Novel alkynyl substituted 3,4-dihydropyrimidin-2(1H)-one derivatives as potential inhibitors of chorismate mutase

V. Mallikarjuna Rao; P. Mahesh Kumar; D. Rambabu; Ravikumar Kapavarapu; S. Shobha Rani; Parimal Misra; Manojit Pal

doi:10.1016/j.bioorg.2013.08.002

Novel alkynyl substituted 3,4-dihydropyrimidin-2(1H)-one derivatives as potential inhibitors of chorismate mutase

V. Mallikarjuna Rao, P. Mahesh Kumar, D. Rambabu, Ravikumar Kapavarapu, S. Shobha Rani, Parimal Misra, Manojit Pal

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

4 Scopus citations

Abstract

A series of novel alkynyl substituted 3,4-dihydropyrimidin-2(1H)-one (DHPM) derivatives were designed, synthesized and evaluated in vitro as potential inhibitors of chorismate mutase (CM). All these compounds were prepared via a multi-component reaction (MCR) involving sequential I₂-mediated Biginelli reaction followed by Cu-free Sonogashira coupling. Some of them showed promising inhibitory activities when tested at 30 μM. One compound showed dose dependent inhibition of CM with IC₅₀ value of 14.76 ± 0.54 μM indicating o-alkynylphenyl substituted DHPM as a new scaffold for the discovery of promising inhibitors of CM.

Original language	English
Pages (from-to)	48-53
Number of pages	6
Journal	Bioorganic Chemistry
Volume	51
DOIs	https://doi.org/10.1016/j.bioorg.2013.08.002
State	Published - 1 Jan 2013
Externally published	Yes

Keywords

Alkyne
Chorismate mutase
Iodine
Palladium
Pyrimidinone

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Drug Discovery
Organic Chemistry

UN SDGs

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

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10.1016/j.bioorg.2013.08.002

Cite this

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title = "Novel alkynyl substituted 3,4-dihydropyrimidin-2(1H)-one derivatives as potential inhibitors of chorismate mutase",

abstract = "A series of novel alkynyl substituted 3,4-dihydropyrimidin-2(1H)-one (DHPM) derivatives were designed, synthesized and evaluated in vitro as potential inhibitors of chorismate mutase (CM). All these compounds were prepared via a multi-component reaction (MCR) involving sequential I2-mediated Biginelli reaction followed by Cu-free Sonogashira coupling. Some of them showed promising inhibitory activities when tested at 30 μM. One compound showed dose dependent inhibition of CM with IC50 value of 14.76 ± 0.54 μM indicating o-alkynylphenyl substituted DHPM as a new scaffold for the discovery of promising inhibitors of CM.",

keywords = "Alkyne, Chorismate mutase, Iodine, Palladium, Pyrimidinone",

author = "\{Mallikarjuna Rao\}, V. and \{Mahesh Kumar\}, P. and D. Rambabu and Ravikumar Kapavarapu and \{Shobha Rani\}, S. and Parimal Misra and Manojit Pal",

year = "2013",

month = jan,

day = "1",

doi = "10.1016/j.bioorg.2013.08.002",

language = "English",

volume = "51",

pages = "48--53",

journal = "Bioorganic Chemistry",

issn = "0045-2068",

publisher = "Academic Press Inc.",

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TY - JOUR

T1 - Novel alkynyl substituted 3,4-dihydropyrimidin-2(1H)-one derivatives as potential inhibitors of chorismate mutase

AU - Mallikarjuna Rao, V.

AU - Mahesh Kumar, P.

AU - Rambabu, D.

AU - Kapavarapu, Ravikumar

AU - Shobha Rani, S.

AU - Misra, Parimal

AU - Pal, Manojit

PY - 2013/1/1

Y1 - 2013/1/1

N2 - A series of novel alkynyl substituted 3,4-dihydropyrimidin-2(1H)-one (DHPM) derivatives were designed, synthesized and evaluated in vitro as potential inhibitors of chorismate mutase (CM). All these compounds were prepared via a multi-component reaction (MCR) involving sequential I2-mediated Biginelli reaction followed by Cu-free Sonogashira coupling. Some of them showed promising inhibitory activities when tested at 30 μM. One compound showed dose dependent inhibition of CM with IC50 value of 14.76 ± 0.54 μM indicating o-alkynylphenyl substituted DHPM as a new scaffold for the discovery of promising inhibitors of CM.

AB - A series of novel alkynyl substituted 3,4-dihydropyrimidin-2(1H)-one (DHPM) derivatives were designed, synthesized and evaluated in vitro as potential inhibitors of chorismate mutase (CM). All these compounds were prepared via a multi-component reaction (MCR) involving sequential I2-mediated Biginelli reaction followed by Cu-free Sonogashira coupling. Some of them showed promising inhibitory activities when tested at 30 μM. One compound showed dose dependent inhibition of CM with IC50 value of 14.76 ± 0.54 μM indicating o-alkynylphenyl substituted DHPM as a new scaffold for the discovery of promising inhibitors of CM.

KW - Alkyne

KW - Chorismate mutase

KW - Iodine

KW - Palladium

KW - Pyrimidinone

UR - https://www.scopus.com/pages/publications/84888305643

U2 - 10.1016/j.bioorg.2013.08.002

DO - 10.1016/j.bioorg.2013.08.002

M3 - Article

C2 - 24012092

AN - SCOPUS:84888305643

SN - 0045-2068

VL - 51

SP - 48

EP - 53

JO - Bioorganic Chemistry

JF - Bioorganic Chemistry

ER -

Novel alkynyl substituted 3,4-dihydropyrimidin-2(1H)-one derivatives as potential inhibitors of chorismate mutase

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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