Thieno[2,3-d]pyrimidines in the synthesis of antitumor and antioxidant agents.
Dimethyl acetylenedicarboxylate, ethyl propiolate, and E-dibenzoylethylene react with thienopyrimidines (cyclo-pentyl, -hexyl, and -heptyl) derivatives to form thiazolo[3,2-a]thieno-[2,3-d]pyrimidin-2-ylidene) acetates, thieno[2,3-d]pyrimidin-2-ylthioacrylates, and thieno[2',3':4,5]pyrimido[2,1-b][1,3]thiazin-6-ones, respectively. Reactions proceed via cyclization and thio-addition processes. Some derivatives of thienopyrimidines showed high inhibition of Hep-G2 cell growth compared with the growth of untreated control cells. However, the fused heptyl of thienopyrimidothiazines indicates a promising specific antitumor agent against Hep-G2 cells with IC(50 )< 20 microM.
Aly
Ashraf A
AA
Chemistry Department, Faculty of Science, El-Minia University, El-Minia, Egypt. ashrafaly63@yahoo.com
Brown
Alan B
AB
Ramadan
Mohamed
M
Gamal-Eldeen
Amira M
AM
Abdel-Aziz
Mohamed
M
Abuo-Rahma
Gamal El-Din A A
Gel-D
Radwan
Mohamed F
MF
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology*; D001713:Biphenyl Compounds / Q000037:antagonists & inhibitors; D049109:Cell Proliferation / Q000187:drug effects; D002478:Cells, Cultured; D003500:Cyclization; D004305:Dose-Response Relationship, Drug; D004353:Drug Evaluation, Preclinical; D004354:Drug Screening Assays, Antitumor / Q000379:methods; D045325:HCT116 Cells; D056945:Hep G2 Cells; D006801:Humans; D010851:Picrates / Q000037:antagonists & inhibitors; D011743:Pyrimidines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D000975:Antioxidants; D001713:Biphenyl Compounds; D010851:Picrates; D011743:Pyrimidines; C476003:thienopyrimidine; C004931:1,1-diphenyl-2-picrylhydrazyl