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185688

Synthesis, Cytotoxic Activity and Molecular Modelling of Novel [1,2,3]triazolo[4,5-d]pyrimidine Compounds, their Glycoside Derivatives and Acyclic Analogs

Article

Last updated: 22 Jan 2023

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Subjects

-

Tags

Organic chemistry

Abstract

Novel substituted [1,2,3]triazolo[4,5-d]pyrimidine-7-one derivatives were synthesized using 1,2,3-triazolo-4-carboxamide derivative (2) by the reaction with carbon disulfide, triethoxymethane, 4-fluorobenzaldehyde and ethyl benzoate respectively. The S-glucoside, N-glycoside derivatives and acyclic sugar analogs of new synthesized [1,2,3]triazolo[4,5-d]pyrimidines were also synthesized. The synthesized compounds were tested for cytotoxicity and in vitro anticancer activity versus human lung (A549), colon (HCT116) and breast (MCF-7) cancer cell lines. The results disclosed that the synthesized compounds apply their activities in A549 and MCF-7. MCF-7 cells are more sensitive to the tested compounds than the other cell lines. Compounds 2, 3, 9 and 10 exposed promising anticancer activities compared to the action of the ordinarily used anticancer drug, doxorubicin in both A549 and MCF-7 cell lines. A good binding affinities for compounds 2, 3, 6, 10 and 11 were noted in docking studies. Results showed a clear effect of N3-substitution in pyrimidine ring on the activities of the synthesized compounds

DOI

10.21608/ejchem.2021.84371.4127

Keywords

Triazolo[4,5-d]pyrimidine, Glycosides, Anticancer, A549, HCT116, MCF-7

Authors

First Name

Ashraf

Last Name

Mohamed

MiddleName

M

Affiliation

Applied Organic Chemistry Department, National Research Centre, Dokki, Cairo, Egypt.

Email

ammewas1@gmail.com

City

Giza

Orcid

0000-0001-7019-5286

First Name

Mohamed

Last Name

Abdelwahab

MiddleName

-

Affiliation

Applied organic chemistry, National Research Center

Email

abdelwahabchem86@gmail.com

City

-

Orcid

-

First Name

dina

Last Name

elnaggar

MiddleName

-

Affiliation

Department of Applied Organic Chemistry, Industrial Chemical Division, National Research Center, Cairo, Dokki 12622, Egypt

Email

elnaggar_d@yahoo.com

City

-

Orcid

-

First Name

Naglaa

Last Name

Abde lHafez

MiddleName

Abdelsamei

Affiliation

Applied Organic Chem, NRC

Email

naglaa1810@gmail.com

City

-

Orcid

-

First Name

Salwa

Last Name

Mahmoud

MiddleName

Faheem

Affiliation

Applied Organic Chemistry Department, National Research Center, Cairo, Dokki, 12622, Egypt

Email

drsalwa.fahim@gmail.com

City

-

Orcid

-

First Name

Mohamed

Last Name

El-Bayaa

MiddleName

-

Affiliation

Photochemistry Department, National Research Centre

Email

mnb6600@yahoo.com

City

-

Orcid

-

First Name

Dina S.

Last Name

El-kady

MiddleName

-

Affiliation

hormones department, medical research division, National research center

Email

dn_science@yahoo.com

City

-

Orcid

0000-0002-5809-5888

First Name

Mervat

Last Name

Omran

MiddleName

Mostafa

Affiliation

Department of Cancer Biology, Pharmacology Unit, National Cancer Institute, Cairo University, Cairo 11796, Egypt

Email

dr.mervatomran@gmail.com

City

Cairo

Orcid

0000-0003-1643-0104

First Name

Wael

Last Name

El-Sayed

MiddleName

A.

Affiliation

Photochemistry Department, Naional Research Centre, Dokki, Cairo, Egypt

Email

waelshendy@gmail.com

City

-

Orcid

-

Volume

65

Article Issue

1

Related Issue

28750

Issue Date

2022-01-01

Receive Date

2021-09-06

Publish Date

2022-01-01

Page Start

645

Page End

656

Print ISSN

0449-2285

Online ISSN

2357-0245

Article File

EJCHEM_Volume 65_Issue 1_Pages 645-656.pdf

PDF . 745.7kB

Link

https://ejchem.journals.ekb.eg/article_185688.html

Detail API

https://ejchem.journals.ekb.eg/service?article_code=185688

Order

62

Type

Original Article

Type Code

297

Publication Type

Journal

Publication Title

Egyptian Journal of Chemistry

Publication Link

https://ejchem.journals.ekb.eg/

MainTitle

-

Details

Type

Article

Created At

22 Jan 2023