The Behavior of Certain Coumarins and Furocoumarins Toward Sulfur Reagents

Ibrahim, Nabila M.

doi:10.1080/10426500500536523

Cited by 13 publications

(7 citation statements)

References 15 publications

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“…Natural products are inexhaustible as a source of chemical structures and for more than a century have been used as scaffolds for the synthesis of new drugs. The coumarins, phenolic compounds which possess a benzopyranone nucleus [4] are one of the major classes of secondary metabolites, which has been highlighted in biological studies as being (anti-HIV [5], hepato-protective [6], anti-inflammatory [7], antimicrobial [8], antimitotic [9] and antitumor [10]), and in part, due to their antifungal properties [11–13] they are believed to exert a role in plant protection against herbivorous, fungal, and bacterial infections [14]. …”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structure-Activity Relationships (SAR) and in Silico Studies of Coumarin Derivatives with Antifungal Activity

Araújo

Guerra

Lima

et al. 2013

IJMS

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The increased incidence of opportunistic fungal infections, associated with greater resistance to the antifungal drugs currently in use has highlighted the need for new solutions. In this study twenty four coumarin derivatives were screened in vitro for antifungal activity against strains of Aspergillus. Some of the compounds exhibited significant antifungal activity with MICs values ranging between 16 and 32 μg/mL. The structure-activity relationships (SAR) study demonstrated that O-substitutions are essential for antifungal activity. It also showed that the presence of a short aliphatic chain and/or electron withdrawing groups (NO2 and/or acetate) favor activity. These findings were confirmed using density functional theory (DFT), when calculating the LUMO density. In Principal Component Analysis (PCA), two significant principal components (PCs) explained more than 60% of the total variance. The best Partial Least Squares Regression (PLS) model showed an r2 of 0.86 and q2cv of 0.64 corroborating the SAR observations as well as demonstrating a greater probe N1 interaction for active compounds. Descriptors generated by TIP correlogram demonstrated the importance of the molecular shape for antifungal activity.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Structure-Activity Relationships (SAR) and in Silico Studies of Coumarin Derivatives with Antifungal Activity

Araújo

Guerra

Lima

et al. 2013

IJMS

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“…Treatment of 4-hydroxycoumarin 1 with Lawesson's reagent in boiling toluene afforded 4-mercapto-2H-chromene-2-thione 136 (Ibrahim, 2006) (Scheme 71). Scheme 72.…”

Section: Thionation Reactionmentioning

confidence: 99%

“…When a mixture of 4-hydroxycoumarin 1 and phosphorus pentasulfide in dry toluene was boiled under reflux, it yielded 3,3-bis-(4-thiohydroxycoumarin)[4-mercapto-3-(4-mercapto-2-oxo-2H-chromen-3-yl)-2H-chromen-2-one] 126 (Ibrahim, 2006) Scheme 66. On the other hand, tetraalkylthiuram disulfides 131 reacted with 4-hydroxycoumarin 1 to yield of 3-dimethylaminothiocarbonylthio-4-hydroxycoumarin 132 (Schnell and Kappe, 1999) (Scheme 69).…”

Section: Thiophenols Formationmentioning

confidence: 99%

Recent advances in 4-hydroxycoumarin chemistry. Part 1: Synthesis and reactions

Abdou

El‐Saeed

Bondock

2019

Arabian Journal of Chemistry

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“…and antimalarial 7 activities. In pursuance of our growing interest in the chemistry of polyfunctional substrates, [8][9][10] we have now attempted the preparation of 2-azidoquinoline-3-carboxaldehyde (2) to examine its reactivity towards certain primary amines (3a-c), hydrazines (4a-d) and active methylene compounds (5, 6) (Scheme 1).…”

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confidence: 99%

“…The reaction of compound (2) with aniline (3a) proceeded in absolute ethanol at ambient temperature to give a pale yellow crystalline product formulated as 3-phenylaminomethylenetetrazolo[1,5-a]quinoline (7) The reaction of (2) with o-phenylenediamine (3b) also proceeded in ethanol in the cold to give a yellowish-brown tetrazolo[1,5-a]quinoline (8). Formation of ( 8) is best explained in terms of molecular reaction of the initially formed anil (9) to give a transient * Correspondent. E-mail: mrh_mahran@yahoo.com intermediate like ( 10) which readily undergoes auto-oxidation 8) (Scheme 2).…”

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confidence: 99%