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Literature DB >> 16122578

New thiophene analogues of kenpaullone: synthesis and biological evaluation in breast cancer cells.

Laurent Brault¹, Evelyne Migianu, Adrien Néguesque, Eric Battaglia, Denyse Bagrel, Gilbert Kirsch.

Abstract

Thieno analogues of kenpaullone have been synthesized using an established method. We investigated the effect of five structural analogues of kenpaullone on vincristine sensitive and resistant MCF7 (human mammary adenocarcinoma) cells. One analogue, 8-Bromo-6,11-dihydro-thieno-[3',2':2,3]azepino[4,5-b]indol-5(4H)-one (3a), showed an antiproliferative activity in the drug sensitive cell line that led to cell accumulation in G2/M phase. In addition, repression of cdk1, a G2/M transition key regulator, as well as induction of p21 were observed at the mRNA level. Programmed cell death (apoptosis) was induced in early time treatments and was accompanied by p53 mRNA induction. The antiproliferative and proapoptotic properties of 3a make this CDK inhibitor an interesting candidate for further investigations.

Entities: Chemical Disease Gene Species

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Year: 2005 PMID： 16122578 DOI： 10.1016/j.ejmech.2005.02.010

Source DB: PubMed Journal: Eur J Med Chem ISSN： 0223-5234 Impact factor: 6.514

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Cited

20 in total

1. 2-[3,4-Dibut-oxy-5-(5-phenyl-1,3,4-oxadiazol-2-yl)-2-thien-yl]-5-phenyl-1,3,4-oxadiazole.

Authors: Hai-Lin Li; Hai-Su Zeng; Si-Shun Kang; Hai-Bo Wang
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-07-05

2. 3-(4-Methoxy-benz-yl)-1-benzothio-phene.

Authors: B Gunasekaran; V Dhayalan; A K Mohanakrishnan; G Chakkaravarthi; V Manivannan
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-05-26

3. 2-{3,4-Dibut-oxy-5-[5-(3-methyl-phen-yl)-1,3,4-oxadiazol-2-yl]thio-phen-2-yl}-5-(3-methyl-phen-yl)-1,3,4-oxadiazole.

Authors: Lu-Na Han; Ran-Zhe Lu; Min Zhang; Hai-Bo Wang
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-02-28

4. Synthesis and antimicrobial studies of some novel bis-[1,3,4]thiadiazole and bis-thiazole pendant to thieno[2,3-b]thiophene moiety.

Authors: Nabila Abdelshafy Kheder; Yahia Nasser Mabkhot
Journal: Int J Mol Sci Date: 2012-03-19 Impact factor: 6.208

5. (2E)-1-(2,5-Dichloro-3-thien-yl)-3-(6-meth-oxy-2-naphth-yl)prop-2-en-1-one.

Authors: Jerry P Jasinski; Albert E Pek; C S Chidan Kumar; H S Yathirajan; A N Mayekar
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-06-18

6. 2-(4-tert-Butyl-phen-yl)-5-{3,4-dibutoxy-5-[5-(4-tert-butyl-phen-yl)-1,3,4-oxadiazol-2-yl]-2-thienyl}-1,3,4-oxadiazole.

Authors: Jian-Ning Guan; Hai-Lin Li; Lu-Na Han; Hai-Bo Wang
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-10-22

New thiophene analogues of kenpaullone: synthesis and biological evaluation in breast cancer cells.

1. 2-[3,4-Dibut-oxy-5-(5-phenyl-1,3,4-oxadiazol-2-yl)-2-thien-yl]-5-phenyl-1,3,4-oxadiazole.

2. 3-(4-Methoxy-benz-yl)-1-benzothio-phene.

3. 2-{3,4-Dibut-oxy-5-[5-(3-methyl-phen-yl)-1,3,4-oxadiazol-2-yl]thio-phen-2-yl}-5-(3-methyl-phen-yl)-1,3,4-oxadiazole.

4. Synthesis and antimicrobial studies of some novel bis-[1,3,4]thiadiazole and bis-thiazole pendant to thieno[2,3-b]thiophene moiety.

5. (2E)-1-(2,5-Dichloro-3-thien-yl)-3-(6-meth-oxy-2-naphth-yl)prop-2-en-1-one.

6. 2-(4-tert-Butyl-phen-yl)-5-{3,4-dibutoxy-5-[5-(4-tert-butyl-phen-yl)-1,3,4-oxadiazol-2-yl]-2-thienyl}-1,3,4-oxadiazole.

7. 2-(4-Chloro-phen-yl)-5-{3,4-dibut-oxy-5-[5-(4-chloro-phen-yl)-1,3,4-oxadiazol-2-yl]thio-phen-2-yl}-1,3,4-oxadiazole.

8. Diethyl 2-{[3-(2-meth-oxy-benz-yl)thio-phen-2-yl]methyl-idene}malonate.

9. (3,4-Dimeth-oxy-phen-yl)[2-(thio-phen-2-ylcarbon-yl)phen-yl]methanone.

10. 6-(4-Meth-oxy-phen-yl)naphtho[2,3-b][1]benzothio-phene.