Activity of 2‐(1‐alkenyl)‐3‐hydroxy‐1,4‐naphthoquinones and related compounds against Musca domestica

Abstract

A series of 2‐(1‐alkenyl)‐3‐hydroxy‐1,4‐naphthoquinones has been prepared and their toxicities assessed against Musca domestica. By comparison with analogous compounds having saturated 2‐alkyl substituents, or unsaturated substituents with an unconjugated double bond (e.g. lapachol), it was demonstrated that the α‐unsaturation of the substituent is responsible for a significant increase in the toxicity. The effect of the compounds against several other insect species and Tetranychus urticae follows completely different patterns.

Novel naphthoquinone derivatives and evaluation of their trypanocidal and leishmanicidal activities

“…18,34 The position and the number of unsaturation of the side chain may also affect the biological activity of the compounds. 20,35 ortho-Quinones are known for having high trypanocidal activity when compared with para-quinone isomers. 18,36 β-lapachone (3) is the most studied and promising molecule of the lapachol group.…”

Reactions of 5-oxo-1-phenylpyrrolidine-3-carbohydrazides with 1,4-naphthoquinone derivatives and the properties of the obtained products

“…Naphthoquinones and their various derivatives as a class display many types of biological activity. They are active against different strains of bacteria and fungi [1][2][3][4][5][6][7][8][9][10], show insecticidal [11,12], molluscicidal [13], and antiproliferative [4,14] properties, and are anticancer agents [15][16][17][18][19][20]. Furthermore, hydrazones have been demonstrated to possess many types of biological activity [21].…”

Insecticidal 2‐hydroxy‐3‐alkyl‐1,4‐naphthoquinones: correlation of inhibition of ubiquinol cytochrome c oxidoreductase (complex III) with insecticidal activity

“…Further work on synthetic analogues of lapachol with relatively lipophilic substituents in the 3‐position has eventually led to the discovery of the new anti‐malarial drug, atovaquone 3. Biological activity against a wide spectrum of organisms and tissues including bacteria,4 fungi,5 parasitic protozoa,6 tumour cells,7 spider mites8 and insects9 has subsequently been described. The mode of action of these compounds and the related hydroxyquinone, 5‐ n ‐undecyl‐6‐hydroxy‐4,7‐dioxobenzthiazole (UHDBT) is by inhibition of the Qo site of mitochondrial complex III (b/c1 complex) by binding near the Rieske iron–sulfur protein 10.…”

“…The 2‐hydroxy group, in conjunction with a hydrophobic 3‐substituent, appears to be essential for activity, but unsaturated bonds in the side chain generally reduce activity 11. Studies on homologous series show that the lipophilicity of the 3‐substituent is a major factor in defining optimum activity against different targets (eg the malarial parasite,1, 2, 12 bovine heart mitochondria,13 fungi5 and houseflies9). However, maximum activity against different targets is often afforded by different homologues within a series, and optimum in vivo and in vitro activities rarely coincide.…”