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Antitumor Benzothiazoles. 3. Synthesis of 2-(4-Aminophenyl)benzothiazoles and Evaluation of Their Activities against Breast Cancer Cell Lines in Vitro and in Vivo
Abstract
A new series of 2-(4-aminophenyl)benzothiazoles substituted in the phenyl ring and benzothiazole moiety has been synthesized by simple, high-yielding routes. The parent molecule 5a shows potent inhibitory activity in vitro in the nanomolar range against a panel of human breast cancer cell lines, but is inactive (IC50 > 30 microM) against other cell types: activity against the sensitive breast lines MCF-7 and MDA 468 is characterized by a biphasic dose-response relationship. Structure-activity relationships derived using these cell types has revealed that activity follows the heterocyclic sequence benzothiazole > benzoxazole >> benzimidazole and that 2-(4-aminophenyl)benzothiazoles bearing a 3'-methyl- 9a, 3'-bromo- 9c, 3'-iodo- 9f, and 3'-chloro-substituent 9i are especially potent and their activity extends to ovarian, lung, and renal cell lines. Four compounds have been evaluated in vivo against human mammary carcinoma models in nude mice. Compound 9a showed the most potent growth inhibition against the ER+ (MCF-7 and BO) and ER- (MT-1 and MT-3) tumors. Our efforts to identify a pharmacological mechanism of action for these intriguing compounds have not, as yet, been successful.
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Citations
Cited by
Keri, R. S., Patil, M. R., Patil, S. A., & Budagumpi, S. (2015) · European Journal of Medicinal Chemistry · doi:10.1016/j.ejmech.2014.10.059 · Cited by 631
Nepali, K., Sharma, S., Sharma, M., Bedi, P. M. S., & Dhar, K. L. (2014) · European Journal of Medicinal Chemistry · doi:10.1016/j.ejmech.2014.03.018 · Cited by 435
Mathis, C. A., Bacskai, B. J., Kajdasz, S. T., McLellan, M. E., Frosch, M. P., Hyman, B. T., Holt, D. P., Wang, Y., Huang, G.-F., Debnath, M. L., et al. (2002) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/s0960-894x(01)00734-x · Cited by 403
Medicinal significance of benzothiazole scaffold: an insight view
Sharma, P. C., Sinhmar, A., Sharma, A., Rajak, H., & Pathak, D. P. (2013) · Journal of Enzyme Inhibition and Medicinal Chemistry · doi:10.3109/14756366.2012.720572 · Cited by 256
Preliminary studies of a novel bifunctional metal chelator targeting Alzheimer's amyloidogenesis
Dedeoglu, A., Cormier, K., Payton, S., Tseitlin, K. A., Kremsky, J. N., Lai, L., Li, X., Moir, R. D., Tanzi, R. E., Bush, A. I., et al. (2004) · Experimental Gerontology · doi:10.1016/j.exger.2004.08.016 · Cited by 141
Metadata
- Authors
- Shi, D.-F., Bradshaw, T. D., Wrigley, S., McCall, C. J., Lelieveld, P., Fichtner, I., & Stevens, M. F. G.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1996-01-01
- Volume
- 39
- Issue
- 17
- Pages
- 3375-3384
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W1982445402
- Cited by
- 370
- References
- 0
- FWCI
- 2.69
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Antitumor Benzothiazoles. 3. Synthesis of 2-(4-Aminophenyl)benzothiazoles and Evaluation of Their Activities against Breast Cancer Cell Lines in Vitro and in Vivo. https://app.cochat.ai/papers/10.1021/jm9600959
- The paper
- Shi, D.-F., Bradshaw, T. D., Wrigley, S., McCall, C. J., Lelieveld, P., Fichtner, I., & Stevens, M. F. G. (1996). Antitumor Benzothiazoles. 3. Synthesis of 2-(4-Aminophenyl)benzothiazoles and Evaluation of Their Activities against Breast Cancer Cell Lines in Vitro and in Vivo. Journal of Medicinal Chemistry. https://doi.org/10.1021/jm9600959
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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