclohexene-fused 1,3-oxazines (cis?1-benzyl-N-phenyl-1,4,4a,5,8,8a-hexahydro-3,1-benzoxazin-2-imine (1) and trans?N-phenyl-1,4,4a,5,8,8a-hexahydro-3,1-benzoxazin-2-imine (2)) in cultures of Bacillus cereus, Enterococcus faecalis, Escherichia coli, Klebsiella pneumoniae, Salmonella enterica, Serratia marcescens, Shigella flexneri and Staphylococcus aureus by the Minimum Inhibitory Concentration (MIC) and Minimum Bactericidal Concentration (MBC). Additionally, the ex vivo antiparasitic activity of oxazines was assessed against Schistosoma mansoni, a helminth that is one of the major agents of the disease schistosomiasis Also, oxazines were evaluated on three tumor cell lines, NCI-H292 (human lung carcinoma), MCF-7 (human breast adenocarcinoma) and HEp-2 (human cervix carcinoma), and two normal cell lines (Vero and red blood cells). Bioassays revealed that oxazine 2 is more effective against bacteria than oxazine 1, with the lowest MIC and MBC values of 3.91 and 32.5 μg/mL, respectively. Similarly, compound 2 demonstrated higher antiparasitic activity than 1, and scanning electron microscopy analysis showed several morphological alterations in the tegument of worms in a concentration-dependent manner. In contrast, both oxazines exhibited low cytotoxic effects on cancer and normal cell lines. These results indicated that oxazines exerted direct effects on bacteria and parasite schistosomes. More importantly, since schistosomiasis control programs rely on one drug, praziquantel, oxazines may have the potential to become new antischistosomal agents.
The Mechanism of Electrochemical Reduction of Partially Saturated Bicyclic 2-Phenylsubstituted-1,3-oxazines
Richter, H.P.,Fueloep, F.,Stajer, G.,Pflegel, P.,Bernath, G.
, p. 601 - 605 (2007/10/02)
Partially saturated bicyclic 2-phenylsubstituted 1,3-oxazines of the type 1-6 are reduced in a 2e step at the azomethine bond by controlled potential electrolysis in acidic electrolytes.By ring-chain tautomerism, the resulting bicyclic tetrahydro-1,3-oxazines (2e products) form the corresponding ring-opened aldimine derivatives, which are reduced in a further 2e step to the corresponding amines (4e products), and which are also hydrolyzed to the aminoalcohols and aldehydes.This explains the poor yields of the 4e products.The behaviour of the bicyclic tetrahydro-1,3-oxazines was rationalized by comparisons with the authentic substances 7 and 8.
STEREOCHEMICAL STUDIES 83. SATURATED HETEROCYCLES 76. PREPARATION AND CONFORMATIONAL STUDY OF PARTIALLY SATURATED 3,1-BENZOXAZINES, 3,1-BENZOXAZIN-2-ONES AND 3,1-BENZOXAZINE-2-THIONES
Bernath, Gabor,Stajer, Geza,Szabo, Angela E.,Fueloep, Ferenc,Sohar, Pal
, p. 1353 - 1366 (2007/10/02)
The cis- and trans-2-amino-4-cyclohexene-1-carboxylic acids 1 and 3 react with imidates to give the condensed-skeleton, bicyclic cis- and trans-pyrimidin-4-ones 8 and 9.The amino acids 1 and 3 were reduced to the cis- and trans-1,3-aminoalcohols 6 and 7, which were cyclized by means of imidates to the bicyclic tetrahydro-4H-3,1-benzoxazines 10 and 11, or were converted, via the corresponding carbamates 14 and 15 into the tetrahydro-4H-3,1-benzoxazin-2(1H)-ones 16 and 17.The 2-thioxo analogues 18 and 19 were prepared by cyclization of the dithiocarbamates obtained from the aminoalcohols 6 and 7 by treatment with carbon disulphide.The trans-aminoalcohol 7 and its saturated analogue reacted with p-chlorobenzaldehyde to furnish the hexahydro 13 and octahydro-4H-3,1-benzoxazine 13a, respectively. 1H and 13C NMR studies showed that, similarly to the earlier-investigated analogues containing oxygen or unsubstituted nitrogen at position 1, the synthesized cis isomers 8, 10, 16 and 18 occurred as the preferred conformer in the heterocyclic twist inverse form of N-inside type (quasiaxal C6-N bond) (B).In the trans isomers containing a saturated C-2 atom (13 and 13a), H-2 and H-6 are in cis relative positions.
