Synthesis and Bioevaluation of Thieno[2,3‐d]pyrimidinone Derivatives as Potential Tumor Cell Growth Inhibitors

Abstract

A series of novel cycloalkylthieno[2,3-d]pyrimidinone derivatives have been conveniently synthesized via three steps including G-3CR, heterocyclization, and alkylation reactions as a part of our ongoing search for new bioactive molecules. The newly synthesized compounds were evaluated for their potential tumor cell growth inhibitory activity by standard MTT assay. The preliminary results show that compound 6b exhibited better inhibitory activities against HepG2, MCF-7, and BCG-823 cell lines compared to the control.

Discovery of New Apoptosis-Inducing Agents for Breast Cancer Based on Ethyl 2-Amino-4,5,6,7-Tetra Hydrobenzo[b]Thiophene-3-Carboxylate: Synthesis, In Vitro, and In Vivo Activity Evaluation

“…3-Benzyl-5,6,7,8-tetrahydrobenzo [4,5]thieno [2,3-d]pyrimidin-4(3H)-one (10) Yield: 73%, m.p. 190 Synthesis of ( 14): A mixture of ester 13 (3.0 mmol) and hydrazine hydrate (6.0 mmol) in 30 mL of ethanol was refluxed for 3 h, the reaction mixture was cooled, the solid product was filtered off, dried, and recrystallized from EtOH/DMF.…”

“…Fused heterocycles, based on pyrimidine scaffolds, have gained significant attention due to a wide range of pharmacological applications [5]. Especially, thienopyrimidines have been discovered as anticancer agents [6,7], EGFR kinase inhibitors (compound I, IC 50 = 2.6 [8]; compound II, IC 50 = 0.008, and compound III, IC 50 = 0.007 µM, respectively) [9], compound IV selective against HepG-2 (IC 50 = 14.9 µM) [10], compound V selective against the MCF-7 breast cancer line (IC 50 = 0.10 µM) [11], and tyrosine kinase inhibitors (compound VI) [12]. TargeGen, Inc. et al have been designed as an JAK2 inhibitor based on the core structure of anilinopyrimidine, and the cell proliferation assay has shown the EC 50 = 3 nM in a JAK2 V617F (compound VI) [13].…”

Recent developments regarding the use of thieno[2,3-d]pyrimidin-4-one derivatives in medicinal chemistry, with a focus on their synthesis and anticancer properties

“…should be a potential lead molecule for the discovery of cycloalkyl TPs as potential drugs [59]. and 123, thereby generating the corresponding drug-enzyme allene intermediates.…”

Synthesis, Characterization and Cytotoxicity of substituted[1]benzothieno[3,2-e][1,2,4]triazolo[4,3-a]pyrimidines

“…11 In addition, the tricyclic system, cycloalkylthieno [2,3-d]pyrimidine, which is considered to be a bioisostere of quinazoline, has been used as a core for the mechanism-based design and synthesis of a variety of compounds for anticancer therapy. [12][13][14][15][16] On the other hand, the 1,2,4-triazole heterocycle is of great value as a building block in the structure of several anticancer drug candidates. 11,17,18 Letrozole, Anastrozole and Ribavirin are representative examples of commercially available anticancer drugs containing triazole scaffolds (Fig.…”