<abstract xml:lang="en" xmlns="http://www.w3.org/1999/xhtml"><p>2-Amino-5-acetyl-4-methyl-thiophene-3-carboxylic acid ethyl ester (<bold>1</bold>) and 5-acetyl-2-amino-4-methylthiophene-3-carbohydrazide (<bold>2</bold>) were synthesized and used as starting materials for the synthesis of new series of 1-(5-amino-4-(3,5-dimethyl-1<italic>H</italic>-pyrazole-1-carbonyl)-3-methylthiophen-2-yl) ethanone (<bold>3a</bold>), 1-(5-amino-4-(4-chloro-3,5-dimethyl-1<italic>H</italic>-pyrazole-1-carbonyl)-3-methylthiophen-2-yl) ethanone (<bold>3b</bold>), 1-(4-methyl-2-amino-5-acetylthiophene-3-carbonyl)pyrazolidine-3,5-dione (<bold>4</bold>), (Z)-<italic>N'</italic>-(4-methyl-2-amino-5-acetylthiophene-3-carbonyl) formohydrazonic acid (<bold>5a</bold>), (Z)-ethyl-<italic>N'</italic>-4-methyl-2-amino-5-acetylthiophene-3-carbonylformo hydrazonate (<bold>5b</bold>), 6-acetyl-3-amino-2,5-dimethylthieno[2,3-<italic>d</italic>]pyrimidin-4(3<italic>H</italic>)-one (<bold>8</bold>), 5-methyl-3-amino-2-mercapto-6-acetylthieno [2,3-<italic>d</italic>]pyrimidin-4(3<italic>H</italic>)-one (<bold>10</bold>) and 5-methyl-6-acetyl-2-thioxo-2,3-dihydrothieno[2,3-<italic>d</italic>]pyrimidin-4(1<italic>H</italic>)-one (<bold>12</bold>) as potential antioxidant and antitumor agents. Pharmacological tests showed that compounds <bold>6a, 6b, 8, 10</bold> and <bold>12</bold> exhibited significant antitumor and antioxidant activity.</p></abstract>

2-Amino-5-acetyl-4-methyl-thiophene-3-carboxylic acid ethyl ester (1) and 5-acetyl-2-amino-4-methylthiophene-3-carbohydrazide (2) were synthesized and used as starting materials for the synthesis of new series of 1-(5-amino-4-(3,5-dimethyl-1H-pyrazole-1-carbonyl)-3-methylthiophen-2-yl) ethanone (3a), 1-(5-amino-4-(4-chloro-3,5-dimethyl-1H-pyrazole-1-carbonyl)-3-methylthiophen-2-yl) ethanone (3b), 1-(4-methyl-2-amino-5-acetylthiophene-3-carbonyl)pyrazolidine-3,5-dione (4), (Z)-N'-(4-methyl-2-amino-5-acetylthiophene-3-carbonyl) formohydrazonic acid (5a), (Z)-ethyl-N'-4-methyl-2-amino-5-acetylthiophene-3-carbonylformo hydrazonate (5b), 6-acetyl-3-amino-2,5-dimethylthieno[2,3-d]pyrimidin-4(3H)-one (8), 5-methyl-3-amino-2-mercapto-6-acetylthieno [2,3-d]pyrimidin-4(3H)-one (10) and 5-methyl-6-acetyl-2-thioxo-2,3-dihydrothieno[2,3-d]pyrimidin-4(1H)-one (12) as potential antioxidant and antitumor agents. Pharmacological tests showed that compounds 6a, 6b, 8, 10 and 12 exhibited significant antitumor and antioxidant activity.

Design and synthesis of novel thiophenecarbohydrazide, thienopyrazole and thienopyrimidine derivatives as antioxidant and antitumor agents

Photochemistry Department (Heterocyclic Unit), National Research Center, 12622 Dokki Giza, Egypt

Green Chemistry Department, National Research Center, 12622 Dokki, Giza, Egypt

Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, 35516 Mansoura, Egypt

Acta Pharmaceutica

2-Amino-5-acetyl-4-methyl-thiophene-3-carboxylic acid ethyl ester (1) and 5-acetyl-2-amino-4-methylthiophene-3-carbohydrazide (2) were synthesized and used as...

Design and synthesis of novel thiophenecarbohydrazide, thienopyrazole and thienopyrimidine derivatives as antioxidant and antitumor agents

Publicado en línea: 06 dic 2010

Páginas: 311 - 323

DOI: https://doi.org/10.2478/v10007-010-0027-6

Palabras clave
tienopirazol, tieno[2,3-]pirimidini, tiofenkarbohidrazid, antioksidativno djelovanje, bleomicin-ovisno DNA oštećenje, antitumorsko djelovanje

This content is open access.

Design and synthesis of novel thiophenecarbohydrazide, thienopyrazole and thienopyrimidine derivatives as antioxidant and antitumor agents

Publicado en línea: 06 dic 2010

Páginas: 311 - 323

DOI: https://doi.org/10.2478/v10007-010-0027-6

Palabras clavetienopirazol, tieno[2,3-]pirimidini, tiofenkarbohidrazid, antioksidativno djelovanje, bleomicin-ovisno DNA oštećenje, antitumorsko djelovanje

This content is open access.

Palabras clave
tienopirazol, tieno[2,3-]pirimidini, tiofenkarbohidrazid, antioksidativno djelovanje, bleomicin-ovisno DNA oštećenje, antitumorsko djelovanje