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Molecules 2010, 15(12), 9427-9436; doi:10.3390/molecules15129427
Article

Synthesis and Antitumor Activity of 3-Methyl-4-oxo-3,4-dihydroimidazo [5,1-d][1,2,3,5]tetrazine-8-carboxylates and -carboxamides

1
, 2
, 1
 and 1,*
1 Key Laboratory of Structure-Based Drugs Design & Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China 2 Zhejiang Jinhua CONBA Bio-pharm Co. Ltd., Jinhua 321016, China
* Author to whom correspondence should be addressed.
Received: 4 November 2010 / Revised: 10 December 2010 / Accepted: 14 December 2010 / Published: 20 December 2010
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Abstract

Seventeen novel 3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylate and -carboxamide derivatives were synthesized and evaluated for their growth inhibition in seven human solid tumor and a human leukemia HL-60 cell lines. Compound IVa showed more activity than the other compounds and the positive control temozolomide. In the presence of 40 mg/mL of IVa, the survival rate of all tested tumor cells was less than 10%. Esters displayed more potent antitumour activity than amides and temozolomide against HL-60 cells. These compounds also exhibited considerably enhanced water-solubility.
Keywords: antitumour activity; 3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]-tetrazine-8-carboxylates; 3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamides; synthesis antitumour activity; 3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]-tetrazine-8-carboxylates; 3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamides; synthesis
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Liu, D.; Yang, J.-G.; Cheng, J.; Zhao, L.-X. Synthesis and Antitumor Activity of 3-Methyl-4-oxo-3,4-dihydroimidazo [5,1-d][1,2,3,5]tetrazine-8-carboxylates and -carboxamides. Molecules 2010, 15, 9427-9436.

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