Antifungal activity of synthetic di(hetero)arylamines based on the benzo[b]thiophene moiety

Pinto, Eugénia; Queiroz, Maria João R. P.; Vale-Silva, Luís A.; Oliveira, João Filipe; Begouin, Agathe; Bégouin, Jeanne-Marie; Kirsch, Gilbert

doi:10.1016/j.bmc.2008.07.042

Cited by 57 publications

(38 citation statements)

References 19 publications

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“…Their natural and synthetic derivatives display a wide spectrum of pharmacological activities like antioxidant, antibacterial, antimicrobial, antifungal, antiviral and anticancer activities etc [13][14][15][16][17]. Moreover substituted benzofurans find application such as of oxidant [18], antioxidants, fluorescent sensor [19], brightening agents, a variety of drugs and in other field of chemistry and agriculture [20].…”

Section: Introductionmentioning

confidence: 99%

<strong>Synthesis of Chiral Heteroaryl-Substituted Dihydropyran Derivatives via Ring Closing Enyne Metathesis Reaction</strong>

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et al. 2017

Proceedings of the 21st International Electronic Conference on Synthetic Organic Chemistry

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The ring closing enyne metathesis reactions have been applied to systems derived from homopropargylic alcohol backbones are described. The key intermediates 2-benzofuranyl and 2-benzothiophenyl homopropargylic alcohols were synthesized from their corresponding carboxyaldehyde derivatives and resolved to give the corresponding enantiopure acetates and the alcohols with high ee values through enzymatic resolution. Then, enantiomerically enriched enyne skeletons derived from homopropargylic alcohols were subjected to the ring closing metathesis reaction via first generation Grubbs' catalysts and corresponding chiral heteroaryl-substituted dihydropyran derivatives were obtained with good yields.

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Section: Introductionmentioning

confidence: 99%

<strong>Synthesis of Chiral Heteroaryl-Substituted Dihydropyran Derivatives via Ring Closing Enyne Metathesis Reaction</strong>

Gümüş

Büyükadalı

et al. 2017

Proceedings of the 21st International Electronic Conference on Synthetic Organic Chemistry

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“…Thiophenes represent many naturally occurring and designed molecules responsible for a diverse range of biological responses [1]- [6] recently; substituted thiophenes [7] [8] are often representing a class of important and well-studied herterocycles [9]. The interest in this kind heterocycles has spread from early dye chemistry [10] to modern drug design [11] biodiagnostics [12], electronic and optoelectronic devices [13], conductivity-based…”

Section: Introductionmentioning

confidence: 99%

New Approaches for the Use of Acetoacetanilide in the Synthesis of Thiophenes and Their Fused Derivatives with Anti-Tumor Activity

Mohareb¹,

Sherif²,

Wardakhan³

2014

OALib

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Acetoacetanilide derivatives 1a-c reacted with either malnonitrile or ethyl cyanoacetate and elemental sulfur to give the thiophene derivatives 3a-f. The reactivity of 3a towards some chemical reagents to give thiophene, theino[2,3-b]pyridine, thieno[2,3-c]pyrimidine and coumarin derivatives was studied. The anti-tumor evaluation of the newly synthesized compounds against the three human tumor cells lines namely breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268) showed that compounds 8a, 8b and 14 exhibit higher inhibitory effects towards the three tumor cell lines than the positive control doxorubicin.

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“…Therefore, the development of new and efficacious antimicrobial drugs is a very important goal, and most of the research efforts in this field are directed towards the design of new agents. A review of the recent literature shows that many effective antimicrobial agents contain a heterocyclic moiety within their structure [4,5] with special emphasis on those agents incorporating a thiophene moiety [6][7][8][9][10]. The thiophene ring system is notably a structural component of the commercial imidazole antifungal agent sertaconazole [11].…”

Section: Introductionmentioning

confidence: 99%

Regioselective synthesis and biological evaluation of some novel thiophene-containing heterocyclic scaffolds as potential chemotherapeutic agents

Gaber

Bagley

2011

Eur. J. Chem.

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KEYWORDSIn the reaction of 2-amino-3-carbethoxythiophene derivative 2b with hydrazine hydrate the respective aminocarbohydrazide 3 was isolated. Treatment of the latter product with carbon disulfide in alkaline medium caused a heterocyclization to give 1,3,4-oxadiazole-2-thione 5 rather than 3-amino-2-thioxothieno[2,3-d]pyrimidin-4-one 4, which could be obtained on treatment of carbohydrazide 3 with thiourea. The structure of products 4 and 5 was proved by spectroscopic methods and chemical transformations. Derivatization led to two novel series of condensed and uncondensed thiophenes, which were of significant interest for biological study. Since compound 4 contains two adjacent reactive functional groups, it reacted readily with different electrophilic reagents to provide a series of thieno[2,3-d]pyrimidin-4-one derivatives with annelated bridgehead nitrogen heterocycles 8-11, whereas a second series of 3-heteroaryl-substituted thiophenes 13-17 was obtained by thioamide functionalization in 1,3,4-oxadiazole derivative 5 using various chemical reagents. The new thiophene-based derivatives were evaluated for their preliminary antimicrobial activity against a representative panel of Gram-positive and Gram-negative bacteria as well as fungi strains. The compounds tested displayed different levels of inhibitory effects, with the assays carried out on two pathogenic bacteria and two pathogenic fungi. Of these compounds, the monocyclic aminothiophene derivative 15 showed the highest effect on pathogenic bacteria, while the tricyclic condensed thiophene derivative 8 was observed to have the same inhibitory effect against pathogenic mould (Aspergillus flavus) as the reference drug Amphotericin B. For those derivatives belonging to first series of condensed thiophenes with annelated bridgehead nitrogen heterocycles, it has been observed that the antibacterial effect was in general found to be significantly higher than the corresponding uncondensed analogues. Although most of the condensed and uncondensed thiophenes under investigation showed generally remarkable in vitro antibacterial activity, unfortunately, no significant antifungal activity was observed with any of the compounds tested except for 8. Surprisingly, compound 8 displayed an excellent effect on fungus (A. flavus) on the one hand, whereas the lowest effect on bacteria on the other. The attachment of a triazolothiadiazine moiety to a thiophene ring could be considered as a promising strategy for the development of new therapeutic antibacterial agents related to the aminothiophene system. Thienopyrimidinone Cyclocondensation Cyclodesulfurization Hydrazinolysis Alkylation Antimicrobial activity

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Antifungal activity of synthetic di(hetero)arylamines based on the benzo[b]thiophene moiety

Cited by 57 publications

References 19 publications

<strong>Synthesis of Chiral Heteroaryl-Substituted Dihydropyran Derivatives via Ring Closing Enyne Metathesis Reaction</strong>

<strong>Synthesis of Chiral Heteroaryl-Substituted Dihydropyran Derivatives via Ring Closing Enyne Metathesis Reaction</strong>

New Approaches for the Use of Acetoacetanilide in the Synthesis of Thiophenes and Their Fused Derivatives with Anti-Tumor Activity

Regioselective synthesis and biological evaluation of some novel thiophene-containing heterocyclic scaffolds as potential chemotherapeutic agents

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