Synthesis of 9-substituted derivatives of berberine as anti-HIV agents

Design, synthesis and biological evaluation of berberine-benzimidazole hybrids as new type of potentially DNA-targeting antimicrobial agents

“…Intermediate 2 could be efficiently prepared in yield of 79% by selective demethylation of berberine chloride 1 at 9-position heated at 190 °C under vacuum (20 mm Hg) for 45 minutes [28]. Berberrubine 2 was further reacted with chloroacetic acid by nucleophilic substitution in dry DMF at 60 °C to produce compound 3 in yield of 50% [29,30], and then cyclized with substituted benzene-1,2-diamines in 4 mol/L hydrochloric acid solution at 110 °C in good yields to afford compounds 4a−c.…”

A Novel Synthetic Route for Berberine Chloride

“…[4] 、抗病毒 [5] 、抗艾滋病毒(HIV)、 糖尿病、抗肥胖症、抗疟疾、抗风湿、抗衰老、抗焦虑、 抗活体器官移植排斥反应等作用, 同时可用于降低腹部 手术后的发炎、保护心脏、减少疼痛的作用以及改善多 囊卵巢综合征、治疗心血管疾病 [6～10] . 在细胞外信号调 节激酶(ERK)中, 它通过低密度脂蛋白信使核糖核酸 (LDLR mRNA)的稳定转录来增加低密度脂蛋白受体的 表达 [11] .…”

“…[13] , 后经霍夫曼重排 得黄连素关键中间体 3,4-亚甲二氧基苯乙胺 [14] . [15] , 5,147.7,146.1,134.0,121.2,108.8,108.4,100.9,36.0,30.4; -).…”

“…3.2.8 N- (2,3-二甲氧基苄基)-3,4-亚甲二氧基苯乙胺(9) 的合成 称取化合物 8 (6.30 g, 0.0382 mol)、2,3-二甲氧基苯 甲醛(6.30 g, 0.0380 mol)置于反应瓶中, 在 105 ℃条件 下反应 0.5 h, 随后冷却至室温, 加入 51 mL 甲醇, 分多 次加入 NaBH 4 (0.800 g, 0.0211 mol), 在 70 ℃的条件下 反应 10 h. 室温下旋转蒸除去多余的甲醇, 残留物用 20 mL 水溶解后用乙醚萃取(50 mL×3), 合并有机层, 用 20 mL 水洗、饱和食盐水洗 (20 mL×2 5,147.5,147.2,145.8,133.6,133.2,123.8,121.7,121.5,111.4,109.0,108.1,100.7,60.6,55.6,50.4,48.4,35.8; ＋ ).…”

Novel berberine triazoles: Synthesis, antimicrobial evaluation and competitive interactions with metal ions to Human Serum Albumin

“…The berberine chloride was demethylated at 190°C under reduced pressure (20 mm Hg) for 2 h to produce berberrubine in 88.2% yield which was in agreement with literature. 4 The latter was reacted with compounds 4a-h in DMF at 110°C for 20 h approximately to afford the target compounds 5a-h. Subsequently, hydrochloride 6 was easily prepared by the reaction of compound 5a with 4 M hydrochloric acid.…”