The synthesis of thioglucosides substituted 1,4-naphthoquinones and their conversion in oxathiane fused quinone-thioglucoside conjugates

Abstract

In this paper we describe a methodology for the preparation of thioglucosides of substituted 1,4-naphthoquinones via condensation of related chloronaphthoquinones with the sodium salt of 1-thio-β-Dglucopyranose in acetone-MeOH solution and subsequent base-catalytic conversion of these mono-and dithioglucosides in the linear tetracyclic quinone-carbohydrate conjugates.

Synthesis and Evaluation of Antimicrobial and Cytotoxic Activity of Oxathiine-Fused Quinone-Thioglucoside Conjugates of Substituted 1,4-Naphthoquinones

“…The starting substituted 2-chloro-3,5,8-trimethoxy-1,4-naphthoquinones 5 and 6 were prepared by treatment of appropriated 2,3-dichloro-5,8-dimethoxynaphtalene-1,4-dione and 2,3,6,7-tetrachloro-5,8-dimethoxynaphtalene-1,4-dione with AcONa in dry methanol at reflux as described earlier [ 27 ] ( Figure 1 ). Bromination of available hydroxyjuglone derivatives 7 and 8 in chloroform solution according to the work in [ 28 ] led to bromoquinones 9 and 10 in good yields, 92%.…”

Tetracyclic 1,4-Naphthoquinone Thioglucoside Conjugate U-556 Blocks the Purinergic P2X7 Receptor in Macrophages and Exhibits Anti-Inflammatory Activity In Vivo

“…13 C NMR (DMSO-d6 , 125 MHz): δ 12.1, 12.2, 60.7, 70.4, 73.4, 73.9, 79. 3, 82.3, 117.3, 107.4, 123.5, 137.8, 137.9, 150.4, 156.3, 157.3, 177.7, 183.0 [14].…”

“…Synthesis of tetracyclic quinone-thioglucoside conjugate U-556 was developed according to our works [12,14]. Briefly, 2-chloro-5,8-dihydroxy-3-methoxy-6,7-dimethyl-1,4naphthoquinone 1 was condensed with tetra-O-acetyl-1-thio-β-D-glucose 2, and acetylthioglucoside of 1,4-naphthoquinone 3 was converted to the tetracyclic quinone-thioglucoside conjugate 4 U-556 by treatment with MeONa.…”