Synthesis, characterization and antibacterial activity of novel heterocycle, coumacine, and two of its derivatives

Mustafa, Yasser Fakri

doi:10.1016/j.jsps.2018.03.010

Cited by 29 publications

(17 citation statements)

References 30 publications

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“…The EtOAc layer was dehydrated over Na2SO4, filtered, and vaporized under reduced pressure. The target product was recrystallized from EtOH [22]. (e): White powder; % yield=92; mp=106-108°C; Rf =0.26; C17H15FN2O7; λmax (MeOH)=302 nm; FTIR (ν, cm - 3-(2-((3-((5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1…”

Section: Synthesis Of (Z)-2-(3-((tert-butyldimethylsilyl)oxy)prop-1-ementioning

confidence: 99%

Synthesis and Kinetic Study of Novel Coumarin- Based Mutual Prodrug of 5-fluorouracil and 5-ethynyluracil

Mustafa¹,

Oglah²,

Bashir³

2021

Rev. Chim.

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The oral use of 5-fluorouracil is being deserted in the last decades due to its atypical intestinal absorption, which is primarily attributed to the mutable activity of dihydropyrimidine dehydrogenase located in the gastrointestinal mucosa. In this work, a coumarin-based prodrug system was utilized to synthesize a novel mutual prodrug of 5-fluorouracil and 5-ethynyluracil. This prodrug was designed to afford a concurrent release of these two active drugs resulting in the improvement of the therapeutic efficacy of both. The synthetic pathway involved 7 linear steps starting from coumarin. The chemical structures of the intermediates and prodrug were established by analyzing their FTIR, 1H-NMR, and 13C-NMR spectra. The in vitro chemical stability of the synthesized prodrug was tested in the HCl buffer (pH 1.2) and phosphate-buffered saline (pH 6.8), while its ability to release the active moieties was studied in human serum. The outcomes of these in vitro studies revealed that the prodrug showed a significant stability in the HCl buffer and phosphate-buffered saline with half-lives of 33.19 h and 18.13 hr respectively, obeying pseudo-first-order kinetics. Also, the prodrug was able to release the two active components in human serum with a half-life of 4.62 h obeying zero-order kinetics. It is concluded that the synthesized prodrug represents a promising oral prodrug of 5-fluorouracil and 5-ethynyluracil to serve better in therapeutics.

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Section: Synthesis Of (Z)-2-(3-((tert-butyldimethylsilyl)oxy)prop-1-ementioning

confidence: 99%

Synthesis and Kinetic Study of Novel Coumarin- Based Mutual Prodrug of 5-fluorouracil and 5-ethynyluracil

Mustafa¹,

Oglah²,

Bashir³

2021

Rev. Chim.

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“…Coumarin-derived compounds of varied structural manifestations have been exhibited a distinct role for managing a number of clinical conditions, such as inflammation [8], Alzheimer [9], high protein edema [10], blood coagulation [11], oxidative stress [12], cancer [13][14][15], and chronic infections [16,17]. Synthesis devised for preparing various coumarin-derived compounds [18].…”

Section: Introductionmentioning

confidence: 99%

Untitled

Mustafa

2021

J. Med. Chem. Sci.

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Coumarin chemical nucleus is a gift awarded from nature to humanity. The multifarious derivatives and the broad range of their bio-medicinal potentials are the basis for this description. In the last several decades, though numerous coumarin-based products have been primarily separated from their biological origins, the laboratory synthesis of the coumarins is developing. Various synthetic trails namely Knoevenagel, Claisen, Perkin, Pechmann, Wittig, and Reformatsky have been reported. Several advanced innovations have been created to maximize yield, minimize overall reaction time, avoid side products, and make synthetic reactions environmentally friendly. These include the employment of ultrasonic, microwave, and solventfree conditions. This brief review focuses on the classic methods for synthesizing coumarins, and the advantages derived from the use of creative catalytic tools.

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“…Since its original isolation via Vogel, coumarin and its based products and compounds have attracted much research concern not only because of their fascinating structural properties but also due to their multifactorial biological activities [1]. Of those, antiinflammatory, anticoagulant [2], anti-HIV [3], antioxidant [4], antidiabetic [5], anticancer [6], antibacterial [7], and antifungal [8] potentials are widely investigated.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and anticoagulant activity of new functionalized biscoumarins

2021

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Despite their rarity and structural complexity, natural and synthetic biscoumarins have polarized much attention from investigators particularly due to their characteristic activity as anticoagulant agents. In this work, a panel of twelve functionalized biscoumarins was synthesized in two schematic steps; the first one started by condensing various phenol-based derivatives with malonic acid via a Pechmann-type reaction yielding alkyl-substituted 4-hydroxycoumarins herein symbolized as (E1-E12). The latter compounds were undergone a self-coupling under the influence of methylene iodide to afford the target functionalized biscoumarins, which were symbolized as (EY1-EY12). The potential of the synthesized biscoumarins as anticoagulant applicants was investigated in vivo using rabbit as an animal model. The employed assay was the prothrombin time that was monitored after three and five days of the last oral treatment. The results gathered from this test revealed that the synthesized biscoumarins have a promising anticoagulant activity compared with warfarin as a standard anticoagulant drug, with privileged influence contributed to those substituted at position 7 of the coumarin framework. The authors concluded that the substitution of an alkyl group at that position of the coumarin monomer may intensify the anticoagulant activity of the prepared biscoumarins. Also, this intensity was directly proportionated to the increase in the molecular weight of this alkyl group. Accordingly, the synthesized biscoumarins possessing this property would provide an efficient base for synthesizing new compounds, which have a promising anticoagulant effect.

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Synthesis, characterization and antibacterial activity of novel heterocycle, coumacine, and two of its derivatives

Cited by 29 publications

References 30 publications

Synthesis and Kinetic Study of Novel Coumarin- Based Mutual Prodrug of 5-fluorouracil and 5-ethynyluracil

Synthesis and Kinetic Study of Novel Coumarin- Based Mutual Prodrug of 5-fluorouracil and 5-ethynyluracil

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Synthesis, characterization, and anticoagulant activity of new functionalized biscoumarins

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