Synthesis and Macrofilaricidal Activity of Substituted 2‐Hydroxy/5‐Hydroxy/2‐Methyl‐1,4‐Naphthoquinones
Identifieur interne : 001115 ( Main/Exploration ); précédent : 001114; suivant : 001116Synthesis and Macrofilaricidal Activity of Substituted 2‐Hydroxy/5‐Hydroxy/2‐Methyl‐1,4‐Naphthoquinones
Auteurs : Twinkle Karunan [Inde] ; Nisha Mathew [Inde] ; Lakshmy Srinivasan [Inde] ; Kalyanasundaram Muthuswamy [Inde]Source :
- Drug Development Research [ 0272-4391 ] ; 2013-05.
English descriptors
- Teeft :
- Adme properties, Adult worm, Adult worms, Adulticidal drug, Amine, Antimalarial, Assay, Chem, Chemical structure, Compound, Derivative, Digitata, Digitata worms, Drug score, Effective compounds, Formazan, Formazan formation, Fresh medium, Human lymphatic system, Hydroxyl group, Incubation period, Indian council, Indira nagar, Kalyanasundaram, Larial, Larial worm, Larial worm setaria digitata, Larial worms, Lower concentrations, Macrofilaricidal activity, Medical research, Methyl group, Molecular weight, Motility, Naphthoquinone, Nisha, Nisha mathew, Online program osiris property explorer, Osiris, Osiris property explorer, Parasitic worms, Polysubstituted derivatives, Preliminary screening, Promising activity, Quinone, Quinone ring, Reduction assay, Reproductive toxicity, Room temperature, Secondary amines, Spectroscopic data, Streblus asper, Substitution, Thermo finnigan, Thin layer chromatography, Toxicity, Trypanosoma cruzi, Vector control research centre, Wiley periodicals, Worm, Worm motility.
Abstract
Preclinical Research Lymphatic filariasis is a disfiguring disease caused by parasitic worms that destroy the human lymphatic system leading to substantial morbidity. The current drug of choice for the treatment of filariasis is diethylcarbamazine and ivermectin with albendazole which are only effective against the microfilaria, leaving the adult worm unaffected, requiring the development of “adulticidal drugs.” Thirty amino substituted 2‐hydroxy/5‐hydroxy/2‐methyl‐1,4‐naphthoquinones were synthesized via the reaction of 2‐hydroxy/5‐hydroxy/2‐methyl‐1,4‐naphthoquinones with different primary and secondary amines. Compounds 1–30 were evaluated for in vitro antifilarial activity against the adult bovine filarial worm Setaria digitata as assessed by worm motility and MTT (3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide) reduction assays. The mutagenecity, tumerogenecity, irritantancy, reproductive toxicity, drug score, druglike, and cLogP properties were calculated using OSIRIS property predictor. Ten compounds showed macrofilaricidal activity with ED50 values ranging between 0.086 and 7.6 μM. Taking into account the biological effects and the promising drug‐like profiles of these compounds, these represent valid leads for the development of antifilarial agents against adult filarial worm.
Url:
DOI: 10.1002/ddr.21065
Affiliations:
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nagar</term><term>Kalyanasundaram</term><term>Larial</term><term>Larial worm</term><term>Larial worm setaria digitata</term><term>Larial worms</term><term>Lower concentrations</term><term>Macrofilaricidal activity</term><term>Medical research</term><term>Methyl group</term><term>Molecular weight</term><term>Motility</term><term>Naphthoquinone</term><term>Nisha</term><term>Nisha mathew</term><term>Online program osiris property explorer</term><term>Osiris</term><term>Osiris property explorer</term><term>Parasitic worms</term><term>Polysubstituted derivatives</term><term>Preliminary screening</term><term>Promising activity</term><term>Quinone</term><term>Quinone ring</term><term>Reduction assay</term><term>Reproductive toxicity</term><term>Room temperature</term><term>Secondary amines</term><term>Spectroscopic data</term><term>Streblus asper</term><term>Substitution</term><term>Thermo finnigan</term><term>Thin layer chromatography</term><term>Toxicity</term><term>Trypanosoma 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The current drug of choice for the treatment of filariasis is diethylcarbamazine and ivermectin with albendazole which are only effective against the microfilaria, leaving the adult worm unaffected, requiring the development of “adulticidal drugs.” Thirty amino substituted 2‐hydroxy/5‐hydroxy/2‐methyl‐1,4‐naphthoquinones were synthesized via the reaction of 2‐hydroxy/5‐hydroxy/2‐methyl‐1,4‐naphthoquinones with different primary and secondary amines. Compounds 1–30 were evaluated for in vitro antifilarial activity against the adult bovine filarial worm Setaria digitata as assessed by worm motility and MTT (3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide) reduction assays. The mutagenecity, tumerogenecity, irritantancy, reproductive toxicity, drug score, druglike, and cLogP properties were calculated using OSIRIS property predictor. Ten compounds showed macrofilaricidal activity with ED50 values ranging between 0.086 and 7.6 μM. Taking into account the biological effects and the promising drug‐like profiles of these compounds, these represent valid leads for the development of antifilarial agents against adult filarial worm.</div></front></TEI><affiliations><list><country><li>Inde</li></country></list><tree><country name="Inde"><noRegion><name sortKey="Karunan, Twinkle" sort="Karunan, Twinkle" uniqKey="Karunan T" first="Twinkle" last="Karunan">Twinkle Karunan</name></noRegion><name sortKey="Mathew, Nisha" sort="Mathew, Nisha" uniqKey="Mathew N" first="Nisha" last="Mathew">Nisha Mathew</name><name sortKey="Muthuswamy, Kalyanasundaram" sort="Muthuswamy, Kalyanasundaram" uniqKey="Muthuswamy K" first="Kalyanasundaram" last="Muthuswamy">Kalyanasundaram Muthuswamy</name><name sortKey="Srinivasan, Lakshmy" sort="Srinivasan, Lakshmy" uniqKey="Srinivasan L" first="Lakshmy" last="Srinivasan">Lakshmy Srinivasan</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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