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

Abstract

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.

Thieno[2,3-d]pyrimidinedione derivatives as antibacterial agents

“…Thienopyrimidines are interesting heterocyclic compounds and a number of derivatives of these compounds display therapeutic activity as antimicrobial [5–7], antiviral [8, 9], anti inflammatory [10] antidiabetic [11] and anti cancer [12, 13] agents. [14–16] Despite the breadth of biological activities displayed by these agents, the antibacterial activity of this class of compounds has been underexplored.…”

Recent Report on Thieno[2,3-d]pyrimidines. Their Preparation Including Microwave and Their Utilities in Fused Heterocycles Synthesis

“…Aly et al . reported that dimethyl acetylenedicarboxylate, ethyl propiolate, and E ‐dibenzoylethylene react with thienopyrimidines (cyclopentyl‐ 119a , hexyl‐ 119b , and heptyl‐ 119c derivatives) to form ( Z )‐methyl (3,5‐dioxo‐cycloalka[4′,5′]thieno[2′,3′:4,5]pyrimido[2,1‐ b ][1,3]thiazol‐2‐ylidene)acetate derivatives ( 120a , 120b , 120c , Scheme ), ( Z )‐ethyl 3′‐((4‐oxo‐cycloalka[4,5]thieno[2,3‐ d ]pyrimidin‐2‐yl)thio)acrylate derivatives ( 121a , 121b , 121c , Scheme ), and 2‐benzoyl‐4‐hydroxy‐4‐phenylcycloalka[4′,5′]thieno‐[2′,3′:4,5]pyrimido[2,1‐ b ][1,3]thiazin‐6‐one derivatives ( 122a , 122b , 122c , Scheme ), respectively. Reaction proceeded 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. Additionally, the heptyl derivative of thiazinothieno‐pyrimidines indicates a promising specific antitumor agent against Hep‐G2 cells because its IC 50 is <20 μM .…”

The Behavior of (cyclic‐alkylidene)hydrazinecarbothioamides in Cyclization with Dimethyl acetylenedicarboxylate

“…The literatures on reactions of hydrazine‐carbothioamides with dialkyl acetylenedicarboxylates contain contradiction in the structure of heterocycles obtained from structurally similar thiocarbonyl substrates . These differences could be attributed to solvent effect, effects condition, and to electronic or structural environment .…”