Copper-catalyzed synthesis and anticancer activity evaluation of indolo[1,2-a]quinoline derivatives

Adisak Thanetchaiyakup; Suparerk Borwornpinyo; Hassayaporn Rattanarat; Phongthon Kanjanasirirat; Kedchin Jearawuttanakul; Sawinee Seemakhan; Nutthawat Chuanopparat; Paiboon Ngernmeesri

doi:10.1016/j.tetlet.2021.153365

Copper-catalyzed synthesis and anticancer activity evaluation of indolo[1,2-a]quinoline derivatives

Adisak Thanetchaiyakup
, Suparerk Borwornpinyo
, Hassayaporn Rattanarat
, Phongthon Kanjanasirirat
, Kedchin Jearawuttanakul
, Sawinee Seemakhan
, Nutthawat Chuanopparat
, Paiboon Ngernmeesri

Kasetsart University
Mahidol University

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

11 Citations (Scopus)

Abstract

A simple and effective one-pot synthesis of substituted indolo[1,2-a]quinolines has been developed. The desired products were obtained in up to 98% yield when substituted 2-methyindoles were treated with 2-iodobenzaldehyde in the presence of Cs₂CO₃, CuI and L-proline. Our mechanistic study confirmed that the reaction sequence involved an intermolecular Knoevenagel reaction followed by an intramolecular Ullmann-type coupling reaction. Moreover, some of the synthesized compounds were found to be active against human breast (MCF-7) and colorectal (HCT-116) cancer cells with IC₅₀ values of 27.96 μM and in the range of 6.21–46.91 μM, respectively.

Original language	English
Article number	153365
Journal	Tetrahedron Letters
Volume	82
DOIs	https://doi.org/10.1016/j.tetlet.2021.153365
Publication status	Published - 12 Oct 2021
Externally published	Yes

UN SDGs

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

SDG 3 Good Health and Well-being

Keywords

Indolo[1,2-a]quinoline
Knoevenagel condensation
One-pot synthesis
Ullmann-type reaction

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10.1016/j.tetlet.2021.153365

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title = "Copper-catalyzed synthesis and anticancer activity evaluation of indolo[1,2-a]quinoline derivatives",

abstract = "A simple and effective one-pot synthesis of substituted indolo[1,2-a]quinolines has been developed. The desired products were obtained in up to 98\% yield when substituted 2-methyindoles were treated with 2-iodobenzaldehyde in the presence of Cs2CO3, CuI and L-proline. Our mechanistic study confirmed that the reaction sequence involved an intermolecular Knoevenagel reaction followed by an intramolecular Ullmann-type coupling reaction. Moreover, some of the synthesized compounds were found to be active against human breast (MCF-7) and colorectal (HCT-116) cancer cells with IC50 values of 27.96 μM and in the range of 6.21–46.91 μM, respectively.",

keywords = "Indolo[1,2-a]quinoline, Knoevenagel condensation, One-pot synthesis, Ullmann-type reaction",

author = "Adisak Thanetchaiyakup and Suparerk Borwornpinyo and Hassayaporn Rattanarat and Phongthon Kanjanasirirat and Kedchin Jearawuttanakul and Sawinee Seemakhan and Nutthawat Chuanopparat and Paiboon Ngernmeesri",

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year = "2021",

month = oct,

day = "12",

doi = "10.1016/j.tetlet.2021.153365",

language = "English",

volume = "82",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Copper-catalyzed synthesis and anticancer activity evaluation of indolo[1,2-a]quinoline derivatives

AU - Thanetchaiyakup, Adisak

AU - Borwornpinyo, Suparerk

AU - Rattanarat, Hassayaporn

AU - Kanjanasirirat, Phongthon

AU - Jearawuttanakul, Kedchin

AU - Seemakhan, Sawinee

AU - Chuanopparat, Nutthawat

AU - Ngernmeesri, Paiboon

PY - 2021/10/12

Y1 - 2021/10/12

N2 - A simple and effective one-pot synthesis of substituted indolo[1,2-a]quinolines has been developed. The desired products were obtained in up to 98% yield when substituted 2-methyindoles were treated with 2-iodobenzaldehyde in the presence of Cs2CO3, CuI and L-proline. Our mechanistic study confirmed that the reaction sequence involved an intermolecular Knoevenagel reaction followed by an intramolecular Ullmann-type coupling reaction. Moreover, some of the synthesized compounds were found to be active against human breast (MCF-7) and colorectal (HCT-116) cancer cells with IC50 values of 27.96 μM and in the range of 6.21–46.91 μM, respectively.

AB - A simple and effective one-pot synthesis of substituted indolo[1,2-a]quinolines has been developed. The desired products were obtained in up to 98% yield when substituted 2-methyindoles were treated with 2-iodobenzaldehyde in the presence of Cs2CO3, CuI and L-proline. Our mechanistic study confirmed that the reaction sequence involved an intermolecular Knoevenagel reaction followed by an intramolecular Ullmann-type coupling reaction. Moreover, some of the synthesized compounds were found to be active against human breast (MCF-7) and colorectal (HCT-116) cancer cells with IC50 values of 27.96 μM and in the range of 6.21–46.91 μM, respectively.

KW - Indolo[1,2-a]quinoline

KW - Knoevenagel condensation

KW - One-pot synthesis

KW - Ullmann-type reaction

UR - https://www.scopus.com/pages/publications/85114674977

U2 - 10.1016/j.tetlet.2021.153365

DO - 10.1016/j.tetlet.2021.153365

M3 - Article

AN - SCOPUS:85114674977

SN - 0040-4039

VL - 82

JO - Tetrahedron Letters

JF - Tetrahedron Letters

M1 - 153365

ER -

Copper-catalyzed synthesis and anticancer activity evaluation of indolo[1,2-a]quinoline derivatives

Abstract

UN SDGs

Keywords

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