Synthesis and biological properties of benzothiazole, benzoxazole, and chromen-4-one analogues of the potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648)

Stefania Aiello; Geoffrey Wells; Erica L. Stone; Hachemi Kadri; Rana Bazzi; David R. Bell; Malcolm F.G. Stevens; Charles S. Matthews; Tracey D. Bradshaw; Andrew D. Westwell

doi:10.1021/jm800418z

Synthesis and biological properties of benzothiazole, benzoxazole, and chromen-4-one analogues of the potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648)

Stefania Aiello, Geoffrey Wells, Erica L. Stone, Hachemi Kadri, Rana Bazzi, David R. Bell, Malcolm F.G. Stevens, Charles S. Matthews, Tracey D. Bradshaw, Andrew D. Westwell

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

Abstract

New fluorinated 2-aryl-benzothiazoles, -benzoxazoles, and -chromen-4-ones have been synthesized and their activity against MCF-7 and MDA 468 breast cancer cell lines compared with the potent antitumor benzothiazole 5. Analogues such as 9a,b and 12a,d yielded submicromolar GI50 values in both cell lines; however, none of the new compounds approached 5 in terms of antitumor potency. For 5, binding to the aryl hydrocarbon receptor appeared to be necessary but not sufficient for growth inhibition.

Original language	English
Pages (from-to)	5135-5139
Journal	Journal of Medicinal Chemistry
Volume	51
Issue number	16
Early online date	31 Jul 2008
DOIs	https://doi.org/10.1021/jm800418z
Publication status	Published - 28 Aug 2008

Keywords

Cancer studies

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https://doi.org/10.1021/jm800418z

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Aiello, S., Wells, G., Stone, E. L., Kadri, H., Bazzi, R., Bell, D. R., Stevens, M. F. G., Matthews, C. S., Bradshaw, T. D., & Westwell, A. D. (2008). Synthesis and biological properties of benzothiazole, benzoxazole, and chromen-4-one analogues of the potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648). Journal of Medicinal Chemistry, 51(16), 5135-5139. https://doi.org/10.1021/jm800418z

@article{cd75475088d2487b8423c036766c5d99,

title = "Synthesis and biological properties of benzothiazole, benzoxazole, and chromen-4-one analogues of the potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648)",

abstract = "New fluorinated 2-aryl-benzothiazoles, -benzoxazoles, and -chromen-4-ones have been synthesized and their activity against MCF-7 and MDA 468 breast cancer cell lines compared with the potent antitumor benzothiazole 5. Analogues such as 9a,b and 12a,d yielded submicromolar GI50 values in both cell lines; however, none of the new compounds approached 5 in terms of antitumor potency. For 5, binding to the aryl hydrocarbon receptor appeared to be necessary but not sufficient for growth inhibition.",

keywords = "Cancer studies",

author = "Stefania Aiello and Geoffrey Wells and Stone, \{Erica L.\} and Hachemi Kadri and Rana Bazzi and Bell, \{David R.\} and Stevens, \{Malcolm F.G.\} and Matthews, \{Charles S.\} and Bradshaw, \{Tracey D.\} and Westwell, \{Andrew D.\}",

year = "2008",

month = aug,

day = "28",

doi = "10.1021/jm800418z",

language = "English",

volume = "51",

pages = "5135--5139",

journal = "Journal of Medicinal Chemistry",

issn = "0022-2623",

publisher = "American Chemical Society",

number = "16",

}

Aiello, S, Wells, G, Stone, EL, Kadri, H, Bazzi, R, Bell, DR, Stevens, MFG, Matthews, CS, Bradshaw, TD & Westwell, AD 2008, 'Synthesis and biological properties of benzothiazole, benzoxazole, and chromen-4-one analogues of the potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648)', Journal of Medicinal Chemistry, vol. 51, no. 16, pp. 5135-5139. https://doi.org/10.1021/jm800418z

Synthesis and biological properties of benzothiazole, benzoxazole, and chromen-4-one analogues of the potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648). / Aiello, Stefania; Wells, Geoffrey; Stone, Erica L. et al.
In: Journal of Medicinal Chemistry, Vol. 51, No. 16, 28.08.2008, p. 5135-5139.

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

TY - JOUR

T1 - Synthesis and biological properties of benzothiazole, benzoxazole, and chromen-4-one analogues of the potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648)

AU - Aiello, Stefania

AU - Wells, Geoffrey

AU - Stone, Erica L.

AU - Kadri, Hachemi

AU - Bazzi, Rana

AU - Bell, David R.

AU - Stevens, Malcolm F.G.

AU - Matthews, Charles S.

AU - Bradshaw, Tracey D.

AU - Westwell, Andrew D.

PY - 2008/8/28

Y1 - 2008/8/28

N2 - New fluorinated 2-aryl-benzothiazoles, -benzoxazoles, and -chromen-4-ones have been synthesized and their activity against MCF-7 and MDA 468 breast cancer cell lines compared with the potent antitumor benzothiazole 5. Analogues such as 9a,b and 12a,d yielded submicromolar GI50 values in both cell lines; however, none of the new compounds approached 5 in terms of antitumor potency. For 5, binding to the aryl hydrocarbon receptor appeared to be necessary but not sufficient for growth inhibition.

AB - New fluorinated 2-aryl-benzothiazoles, -benzoxazoles, and -chromen-4-ones have been synthesized and their activity against MCF-7 and MDA 468 breast cancer cell lines compared with the potent antitumor benzothiazole 5. Analogues such as 9a,b and 12a,d yielded submicromolar GI50 values in both cell lines; however, none of the new compounds approached 5 in terms of antitumor potency. For 5, binding to the aryl hydrocarbon receptor appeared to be necessary but not sufficient for growth inhibition.

KW - Cancer studies

U2 - 10.1021/jm800418z

DO - 10.1021/jm800418z

M3 - Article

C2 - 18666770

SN - 0022-2623

VL - 51

SP - 5135

EP - 5139

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

IS - 16

ER -

Synthesis and biological properties of benzothiazole, benzoxazole, and chromen-4-one analogues of the potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648)

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