Thieno[2,3-d]pyrimidines in the Synthesis of Antitumor and Antioxidant Agents

• Published in: Archiv der Pharmazie (Weinheim) Vol. 343; no. 5; pp. 301 - 309
• Main Authors: Aly, Ashraf A., Brown, Alan B., Ramadan, Mohamed, Gamal-Eldeen, Amira M., Abdel-Aziz, Mohamed, Abuo-Rahma, Gamal El-Din A. A., Radwan, Mohamed F.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.05.2010; WILEY‐VCH Verlag; Wiley
• Subjects: Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - pharmacology; Antioxidants - chemical synthesis; Antioxidants - pharmacology; Antitumor activity; Biphenyl Compounds - antagonists & inhibitors; Cell Proliferation - drug effects; Cells, Cultured; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Cyclization; Dimethyl acetylenedicarboxylate; Dose-Response Relationship, Drug; Drug Evaluation, Preclinical; Drug Screening Assays, Antitumor - methods; E-Dibenzoylethylene; HCT116 Cells; Hep G2 Cells; Humans; Life Sciences & Biomedicine; Pharmacology & Pharmacy; Physical Sciences; Picrates - antagonists & inhibitors; Pyrimidines - chemical synthesis; Pyrimidines - chemistry; Pyrimidines - pharmacology; Science & Technology; Structure-Activity Relationship; Thienopyrimidines; ACID-DERIVATIVES; E-Dibenzoylethylene; Cyclization; GROWTH; PYRIMIDINES; Antitumor activity; Dimethyl acetylenedicarboxylate; Thienopyrimidines; PHARMACOLOGICAL ACTIVITIES
• ISSN: 0365-6233; 1521-4184
• DOI: 10.1002/ardp.200900245

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 IC50 < 20 μM.