Cu-mediated synthesis of 2,3-dihydro-1h-pyrrolo[3,2,1-ij]quinolin-1-ones as potential inhibitors of sirtuins

Sreerama Srinivas Rao; Dandela Rambabu; Mohosin Layek; Kummari Lalith Kumar; Mandava Venkata Basaveswara Rao; Devyani Haldar; Manojit Pal

doi:10.2174/15701808113109990065

Cu-mediated synthesis of 2,3-dihydro-1h-pyrrolo[3,2,1-ij]quinolin-1-ones as potential inhibitors of sirtuins

Sreerama Srinivas Rao, Dandela Rambabu, Mohosin Layek, Kummari Lalith Kumar, Mandava Venkata Basaveswara Rao, Devyani Haldar, Manojit Pal

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

4 Scopus citations

Abstract

CuI facilitated the intramolecular cyclization of 8-alkynyl substituted 2,3-dihydroquinolin-4(1H)-ones leading to 5-subtituted 2,3-dihydro-1H-pyrrolo[3, 2,1-ij]quinolin-1-ones via intramolecular C-N bond forming reaction. Some of the synthesized compounds have shown encouraging inhibition of Sir 2 protein (a yeast homolog of mammalian SIRT1) when tested using a yeast cell based assay. A representative compound showed dose dependent inhibition of yeast Sir 2 (IC50 = 30.09 μM) and cell growth inhibition properties when tested against different cancer cell lines. It's in silico interactions with sirtuins are presented.

Original language	English
Pages (from-to)	199-206
Number of pages	8
Journal	Letters in Drug Design and Discovery
Volume	11
Issue number	2
DOIs	https://doi.org/10.2174/15701808113109990065
State	Published - 1 Feb 2014
Externally published	Yes

Keywords

Alkyne
CuI
Cyclization
Docking
Pyrroloquinolines
Sirtuins

ASJC Scopus subject areas

Molecular Medicine
Pharmaceutical Science
Drug Discovery

UN SDGs

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

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10.2174/15701808113109990065

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title = "Cu-mediated synthesis of 2,3-dihydro-1h-pyrrolo[3,2,1-ij]quinolin-1-ones as potential inhibitors of sirtuins",

abstract = "CuI facilitated the intramolecular cyclization of 8-alkynyl substituted 2,3-dihydroquinolin-4(1H)-ones leading to 5-subtituted 2,3-dihydro-1H-pyrrolo[3, 2,1-ij]quinolin-1-ones via intramolecular C-N bond forming reaction. Some of the synthesized compounds have shown encouraging inhibition of Sir 2 protein (a yeast homolog of mammalian SIRT1) when tested using a yeast cell based assay. A representative compound showed dose dependent inhibition of yeast Sir 2 (IC50 = 30.09 μM) and cell growth inhibition properties when tested against different cancer cell lines. It's in silico interactions with sirtuins are presented.",

keywords = "Alkyne, CuI, Cyclization, Docking, Pyrroloquinolines, Sirtuins",

author = "Rao, {Sreerama Srinivas} and Dandela Rambabu and Mohosin Layek and Kumar, {Kummari Lalith} and {Basaveswara Rao}, {Mandava Venkata} and Devyani Haldar and Manojit Pal",

year = "2014",

month = feb,

day = "1",

doi = "10.2174/15701808113109990065",

language = "English",

volume = "11",

pages = "199--206",

journal = "Letters in Drug Design and Discovery",

issn = "1570-1808",

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T1 - Cu-mediated synthesis of 2,3-dihydro-1h-pyrrolo[3,2,1-ij]quinolin-1-ones as potential inhibitors of sirtuins

AU - Rao, Sreerama Srinivas

AU - Rambabu, Dandela

AU - Layek, Mohosin

AU - Kumar, Kummari Lalith

AU - Basaveswara Rao, Mandava Venkata

AU - Haldar, Devyani

AU - Pal, Manojit

PY - 2014/2/1

Y1 - 2014/2/1

N2 - CuI facilitated the intramolecular cyclization of 8-alkynyl substituted 2,3-dihydroquinolin-4(1H)-ones leading to 5-subtituted 2,3-dihydro-1H-pyrrolo[3, 2,1-ij]quinolin-1-ones via intramolecular C-N bond forming reaction. Some of the synthesized compounds have shown encouraging inhibition of Sir 2 protein (a yeast homolog of mammalian SIRT1) when tested using a yeast cell based assay. A representative compound showed dose dependent inhibition of yeast Sir 2 (IC50 = 30.09 μM) and cell growth inhibition properties when tested against different cancer cell lines. It's in silico interactions with sirtuins are presented.

AB - CuI facilitated the intramolecular cyclization of 8-alkynyl substituted 2,3-dihydroquinolin-4(1H)-ones leading to 5-subtituted 2,3-dihydro-1H-pyrrolo[3, 2,1-ij]quinolin-1-ones via intramolecular C-N bond forming reaction. Some of the synthesized compounds have shown encouraging inhibition of Sir 2 protein (a yeast homolog of mammalian SIRT1) when tested using a yeast cell based assay. A representative compound showed dose dependent inhibition of yeast Sir 2 (IC50 = 30.09 μM) and cell growth inhibition properties when tested against different cancer cell lines. It's in silico interactions with sirtuins are presented.

KW - Alkyne

KW - CuI

KW - Cyclization

KW - Docking

KW - Pyrroloquinolines

KW - Sirtuins

UR - http://www.scopus.com/inward/record.url?scp=84893808069&partnerID=8YFLogxK

U2 - 10.2174/15701808113109990065

DO - 10.2174/15701808113109990065

M3 - Article

AN - SCOPUS:84893808069

SN - 1570-1808

VL - 11

SP - 199

EP - 206

JO - Letters in Drug Design and Discovery

JF - Letters in Drug Design and Discovery

IS - 2

ER -

Cu-mediated synthesis of 2,3-dihydro-1h-pyrrolo[3,2,1-ij]quinolin-1-ones as potential inhibitors of sirtuins

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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