Synthesis of 8-benzylamino-1,2-dihydro-10-oxo-2,2,5-trimethyl-4H-pyrano[4′3′∶4,5]pyrido[3,2-e]-1,3-thiazine and its psychotropic activity

Paronikyan, E. G.; Sirakanyan, S. N.; Noravyan, A. S.; Arzanunts, E. M.; Paronikyan, R. G.; Sarikisyan, I. S.; Akopyan, N. E.

doi:10.1007/bf02218947

Cited by 3 publications

(4 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…There are limited examples in the literature for the synthesis of electron‐neutral or electron‐rich benzothiazinones via a traditional S N Ar approach. There are two reports that use a strong base [18a,27] and another one that utilizes a 2‐chloropyridine derivative as activated system [28] . There are other reported conditions to synthesize these benzothiazinones such as using photochemistry [29a,b] or electrochemistry [29c] …”

Section: Resultsmentioning

confidence: 99%

“…A PEG-linker type amine (26) worked in good yield. Finally, alkyl amines such as propylamine ( 27) and a branched substrate, isopropylamine (28), were viable under the standard conditions.…”

Section: Resultsmentioning

confidence: 99%

“…There are two reports that use a strong base [18a,27] and another one that utilizes a 2-chloropyridine derivative as activated system. [28] There are other reported conditions to synthesize these benzothiazinones such as using photochemistry [29a,b] or electrochemistry. [29c] Finally, this methodology was applied to the synthesis of the anti-tuberculosis APIs BTZ-043 1 and Macozinone 2 (Scheme Benzoyl chloride 39 (synthesized in one-step from the corresponding commercially available carboxylic acid) was reacted under the standard conditions of ammonium thiocyanate addition followed by treatment with EtOH to afford the putative benzoyl thiocarbamate 40, which spontaneously cyclized to ethoxy benzothiazinone 41 at room temperature without the use of exogenous base.…”

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of Benzothiazinones from Benzoyl Thiocarbamates: Application to Clinical Candidates for Tuberculosis Treatment

et al. 2022

View full text Add to dashboard Cite

Benzothiazinones are a structural motif found in biologically active compounds, such as the clinical candidates BTZ-043 and Macozinone for the treatment of tuberculosis. We describe a robust, two-step method to synthesize 2-amino-substituted benzothiazinones from benzoyl thiocarbamates, which were prepared in a one-pot procedure from benzoyl chlorides. The intramolecular cyclization and ethoxy displacement steps were also amenable to adoption in continuous flow as exemplified by select substrates.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of Benzothiazinones from Benzoyl Thiocarbamates: Application to Clinical Candidates for Tuberculosis Treatment

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Formation of the product was confirmed by TLC method of estimation. Finally the solvent was removed by distillation and the residue obtained was treated with ice cold water, filtered, dried and the dried residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give respective compound 1,3thiazine derivative 29,28,30 .…”

Section: General Procedures For the Preparation Of 8-benzylidene-6-termentioning

confidence: 99%

Untitled

2017

IJPSR

View full text Add to dashboard Cite

In the present study, a series of novel biologically active 8benzylidene-6-tert-butyl-4-phenyl-5, 6, 7, 8-tetrahydro-benzo-1, 3-thiazin-2-imines (TB 1-TB 12) were synthesized and evaluated for their biological activities. Initially, 2,6-dibenzylidene-4-tert-butylcyclohexanones were synthesized by Claisen-Schmidt condensation of 4-tert-butylcyclohexanone with various aromatic aldehydes in the presence of dilute sodium hydroxide. Further these compounds were subjected to cyclocondensation with thiourea, in isopropyl alcohol, catalyzed by aqueous potassium hydroxide to form 4aryl-8-arylidene-5,6,7,8-tetrahydro-1H-benzo[d][1,3]thiazin-2(4H)-imines (TB 1-TB 12). The structures of the newly synthesized compounds have been established on the basis of their spectral data and elemental analysis. Anticonvulsant activity was performed by Maximal electroshocks (MES) method by using Diazepam as standard reference. These compounds were subjected to molecular properties prediction, drug-likeness, lipophilicity and solubility parameters determination using Molinspiration, Osiris program was used for prediction of the toxicity, and also Molsoft and ALOGPS 2.1 softwares. Among all compounds TB 5 and TB 8 containing lipophilic methoxyl and isopropyl group were more potent whereas TB 12 containing hydroxyl groups were least potent among the series.

show abstract

Synthesis, Characterization, Biological Evaluation and Docking of Some Novel Substituted 1, 3-Thiazine Derivatives

Bairam

Muppavarapu²,

Sivan

2017

Int J Pharm Pharm Sci

View full text Add to dashboard Cite

Objective: Chalcones and their heterocyclic analogs represent an important class of small molecules which have a wide range of pharmacological activities. Therefore, in this study, synthesis and anticonvulsant and antimicrobial activities of some new 1, 3-thiazines have been extensively discussed.Methods: The reaction mixture of 4-tert-butylcyclohexanone on Claisen-Schmidt condensation with various aromatic aldehydes in the presence of dilute sodium hydroxide afforded the corresponding chalcones. Further, these compounds were subjected to cocondensation with thiourea, in the presence of isopropanol, catalyzed by aqueous potassium hydroxide to form 4-aryl 8-arylidene-5, 6-dihydro-2-imino-6-methyl-4H, 7H-(1, 3) benzothiazines. The structures of the newly synthesized compounds have been established on the basis of their spectral analysis. The newly synthesized compounds have been tested for their biological screening. Antimicrobial activity by cup plate agar diffusion method and antiepileptic activity by pentylenetetrazole (PTZ) induced seizures model, using diphenyl hydantain as standard, and also they are subjected to molecular properties prediction, toxicity, drug-likeness, lipophilicity and solubility parameters determination were done by using Osiris program, Molsoft, Prototox and ALOGPS 2.1 software. The binding mode of the synthesized compounds with active protein site has been predicted using docking method.Results: Most of the compounds have shown good anticonvulsant as well as antimicrobial activities, but it is less than the standard drugs. 1, 3-thiazines derivatives were more potent, and among them, compounds TB5 andTB7 were the most active compounds in these series; TB5 whichcontains isopropyl phenyl moiety, was shown moderate potent activity with onset of convulsion at 14.1 min and TB7 containing 3, 4, 5-trimethoxyphenyl substituents on the thiazine moiety was more potent as it has prolonged the onset of convulsions by 18.7 min. Whereas in the case of antimicrobial activity of the compounds, from the results we have observed that TB5 have been shown greatest antimicrobial activity in all the bacterial and fungal strains, TB2 also shown superior activity, the others have been shown good antimicrobial activity.Conclusion: According to the activity studies, it is observed that the synthesis and antimicrobial as well as anticonvulsant activities of novel 1, 3-thiazine derivatives have been shown better activity. Moreover molecular docking results give an insight into how further modification of the lead compound can be carried out for higher inhibitory activity. In particular, compounds with electron withdrawing substituents along with lipophilic methoxyl and isopropyl groups were more potent.

show abstract

Synthesis of 8-benzylamino-1,2-dihydro-10-oxo-2,2,5-trimethyl-4H-pyrano[4′3′∶4,5]pyrido[3,2-e]-1,3-thiazine and its psychotropic activity

Cited by 3 publications

References 2 publications

Synthesis of Benzothiazinones from Benzoyl Thiocarbamates: Application to Clinical Candidates for Tuberculosis Treatment

Synthesis of Benzothiazinones from Benzoyl Thiocarbamates: Application to Clinical Candidates for Tuberculosis Treatment

Untitled

Synthesis, Characterization, Biological Evaluation and Docking of Some Novel Substituted 1, 3-Thiazine Derivatives

Contact Info

Product

Resources

About