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

Department of Drug Design and Pharmacology

48 Citations (Scopus)

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
Journal	Bioorganic & Medicinal Chemistry
Volume	16
Issue number	13
Pages (from-to)	6535-43
Number of pages	9
ISSN	0968-0896
DOIs	https://doi.org/10.1016/j.bmc.2008.05.030
Publication status	Published - 1 Jul 2008

Keywords

Amides
Bacterial Proteins
Ciprofloxacin
Molecular Structure
Multidrug Resistance-Associated Proteins
Staphylococcus aureus
Structure-Activity Relationship
Journal Article

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10.1016/j.bmc.2008.05.030

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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 = "Amides, Bacterial Proteins, Ciprofloxacin, Molecular Structure, Multidrug Resistance-Associated Proteins, Staphylococcus aureus, Structure-Activity Relationship, Journal Article",

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",

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

language = "English",

volume = "16",

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journal = "Bioorganic & Medicinal Chemistry",

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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 - Amides

KW - Bacterial Proteins

KW - Ciprofloxacin

KW - Molecular Structure

KW - Multidrug Resistance-Associated Proteins

KW - Staphylococcus aureus

KW - Structure-Activity Relationship

KW - Journal Article

U2 - 10.1016/j.bmc.2008.05.030

DO - 10.1016/j.bmc.2008.05.030

M3 - Journal article

C2 - 18524600

SN - 0968-0896

VL - 16

SP - 6535

EP - 6543

JO - Bioorganic & Medicinal Chemistry

JF - Bioorganic & Medicinal Chemistry

IS - 13

ER -

Citral derived amides as potent bacterial NorA efflux pump inhibitors

Abstract

Keywords

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