Synthesis and antitumor evaluation of trimethoxyanilides based on 4(3H)-quinazolinone scaffolds

Menshawy A Mohamed; Rezk R Ayyad; Taghreed Z Shawer; Alaa A-M Abdel-Aziz; Adel S El-Azab

doi:10.1016/j.ejmech.2016.02.002

Synthesis and antitumor evaluation of trimethoxyanilides based on 4(3H)-quinazolinone scaffolds

Eur J Med Chem. 2016 Apr 13:112:106-113. doi: 10.1016/j.ejmech.2016.02.002. Epub 2016 Feb 4.

Authors

Menshawy A Mohamed¹, Rezk R Ayyad², Taghreed Z Shawer², Alaa A-M Abdel-Aziz³, Adel S El-Azab⁴

Affiliations

¹ Department of Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo, Egypt; Department of Pharmaceutical Chemistry, College of Pharmacy, Salman Bin Abdulaziz University, AlKharj, Saudi Arabia.
² Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo, Egypt.
³ Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia; Department of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura, Egypt.
⁴ Department of Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo, Egypt; Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia. Electronic address: adelazaba@yahoo.com.

PMID: 26890117
DOI: 10.1016/j.ejmech.2016.02.002

Abstract

A novel series of 2-[(3-substituted-4(3H)-quinazolin-2-yl)thio]-N-(3,4,5-trimethoxyphenyl)acetamide (15-21) and 3-[(3-substituted-4(3H)-quinazolin-2-yl)thio])-N-(3,4,5-trimethoxyphenyl)propanamide (23-29) were designed, prepared and estimated for their anticancer activity in a solo dose 10 μM of the test compounds in the NCI 57 cell lines panel assay. Compounds 20, 23, 26, 27 and 28 revealed extensive-spectrum antitumor efficiency to numerous cell lines that belong to various tumor subpanels, while compounds 15, 16 and 19 possessed perceptive activity toward A498 and UO-31 renal cancer cell lines, and compound 17 showed selective effectiveness against NSC lung cancer NCI-H522 cell line. Additionally, compound 18 showed advanced activity against SR leukemia cell line, NSC lung cancer HOP-92 and renal cancer UO-31 cell lines.

Keywords: Anticancer; Broad spectrum; NCI; Quinazoline scaffolds; Synthesis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents / chemical synthesis
Antineoplastic Agents / chemistry*
Antineoplastic Agents / pharmacology*
Cell Line, Tumor
Cell Proliferation / drug effects*
Drug Screening Assays, Antitumor
Humans
Neoplasms / drug therapy
Neoplasms / metabolism
Quinazolinones / chemical synthesis
Quinazolinones / chemistry*
Quinazolinones / pharmacology*
Structure-Activity Relationship

Substances

Antineoplastic Agents
Quinazolinones
4-hydroxyquinazoline