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A Novel Family of [1,4]Thiazino[2,3,4-ij]quinolin-4-ium Derivatives: Regioselective Synthesis Based on Unsaturated Heteroatom and Heterocyclic Compounds and Antibacterial Activity.

ABSTRACT: A novel family of [1,4]thiazino[2,3,4-ij]quinolin-4-ium derivatives was synthesized by annulation reactions of 8-quinolinesulfenyl chloride with unsaturated heteroatom and heterocyclic compounds. It was found that the reactions with 4-pentenoic and 5-hexenoic acids, allyl chloride and bromide, allyl cyanate and vinyl heterocyclic compounds (N-vinyl pyrrolidin-2-one and 1-vinylimidazole) proceeded in a regioselective mode but with the opposite regiochemistry. The reactions with vinyl heterocyclic compounds included electrophilic addition of the sulfur atom of 8-quinolinesulfenyl chloride to the β-carbon atom of the vinyl group. In the case of other substrates, the annulation proceeded with the attachment of the sulfur atom to the α-carbon atom of the vinyl group. The antibacterial activity of novel water-soluble compounds against Enterococcus durans, Bacillus subtilis and Escherichia coli was evaluated. Compounds with high antibacterial activity were found.

SUBMITTER: Potapov VA

PROVIDER: S-EPMC8472155 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Efficient Regioselective Synthesis of Novel Water-Soluble 2H,3H-[1,4]thiazino[2,3,4-ij]quinolin-4-ium Derivatives by Annulation Reactions of 8-quinolinesulfenyl Halides.

Project description:Regioselective synthesis of novel 2H,3H-[1,4]thiazino[2,3,4-ij]quinolin-4-ium derivatives has been developed by annulation reactions of 8-quinolinesulfenyl halides with vinyl chalcogenides (vinyl ethers, divinyl sulfide, divinyl selenide and phenyl vinyl sulfide) and tetravinyl silane. The novel reagent 8-quinolinesulfenyl bromide was used in the annulation reactions. The influence of the substrate structure and the nature of heteroatoms on the direction of the reactions and on product yields has been studied. The opposite regiochemistry was observed in the reactions with vinyl chalcogenides and tetravinyl silane. The obtained condensed heterocycles are novel water-soluble functionalized compounds with promising biological activity.

| S-EPMC7923262 | biostudies-literature

(7aR*,12bS*)-8,12b-Dihydro-7aH-indeno-[1',2':5,6][1,4]selenazino[2,3,4-ij]quinolin-13-ium hydrogen sulfate.

Project description:In the title compound, C(18)H(14)NSe(+)·HSO(4) (-), the cyclo-pentene ring in the cation has an envelope conformation while the central six-membered 1,4-selenazine ring adopts a sofa conformation. The dihedral angle between the planes of the terminal benzene rings is 68.08 (11)°. In the crystal, the anions form chains along the c axis through O-H⋯O hydrogen bonds. Weak C-H⋯O and C-H⋯π hydrogen bonds, as well as attractive Se⋯Se [3.5608 (8) Å] inter-actions, further consolidate the crystal structure.

| S-EPMC3238942 | biostudies-literature

2<i>H</i>-[1,3]Thia-zolo[5,4,3-<i>ij</i>]quinolin-3-ium chloride monohydrate.

Project description:The structure of the title hydrated mol-ecular salt, C10H8NS+·Cl-·H2O, obtained by the reaction of sodium quinoline-8-thiolate Na(Quin-8-S) with CH2Cl2 and an aqueous solution of [Bu4N]Cl, contains π-stacked cations [plane-to-plane separation = 3.338 (4)-3.356 (4) Å] and features chains built by alternating Cl- anions and H2O mol-ecules connected by O-H⋯O hydrogen bonds. The cation shows whole-mol-ecule disorder over two flipped orientations in a 0.853 (3):0.147 (3) ratio.

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Regioselective 1,4-trifluoromethylation of ?,?-unsaturated ketones via a S-(trifluoromethyl)diphenylsulfonium salts/copper system.

Project description:Regioselective conjugate 1,4-trifluoromethylation of ?,?-unsaturated ketones by the use of shelf-stable electrophilic trifluoromethylating reagents, S-(trifluoromethyl)diphenylsulfonium salts and copper under mild conditions is described. A wide range of acyclic aryl-aryl-enones and aryl-alkyl-enones were converted into ?-trifluoromethylated ketones in low to moderate yields.

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6-Hy-droxy-1,2-dihydro-4H-pyrrolo-[3,2,1-ij]quinolin-4-one.

Project description:The mol-ecule of the title compound, C11H9NO2, is essentially planar [r.m.s. deviation of the non-H atoms = 0.056?(1)?Å]. In the crystal, strong O-H?O hydrogen bonds form zigzag chains along the b axis. The mol-ecules form stacks along the a axis due to ?-? inter-actions, the shortest distance between the centroids of the benzene and pyridinone rings being 3.6146?(7)?Å.

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2-Cyano-quinolin-1-ium hydrogen sulfate.

Project description:The title salt, C(10)H(7)N(2) (+)·HSO(4) (-), is formed by the transfer of a proton from H(2)SO(4) to the N atom of 2-cyano-quinoline during crystallization. The quinoline ring system is approximately planar with a maximum deviation of 0.013?(3)?Å. In the crystal, the cations are linked to the anions via inter-molecular N-H?O, O-H?O and C-H?O hydrogen bonds, forming a layered network.

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8-Hy-droxy-quinolin-1-ium nitrate.

Project description:In the title salt, C(9)H(8)NO(+)·NO(3) (-), the quinoline ring system is essentially planar with a maximum deviation of 0.043?(1)?Å. In the crystal, an R(2) (2)(7) ring motif is formed by inter-molecular N-H?O and C-H?O hydrogen bonds between the cation and the anion. In addition, inter-molecular O-H?O and C-H?O hydrogen bonds link the two ions, generating an R(2) (2)(8) ring motif. These sets of ring motifs are further linked into a ribbon along the a axis via inter-molecular C-H?O hydrogen bonds.

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8-Hy-droxy-quinolin-1-ium hydrogen sulfate monohydrate.

Project description:In the crystal structure of the title salt hydrate, C9H8NO(+)·HSO4 (-)·H2O, the quinoline N-H atoms are hydrogen bonded to the bis-ulfate anions. The bis-ulfate anions and water mol-ecules are linked together by O-H?O hydrogen-bonding inter-actions. The cations and anions form separate layers alternating along the c axis, which are linked by N-H?O and O-H?O hydrogen bonds into a two-dimensional network parallel to (100). Further O-H?O contacts connect these layers, forming a three-dimensional network, in which two R 4 (4)(12) rings and C 2 (2)(13) infinite chains can be identified.

| S-EPMC3884397 | biostudies-literature

3-Acetyl-2,4-di-methyl-quinolin-1-ium chloride.

Project description:In the title salt, C13H14NO(+)·Cl(-), the dihedral angle between the fused ring system (r.m.s. deviation = 0.039?Å) and the attached aldehyde group is 75.27?(16)°. In the crystal, the cation and anion are linked by an N-H?Cl hydrogen bond and the resulting pairs are connected into four-ion aggregates by ?-? inter-actions between the C6 and pyridinium rings [3.6450?(9)?Å] of inversion-related quinolinium residues.

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2-Cyano-quinolin-1-ium nitrate.

Project description:A proton is transferred from the nitric acid to the N atom of 2-cyano-quinoline during crystallization, resulting in the formation of the title salt, C(10)H(7)N(2) (+)·NO(3) (-). The quinolinium ring system is approximately planar, with a maximum deviation of 0.013?(3)?Å. In the crystal, a very asymmetric bifurcated N-H?(O,O) hydrogen bond to two O atoms of an adjacent nitrate anion occurs, generating an R(2) (1)(4) ring motif. C-H?O hydrogen bonds link the ions into sheets stacking along the a axis.

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