Antiparasitic activities of new lawsone Mannich bases

A series of new lawsone Mannich bases derived from salicylaldehydes or nitrofurfural were prepared and tested for their activities against Leishmania major, Toxoplasma gondii, and Trypanosoma brucei brucei parasites. The hydrochloride salts 5a and 6a of the Mannich bases 2a and 3a, derived from unsu...

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Veröffentlicht in:Archiv der Pharmazie (Weinheim) 2019-11, Vol.352 (11), p.e1900128-n/a
Hauptverfasser: Al Nasr, Ibrahim, Jentzsch, Jana, Winter, Isabel, Schobert, Rainer, Ersfeld, Klaus, Koko, Waleed S., Mujawah, Adil A. H., Khan, Tariq A., Biersack, Bernhard
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container_issue 11
container_start_page e1900128
container_title Archiv der Pharmazie (Weinheim)
container_volume 352
creator Al Nasr, Ibrahim
Jentzsch, Jana
Winter, Isabel
Schobert, Rainer
Ersfeld, Klaus
Koko, Waleed S.
Mujawah, Adil A. H.
Khan, Tariq A.
Biersack, Bernhard
description A series of new lawsone Mannich bases derived from salicylaldehydes or nitrofurfural were prepared and tested for their activities against Leishmania major, Toxoplasma gondii, and Trypanosoma brucei brucei parasites. The hydrochloride salts 5a and 6a of the Mannich bases 2a and 3a, derived from unsubstituted salicylaldehyde and long‐chained alkyl amines, were selectively and strongly active against T. gondii cells and appear to be new promising drug candidates against this parasite. Compound 6a showed an even higher activity against T. gondii than the known lawsone Mannich base 1b. Compound 4a, derived from salicylaldehyde and 2‐methylaminopyridine, was also distinctly active against T. gondii cells. The derivatives 3a (salicyl derivative), 3b (3,5‐dichloro‐2‐hydroxyphenyl derivative), and 3d (5‐nitrofuranyl derivative) as well as the hydrochlorides 6a and 6b were also efficacious against T. b. brucei cells with compounds 3a and 3b being more selective for T. b. brucei over Vero cells when compared with the known control compound 1b. The derivatives 5a, 5c, 6a, and 6c proved to be up to five times more active than 1b against L. major promastigotes and up to four times more efficacious against L. major amastigotes. New lawsone Mannich bases derived from salicylic aldehydes and long‐chained primary alkyl amines were prepared by simple methods. Some promising derivatives were distinctly more active against and selective for Toxoplasma gondii and Leishmania major cells than a known antiparasitic lawsone Mannich base.
doi_str_mv 10.1002/ardp.201900128
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The derivatives 3a (salicyl derivative), 3b (3,5‐dichloro‐2‐hydroxyphenyl derivative), and 3d (5‐nitrofuranyl derivative) as well as the hydrochlorides 6a and 6b were also efficacious against T. b. brucei cells with compounds 3a and 3b being more selective for T. b. brucei over Vero cells when compared with the known control compound 1b. The derivatives 5a, 5c, 6a, and 6c proved to be up to five times more active than 1b against L. major promastigotes and up to four times more efficacious against L. major amastigotes. New lawsone Mannich bases derived from salicylic aldehydes and long‐chained primary alkyl amines were prepared by simple methods. 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Compound 6a showed an even higher activity against T. gondii than the known lawsone Mannich base 1b. Compound 4a, derived from salicylaldehyde and 2‐methylaminopyridine, was also distinctly active against T. gondii cells. The derivatives 3a (salicyl derivative), 3b (3,5‐dichloro‐2‐hydroxyphenyl derivative), and 3d (5‐nitrofuranyl derivative) as well as the hydrochlorides 6a and 6b were also efficacious against T. b. brucei cells with compounds 3a and 3b being more selective for T. b. brucei over Vero cells when compared with the known control compound 1b. The derivatives 5a, 5c, 6a, and 6c proved to be up to five times more active than 1b against L. major promastigotes and up to four times more efficacious against L. major amastigotes. New lawsone Mannich bases derived from salicylic aldehydes and long‐chained primary alkyl amines were prepared by simple methods. 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subjects Antiparasitic Agents - chemical synthesis
Antiparasitic Agents - chemistry
Antiparasitic Agents - pharmacology
antiparasitic drugs
Dose-Response Relationship, Drug
lawsone
Leishmania major - drug effects
Mannich base
Mannich Bases - chemical synthesis
Mannich Bases - chemistry
Mannich Bases - pharmacology
Molecular Structure
Naphthoquinones - chemical synthesis
Naphthoquinones - chemistry
Naphthoquinones - pharmacology
neglected tropical diseases
Parasitic Sensitivity Tests
Protozoa
salicyl derivatives
Structure-Activity Relationship
Toxoplasma - drug effects
Trypanosoma brucei brucei - drug effects
title Antiparasitic activities of new lawsone Mannich bases
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