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Quinolonecarboxylic Acids. 2. Synthesis and Antibacterial Evaluation of 7-Oxo-2,3-dihydro-7H-pyrido<1,2,3-de><1,4>benzothiazine-6-carboxylic Acids

A series of pyridobenzothiazine acid derivatives was synthesized and their in vitro antibacterial activity was evaluated.The 1,4-benzothiazine intermediates, which by Gould-Jacobs quinoline synthesis produced pyridobenzothiazine acids, were prepared by hydrolytic basic cleavage of substituted 2-aminobenzothiazoles and successive cyclocondensation with 1-bromo-2-chloroethane or alternatively with monochloroacetic acid, hence reduction by LiAlH4.The pyridobenzothiazine acids 10c, 30, and 31 show potent antibacterial activities against Gram-positive and Gram-negative pathogens.Structure-activity relationships are discussed.The compound 9-fluoro-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido<1,2,3-de><1,4>benzothiazine-6-carboxylic acid (31) (MF-934) has been found to possess, together with the antibacterial activity, a weak acute toxicity and interesting pharmacokinetic characteristics in several animal species (rat, dog, monkey, man).

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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Biotransformation of organic sulfides. Part 12. Conversion of heterocyclic sulfides to chiral sulfoxides by Helminthosporium sp. NRRL 4671 and Mortierella isabellina ATCC 42613

The enantioselective oxidation of a series of heterocyclic prochiral sulfides to chiral sulfoxides has been examined using the fungal biocatalysts Helminthosporium species NRRL 4671 and Mortierella isabellina ATCC 42613. Methylthiofuranyl and -thiophenyl substrates gave (S)-configuration products in low to moderate enantiomeric purity on biotransformation with H. species, but pyridyl sulfides with the nitrogen atom located at an optimal distance of 8-10 A from the sulfur centre gave (S) sulfoxides of high enantiomeric purity. The biotransformation of appropriately substituted benzothiane substrates by M. isabellina also gave products of high enantiomeric purity, but with (R) configuration at sulfur. The acceptability of the substrate and the configuration of sulfur oxidation by both H. species and M. isabellina for the range of substrates examined were found to be consistent with predictions based on cubic space models for these oxidations.

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Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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Access to Phenothiazine Derivatives via Iodide-Mediated Oxidative Three-Component Annulation Reaction

Herein, a new iodide-mediated three-component annulation reaction of secondary anilines, cyclohexanones, and elemental sulfur is demonstrated, which allows access to various phenothiazines with the merits of formation of multiple chemical bonds in one single operation, high step and atom efficiency, readily available feedstocks and catalyst system, and good substrate and functional group compatibility. The developed chemistry capable of constructing novel phenothiazines with structural diversity offers a significant basis for further applications.

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Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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1-PROPANOL AND 1-PROPYLAMINE DERIVATIVES AND THEIR USE AS GLUCOCORTICOID LIGANDS

Compounds of Formula (I) wherein R1, R2 R3, R4, R5, R6, and X are as defiend herein for Formula (IA) and Formula (IB), or a tautomer, prodrug, solvate, or salt thereof; pharmaceutical compositions containing such compounds, and methods of modulating the glucocoricoid receptor function and methods of treating disease-states or conditions mediated by the glucocorticoid receptor function or characterized by inflammatory, allergic, or proliferative processes in a patient using these compounds.

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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Process for introducing a thiocarboxylic ester group at the orthoposition of phenols or phenylamines

A process for introducing thiocarboxylic ester at ortho-position of phenols or phenylamines which comprises reacting a phenyl compound having group or optionally substituted amino or cyclic amino group, of which at least one ortho-position is vacant, with C1 -C5 alkyl thiocyanate, C7 -C13 aralkyl thiocyanate or C6 -C12 aryl thiocyanate in the presence of a boron trihalide and hydrolyzing the resultant product under acidic conditions is provided, and said process is useful in the synthesis of medicinals, pesticides and dyes.

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Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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Eliminative Ring Fission of 4-Acyl-2,3-dihydro-4H-1,4-benzothiazines

The behavior of 4-acyl-2,3-dihydro-1,4-benzothiazines 1-11 upon treatment with lithium diisopropylamide (LDA) in THF at -78 deg C has been examined.Very marked differences have been observed.Whereas unsubstituted and monosubstituted derivatives (1-4) readily undergo “eliminative ring fission”, providing 2-(alkylthio)phenylenamides 12, 2-aminophenyl vinyl sulfides 16, and 3-acylbenzothiazolines 13, 2,3-disubstituted derivatives (5-7) do not react at all.The relationship between structural features of the above-mentioned dihydrobenzothiazines and their reactivity is considered.Lithium ion plays a fundamental role in providing activation for the ring-opening reaction.

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Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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SINTESI ED ATTIVITA ANTIINFIAMMATORIA DI ALCUNI DERIVATI 1,4-BENZOTIAZINICI

A new series of dihydro-4H-1,4-benzothiazine derivatives was prepared.These compounds were obtained by reductive N-alkylation reaction with sodium borohydride in acetic acid of the corresponding 4H-1,4-benzothiazine.Some of the latter compounds were synthesized by a new synthetic method employing 2-aminobenzenethiol and alkynes as starting material. – Preliminary pharmacological data on the antiinflammatory activity of these compounds by using carrageenin paw edema assay are reported.

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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Conjugate-base-stabilized bronsted acids as asymmetric catalysts: Enantioselective povarov reactions with secondary aromatic amines

Caught in the act: A new concept for asymmetric Bronsted acid catalysis is presented. Compounds containing an acidic functionality in addition to an anion recognition site act as powerful conjugate-base-stabilized Bronsted acid catalysts. This strategy was applied to the first catalytic enantioselective three-component Povarov reaction of indoline and other secondary aromatic amines (see scheme; M.S.=molecular sieves). Copyright

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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Selective N-alkylation of arylamines with alkyl chloride in ionic liquids: Scope and applications

An efficient N-selective alkylation of primary aromatic amines in molten quaternary ammonium salts, as the solvent, under relatively mild and base-free conditions is presented. On the basis of the Kamlet-Taft parameters and the nucleophilicity of the IL (ionic liquid) anions, the influence of the ionic liquid was evaluated. This protocol was validated on a larger multigram scale and with the syntheses of bioactive heterocycles (e.g., 1,4-benzothiazine and quinoxalines) and new efficient MALDI matrixes. Copyright

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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REMEDIES OR PREVENTIVES FOR URINARY FREQUENCY OR URINARY INCONTINENCE AND MORPHINAN DERIVATIVES HAVING NITROGEN-CONTAINING HETEROCYCLIC GROUP

The invention provides a morphinan derivative of the Formula (I): [wherein R1 is methyl, cyclopropylmethyl or the like; R2 and R3 are hydroxy, methoxy, acetoxy or the like; both Y and Z are valence bonds, -C(=O)- or the like; X is C2-C5 carbon chain (one of the carbon atoms may be substituted by oxygen, sulfur or nitrogen) constituting a part of the ring structure, or the like; (R4)k is substituted or non-substituted benzene fused ring, carbonyl group or the like; R9 is hydrogen or the like; R10 and R11 are bound to represent -O-, or the like, and R6 is hydrogen or the like] or a pharmaceutically acceptable acid addition salt thereof. The invention also provides a therapeutic or prophylactic agent for urinary frequency or urinary incontinence, comprising as an effective ingredient the morphinan derivative or the pharmaceutically acceptable acid addition salt thereof; a method for therapy or prophylaxis of the diseases, and use for the diseases.psiThe compounds of the invention are useful as a new therapeutic or prophylactic agent for urinary frequency or urinary incontinence, free from side effects, and useful for the method for therapy or prophylaxis of the diseases and for use for the diseases.

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem