Citral derived amides as potent bacterial NorA efflux pump inhibitors

Niranjan Thota; Surrinder Koul; Mallepally V. Reddy; Payare L. Sangwan; Inshad A. Khan; Ashwani Kumar; Alsaba F. Raja; Samar S. Andotra; Ghulam N. Qazi

doi:10.1016/j.bmc.2008.05.030

Citral derived amides as potent bacterial NorA efflux pump inhibitors

Niranjan Thota
, Surrinder Koul
, Mallepally V. Reddy
, Payare L. Sangwan
, Inshad A. Khan
, Ashwani Kumar
, Alsaba F. Raja
, Samar S. Andotra
, Ghulam N. Qazi

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

52 Scopus citations

Abstract

Monoterpene citral and citronellal have been used as starting material for the preparation of 5,9-dimethyl-deca-2,4,8-trienoic acid amides and 9-formyl-5-methyl-deca-2,4,8-trienoic acid amides. The amides on bioevaluation as efflux pump inhibitors (EPIs) against Staphylococcus aureus 1199 and NorA overexpressing S. aureus 1199B bacteria resulted in the identification of several of these as potent EPIs. Many of these amides have been shown to possess potency higher or equivalent to known EPIs such as reserpine, verapamil, carsonic acid, and piperine. In this communication, we report a convenient synthesis of alkenyl amides, their bioevaluation and identification as efflux pump inhibitors against S. aureus.

Original language	English
Pages (from-to)	6535-6543
Number of pages	9
Journal	Bioorganic and Medicinal Chemistry
Volume	16
Issue number	13
DOIs	https://doi.org/10.1016/j.bmc.2008.05.030
State	Published - 1 Jul 2008
Externally published	Yes

Keywords

Antibacterial agent
Citral derived amides
NorA efflux pump inhibitors
Potentiators

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10.1016/j.bmc.2008.05.030

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@article{dc26599e714d4511a43cdb2db6a28431,

title = "Citral derived amides as potent bacterial NorA efflux pump inhibitors",

abstract = "Monoterpene citral and citronellal have been used as starting material for the preparation of 5,9-dimethyl-deca-2,4,8-trienoic acid amides and 9-formyl-5-methyl-deca-2,4,8-trienoic acid amides. The amides on bioevaluation as efflux pump inhibitors (EPIs) against Staphylococcus aureus 1199 and NorA overexpressing S. aureus 1199B bacteria resulted in the identification of several of these as potent EPIs. Many of these amides have been shown to possess potency higher or equivalent to known EPIs such as reserpine, verapamil, carsonic acid, and piperine. In this communication, we report a convenient synthesis of alkenyl amides, their bioevaluation and identification as efflux pump inhibitors against S. aureus.",

keywords = "Antibacterial agent, Citral derived amides, NorA efflux pump inhibitors, Potentiators",

author = "Niranjan Thota and Surrinder Koul and Reddy, \{Mallepally V.\} and Sangwan, \{Payare L.\} and Khan, \{Inshad A.\} and Ashwani Kumar and Raja, \{Alsaba F.\} and Andotra, \{Samar S.\} and Qazi, \{Ghulam N.\}",

year = "2008",

month = jul,

day = "1",

doi = "10.1016/j.bmc.2008.05.030",

language = "English",

volume = "16",

pages = "6535--6543",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier Ltd.",

number = "13",

}

TY - JOUR

T1 - Citral derived amides as potent bacterial NorA efflux pump inhibitors

AU - Thota, Niranjan

AU - Koul, Surrinder

AU - Reddy, Mallepally V.

AU - Sangwan, Payare L.

AU - Khan, Inshad A.

AU - Kumar, Ashwani

AU - Raja, Alsaba F.

AU - Andotra, Samar S.

AU - Qazi, Ghulam N.

PY - 2008/7/1

Y1 - 2008/7/1

N2 - Monoterpene citral and citronellal have been used as starting material for the preparation of 5,9-dimethyl-deca-2,4,8-trienoic acid amides and 9-formyl-5-methyl-deca-2,4,8-trienoic acid amides. The amides on bioevaluation as efflux pump inhibitors (EPIs) against Staphylococcus aureus 1199 and NorA overexpressing S. aureus 1199B bacteria resulted in the identification of several of these as potent EPIs. Many of these amides have been shown to possess potency higher or equivalent to known EPIs such as reserpine, verapamil, carsonic acid, and piperine. In this communication, we report a convenient synthesis of alkenyl amides, their bioevaluation and identification as efflux pump inhibitors against S. aureus.

AB - Monoterpene citral and citronellal have been used as starting material for the preparation of 5,9-dimethyl-deca-2,4,8-trienoic acid amides and 9-formyl-5-methyl-deca-2,4,8-trienoic acid amides. The amides on bioevaluation as efflux pump inhibitors (EPIs) against Staphylococcus aureus 1199 and NorA overexpressing S. aureus 1199B bacteria resulted in the identification of several of these as potent EPIs. Many of these amides have been shown to possess potency higher or equivalent to known EPIs such as reserpine, verapamil, carsonic acid, and piperine. In this communication, we report a convenient synthesis of alkenyl amides, their bioevaluation and identification as efflux pump inhibitors against S. aureus.

KW - Antibacterial agent

KW - Citral derived amides

KW - NorA efflux pump inhibitors

KW - Potentiators

UR - https://www.scopus.com/pages/publications/44849104070

U2 - 10.1016/j.bmc.2008.05.030

DO - 10.1016/j.bmc.2008.05.030

M3 - Article

C2 - 18524600

AN - SCOPUS:44849104070

SN - 0968-0896

VL - 16

SP - 6535

EP - 6543

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 13

ER -

Citral derived amides as potent bacterial NorA efflux pump inhibitors

Abstract

Keywords

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