Synthesis of thiophene-2-carboxamidines containing 2-aminothiazoles and their biological evaluation as urokinase inhibitors

Kenneth J. Wilson; Carl R. Illig; Nalin Subasinghe; James B. Hoffman; M. Jonathan Rudolph; Richard Soll; Christopher J. Molloy; Roger Bone; David Green; Troy Randall; Marie Zhang; Frank A. Lewandowski; Zhao Zhou; Celia Sharp; Diane Maguire; Bruce Grasberger; Renee L. DesJarlais; John Spurlino

doi:10.1016/S0960-894X(01)00102-0

Synthesis of thiophene-2-carboxamidines containing 2-aminothiazoles and their biological evaluation as urokinase inhibitors

Kenneth J. Wilson, Carl R. Illig, Nalin Subasinghe, James B. Hoffman, M. Jonathan Rudolph, Richard Soll, Christopher J. Molloy, Roger Bone, David Green, Troy Randall, Marie Zhang, Frank A. Lewandowski, Zhao Zhou, Celia Sharp, Diane Maguire, Bruce Grasberger, Renee L. DesJarlais, John Spurlino

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

116 Scopus citations

Abstract

The serine protease urokinase (uPa) has been implicated in the progression of both breast and prostate cancer. Utilizing structure based design, the synthesis of a series of substituted 4-[2-amino-1, 3-thiazolyl]-thiophene-2-carboxamidines is described. Further optimization of this series by substitution of the terminal amine yielded urokinase inhibitors with excellent activities.

Original language	English (US)
Pages (from-to)	915-918
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	11
Issue number	7
DOIs	https://doi.org/10.1016/S0960-894X(01)00102-0
State	Published - Apr 9 2001
Externally published	Yes

All Science Journal Classification (ASJC) codes

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

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Wilson, K. J., Illig, C. R., Subasinghe, N., Hoffman, J. B., Jonathan Rudolph, M., Soll, R., Molloy, C. J., Bone, R., Green, D., Randall, T., Zhang, M., Lewandowski, F. A., Zhou, Z., Sharp, C., Maguire, D., Grasberger, B., DesJarlais, R. L., & Spurlino, J. (2001). Synthesis of thiophene-2-carboxamidines containing 2-aminothiazoles and their biological evaluation as urokinase inhibitors. Bioorganic and Medicinal Chemistry Letters, 11(7), 915-918. https://doi.org/10.1016/S0960-894X(01)00102-0

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title = "Synthesis of thiophene-2-carboxamidines containing 2-aminothiazoles and their biological evaluation as urokinase inhibitors",

abstract = "The serine protease urokinase (uPa) has been implicated in the progression of both breast and prostate cancer. Utilizing structure based design, the synthesis of a series of substituted 4-[2-amino-1, 3-thiazolyl]-thiophene-2-carboxamidines is described. Further optimization of this series by substitution of the terminal amine yielded urokinase inhibitors with excellent activities.",

author = "Wilson, {Kenneth J.} and Illig, {Carl R.} and Nalin Subasinghe and Hoffman, {James B.} and {Jonathan Rudolph}, M. and Richard Soll and Molloy, {Christopher J.} and Roger Bone and David Green and Troy Randall and Marie Zhang and Lewandowski, {Frank A.} and Zhao Zhou and Celia Sharp and Diane Maguire and Bruce Grasberger and DesJarlais, {Renee L.} and John Spurlino",

year = "2001",

month = apr,

day = "9",

doi = "10.1016/S0960-894X(01)00102-0",

language = "English (US)",

volume = "11",

pages = "915--918",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Limited",

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}

Wilson, KJ, Illig, CR, Subasinghe, N, Hoffman, JB, Jonathan Rudolph, M, Soll, R, Molloy, CJ, Bone, R, Green, D, Randall, T, Zhang, M, Lewandowski, FA, Zhou, Z, Sharp, C, Maguire, D, Grasberger, B, DesJarlais, RL & Spurlino, J 2001, 'Synthesis of thiophene-2-carboxamidines containing 2-aminothiazoles and their biological evaluation as urokinase inhibitors', Bioorganic and Medicinal Chemistry Letters, vol. 11, no. 7, pp. 915-918. https://doi.org/10.1016/S0960-894X(01)00102-0

TY - JOUR

T1 - Synthesis of thiophene-2-carboxamidines containing 2-aminothiazoles and their biological evaluation as urokinase inhibitors

AU - Wilson, Kenneth J.

AU - Illig, Carl R.

AU - Subasinghe, Nalin

AU - Hoffman, James B.

AU - Jonathan Rudolph, M.

AU - Soll, Richard

AU - Molloy, Christopher J.

AU - Bone, Roger

AU - Green, David

AU - Randall, Troy

AU - Zhang, Marie

AU - Lewandowski, Frank A.

AU - Zhou, Zhao

AU - Sharp, Celia

AU - Maguire, Diane

AU - Grasberger, Bruce

AU - DesJarlais, Renee L.

AU - Spurlino, John

PY - 2001/4/9

Y1 - 2001/4/9

N2 - The serine protease urokinase (uPa) has been implicated in the progression of both breast and prostate cancer. Utilizing structure based design, the synthesis of a series of substituted 4-[2-amino-1, 3-thiazolyl]-thiophene-2-carboxamidines is described. Further optimization of this series by substitution of the terminal amine yielded urokinase inhibitors with excellent activities.

AB - The serine protease urokinase (uPa) has been implicated in the progression of both breast and prostate cancer. Utilizing structure based design, the synthesis of a series of substituted 4-[2-amino-1, 3-thiazolyl]-thiophene-2-carboxamidines is described. Further optimization of this series by substitution of the terminal amine yielded urokinase inhibitors with excellent activities.

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UR - http://www.scopus.com/inward/citedby.url?scp=0035832101&partnerID=8YFLogxK

U2 - 10.1016/S0960-894X(01)00102-0

DO - 10.1016/S0960-894X(01)00102-0

M3 - Article

C2 - 11294390

AN - SCOPUS:0035832101

SN - 0960-894X

VL - 11

SP - 915

EP - 918

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 7

ER -

Synthesis of thiophene-2-carboxamidines containing 2-aminothiazoles and their biological evaluation as urokinase inhibitors

Abstract

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