Synthesis of 3-phenylpyrazolopyrimidine-1,2,3-triazole conjugates and evaluation of their Src kinase inhibitory and anticancer activities

Anil Kumar; Israr Ahmad; Bhupender S. Chhikara; Rakesh Tiwari; Deendayal Mandal; Keykavous Parang

doi:10.1016/j.bmcl.2011.01.047

Synthesis of 3-phenylpyrazolopyrimidine-1,2,3-triazole conjugates and evaluation of their Src kinase inhibitory and anticancer activities

Anil Kumar, Israr Ahmad, Bhupender S. Chhikara, Rakesh Tiwari, Deendayal Mandal, Keykavous Parang

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

84 Scopus citations

Abstract

A series of two classes of 3-phenylpyrazolopyrimidine-1,2,3-triazole conjugates were synthesized using click chemistry approach. All compounds were evaluated for inhibition of Src kinase and human ovarian adenocarcinoma (SK-Ov-3), breast carcinoma (MDA-MB-361), and colon adenocarcinoma (HT-29). Hexyl triazolyl-substituted 3-phenylpyrazolopyrimidine exhibited inhibition of Src kinase with an IC₅₀ value of 5.6 μM. 4-Methoxyphenyl triazolyl-substituted 3-phenylpyrazolopyrimidine inhibited the cell proliferation of HT-29 and SK-Ov-3 by 73% and 58%, respectively, at a concentration of 50 μM.

Original language	English (US)
Pages (from-to)	1342-1346
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	21
Issue number	5
DOIs	https://doi.org/10.1016/j.bmcl.2011.01.047
State	Published - Mar 1 2011
Externally published	Yes

Keywords

1,2,3-Triazole
Anticancer activity
Click reaction
Phenylpyrazolopyrimidine
Src kinase
Tyrosine kinase

ASJC Scopus subject areas

Pharmaceutical Science
Drug Discovery
Organic Chemistry
Molecular Medicine
Molecular Biology
Clinical Biochemistry
Biochemistry

Access to Document

10.1016/j.bmcl.2011.01.047

Cite this

@article{f48664eebf3a4c5690adb9a4a32821c5,

title = "Synthesis of 3-phenylpyrazolopyrimidine-1,2,3-triazole conjugates and evaluation of their Src kinase inhibitory and anticancer activities",

abstract = "A series of two classes of 3-phenylpyrazolopyrimidine-1,2,3-triazole conjugates were synthesized using click chemistry approach. All compounds were evaluated for inhibition of Src kinase and human ovarian adenocarcinoma (SK-Ov-3), breast carcinoma (MDA-MB-361), and colon adenocarcinoma (HT-29). Hexyl triazolyl-substituted 3-phenylpyrazolopyrimidine exhibited inhibition of Src kinase with an IC50 value of 5.6 μM. 4-Methoxyphenyl triazolyl-substituted 3-phenylpyrazolopyrimidine inhibited the cell proliferation of HT-29 and SK-Ov-3 by 73% and 58%, respectively, at a concentration of 50 μM.",

keywords = "1,2,3-Triazole, Anticancer activity, Click reaction, Phenylpyrazolopyrimidine, Src kinase, Tyrosine kinase",

author = "Anil Kumar and Israr Ahmad and Chhikara, {Bhupender S.} and Rakesh Tiwari and Deendayal Mandal and Keykavous Parang",

year = "2011",

month = mar,

day = "1",

doi = "10.1016/j.bmcl.2011.01.047",

language = "English (US)",

volume = "21",

pages = "1342--1346",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Limited",

number = "5",

}

TY - JOUR

T1 - Synthesis of 3-phenylpyrazolopyrimidine-1,2,3-triazole conjugates and evaluation of their Src kinase inhibitory and anticancer activities

AU - Kumar, Anil

AU - Ahmad, Israr

AU - Chhikara, Bhupender S.

AU - Tiwari, Rakesh

AU - Mandal, Deendayal

AU - Parang, Keykavous

PY - 2011/3/1

Y1 - 2011/3/1

N2 - A series of two classes of 3-phenylpyrazolopyrimidine-1,2,3-triazole conjugates were synthesized using click chemistry approach. All compounds were evaluated for inhibition of Src kinase and human ovarian adenocarcinoma (SK-Ov-3), breast carcinoma (MDA-MB-361), and colon adenocarcinoma (HT-29). Hexyl triazolyl-substituted 3-phenylpyrazolopyrimidine exhibited inhibition of Src kinase with an IC50 value of 5.6 μM. 4-Methoxyphenyl triazolyl-substituted 3-phenylpyrazolopyrimidine inhibited the cell proliferation of HT-29 and SK-Ov-3 by 73% and 58%, respectively, at a concentration of 50 μM.

AB - A series of two classes of 3-phenylpyrazolopyrimidine-1,2,3-triazole conjugates were synthesized using click chemistry approach. All compounds were evaluated for inhibition of Src kinase and human ovarian adenocarcinoma (SK-Ov-3), breast carcinoma (MDA-MB-361), and colon adenocarcinoma (HT-29). Hexyl triazolyl-substituted 3-phenylpyrazolopyrimidine exhibited inhibition of Src kinase with an IC50 value of 5.6 μM. 4-Methoxyphenyl triazolyl-substituted 3-phenylpyrazolopyrimidine inhibited the cell proliferation of HT-29 and SK-Ov-3 by 73% and 58%, respectively, at a concentration of 50 μM.

KW - 1,2,3-Triazole

KW - Anticancer activity

KW - Click reaction

KW - Phenylpyrazolopyrimidine

KW - Src kinase

KW - Tyrosine kinase

UR - http://www.scopus.com/inward/record.url?scp=79951689971&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79951689971&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2011.01.047

DO - 10.1016/j.bmcl.2011.01.047

M3 - Article

C2 - 21300544

AN - SCOPUS:79951689971

SN - 0960-894X

VL - 21

SP - 1342

EP - 1346

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 5

ER -

Synthesis of 3-phenylpyrazolopyrimidine-1,2,3-triazole conjugates and evaluation of their Src kinase inhibitory and anticancer activities

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this