A chiral benzoquinolizine-2-carboxylic acid arginine salt active against vancomycin-resistant Staphylococcus aureus

Noel J. De Souza; Shrikant V. Gupte; Prasad K. Deshpande; Vijaya N. Desai; Satish B. Bhawsar; Ravindra D. Yeole; Milind C. Shukla; Jacob Strahilevitz; David C. Hooper; Bülent Bozdogan; Peter C. Appelbaum; Michael R. Jacobs; Nitin Shetty; Mahesh V. Patel; Rasendrakumar Jha; Habil F. Khorakiwala

doi:10.1021/jm050035f

A chiral benzoquinolizine-2-carboxylic acid arginine salt active against vancomycin-resistant Staphylococcus aureus

Noel J. De Souza
, Shrikant V. Gupte
, Prasad K. Deshpande
, Vijaya N. Desai
, Satish B. Bhawsar
, Ravindra D. Yeole
, Milind C. Shukla
, Jacob Strahilevitz
, David C. Hooper
, Bülent Bozdogan
, Peter C. Appelbaum
, Michael R. Jacobs
, Nitin Shetty
, Mahesh V. Patel^*
, Rasendrakumar Jha
, Habil F. Khorakiwala

^*Corresponding author for this work

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

49 Scopus citations

Abstract

There is an urgent medical need for novel antibacterial agents to treat hospital infections, specially those caused by multidrug-resistant Gram-positive pathogens. The need may also be fulfilled by either exploring antibacterial agents having new mechanism of action or expanding known classes of antibacterial drugs. The paper describes a new chemical entity, compound 21, derived from hitherto little known "floxacin". The choice of the entity was made from a series of synthesized prodrugs and salts of the active chiral benzoquinolizine carboxylic acid, S-(-)-nadifloxacin. The chemistry, physicochemical characteristics, and essential bioprofile of 21 qualifies it for serious consideration as a novel drug entity against hospital infections of multi-drug-resistant Staphylococcus aureus, and its progress up to clinical phase I trials in humans is described.

Original language	English
Pages (from-to)	5232-5242
Number of pages	11
Journal	Journal of Medicinal Chemistry
Volume	48
Issue number	16
DOIs	https://doi.org/10.1021/jm050035f
State	Published - 11 Aug 2005
Externally published	Yes

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

SDG 3 Good Health and Well-being

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10.1021/jm050035f

Cite this

De Souza, N. J., Gupte, S. V., Deshpande, P. K., Desai, V. N., Bhawsar, S. B., Yeole, R. D., Shukla, M. C., Strahilevitz, J., Hooper, D. C., Bozdogan, B., Appelbaum, P. C., Jacobs, M. R., Shetty, N., Patel, M. V., Jha, R., & Khorakiwala, H. F. (2005). A chiral benzoquinolizine-2-carboxylic acid arginine salt active against vancomycin-resistant Staphylococcus aureus. Journal of Medicinal Chemistry, 48(16), 5232-5242. https://doi.org/10.1021/jm050035f

@article{a60d14ea83c74a88849c9cf3e5cd02c9,

title = "A chiral benzoquinolizine-2-carboxylic acid arginine salt active against vancomycin-resistant Staphylococcus aureus",

abstract = "There is an urgent medical need for novel antibacterial agents to treat hospital infections, specially those caused by multidrug-resistant Gram-positive pathogens. The need may also be fulfilled by either exploring antibacterial agents having new mechanism of action or expanding known classes of antibacterial drugs. The paper describes a new chemical entity, compound 21, derived from hitherto little known {"}floxacin{"}. The choice of the entity was made from a series of synthesized prodrugs and salts of the active chiral benzoquinolizine carboxylic acid, S-(-)-nadifloxacin. The chemistry, physicochemical characteristics, and essential bioprofile of 21 qualifies it for serious consideration as a novel drug entity against hospital infections of multi-drug-resistant Staphylococcus aureus, and its progress up to clinical phase I trials in humans is described.",

author = "\{De Souza\}, \{Noel J.\} and Gupte, \{Shrikant V.\} and Deshpande, \{Prasad K.\} and Desai, \{Vijaya N.\} and Bhawsar, \{Satish B.\} and Yeole, \{Ravindra D.\} and Shukla, \{Milind C.\} and Jacob Strahilevitz and Hooper, \{David C.\} and B{\"u}lent Bozdogan and Appelbaum, \{Peter C.\} and Jacobs, \{Michael R.\} and Nitin Shetty and Patel, \{Mahesh V.\} and Rasendrakumar Jha and Khorakiwala, \{Habil F.\}",

year = "2005",

month = aug,

day = "11",

doi = "10.1021/jm050035f",

language = "אנגלית",

volume = "48",

pages = "5232--5242",

journal = "Journal of Medicinal Chemistry",

issn = "0022-2623",

publisher = "American Chemical Society",

number = "16",

}

De Souza, NJ, Gupte, SV, Deshpande, PK, Desai, VN, Bhawsar, SB, Yeole, RD, Shukla, MC, Strahilevitz, J, Hooper, DC, Bozdogan, B, Appelbaum, PC, Jacobs, MR, Shetty, N, Patel, MV, Jha, R & Khorakiwala, HF 2005, 'A chiral benzoquinolizine-2-carboxylic acid arginine salt active against vancomycin-resistant Staphylococcus aureus', Journal of Medicinal Chemistry, vol. 48, no. 16, pp. 5232-5242. https://doi.org/10.1021/jm050035f

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T1 - A chiral benzoquinolizine-2-carboxylic acid arginine salt active against vancomycin-resistant Staphylococcus aureus

AU - De Souza, Noel J.

AU - Gupte, Shrikant V.

AU - Deshpande, Prasad K.

AU - Desai, Vijaya N.

AU - Bhawsar, Satish B.

AU - Yeole, Ravindra D.

AU - Shukla, Milind C.

AU - Strahilevitz, Jacob

AU - Hooper, David C.

AU - Bozdogan, Bülent

AU - Appelbaum, Peter C.

AU - Jacobs, Michael R.

AU - Shetty, Nitin

AU - Patel, Mahesh V.

AU - Jha, Rasendrakumar

AU - Khorakiwala, Habil F.

PY - 2005/8/11

Y1 - 2005/8/11

N2 - There is an urgent medical need for novel antibacterial agents to treat hospital infections, specially those caused by multidrug-resistant Gram-positive pathogens. The need may also be fulfilled by either exploring antibacterial agents having new mechanism of action or expanding known classes of antibacterial drugs. The paper describes a new chemical entity, compound 21, derived from hitherto little known "floxacin". The choice of the entity was made from a series of synthesized prodrugs and salts of the active chiral benzoquinolizine carboxylic acid, S-(-)-nadifloxacin. The chemistry, physicochemical characteristics, and essential bioprofile of 21 qualifies it for serious consideration as a novel drug entity against hospital infections of multi-drug-resistant Staphylococcus aureus, and its progress up to clinical phase I trials in humans is described.

AB - There is an urgent medical need for novel antibacterial agents to treat hospital infections, specially those caused by multidrug-resistant Gram-positive pathogens. The need may also be fulfilled by either exploring antibacterial agents having new mechanism of action or expanding known classes of antibacterial drugs. The paper describes a new chemical entity, compound 21, derived from hitherto little known "floxacin". The choice of the entity was made from a series of synthesized prodrugs and salts of the active chiral benzoquinolizine carboxylic acid, S-(-)-nadifloxacin. The chemistry, physicochemical characteristics, and essential bioprofile of 21 qualifies it for serious consideration as a novel drug entity against hospital infections of multi-drug-resistant Staphylococcus aureus, and its progress up to clinical phase I trials in humans is described.

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IS - 16

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A chiral benzoquinolizine-2-carboxylic acid arginine salt active against vancomycin-resistant Staphylococcus aureus

Abstract

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