332017-62-6Relevant academic research and scientific papers
Synthesis and biological activity of a series of new thieno[2,3-d] pyrimidines
Wang, Tao,Zheng, Cai Hua,Liu, Sue,Chen, Hui Zong
, p. 1543 - 1549 (2010)
Ethyl 2-amino-5-ethylthiophene-3- carboxylate 1, obtained from the reaction of butyraldehyde, ethyl cyanoacetate, sulfur, and triethylamine, reacted with benzoylisothiocyanate to give the corresponding ureido derivatives 2 in a high yield. Further reactions of the compound 2 with an aqueous-alcohol solution of potassium hydroxide and then with hydrochloric acid gave the 2-thio-thieno[2,3-d]pyrimidine-4-ones 3, which were reacted with RX to give novel compounds 4a-4i. Treating the compound 3 with dibromoalkane led to the formation of triacylic compounds 5j-5m. Their structures were clearly verified by IR, 1H NMR, EI-MS spectroscopy, and elemental analysis. The results of a preliminary bioassay indicated that some compounds possess excellent inhibitory activities against the root and the stalk of Brassica napus (rape) and Echinochloa crusgalli (barnyard grass) at a dosage of 100 mg/L. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
Synthesis and receptor binding of new thieno[2,3-d]-pyrimidines as selective ligands of 5-HT3 receptors
Modica, Maria N.,Romeo, Giuseppe,Salerno, Loredana,Pittala, Valeria,Siracusa, Maria A.,Mereghetti, Ilario,Cagnotto, Alfredo,Mennini, Tiziana,Gaspar, Robert,Gal, Adrienn,Falkay, George,Palko, Marta,Maksay, Gabor,Fueluep, Ferenc
experimental part, p. 333 - 343 (2009/04/04)
With the aim to develop new potent and selective ligands of 5-HT 3-type serotonin receptors and to acquire more information on their structure-affinity relationships, new thieno[2,3-d]pyrimidine derivatives 32-39 were synthesized and their binding to 5-HT3 versus 5-HT4 receptors was studied. Some of these new compounds exhibit good affinity for cortical 5-HT3 receptors, but not for 5-HT4 receptors. Among these derivatives, 6-ethyl-4-(4-methyl-1-piperazinyl)-2-(methylthio)- thieno[2,3-d]pyrimidine 32 is the most potent ligand (Ki = 67 nM); it behaves as a competitive antagonist of the 5-HT3 receptor function in the guinea pig colon. Its binding interactions with 5-HT3A receptors were analysed by using receptor modelling and comparative docking.
