Prodrugs for amidines: synthesis and anti-Pneumocystis carinii activity of carbamates of 2,5-bis(4-amidinophenyl)furan.

doi:10.1021/JM990237+

Paper

Prodrugs for amidines: synthesis and anti-Pneumocystis carinii activity of carbamates of 2,5-bis(4-amidinophenyl)furan.

Published 1999 · Syed M. Rahmathullah, James Edwin Hall, B. C. Bender

Journal of Medicinal Chemistry

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Abstract

Syntheses of several carbamate analogues of 2,5-bis(4-amidinophenyl)furan (1) under mild conditions and their evaluation as prodrugs against Pneumocystis carinii pneumonia (PCP) in an immunosuppressed rat model are described. Thus, nine new bis-carbamates: methoxycarbonyl (2), 2,2,2-trichloroethoxycarbonyl (3), ethylthiocarbonyl (4), benzyloxycarbonyl (5), (4-methyl-2-oxo-1,3-dioxol-4-en-5-yl)methoxycarbonyl (6), phenoxycarbonyl (7), 4-fluorophenoxycarbonyl (8), 4-methoxyphenoxycarbonyl (9), and (1-acetoxy)ethoxycarbonyl (10) and a bis-carbonate ethoxycarbonyloxy (11) of the bis-amidine 1 have been synthesized and evaluated. The in vivo results show that the 4-fluorophenyl carbamate 8 and the 4-methoxyphenyl carbamate 9 in this series had the best anti-PCP activity by both intravenous and oral administration at a dosage level of 22 mol and 33 μmol/kg/day, respectively. Compounds 3−7 were also more active than the parent drug (1) on oral administration. The acute toxicity usually exhibited by the parent a...

Study Snapshot

Carbamates of 2,5-bis(4-amidinophenyl)furan show promising anti-Pneumocystis carinii activity, with 4-fluorophenyl carbamate 8 and 4-methoxyphenoxycarbonyl 9 showing the best anti-PCP activity

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Prodrugs for amidines: synthesis and anti-Pneumocystis carinii activity of carbamates of 2,5-bis(4-amidinophenyl)furan.

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References

Citations

Manganese-Promoted Cyclization Reaction of Enynones with Tetrasulfides: Synthesis of Multisubstituted Furanmethyl Disulfides.

A manganese-promoted tandem cyclization reaction of enynones with tetrasulfides leads to high-yield formation of various furanmethyl disulfides, offering a practical strategy for synthesis of disulfide-containing functionalized furans.

Amide bioisosteric replacement in the design and synthesis of quorum sensing modulators.

Amide bond bioisosteric replacement can be used to design and synthesize novel quorum sensing inhibitors, potentially improving antibacterial strategies.

Energy-saving improvement of heat integration and heat pump for separating multi-azeotropes mixture via novel pressure swing distillation

The novel pressure swing distillation process (NPSD) with heat integration and heat pump technology significantly reduces energy consumption and emissions compared to the traditional triple-columns process.

Nickel catalysis synthesis of 2,5-disubstituted furans from aryl (alkyl) iodide

This study developed a new method for preparing 2,5-disubstituted furans in good to excellent yields using various aryl(alkyl) iodides and CaC2 as coupling partners, offering a versatile approach for biologically active compounds and functional materials.

Recyclable gold(I)-catalyzed oxidative cyclization of 1,4-diyn-3-ols leading to highly substituted 3-formylfurans

Gold(I)-catalyzed oxidative cyclization of 1,4-diyn-3-ols in toluene effectively synthesizes various 3-formylfurans with high yields and can be reused up to six times without significant loss of catalytic efficiency.