Carboxylic acid bioisosteres acylsulfonamides, acylsulfamides, and sulfonylureas as novel antagonists of the CXCR2 receptor

Michael P. Winters; Carl Crysler; Nalin Subasinghe; Declan Ryan; Lynette Leong; Shuyuan Zhao; Robert Donatelli; Edward Yurkow; Marie Mazzulla; Lisa Boczon; Carl L. Manthey; Christopher Molloy; Holly Raymond; Lynne Murray; Laura McAlonan; Bruce Tomczuk

doi:10.1016/j.bmcl.2008.01.127

Carboxylic acid bioisosteres acylsulfonamides, acylsulfamides, and sulfonylureas as novel antagonists of the CXCR2 receptor

Michael P. Winters, Carl Crysler, Nalin Subasinghe, Declan Ryan, Lynette Leong, Shuyuan Zhao, Robert Donatelli, Edward Yurkow, Marie Mazzulla, Lisa Boczon, Carl L. Manthey, Christopher Molloy, Holly Raymond, Lynne Murray, Laura McAlonan, Bruce Tomczuk

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Abstract

A series of novel acylsulfonamide, acylsulfamide, and sulfonylurea bioisosteres of carboxylic acids were prepared as CXCR2 antagonists. Structure-activity relationships are reported for these series. One potent orally bioavailable inhibitor had excellent PK properties and was active in a lung injury model in hyperoxia-exposed newborn rats.

Original language	English (US)
Pages (from-to)	1926-1930
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	18
Issue number	6
DOIs	https://doi.org/10.1016/j.bmcl.2008.01.127
State	Published - Mar 15 2008

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

Keywords

Acylsulfamides
Acylsulfonamides
Asthma
COPD
CXCR1
CXCR2
Carboxylic acid bioisosteres
Chemokine
IL-8
Indole
Neutrophils
Sulfonylureas

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10.1016/j.bmcl.2008.01.127

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Winters, M. P., Crysler, C., Subasinghe, N., Ryan, D., Leong, L., Zhao, S., Donatelli, R., Yurkow, E., Mazzulla, M., Boczon, L., Manthey, C. L., Molloy, C., Raymond, H., Murray, L., McAlonan, L., & Tomczuk, B. (2008). Carboxylic acid bioisosteres acylsulfonamides, acylsulfamides, and sulfonylureas as novel antagonists of the CXCR2 receptor. Bioorganic and Medicinal Chemistry Letters, 18(6), 1926-1930. https://doi.org/10.1016/j.bmcl.2008.01.127

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title = "Carboxylic acid bioisosteres acylsulfonamides, acylsulfamides, and sulfonylureas as novel antagonists of the CXCR2 receptor",

abstract = "A series of novel acylsulfonamide, acylsulfamide, and sulfonylurea bioisosteres of carboxylic acids were prepared as CXCR2 antagonists. Structure-activity relationships are reported for these series. One potent orally bioavailable inhibitor had excellent PK properties and was active in a lung injury model in hyperoxia-exposed newborn rats.",

keywords = "Acylsulfamides, Acylsulfonamides, Asthma, COPD, CXCR1, CXCR2, Carboxylic acid bioisosteres, Chemokine, IL-8, Indole, Neutrophils, Sulfonylureas",

author = "Winters, {Michael P.} and Carl Crysler and Nalin Subasinghe and Declan Ryan and Lynette Leong and Shuyuan Zhao and Robert Donatelli and Edward Yurkow and Marie Mazzulla and Lisa Boczon and Manthey, {Carl L.} and Christopher Molloy and Holly Raymond and Lynne Murray and Laura McAlonan and Bruce Tomczuk",

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doi = "10.1016/j.bmcl.2008.01.127",

language = "English (US)",

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Winters, MP, Crysler, C, Subasinghe, N, Ryan, D, Leong, L, Zhao, S, Donatelli, R, Yurkow, E, Mazzulla, M, Boczon, L, Manthey, CL, Molloy, C, Raymond, H, Murray, L, McAlonan, L & Tomczuk, B 2008, 'Carboxylic acid bioisosteres acylsulfonamides, acylsulfamides, and sulfonylureas as novel antagonists of the CXCR2 receptor', Bioorganic and Medicinal Chemistry Letters, vol. 18, no. 6, pp. 1926-1930. https://doi.org/10.1016/j.bmcl.2008.01.127

TY - JOUR

T1 - Carboxylic acid bioisosteres acylsulfonamides, acylsulfamides, and sulfonylureas as novel antagonists of the CXCR2 receptor

AU - Winters, Michael P.

AU - Crysler, Carl

AU - Subasinghe, Nalin

AU - Ryan, Declan

AU - Leong, Lynette

AU - Zhao, Shuyuan

AU - Donatelli, Robert

AU - Yurkow, Edward

AU - Mazzulla, Marie

AU - Boczon, Lisa

AU - Manthey, Carl L.

AU - Molloy, Christopher

AU - Raymond, Holly

AU - Murray, Lynne

AU - McAlonan, Laura

AU - Tomczuk, Bruce

PY - 2008/3/15

Y1 - 2008/3/15

N2 - A series of novel acylsulfonamide, acylsulfamide, and sulfonylurea bioisosteres of carboxylic acids were prepared as CXCR2 antagonists. Structure-activity relationships are reported for these series. One potent orally bioavailable inhibitor had excellent PK properties and was active in a lung injury model in hyperoxia-exposed newborn rats.

AB - A series of novel acylsulfonamide, acylsulfamide, and sulfonylurea bioisosteres of carboxylic acids were prepared as CXCR2 antagonists. Structure-activity relationships are reported for these series. One potent orally bioavailable inhibitor had excellent PK properties and was active in a lung injury model in hyperoxia-exposed newborn rats.

KW - Acylsulfamides

KW - Acylsulfonamides

KW - Asthma

KW - COPD

KW - CXCR1

KW - CXCR2

KW - Carboxylic acid bioisosteres

KW - Chemokine

KW - IL-8

KW - Indole

KW - Neutrophils

KW - Sulfonylureas

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U2 - 10.1016/j.bmcl.2008.01.127

DO - 10.1016/j.bmcl.2008.01.127

M3 - Article

C2 - 18308567

AN - SCOPUS:40749109329

SN - 0960-894X

VL - 18

SP - 1926

EP - 1930

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 6

ER -

Carboxylic acid bioisosteres acylsulfonamides, acylsulfamides, and sulfonylureas as novel antagonists of the CXCR2 receptor

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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