A Simple Synthesis of Angular Anthrathiophenediones via Acetylenic Derivatives of Anthraquinone

Ivanchikova, Irina D.; Lebedeva, Nadezhda I.; Shvartsberg, M. S.

doi:10.1055/s-2004-829187

Cited by 6 publications

(1 citation statement)

References 18 publications

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“…In addition, different transition metal catalysts such as PdCl 2 , CuCl 2 , and AuCl were used for the electrophilic cyclization of o -alkynyl aryl thioether to synthesize benzothiophene . The reaction of o -bromo alkynyl benzenes with elemental chalcogens (sulfur, selenium, and tellurium) to synthesize benzo[ b ]chalcogenophenes has been reported. , Other inorganic sulfur sources such as sodium sulfide (Na 2 S·9H 2 O), − thionyl chloride, hydrogen sulfide, thiourea, and carbon disulfide were reacted with o -halo alkynyl benzenes to synthesize benzothiophenes. 2-Halo benzonitrile derivatives were reacted with ethyl mercaptoacetate to synthesize 3-amino-2-ester-functionalized benzothiophenes. − …”

Section: Introductionmentioning

confidence: 99%

Domino Reaction Protocol to Synthesize Benzothiophene-Derived Chemical Entities as Potential Therapeutic Agents

Roy,

Budhathoki,

Iqbal

et al. 2024

J. Org. Chem.

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An efficient synthesis of 3-amino-2-formyl-functionalized benzothiophenes by a domino reaction protocol and their use to synthesize a library of novel scaffolds have been reported. Reactions of ketones and 1,3-diones with these amino aldehyde derivatives formed a series of benzothieno[3,2-b]pyridine and 3,4-dihydro-2H-benzothiopheno [3,2-b]quinolin-1-one, respectively. A plausible mechanism for the formation of fused pyridine derivatives by the Friedlander reaction has been elucidated by density functional theory (DFT) calculations. Furthermore, hydrazones were obtained by reacting the aldehyde functional group of benzothiophenes with different hydrazine derivatives. Preliminary screening of these compounds against several bacterial strains and cancer cell lines led to the discovery of several hit molecules. Hydrazone and benzothieno [3,2-b]pyridine derivatives are potent cytotoxic and antibacterial agents, respectively. One of the potent compounds effected ∼97% growth inhibition of the LOX IMVI cell line at 10 μM concentration.

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