Synthesis and in vitro anti-hepatitis B virus activities of some ethyl 6-bromo-5-hydroxy-1H-indole-3-carboxylates

Chai, Huifang; Zhao, Yanfang; Zhao, Chunshen; Gong, Ping

doi:10.1016/j.bmc.2005.08.041

Cited by 100 publications

(70 citation statements)

References 10 publications

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“…They separated the center of mass movement of ligand from its internal and rotational motions. (Friedman and Caflisch, 2009), target for malaria Flavivirus Proteases (Ekonomiuk et al, 2009a,b), target for WNV and Dengue virus Tyrosine kinase erythropoietin-producing human hepatocellular carcinoma receptor B4 (EphB4) (Lafleur et al, 2009) FlexX Plasmepsin II and IV inhibitors (Luksch et al, 2008), malaria Anthrax edema factor Pneumococcal peptidoglycan deacetylase inhibitors (Bui et al, 2011) Glide Aurora kinases inhibitors (Warner et al, 2006) Falcipain inhibitors (Shah et al, 2011) Cytochrome P450 inhibitors (Caporuscioi et al, 2011) Surflex Topoisomerase I, anticancer (optimization) DOCK FK506 immunophilin (Zhao et al, 2006) BCL6, oncogene in B-cell lymphomas (Cerchietti et al, 2010) 348…”

Section: Sampling Algorithms For Protein-ligand Dockingmentioning

confidence: 99%

“…SB-vHTS has been used successfully in identifying novel and potent hits in several drug discovery campaigns Lu et al, 2006;Zhao et al, 2006;Ruiz et al, 2008;Triballeau et al, 2008;Li et al, 2009;Budzik et al, 2010;Izuhara et al, 2010;Simmons et al, 2010;Roughley et al, 2012). We discuss two examples in which SB-vHTS played pivotal role in discovery of lead compounds.…”

Section: E Structure-based Virtual High-throughput Screeningmentioning

confidence: 99%

“…This compound was tested in vitro and displayed an IC 50 of 25 nM against aurora kinase A. Additionally, compound 67 displayed antiproliferative activity with an IC 50 of 23 nM against the HCT-116 colon cancer cell line. Chai et al (2011) used 26 previously identified antihepatitis B (HBV) compounds (Chai et al, 2006;Zhao et al, 2006a,b) to generate CoMFA models based on steric and electrostatic fields and CoMSIA models based on steric, electrostatic, hydrophobic, and H-bond acceptor fields. Three compounds were designed using Computational Methods in Drug Discovery these models and subsequently tested against replication of HBV DNA in HBV-infected 2.2.15 cells.…”

Section: Quantitative Structure-activity Relationship Modelsmentioning

confidence: 99%

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Computational Methods in Drug Discovery

et al. 2013

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Section: Sampling Algorithms For Protein-ligand Dockingmentioning

confidence: 99%

Section: E Structure-based Virtual High-throughput Screeningmentioning

confidence: 99%

Section: Quantitative Structure-activity Relationship Modelsmentioning

confidence: 99%

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Computational Methods in Drug Discovery

et al. 2013

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“…It is less likely to induce drug resistance than other compounds, such as adamantine and oseltamivir [11,12,16,18] . However, its mechanism is complicated: earlier reports indicated that ARB could inhibit the membrane fusion of enveloped viruses in vitro and strengthen the interactions between virus glycoprotein and the membrane of host during the endocytosis [17,19,20] .…”

Section: Introductionmentioning

confidence: 99%

Antiviral and anti-inflammatory activity of arbidol hydrochloride in influenza A (H1N1) virus infection

et al. 2013

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Aim: To investigate the effects of arbidol hydrochloride (ARB), a widely used antiviral agent, on the inflammation induced by influenza virus. Methods: MDCK cells were infected with seasonal influenza A/FM/1/47 (H1N1) or pandemic influenza A/Hubei/71/2009 (H1N1). In vitro cytotoxicity and antiviral activity of ARB was determined using MTT assay. BALB/c mice were infected with A/FM/1/47 (H1N1). Four hours later the mice were administered ARB (45, 90, and 180 mg·kg -1 ·d -1 ) or the neuraminidase inhibitor oseltamivir (22.5 mg·kg -1 ·d -1 ) via oral gavage once a day for 5 d. Body-weight, median survival time, viral titer, and lung index of the mice were measured. The levels of inflammatory cytokines were examined using real-time RT-PCR and ELISA. Results: Both H1N1 stains were equally sensitive to ARB as tested in vitro. In the infected mice, ARB (90 and 180 mg·kg -1 ·d -1 ) significantly decreased the mortality, alleviated virus-induced lung lesions and viral titers. Furthermore, ARB suppressed the levels of IL-1β, IL-6, IL-12, and TNF-α, and elevated the level of IL-10 in the bronchoalveolar lavage fluids and lung tissues. However, ARB did not significantly affect the levels of IFN-α and IFN-γ, but reduced the level of IFN-β1 in lung tissues at 5 dpi. In peritoneal macrophages challenged with A/FM/1/47 (H1N1) or poly I:C, ARB (20 µmol/L) suppressed the levels of IL-1β, IL-6, IL-12, and TNF-α, and elevated the level of IL-10. Oseltamivir produced comparable alleviation of virus-induced lung lesions with more reduction in the viral titers, but less effective modulation of the inflammatory cytokines. Conclusion: ARB efficiently inhibits both H1N1 stains and diminishes both viral replication and acute inflammation through modulating the expression of inflammatory cytokines.

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“…Today, analogues based on indole are significant players in a diverse array of markets such as dyes, plastics, agriculture, vitamin supplements, over-thecounter drugs, flavour enhancers and perfumery (Barden, 2011). Indole derivatives exhibit antibacterial, antifungal (Singh et al 2000), antitumor (Andreani et al, 2001), antihepatitis B virus (Chai et al, 2006) and anti-inflammatory (Rodriguez et al, 1985) activities. They are also used as bioactive drugs (Stevenson et al, 2000) and exhibit high aldose reductase inhibitory (Rajeswaran et al, 1999) and antimicrobial activities (Amal Raj et al, 2003).…”

Section: Structure Descriptionmentioning

confidence: 99%

5-Benzoyl-2-(5-bromo-1H-indol-3-yl)-4-(4-methoxyphenyl)-1H-pyrrole-3-carbonitrile

et al. 2016

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In the title compound, C27H18BrN3O, the indole and central pyrrole ring systems are inclined to one another by 13.15 (15)°. The carbonitrile group is almost coplanar with its attached pyrrole ring, the C[triple-bond]N bond making a dihedral angle of 1.9 (2)° with the ring plane. The 4-methoxybenzene ring and the benzoyl ring are inclined to the central pyrrole ring by 55.1 (2) and 51.5 (2)°, respectively. The dihedral angle between these two benzene rings is 37.68 (17)°. In the crystal, molecules are linked by pairs of N—H...N hydrogen bonds, forming inversion dimers with anR22(16) ring motif. The dimers are linked by offset π–π interactions [intercentroid distance = 3.614 (2) Å], which leads to the formation of chains propagating in the [010] direction.

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Synthesis and in vitro anti-hepatitis B virus activities of some ethyl 6-bromo-5-hydroxy-1H-indole-3-carboxylates

Cited by 100 publications

References 10 publications

Computational Methods in Drug Discovery

Computational Methods in Drug Discovery

Antiviral and anti-inflammatory activity of arbidol hydrochloride in influenza A (H1N1) virus infection

5-Benzoyl-2-(5-bromo-1H-indol-3-yl)-4-(4-methoxyphenyl)-1H-pyrrole-3-carbonitrile

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