Design and synthesis of novel benzimidazole derivatives as inhibitors of hepatitis B virus

Luo, Yu; Yao, Jia-Ping; Li, Yang; Feng, Chen‐Guo; Tang, Wei; Wang, Guifeng; Zuo, J. M.; Lü, Wei

doi:10.1016/j.bmc.2010.05.076

Cited by 46 publications

(27 citation statements)

References 33 publications

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“…The CEP‐based small molecules, such as CEP03, were synthesized in the laboratory from commercially available starting materials12, 13 and reconstituted in DMSO (dimethyl sulfoxide). These small molecules were fully characterized by nuclear magnetic resonance spectroscopy and liquid chromatography–mass spectrometry: hydrogen 1 ( 1 H) nuclear magnetic resonance (400 MHz, CD3OD) δ 9.92 (s, 1 H), 6.58 (m, 1 H), 5.95 (m, 1 H), 5.81 (m, 1 H), 2.86 (t, J=7.6 Hz, 2 H), 2.58 (t, J=7.6 Hz, 2 H); mass spectrometry (electrospray ionization): m/z 138.3 [M−H] − .…”

Section: Methodsmentioning

confidence: 99%

Small Molecule Derived From Carboxyethylpyrrole Protein Adducts Promotes Angiogenesis in a Mouse Model of Peripheral Arterial Disease

Hou

Yang

Tang

et al. 2018

JAHA

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BackgroundCEP (ω‐[2‐carboxyethyl]pyrrole) protein adducts are the end products of lipid oxidation associated with inflammation and have been implicated in the induction of angiogenesis in pathological conditions such as tissue ischemia. We synthesized small molecules derived from CEP protein adducts and evaluated the angiogenic effect of the CEP analog CEP03 in the setting of peripheral arterial disease.Methods and ResultsThe angiogenic effect of CEP03 was assessed by in vitro analysis of primary human microvascular endothelial cell proliferation and tubelike formation in Matrigel (Corning). In the presence of CEP03, proliferation of endothelial cells in vitro increased by 27±18% under hypoxic (1% O2) conditions, reaching similar levels to that of VEGFA (vascular endothelial growth factor A) stimulation (22±10%), relative to the vehicle control treatment. A similar effect of CEP03 was demonstrated in the increased number of tubelike branches in Matrigel, reaching >70% induction in hypoxia, compared with the vehicle control. The therapeutic potential of CEP03 was further evaluated in a mouse model of peripheral arterial disease by quantification of blood perfusion recovery and capillary density. In the ischemic hind limb, treatment of CEP03 encapsulated within Matrigel significantly enhanced blood perfusion by 2‐fold after 14 days compared with those treated with Matrigel alone. Moreover, these results concurred with histological finding that treatment of CEP03 in Matrigel resulted in a significant increase in microvessel density compared with Matrigel alone.ConclusionsOur data suggest that CEP03 has a profound positive effect on angiogenesis and neovessel formation and thus has therapeutic potential for treatment of peripheral arterial disease.

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Section: Methodsmentioning

confidence: 99%

Small Molecule Derived From Carboxyethylpyrrole Protein Adducts Promotes Angiogenesis in a Mouse Model of Peripheral Arterial Disease

Hou

Yang

Tang

et al. 2018

JAHA

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“…Compound 1, with IC 50 <0.41 µM and SI >81.2 surfaced out as the most promising one. Its cytotoxicity (CC 50 = 33.3 µM) was over six times less than lamivudine (CC 50 = 5 µM), it had nearly three times higher selectivity than lamivudine [45]. SAR study is depicted in Fig.5 Amongst the series, compound 9 exhibited potent activity [47].…”

Section: Antiviral Activitymentioning

confidence: 95%

Structure activity relationship (SAR) study of benzimidazole scaffold for different biological activities: A mini-review

Yadav

Ganguly

2015

European Journal of Medicinal Chemistry

322

141

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“…The results demonstrated that compound 63 (Figure 14) was the most promising anti-HBV compound (IC 50 < 0.41 μM and SI > 81.2), and selected as the lead compound for further optimization [147]. A series of novel thiazolylbenzimidazole derivatives were synthesized and evaluated for their anti-HBV activity and cytotoxicity in the HepG2.2.15 cells.…”

Section: Others Hbv Inhibitorsmentioning

confidence: 99%

Recent Advance of the Hepatitis B Virus Inhibitors: A Medicinal Chemistry Overview

et al. 2015

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Hepatitis B Virus (HBV) is one of the most prevalent viral infections of human worldwide. The therapies are limited in the clinical context because of negative side effects of interferons and the development of viral resistance to the nucleoside/nucleotide inhibitors. In this review, we summarize the recent advances in design and development of potent anti-HBV inhibitors from natural sources and synthetic compounds, targeting different steps in the life cycle of HBV. We attempt to emphasize the major structural modifications, mechanisms of action and computer-aided docking analysis of novel potent inhibitors that need to be addressed in the future to design potent anti-HBV molecules.

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Design and synthesis of novel benzimidazole derivatives as inhibitors of hepatitis B virus

Cited by 46 publications

References 33 publications

Small Molecule Derived From Carboxyethylpyrrole Protein Adducts Promotes Angiogenesis in a Mouse Model of Peripheral Arterial Disease

Small Molecule Derived From Carboxyethylpyrrole Protein Adducts Promotes Angiogenesis in a Mouse Model of Peripheral Arterial Disease

Structure activity relationship (SAR) study of benzimidazole scaffold for different biological activities: A mini-review

Recent Advance of the Hepatitis B Virus Inhibitors: A Medicinal Chemistry Overview

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