Synthesis and cytotoxicity of 2-acetyl-4,8-dihydrobenzodithiophene-4, 8-dione derivatives.
2-Acetyl-4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione (9) and 2-acetyl-4,8-dihydrobenzo[1,2-b:5,4-b']dithiophene-4,8-dione (19), together with 10 related mono- and disubstituted derivatives, were synthesized and evaluated in vitro by NCI against eight cancer types. All compounds showed significant activity against melanoma, HL-60 leukemia, NCI-H23 non-small-cell lung cancer, OVCAR-3 ovarian cancer, and MDA-MB-435 and MDA-N breast cancer cell lines. Compound 11, 2-(1'-acetoxyethyl)-4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4, 8-dione, showed the highest overall potency (mean GI50 = 40 nM).
Chao
Y H
YH
Natural Products Laboratory, Division of Medicinal Chemistry and Natural Products, School of Pharmacy CB#7360, University of North Carolina, Chapel Hill, North Carolina 27599-7360, USA.
Kuo
S C
SC
Wu
C H
CH
Lee
C Y
CY
Mauger
A
A
Sun
I C
IC
Morris-Natschke
S L
SL
Lee
K H
KH
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D020128:Inhibitory Concentration 50; D013329:Structure-Activity Relationship; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D014407:Tumor Cells, Cultured
C115594:2-(1'-acetoxyethyl)-4,8-dihydrobenzo(1,2--4,5-b')dithiophene-4,8-dione; D000970:Antineoplastic Agents; D013876:Thiophenes