Synthesis of Some New 1,5-Benzothiazepines Containing 2h-1- Benzopyran-2-One Heterocycle

Prashant, A.; Rao, S. Srinivas; Chowdary, K. S.; Krishnan, V.

doi:10.1515/hc.2001.7.1.61

Cited by 4 publications

(2 citation statements)

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“…A solution of 8-acetyl-7-hydroxyco umarin (3, F igure 1) (Prashant et al 2001) (1.7 g, 8.33 mmol), cyclopentanone (0.91 g, 10.87 mmol) and pyrrolidine (0.18 mL, 2.17 mmol) in anhydrou s toluene was refluxed for 1 h using a Dean-Stark apparatus. The reaction mixture was extracted with HCl 9% to remove the bulk of pyrr olidine, the organic phase was dried (Na 2 SO 4 ) and evaporated to dryness.…”

Section: '10'-dihydrospiro[cyclopentane-18'(8'h)pyran[23-h]benzo[mentioning

confidence: 99%

“…The preparation of the target derivatives is depicted in F igures 1 and 2. We used 8-acetyl-7-hydroxycou marin (3) as starting material, which was obtained together with its regioisom er 4, according to known procedur es starting from commercial 7-hydr oxycouma rin (1) through a F ries rearrangement of the intermediate acetate 2 (F igure 1) (Bender et al 1983;Prashant et al 2001). A solution of compoun d 3 in toluene was then treated at reflux with the appropriate carbocyclic ketone in the presence of pyrrolidine (Kabbe 1978) to provide the spiropyra nobenzop yranodion es 5a-c in very good yield.…”

Section: Chemistrymentioning

confidence: 99%

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Interactions of a series of novel spiropyranocoumarin derivatives with reactive oxygen species

Panteleon

Marakos

Pouli

et al. 2003

Journal of Pharmacy and Pharmacology

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A series of new spiro-substituted pyranocoumarin derivatives have been synthesized starting from the commercially available 7-hydroxycoumarin and the conformation of the pyran ring was investigated. The antioxidant activity of the compounds was evaluated in-vitro, by means of three different tests: the interaction with the stable free radical 1,1-diphenyl-2-picrylhydrazyl (DPPH), the competition with DMSO for hydroxyl radicals scavenging ability and the quenching of superoxide anions generated by the enzymic xanthine-xanthine oxidase system. In the DPPH test the spiroadamantane derivative 13 was the most active and possessed a 40% inhibition at a concentration of 400 microM. All compounds successfully compete with DMSO for hydroxyl radicals generated by the Fe(3+)/ascorbic acid system. Compound 13 inhibited the oxidation of DMSO (3.125 mM) by 93% at 2 mM and by 71% at 0.25 mM. The corresponding second-order rate constants have been estimated and all compounds demonstrated higher rate constants compared with the reference compounds, 7-hydroxycoumarin and mannitol. Derivatives possessing extended conjugation showed the highest inhibitory activity for superoxide anions generated by the xanthine-xanthine oxidase system, although the results of this experiment possessed partial parallelism with the results observed in the other two tests. The overall obtained data indicate that the size of the different spiro- substituents influence the degree of free radical scavenging and demonstrate the importance of extended conjugation for the antioxidant activity. Due to its multiple mechanism of protective action, derivative 13 may serve as a lead for the development of analogues that could be useful for the treatment of pathophysiological processes dependent upon reactive oxygen species.

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Section: '10'-dihydrospiro[cyclopentane-18'(8'h)pyran[23-h]benzo[mentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Interactions of a series of novel spiropyranocoumarin derivatives with reactive oxygen species

Panteleon

Marakos

Pouli

et al. 2003

Journal of Pharmacy and Pharmacology

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Synthesis of 1-substituted 5-aryl-3-(3-coumarinyl)-2-pyrazolines by the reaction of 3-aryl-1-(3-coumarinyl)propen-1-ones with hydrazines

Lévai

Jekő²,

Brahmbhatt

2005

Journal of Heterocyclic Chemistry

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Dedicated to Professor Dr. Fritz Sauter on the occasion of his 75 th birthday 1-Acetyl-and 1-propionyl-2-pyrazolines 11-27 have been synthesized by the reaction of (3-coumarinyl)chalcones 1-10 with hydrazine in hot acetic acid or propionic acid. While 5-aryl-3-(3-coumarinyl)-1-phenyl-2-pyrazolines 28-35 have been prepared by the reaction of (3-coumarinyl)chalcones 1,3,5-10 with phenylhydrazine in hot pyridine. Structures of all new compounds have been elucidated by microanalyses, 1 H and 13 C nmr spectroscopies.

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Synthesis of benzo[b][1,4]thiazepines by the reaction of 3‐aryl‐1‐(3‐coumarinyl)propen‐1‐ones with 2‐aminothiophenol

Lévai

Jekő

Gondos

et al. 2007

Journal of Heterocyclic Chem

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3‐(2‐Aryl‐2,3‐dihydro‐benzo[b][1,4]thiazepin‐4‐yl)chromen‐2‐ones (2a, e, f) and (Z)‐3‐(2,3‐dihydro‐2‐arylbenzo[b][1,4]thiazepin‐4(5H)‐ylidene)chroman‐2‐ones (3a‐f) have been synthesized by the reaction of 3‐aryl‐1‐(3‐coumarinyl)propen‐1‐ones (1a‐f) with 2‐aminothiophenol in a hot mixture of toluene and acetic acid. Structures of all new compounds and their complete 1H and 13C assignments were achieved applying different one‐ and two‐dimensional nmr experiments in combination with various spectroscopic techniques.

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Synthesis of Some New 1,5-Benzothiazepines Containing 2h-1- Benzopyran-2-One Heterocycle

Cited by 4 publications

References 1 publication

Interactions of a series of novel spiropyranocoumarin derivatives with reactive oxygen species

Interactions of a series of novel spiropyranocoumarin derivatives with reactive oxygen species

Synthesis of 1-substituted 5-aryl-3-(3-coumarinyl)-2-pyrazolines by the reaction of 3-aryl-1-(3-coumarinyl)propen-1-ones with hydrazines

Synthesis of benzo[b][1,4]thiazepines by the reaction of 3‐aryl‐1‐(3‐coumarinyl)propen‐1‐ones with 2‐aminothiophenol

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