Anti-HAV evaluation and molecular docking of newly synthesized 3-benzyl(phenethyl)benzo[g]quinazolines

Rashad Al-Salahi; El Hassane Anouar; Mohamed Marzouk; Hatem A. Abuelizz

doi:10.1016/j.bmcl.2019.04.043

Anti-HAV evaluation and molecular docking of newly synthesized 3-benzyl(phenethyl)benzo[g]quinazolines

Rashad Al-Salahi, El Hassane Anouar, Mohamed Marzouk, Hatem A. Abuelizz

Chemistry

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

Synthesized 3-benzyl(phenethyl)benzo[g]quinazolines (1–17)were evaluated in vitro to determine their effects against the anti-hepatitis A virus (HAV)using a cytopathic effect inhibition assay. Of the synthesized compounds, 16 and 17 showed considerably high anti-HAV activity, as indicated by their EC₅₀ values of 27.59 and 18 μM, respectively, when compared to that of amantadine (37.3 μM), the standard therapeutic agent. In addition, they exhibited low cytotoxicity as indicated by their CC₅₀ values, 290.63 and 569.45 μM, respectively. Compounds 1, 2, and 5 exhibited remarkable activity compared to the active compounds (16, 17)and amantadine. The selectivity index (SI)values were calculated and applied as a parameter for classifying the activity of the targets. In addition, molecular docking was performed to rationalize the SAR of the target compounds and analyze the binding modes between the docked-selected compounds and amino acid residues in the active site of the HAV-3C proteinase enzyme.

Original language	English
Pages (from-to)	1614-1619
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	29
Issue number	13
DOIs	https://doi.org/10.1016/j.bmcl.2019.04.043
State	Published - 1 Jul 2019

Keywords

3C proteinase
Antiviral
Benzoquinazolines
Cytopathic effect
Cytotoxicity
Molecular docking

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1016/j.bmcl.2019.04.043

Cite this

@article{aba32183937f4668a4843b5f161c2917,

title = "Anti-HAV evaluation and molecular docking of newly synthesized 3-benzyl(phenethyl)benzo[g]quinazolines",

abstract = "Synthesized 3-benzyl(phenethyl)benzo[g]quinazolines (1–17)were evaluated in vitro to determine their effects against the anti-hepatitis A virus (HAV)using a cytopathic effect inhibition assay. Of the synthesized compounds, 16 and 17 showed considerably high anti-HAV activity, as indicated by their EC50 values of 27.59 and 18 μM, respectively, when compared to that of amantadine (37.3 μM), the standard therapeutic agent. In addition, they exhibited low cytotoxicity as indicated by their CC50 values, 290.63 and 569.45 μM, respectively. Compounds 1, 2, and 5 exhibited remarkable activity compared to the active compounds (16, 17)and amantadine. The selectivity index (SI)values were calculated and applied as a parameter for classifying the activity of the targets. In addition, molecular docking was performed to rationalize the SAR of the target compounds and analyze the binding modes between the docked-selected compounds and amino acid residues in the active site of the HAV-3C proteinase enzyme.",

keywords = "3C proteinase, Antiviral, Benzoquinazolines, Cytopathic effect, Cytotoxicity, Molecular docking",

author = "Rashad Al-Salahi and Anouar, \{El Hassane\} and Mohamed Marzouk and Abuelizz, \{Hatem A.\}",

note = "Publisher Copyright: {\textcopyright} 2019 Elsevier Ltd",

year = "2019",

month = jul,

day = "1",

doi = "10.1016/j.bmcl.2019.04.043",

language = "English",

volume = "29",

pages = "1614--1619",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Ltd",

number = "13",

}

TY - JOUR

T1 - Anti-HAV evaluation and molecular docking of newly synthesized 3-benzyl(phenethyl)benzo[g]quinazolines

AU - Al-Salahi, Rashad

AU - Anouar, El Hassane

AU - Marzouk, Mohamed

AU - Abuelizz, Hatem A.

PY - 2019/7/1

Y1 - 2019/7/1

N2 - Synthesized 3-benzyl(phenethyl)benzo[g]quinazolines (1–17)were evaluated in vitro to determine their effects against the anti-hepatitis A virus (HAV)using a cytopathic effect inhibition assay. Of the synthesized compounds, 16 and 17 showed considerably high anti-HAV activity, as indicated by their EC50 values of 27.59 and 18 μM, respectively, when compared to that of amantadine (37.3 μM), the standard therapeutic agent. In addition, they exhibited low cytotoxicity as indicated by their CC50 values, 290.63 and 569.45 μM, respectively. Compounds 1, 2, and 5 exhibited remarkable activity compared to the active compounds (16, 17)and amantadine. The selectivity index (SI)values were calculated and applied as a parameter for classifying the activity of the targets. In addition, molecular docking was performed to rationalize the SAR of the target compounds and analyze the binding modes between the docked-selected compounds and amino acid residues in the active site of the HAV-3C proteinase enzyme.

AB - Synthesized 3-benzyl(phenethyl)benzo[g]quinazolines (1–17)were evaluated in vitro to determine their effects against the anti-hepatitis A virus (HAV)using a cytopathic effect inhibition assay. Of the synthesized compounds, 16 and 17 showed considerably high anti-HAV activity, as indicated by their EC50 values of 27.59 and 18 μM, respectively, when compared to that of amantadine (37.3 μM), the standard therapeutic agent. In addition, they exhibited low cytotoxicity as indicated by their CC50 values, 290.63 and 569.45 μM, respectively. Compounds 1, 2, and 5 exhibited remarkable activity compared to the active compounds (16, 17)and amantadine. The selectivity index (SI)values were calculated and applied as a parameter for classifying the activity of the targets. In addition, molecular docking was performed to rationalize the SAR of the target compounds and analyze the binding modes between the docked-selected compounds and amino acid residues in the active site of the HAV-3C proteinase enzyme.

KW - 3C proteinase

KW - Antiviral

KW - Benzoquinazolines

KW - Cytopathic effect

KW - Cytotoxicity

KW - Molecular docking

UR - http://www.scopus.com/inward/record.url?scp=85064880576&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2019.04.043

DO - 10.1016/j.bmcl.2019.04.043

M3 - Article

C2 - 31054861

AN - SCOPUS:85064880576

SN - 0960-894X

VL - 29

SP - 1614

EP - 1619

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 13

ER -

Anti-HAV evaluation and molecular docking of newly synthesized 3-benzyl(phenethyl)benzo[g]quinazolines

Abstract

Keywords

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this