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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10.1021/jm800418z

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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