3-Substitued indoles: One-pot synthesis and evaluation of anticancer and Src kinase inhibitory activities

V. Kameshwara Rao; Bhupender S. Chhikara; Amir Nasrolahi Shirazi; Rakesh Tiwari; Keykavous Parang; Anil Kumar

doi:10.1016/j.bmcl.2011.05.010

3-Substitued indoles: One-pot synthesis and evaluation of anticancer and Src kinase inhibitory activities

V. Kameshwara Rao, Bhupender S. Chhikara, Amir Nasrolahi Shirazi, Rakesh Tiwari, Keykavous Parang, Anil Kumar

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

49 Scopus citations

Abstract

An efficient and economical method was developed for the synthesis of 3-substituted indoles by one-pot three-component coupling reaction of a substituted or unsubstituted benzaldehyde, N-methylaniline, and indole or N-methylindole using Yb(OTf) ₃-SiO ₂ as a catalyst. All the synthesized compounds were evaluated for inhibition of cell proliferation of human colon carcinoma (HT-29), human ovarian adenocarcinoma (SK-OV-3), and c-Src kinase activity. The 4-methylphenyl (4o and 4p) and 4-methoxyphenyl (4q) indole derivatives inhibited the cell proliferation of SK-OV-3 and HT-29 cells by 70-77% at a concentration of 50 μM. The unsubstituted phenyl (4d) and 3-nitrophenyl (4l) derivatives showed the inhibition of c-Src kinase with IC ₅₀ values of 50.6 and 58.3 μM, respectively.

Original language	English (US)
Pages (from-to)	3511-3514
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	21
Issue number	12
DOIs	https://doi.org/10.1016/j.bmcl.2011.05.010
State	Published - Jun 15 2011
Externally published	Yes

Keywords

Anticancer
Cancer
Indole
One-pot
Src kinase
Synthesis

ASJC Scopus subject areas

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

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10.1016/j.bmcl.2011.05.010

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title = "3-Substitued indoles: One-pot synthesis and evaluation of anticancer and Src kinase inhibitory activities",

abstract = "An efficient and economical method was developed for the synthesis of 3-substituted indoles by one-pot three-component coupling reaction of a substituted or unsubstituted benzaldehyde, N-methylaniline, and indole or N-methylindole using Yb(OTf) 3-SiO 2 as a catalyst. All the synthesized compounds were evaluated for inhibition of cell proliferation of human colon carcinoma (HT-29), human ovarian adenocarcinoma (SK-OV-3), and c-Src kinase activity. The 4-methylphenyl (4o and 4p) and 4-methoxyphenyl (4q) indole derivatives inhibited the cell proliferation of SK-OV-3 and HT-29 cells by 70-77% at a concentration of 50 μM. The unsubstituted phenyl (4d) and 3-nitrophenyl (4l) derivatives showed the inhibition of c-Src kinase with IC 50 values of 50.6 and 58.3 μM, respectively.",

keywords = "Anticancer, Cancer, Indole, One-pot, Src kinase, Synthesis",

author = "Rao, {V. Kameshwara} and Chhikara, {Bhupender S.} and Shirazi, {Amir Nasrolahi} and Rakesh Tiwari and Keykavous Parang and Anil Kumar",

year = "2011",

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doi = "10.1016/j.bmcl.2011.05.010",

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T2 - One-pot synthesis and evaluation of anticancer and Src kinase inhibitory activities

AU - Rao, V. Kameshwara

AU - Chhikara, Bhupender S.

AU - Shirazi, Amir Nasrolahi

AU - Tiwari, Rakesh

AU - Parang, Keykavous

AU - Kumar, Anil

PY - 2011/6/15

Y1 - 2011/6/15

N2 - An efficient and economical method was developed for the synthesis of 3-substituted indoles by one-pot three-component coupling reaction of a substituted or unsubstituted benzaldehyde, N-methylaniline, and indole or N-methylindole using Yb(OTf) 3-SiO 2 as a catalyst. All the synthesized compounds were evaluated for inhibition of cell proliferation of human colon carcinoma (HT-29), human ovarian adenocarcinoma (SK-OV-3), and c-Src kinase activity. The 4-methylphenyl (4o and 4p) and 4-methoxyphenyl (4q) indole derivatives inhibited the cell proliferation of SK-OV-3 and HT-29 cells by 70-77% at a concentration of 50 μM. The unsubstituted phenyl (4d) and 3-nitrophenyl (4l) derivatives showed the inhibition of c-Src kinase with IC 50 values of 50.6 and 58.3 μM, respectively.

AB - An efficient and economical method was developed for the synthesis of 3-substituted indoles by one-pot three-component coupling reaction of a substituted or unsubstituted benzaldehyde, N-methylaniline, and indole or N-methylindole using Yb(OTf) 3-SiO 2 as a catalyst. All the synthesized compounds were evaluated for inhibition of cell proliferation of human colon carcinoma (HT-29), human ovarian adenocarcinoma (SK-OV-3), and c-Src kinase activity. The 4-methylphenyl (4o and 4p) and 4-methoxyphenyl (4q) indole derivatives inhibited the cell proliferation of SK-OV-3 and HT-29 cells by 70-77% at a concentration of 50 μM. The unsubstituted phenyl (4d) and 3-nitrophenyl (4l) derivatives showed the inhibition of c-Src kinase with IC 50 values of 50.6 and 58.3 μM, respectively.

KW - Anticancer

KW - Cancer

KW - Indole

KW - One-pot

KW - Src kinase

KW - Synthesis

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ER -

3-Substitued indoles: One-pot synthesis and evaluation of anticancer and Src kinase inhibitory activities

Abstract

Keywords

ASJC Scopus subject areas

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