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

7 Citations (Web of Science)

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

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10.1016/j.bioorg.2013.08.002

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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",

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day = "1",

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

language = "English",

volume = "51",

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journal = "Bioorganic Chemistry",

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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

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