Synthesis and evaluation of substituted 4-aryloxy- and 4-arylsulfanyl- phenyl-2-aminothiazoles as inhibitors of human breast cancer cell proliferation

Michael J. Gorczynski; Rachel M. Leal; Susan L. Mooberry; John H. Bushweller; Milton L. Brown

doi:10.1016/j.bmc.2003.12.003

Synthesis and evaluation of substituted 4-aryloxy- and 4-arylsulfanyl- phenyl-2-aminothiazoles as inhibitors of human breast cancer cell proliferation

Michael J. Gorczynski, Rachel M. Leal, Susan L. Mooberry, John H. Bushweller, Milton L. Brown

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

63 Scopus citations

Abstract

Several substituted 4-aryloxy- and 4-arylsulfanyl-phenyl-2-aminothiazoles were synthesized and evaluated for cytotoxic activity against estrogen-positive, estrogen-negative, and adriamycin-resistant human breast cancer cell lines. 4-[4′-(3,4-Dichlorophenoxy)-phenyl]-thiazol-2-yl ammonium iodide demonstrated potent activity against both estrogen-positive and negative breast cancer cell lines with low micromolar (μM) GI₅₀ values. In addition, we have identified several 2-aminothiazoles that demonstrated selective potency for the adriamycin-resistant and estrogen-negative breast cancer cell lines. The results suggest that these 2-aminothiazoles represent lead compounds for evaluation in animal models of breast cancer.

Original language	English (US)
Pages (from-to)	1029-1036
Number of pages	8
Journal	Bioorganic and Medicinal Chemistry
Volume	12
Issue number	5
DOIs	https://doi.org/10.1016/j.bmc.2003.12.003
State	Published - Mar 1 2004
Externally published	Yes

Keywords

2-Aminothiazoles
Breast cancer
Diaryl ethers
Substituent effects

ASJC Scopus subject areas

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

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10.1016/j.bmc.2003.12.003

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Synthesis and evaluation of substituted 4-aryloxy- and 4-arylsulfanyl- phenyl-2-aminothiazoles as inhibitors of human breast cancer cell proliferation. / Gorczynski, Michael J.; Leal, Rachel M.; Mooberry, Susan L. et al.

In: Bioorganic and Medicinal Chemistry, Vol. 12, No. 5, 01.03.2004, p. 1029-1036.

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

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title = "Synthesis and evaluation of substituted 4-aryloxy- and 4-arylsulfanyl- phenyl-2-aminothiazoles as inhibitors of human breast cancer cell proliferation",

abstract = "Several substituted 4-aryloxy- and 4-arylsulfanyl-phenyl-2-aminothiazoles were synthesized and evaluated for cytotoxic activity against estrogen-positive, estrogen-negative, and adriamycin-resistant human breast cancer cell lines. 4-[4′-(3,4-Dichlorophenoxy)-phenyl]-thiazol-2-yl ammonium iodide demonstrated potent activity against both estrogen-positive and negative breast cancer cell lines with low micromolar (μM) GI50 values. In addition, we have identified several 2-aminothiazoles that demonstrated selective potency for the adriamycin-resistant and estrogen-negative breast cancer cell lines. The results suggest that these 2-aminothiazoles represent lead compounds for evaluation in animal models of breast cancer.",

keywords = "2-Aminothiazoles, Breast cancer, Diaryl ethers, Substituent effects",

author = "Gorczynski, {Michael J.} and Leal, {Rachel M.} and Mooberry, {Susan L.} and Bushweller, {John H.} and Brown, {Milton L.}",

note = "Funding Information: We thank the National Cancer Institute's Developmental Therapeutics Program for testing the thiazoles, the Leukemia and Lymphoma Society for funding, the Leukemia and Lymphoma Society for funding, the William Randolph Hearst Foundation for funding to SLM, the University of Virginia Department of Chemistry, and the Burger Center of Biological Sciences for support.",

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AU - Gorczynski, Michael J.

AU - Leal, Rachel M.

AU - Mooberry, Susan L.

AU - Bushweller, John H.

AU - Brown, Milton L.

N1 - Funding Information: We thank the National Cancer Institute's Developmental Therapeutics Program for testing the thiazoles, the Leukemia and Lymphoma Society for funding, the Leukemia and Lymphoma Society for funding, the William Randolph Hearst Foundation for funding to SLM, the University of Virginia Department of Chemistry, and the Burger Center of Biological Sciences for support.

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N2 - Several substituted 4-aryloxy- and 4-arylsulfanyl-phenyl-2-aminothiazoles were synthesized and evaluated for cytotoxic activity against estrogen-positive, estrogen-negative, and adriamycin-resistant human breast cancer cell lines. 4-[4′-(3,4-Dichlorophenoxy)-phenyl]-thiazol-2-yl ammonium iodide demonstrated potent activity against both estrogen-positive and negative breast cancer cell lines with low micromolar (μM) GI50 values. In addition, we have identified several 2-aminothiazoles that demonstrated selective potency for the adriamycin-resistant and estrogen-negative breast cancer cell lines. The results suggest that these 2-aminothiazoles represent lead compounds for evaluation in animal models of breast cancer.

AB - Several substituted 4-aryloxy- and 4-arylsulfanyl-phenyl-2-aminothiazoles were synthesized and evaluated for cytotoxic activity against estrogen-positive, estrogen-negative, and adriamycin-resistant human breast cancer cell lines. 4-[4′-(3,4-Dichlorophenoxy)-phenyl]-thiazol-2-yl ammonium iodide demonstrated potent activity against both estrogen-positive and negative breast cancer cell lines with low micromolar (μM) GI50 values. In addition, we have identified several 2-aminothiazoles that demonstrated selective potency for the adriamycin-resistant and estrogen-negative breast cancer cell lines. The results suggest that these 2-aminothiazoles represent lead compounds for evaluation in animal models of breast cancer.

KW - 2-Aminothiazoles

KW - Breast cancer

KW - Diaryl ethers

KW - Substituent effects

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Synthesis and evaluation of substituted 4-aryloxy- and 4-arylsulfanyl- phenyl-2-aminothiazoles as inhibitors of human breast cancer cell proliferation

Abstract

Keywords

ASJC Scopus subject areas

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