Synthesis of the novel thieno[4,3,2‐ef][1,4]benzoxazepine ring system: 4,5‐Dihydro‐3‐(4‐pyridinyl)thieno[4,3,2‐ef][1,4]benzox‐azepine maleate

Tomer, John D.; Shutske, Gregory M.; Friedrich, Dirk

doi:10.1002/jhet.5570340621

Cited by 10 publications

(2 citation statements)

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“…Benzo [b]thiophenes are important heterocycles as biological active molecules. [1][2][3][4][5] Recently we have been interested in the palladium-catalyzed aryl amination of benzo [b]thiophenes either in the benzene or in the thiophene ring to obtain the corresponding diarylamines and in some cases the tetracyclic aromatic compounds resulting from intramolecular cyclizations. 6,7 We have been able to establish that under the same C-N coupling conditions [Pd(OAc) 2 (3 mol %), Cs 2 CO 3 (1.4 equiv), and BINAP (4 mol %) in toluene] it was possible to obtain either primary amines 8 or diarylamines 7,8 in the benzene ring of the benzo[b]thiophene moiety.…”

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Screening of antimicrobial activity of diarylamines in the 2,3,5-trimethylbenzo[b]thiophene series: a structure–activity evaluation study

Ferreira

Calhelha

Estevinho

et al. 2004

Bioorganic & Medicinal Chemistry Letters

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Abstract-Gram positive (Bacillus cereus, B. subtilis), Gram negative (Pseudomonas aeruginosa, Escherichia coli) bacteria, and Candida albicans as a representative of fungi were used for screening the in vitro antimicrobial activity of diarylamines in the 2,3,5-trimethylbenzo [b]thiophene series bearing different substituents, synthesized by us using the palladium-catalyzed C-N coupling methodology. The minimal inhibitory concentration (MIC) and structure-activity relationships (SARs) were evaluated. Ó 2004 Elsevier Ltd. All rights reserved.The enhance prevalence of infectious diseases is becoming a world wide problem. Additionally, the resistance problem demands that a renewed effort should be made to seek antimicrobial agents effective against pathogenic microorganisms resistant to current treatment. Benzo[b]thiophenes are important heterocycles as biological active molecules. 1-5 Recently we have been interested in the palladium-catalyzed aryl amination of benzo [b]thiophenes either in the benzene or in the thiophene ring to obtain the corresponding diarylamines and in some cases the tetracyclic aromatic compounds resulting from intramolecular cyclizations. 6,7 We have been able to establish that under the same C-N coupling conditions [Pd(OAc) 2 (3 mol %), Cs 2 CO 3 (1.4 equiv), and BINAP (4 mol %) in toluene] it was possible to obtain either primary amines 8 or diarylamines 7,8 in the benzene ring of the benzo[b]thiophene moiety.Herein, we describe the structure-activity relationship of a novel series of diarylamines as antimicrobial agents. Differently substituted diarylamines derivatives of 2,3,5-trimethylbenzo[b]thiophene 1 were obtained by C-N palladium-catalyzed cross-couplings in good to high yields (50%-quantitative yield) using either the bromo compound 2 or the amino derivative 3 as coupling components. 8 The latter was prepared from compound 2 using also a C-N palladium-catalyzed cross-coupling with benzophenone imine, followed by acidic hydrolysis in a 60% overall yield (Scheme 1). 8 A screening of antibacterial activities using two Gram negative (Escherichia coli and Pseudomonas aeruginosa) and two Gram positive bacteria (Bacillus subtilis and B. cereus) and antifungal using Candida albicans was performed for the diarylamines 4-8 and for their benzo[b]thiophene precursors 1-3, to determine the importance of the diarylamine skeleton in this series. The minimal inhibitory concentration (MIC in lg/mL) was determined (Table 1) using an adaptation of agar streak dilution method based on radial diffusion. 9,10 Suspensions of the microorganism were prepared to contain approximately 10 8 cfu/mL and the plates were inoculated. A stock solution of the synthesized compound (1000 lg/mL) in DMSO was prepared and graded dilutions of the tested compounds were incorporated in a cavity (depth 3 mm, diameter 4 mm) made in the center of the petridish (nutrient agar for antibacterial activity and sabouraud dextrose agar medium for antifungal activity). The plates were incubated at 37°C (bacteria) or 30°C (fungi) for ...

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confidence: 99%

Screening of antimicrobial activity of diarylamines in the 2,3,5-trimethylbenzo[b]thiophene series: a structure–activity evaluation study

Ferreira

Calhelha

Estevinho

et al. 2004

Bioorganic & Medicinal Chemistry Letters

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“…The initial methyl 3-amino-4-fluorobenzo[b]thiophene-2-carboxylate (1) was obtained according to the method described earlier [25]. Then 3-amino-4-fluorobenzo[b]thiophene-2-carboxylate (1) was diazotized and treated with SO 2 to give methyl 3-(chlorosulfonyl)-4-fluorobenzo[b]thiophene-2-carboxylate (2) which was employed in the next reaction stage without additional purification.…”

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confidence: 99%

Synthesis, X-ray crystal structure, Hirshfeld surface analysis, and molecular docking study of novel inhibitor of hepatitis B: methyl 4-fluoro-3-(morpholinosulfonyl)benzo[b]thiophene-2-carboxylate

Ivachtchenko¹,

Mitkin²,

Kravchenko

et al. 2019

Heliyon

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A method of 4-fluoro-3-(morpholinosulfonyl)benzo[b]thiophene-2-carboxylate synthesis has been developed and the electronic and spatial structure of a new biologically active molecule has been studied both theoretically and experimentally. The title compound was crystallized from acetonitrile and the single crystal X-ray analysis has revealed that it exists in a monoclinic P21/c space group, with one molecule in the asymmetric part of the unit cell. Hirshfeld surface analysis was used to study intermolecular interactions in the crystal. Molecular docking study evaluates the investigated compound as a new potential inhibitor of hepatitis B. Testing for anti-hepatitis B virus activity has shown that this substance demonstrates in vitro nanomolar inhibitory activity against HBV.

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ChemInform Abstract: Synthesis of the Novel Thieno[4,3,2‐ef][1,4]benzoxazepine Ring System: 4,5‐Dihydro‐3‐(4‐pyridinyl)thieno[4,3,2‐ef][1,4]benzoxazepine Maleate.

Tomer¹,

Shutske²,

Friedrich³

1998

ChemInform

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Synthesis of the novel thieno[4,3,2‐ef][1,4]benzoxazepine ring system: 4,5‐Dihydro‐3‐(4‐pyridinyl)thieno[4,3,2‐ef][1,4]benzox‐azepine maleate

Cited by 10 publications

References 2 publications

Screening of antimicrobial activity of diarylamines in the 2,3,5-trimethylbenzo[b]thiophene series: a structure–activity evaluation study

Screening of antimicrobial activity of diarylamines in the 2,3,5-trimethylbenzo[b]thiophene series: a structure–activity evaluation study

Synthesis, X-ray crystal structure, Hirshfeld surface analysis, and molecular docking study of novel inhibitor of hepatitis B: methyl 4-fluoro-3-(morpholinosulfonyl)benzo[b]thiophene-2-carboxylate

ChemInform Abstract: Synthesis of the Novel Thieno[4,3,2‐ef][1,4]benzoxazepine Ring System: 4,5‐Dihydro‐3‐(4‐pyridinyl)thieno[4,3,2‐ef][1,4]benzoxazepine Maleate.

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