Synthesis and anti-hepatitis B virus evaluation of novel ethyl 6-hydroxyquinoline-3-carboxylates in vitro

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

“…2015, 348, 776-785 7-Methoxy-3-heterocyclic quinolin-6-ols as Anti-HBV Agents Archiv der Pharmazie derivatives 14a-f were synthesized through intermediates 8b,c, which were shown in Scheme 4. 8b,c were reacted with Lawesson's reagent in THF to give 12a,b [23], which were deprotected with a 2:1 mixture of acetic acid and hydrochloric acid to produce intermediates 13a,b [8]. Then, the target compounds 14a-f were obtained via a Mannich reaction as previously demonstrated.…”

“…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.…”

“…Our previous study revealed that pyrrolidinyl, piperidinyl, and imidazolyl substituents at 5-position could exhibit more potent activities than other Mannich basic groups [8], so they were introduced into the new series of compounds. We also found that the oxidation state of sulfur at 2-position would influence the anti-HBV activity [8], therefore some sulfinyl group derivatives were prepared.…”

“…We also found that the oxidation state of sulfur at 2-position would influence the anti-HBV activity [8], therefore some sulfinyl group derivatives were prepared.…”

“…Then the indole ring was expanded to a quinoline moiety to achieve a series of ethyl 6-hydroxyquinoline-3-carboxylate derivatives ( Fig. 1A) with excellent potency (IC 50 < 20 mM) [8]. The main modification of these indole and quinoline derivatives was focused on the positions 2 and 4 (indole) or 5 (quinoline), while there is no change to the carboxylate moiety on 3-position.…”