Synthesis and in vitro anti-hepatitis B virus activities of some ethyl 5-hydroxy-1H-indole-3-carboxylates

Abstract

A series of ethyl 5-hydroxy-1H-indole-3-carboxylates 6A-10T were synthesized and evaluated for their anti-hepatitis B virus (HBV) activities in 2.2.15 cells. The IC50 and selective index of inhibition on replication of HBV DNA of compounds 10(L) (1.52 microg/ml, 9.38) and 10(P) (2.00 microg/ml, 8.85) were higher than those of the other evaluated compounds including lamivudine (7.02). Compounds 7E and 10J exhibited significant anti-HBV activities, and the IC50 values on replication of HBV DNA of these compounds were 24.90 and 15.41 microg/ml, respectively, which were far more potent than the positive control lamivudine 228.00 microg/ml.

Synthesis and Anti‐Hepatitis B Virus Evaluation of 7‐Methoxy‐3‐heterocyclic quinolin‐6‐ols

“…The synthesis of important intermediates 8a-c was achieved using a convenient six-step procedure starting from 3-hydroxy-4-methoxylbenzaldehyde (1) depicted in Scheme 1, in which the synthesis of the key intermediate 6 was illustrated in detail in our previous study [15][16][17][18], which was treated with hydrazine hydrate to afford compound 7 [19]. Furthermore, compound 7 reacted with formic acid or acyl chloride to afford the intermediates 8a-c [20,21].…”

“…Furthermore, compound 7 reacted with formic acid or acyl chloride to afford the intermediates 8a-c [20,21]. The thioether 5 was obtained via etherification of ethyl 4-chloro-3-oxobutanoate 18 and thiophenol 17 (Scheme 2) [15]. The oxadiazol derivatives 11a-g were synthesized from 8a-b (Scheme 3).…”

“…Cyclization of 8a or 8b in POCl 3 at 60°C led to the formation of 9a,b [19], which were deprotected with trifluoroacetic acid and boron tribromide to produce compounds 10a,b [22]. Finally, the target compounds 11a-g were achieved via a Mannich reaction [8,15]. The thiadiazol Arch.…”

“…C NMR spectra were determined for solutions in DMSOd 6 or CDCl 3 using Bruker 400 MHz spectrometers (Bruker Bioscience, Billerica, MA, USA) with TMS as an internal standard. Compound 6 was synthesized according to the literature [15][16][17][18].…”

Synthesis and in‐vitro Anti‐hepatitis B Virus Activity of Ethyl 6‐Bromo‐8‐hydroxyimidazo[1,2‐a]pyridine‐3‐carboxylates

“…1), which exhibited significant anti-HBV activity [8,9]. In view of the novel structural template, which differs from those of all reported anti-HBV agents, we were interested to further study the structureactivity relationship (SAR) of the related class of compounds.…”