Synthesis and in vitro anti-hepatitis B virus activity of 6H-[1]benzothiopyrano[4,3-b]quinolin-9-ols

Wei, Jia; Liu, Yajing; Li, Wei; Liu, Yan; Zhang, Dajun; Zhang, Peng; Gong, Ping

doi:10.1016/j.bmc.2009.05.001

Cited by 27 publications

(11 citation statements)

References 11 publications

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“…Compound 32 was obtained through caudatin reaction with gallic acid in the presence of diisopropyl azodicarboxylate (DIAD) and triphenylphosphine (TPP). As oxygen and sulfur heterocylic rings were effect functional groups to search potential anti-HBV activity according to previous investigation [18][19][20][21][22], some heterocylic rings containing oxygen and sulfur atoms were introduced into the caudatin in order to obtain the active analogs. In order to further evaluate the effect of hydroxyl groups at C-3 and C-17 for biological activity, the C-3, 17 diesters (33-39) of caudatin were synthesized.…”

Section: Chemistrymentioning

confidence: 99%

Design, Synthesis and Biological Evaluation of Caudatin Analogs as Potent Hepatitis B Virus Inhibitors

Wang¹,

Chen²,

Ma³

et al. 2015

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Thirty-nine caudatin analogs were designed and synthesized. Their anti-hepatitis B virus (HBV) activities were evaluated in vitro. Among them, twenty-three compounds showed much better anti-HBV activity than caudatin, and eleven compounds significantly inhibited the HBV DNA replication with IC50 values < 10 μM. Interestingly, three compounds (22, 28, 29) exhibited excellent activity against the secretion of HBsAg (IC50 = 63.02 μM, 52.81 μM, 56.08 μM), HBeAg (IC50 = 204.80 μM, 173.51 μM, 70.39 μM), along with HBV DNA replication (IC50 = 24.55 μM, 5.69 μM, 8.23 μM) with lower cytotoxicity. The structure-activity relationships (SARs) of these caudatin analogs were also discussed.

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Section: Chemistrymentioning

confidence: 99%

Design, Synthesis and Biological Evaluation of Caudatin Analogs as Potent Hepatitis B Virus Inhibitors

Wang¹,

Chen²,

Ma³

et al. 2015

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“…Mannich bases have applications the field medicinal chemistry, the product synthetic polymers, the petroleum industry, as products used in water treatment, cosmetics, the dyes industry, etc 1 . In addition, Mannich bases have biological activity such as anticancer 2,3 , antibacterial [4][5][6] , antimycobacterial [7][8][9] , anti inflammatory [10][11][12] , analgesic 13,14 , antifungal 15,16 , antitumor 17,18 namely the 1-aryl-2-dimethylaminomethyl-2-propen-1-one hydrochlorides 1a-e and 1-aryl-3-dimethylamino-2-hydroxymethyl-1-propanone hydrochlorides 2a-e. A number of these compounds possess marked cytotoxic potencies (IC(50, antiviral [19][20][21] , antidepressant 22,23 , antiulcer 24 , anticonvulsant 25 , antimalarial 26,27 and antioxidant activities 28 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and investigations of antimicrobial, antioxidant activities of novel di-[2-(3-alkyl/ aryl-4,5-dihydro-1h-1,2,4-triazol-5-one-4-yl)- azomethinephenyl] isophtalates and mannich base derivatives

Yüksek¹,

Özdemir²,

Manap³

et al. 2020

actapharm

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In this study, the synthesis of di-[2-(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)-azomethinephenyl] isophtalates (2a-g) from the reactions of 3-alkyl/ aryl-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (1a-g) with di-(2-formylphenyl) isophtalate is described. Then, the compounds 2 were treated with morpholine in the presence of formaldehyde to synthesize di-{2-[1-(morpholine-4-yl-methyl)-3alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-azomethinephenyl} isophtalates (3a-g). The newly synthesized compounds were characterized using IR, 1 H-NMR and 13 C-NMR spectral data. In addition, the compounds synthesized were screened for their antimicrobial activities. Furthermore, the antioxidant properties of the newly synthesized compounds were analysed for their in-vitro potential antioxidant activities in three different methods (reducing power, free radical scavenging and metal chelating activity). These antioxidant activities were compared to those from standard antioxidants, such as BHA, BHT, EDTA and α-tocopherol.

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“…Integration of hepatitis B virus into the genome of hepatocellular carcinoma patients will likely increase carcinogenic opportunities in HBVinfected individuals [2]. HBV infection is a worldwide health problem and may lead to lifelong infection, cirrhosis of liver, liver cancer, hepatocellular carcinoma, liver failure and death [3]. Recent epidemiological data have demonstrated that liver cancer incidence has been continuously rising for more than a decade, not only in Asia and Africa but also in America and Europe [4].…”

Section: Introductionmentioning

confidence: 99%

Virtual screening of natural inhibitors to the predicted HBx protein structure of Hepatitis B Virus using molecular docking for identification of potential lead molecules for liver cancer

Pathak¹,

Baunthiyal²,

Taj

et al. 2014

Bioinformation

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The HBx protein in Hepatitis B Virus (HBV) is a potential target for anti-liver cancer molecules. Therefore, it is of interest to screen known natural compounds against the HBx protein using molecular docking. However, the structure of HBx is not yet known. Therefore, the predicted structure of HBx using threading in LOMET was used for docking against plant derived natural compounds (curcumin, oleanolic acid, resveratrol, bilobetin, luteoline, ellagic acid, betulinic acid and rutin) by Molegro Virtual Docker. The screening identified rutin with binding energy of -161.65 Kcal/mol. Thus, twenty derivatives of rutin were further designed and screened against HBx. These in silico experiments identified compounds rutin01 (-163.16 Kcal/mol) and rutin08 (- 165.76 Kcal/mol) for further consideration and downstream validation.

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Synthesis and in vitro anti-hepatitis B virus activity of 6H-[1]benzothiopyrano[4,3-b]quinolin-9-ols

Cited by 27 publications

References 11 publications

Design, Synthesis and Biological Evaluation of Caudatin Analogs as Potent Hepatitis B Virus Inhibitors

Design, Synthesis and Biological Evaluation of Caudatin Analogs as Potent Hepatitis B Virus Inhibitors

Synthesis and investigations of antimicrobial, antioxidant activities of novel di-[2-(3-alkyl/ aryl-4,5-dihydro-1h-1,2,4-triazol-5-one-4-yl)- azomethinephenyl] isophtalates and mannich base derivatives

Virtual screening of natural inhibitors to the predicted HBx protein structure of Hepatitis B Virus using molecular docking for identification of potential lead molecules for liver cancer

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