Design, synthesis and biological evaluation of 2-mercapto-3- phenethylquinazoline bearing anilide fragments as potential antitumor agents: Molecular docking study

Ibrahim A. Al-Suwaidan; Amer M. Alanazi; Alaa A.M. Abdel-Aziz; Menshawy A. Mohamed; Adel S. El-Azab

doi:10.1016/j.bmcl.2013.04.056

Design, synthesis and biological evaluation of 2-mercapto-3- phenethylquinazoline bearing anilide fragments as potential antitumor agents: Molecular docking study

Ibrahim A. Al-Suwaidan
, Amer M. Alanazi
, Alaa A.M. Abdel-Aziz
, Menshawy A. Mohamed
, Adel S. El-Azab

Pharmaceutical Chemistry

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

65 Scopus citations

Abstract

A novel series of 2-(3-phenethyl-4(3H)quinazolin-2-ylthio)-N-substituted anilide and substituted phenyl 2-(3-phenethyl-4(3H) quinazolin-2-ylthio)acetate were designed, synthesized and evaluated for their in-vitro antitumor activity. Compound 15 possessed remarkable broad-spectrum antitumor activity which almost sevenfold more active than the known drug 5-FU with GI₅₀ values of 3.16 and 22.60 μM, respectively. Compound 15 exhibited remarkable growth inhibitory activity pattern against renal cancer (GI₅₀ = 1.77 μM), colon cancer (GI₅₀ = 2.02 μM), non-small cell lung cancer (GI₅₀ = 2.04 μM), breast cancer (GI₅₀ = 2.77 μM), ovarian cancer (GI₅₀ = 2.55 μM) and melanoma cancer (GI ₅₀ = 3.30 μM). Docking study was performed for compound 15 into ATP binding site of EGFR-TK which showed similar binding mode to erlotinib.

Original language	English
Pages (from-to)	3935-3941
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	23
Issue number	13
DOIs	https://doi.org/10.1016/j.bmcl.2013.04.056
State	Published - 1 Jul 2013

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

SDG 3 Good Health and Well-being

Keywords

In-vitro antitumor evaluation
Molecular docking
NCI
Quinazoline
Synthesis

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10.1016/j.bmcl.2013.04.056

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title = "Design, synthesis and biological evaluation of 2-mercapto-3- phenethylquinazoline bearing anilide fragments as potential antitumor agents: Molecular docking study",

abstract = "A novel series of 2-(3-phenethyl-4(3H)quinazolin-2-ylthio)-N-substituted anilide and substituted phenyl 2-(3-phenethyl-4(3H) quinazolin-2-ylthio)acetate were designed, synthesized and evaluated for their in-vitro antitumor activity. Compound 15 possessed remarkable broad-spectrum antitumor activity which almost sevenfold more active than the known drug 5-FU with GI50 values of 3.16 and 22.60 μM, respectively. Compound 15 exhibited remarkable growth inhibitory activity pattern against renal cancer (GI50 = 1.77 μM), colon cancer (GI50 = 2.02 μM), non-small cell lung cancer (GI50 = 2.04 μM), breast cancer (GI50 = 2.77 μM), ovarian cancer (GI50 = 2.55 μM) and melanoma cancer (GI 50 = 3.30 μM). Docking study was performed for compound 15 into ATP binding site of EGFR-TK which showed similar binding mode to erlotinib.",

keywords = "In-vitro antitumor evaluation, Molecular docking, NCI, Quinazoline, Synthesis",

author = "Al-Suwaidan, \{Ibrahim A.\} and Alanazi, \{Amer M.\} and Abdel-Aziz, \{Alaa A.M.\} and Mohamed, \{Menshawy A.\} and El-Azab, \{Adel S.\}",

year = "2013",

month = jul,

day = "1",

doi = "10.1016/j.bmcl.2013.04.056",

language = "English",

volume = "23",

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journal = "Bioorganic and Medicinal Chemistry Letters",

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}

Design, synthesis and biological evaluation of 2-mercapto-3- phenethylquinazoline bearing anilide fragments as potential antitumor agents: Molecular docking study. / Al-Suwaidan, Ibrahim A.; Alanazi, Amer M.; Abdel-Aziz, Alaa A.M. et al.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 23, No. 13, 01.07.2013, p. 3935-3941.

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

TY - JOUR

T1 - Design, synthesis and biological evaluation of 2-mercapto-3- phenethylquinazoline bearing anilide fragments as potential antitumor agents

T2 - Molecular docking study

AU - Al-Suwaidan, Ibrahim A.

AU - Alanazi, Amer M.

AU - Abdel-Aziz, Alaa A.M.

AU - Mohamed, Menshawy A.

AU - El-Azab, Adel S.

PY - 2013/7/1

Y1 - 2013/7/1

N2 - A novel series of 2-(3-phenethyl-4(3H)quinazolin-2-ylthio)-N-substituted anilide and substituted phenyl 2-(3-phenethyl-4(3H) quinazolin-2-ylthio)acetate were designed, synthesized and evaluated for their in-vitro antitumor activity. Compound 15 possessed remarkable broad-spectrum antitumor activity which almost sevenfold more active than the known drug 5-FU with GI50 values of 3.16 and 22.60 μM, respectively. Compound 15 exhibited remarkable growth inhibitory activity pattern against renal cancer (GI50 = 1.77 μM), colon cancer (GI50 = 2.02 μM), non-small cell lung cancer (GI50 = 2.04 μM), breast cancer (GI50 = 2.77 μM), ovarian cancer (GI50 = 2.55 μM) and melanoma cancer (GI 50 = 3.30 μM). Docking study was performed for compound 15 into ATP binding site of EGFR-TK which showed similar binding mode to erlotinib.

AB - A novel series of 2-(3-phenethyl-4(3H)quinazolin-2-ylthio)-N-substituted anilide and substituted phenyl 2-(3-phenethyl-4(3H) quinazolin-2-ylthio)acetate were designed, synthesized and evaluated for their in-vitro antitumor activity. Compound 15 possessed remarkable broad-spectrum antitumor activity which almost sevenfold more active than the known drug 5-FU with GI50 values of 3.16 and 22.60 μM, respectively. Compound 15 exhibited remarkable growth inhibitory activity pattern against renal cancer (GI50 = 1.77 μM), colon cancer (GI50 = 2.02 μM), non-small cell lung cancer (GI50 = 2.04 μM), breast cancer (GI50 = 2.77 μM), ovarian cancer (GI50 = 2.55 μM) and melanoma cancer (GI 50 = 3.30 μM). Docking study was performed for compound 15 into ATP binding site of EGFR-TK which showed similar binding mode to erlotinib.

KW - In-vitro antitumor evaluation

KW - Molecular docking

KW - NCI

KW - Quinazoline

KW - Synthesis

UR - https://www.scopus.com/pages/publications/84878849267

U2 - 10.1016/j.bmcl.2013.04.056

DO - 10.1016/j.bmcl.2013.04.056

M3 - Article

C2 - 23683592

AN - SCOPUS:84878849267

SN - 0960-894X

VL - 23

SP - 3935

EP - 3941

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 13

ER -

Design, synthesis and biological evaluation of 2-mercapto-3- phenethylquinazoline bearing anilide fragments as potential antitumor agents: Molecular docking study

Abstract

UN SDGs

Keywords

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