126277-86-9Relevant academic research and scientific papers
Synthesis of New Fused Thienopyrimidines Derivatives as Anti-inflammatory Agents
Tolba, Mahmoud S.,Ahmed, Mostafa,Kamal El-Dean, Adel M.,Hassanien, Reda,Farouk, Mahmoud
, p. 408 - 418 (2018)
5-Amino-2-(p-tolylamino)-4-phenylthieno[2,3-d]pyrimidine-6-carbonitrile 9, which was synthesized by an innovative method, was used as a versatile precursor for synthesizing pyrimido-thienopyrimidine, triazolopyrimidothienopyrimidine, and pyrimidothienotriazine compounds. Thus, reaction of aminothienopyrimidinecarbonitrile 9 with chloroacetylchloride in dioxane afforded the chloroacetylaminocarbonitrile derivative 10, which underwent nucleophilic substitution reactions with various primary and secondary amines gave the corresponding N-alkyl-(aryl)amino acetamides 11a,b. On the other hand, the reaction of aminocarbonitrile 9 with triethyl orthoformate followed by cyclization with hydrazine yielded an aminoiminopyrimidine derivative 13. The latter was used as versatile precursor for synthesis of new heterocyclic compounds. The structures of all the new compounds have been established on the basis of their analytical and spectral data (IR, 1H NMR, 13C NMR, and MS). Some of the synthesized compounds were evaluated in vitro for their anti-inflammatory activity. All the tested compounds exhibited remarkable anti-inflammatory activity.
Quantitative analysis of hydrogen and chalcogen bonds in two pyrimidine-5-carbonitrile derivatives, potential DHFR inhibitors: An integrated crystallographic and theoretical study
Al-Mutairi, Aamal A.,Al-Shaalan, Nora H.,Al-Wahaibi, Lamya H.,Blacque, Olivier,Chakraborty, Kushumita,El-Emam, Ali A.,Percino, M. Judith,Syed Majeed, Mohamed Yehya Annavi,Thamotharan, Subbiah
, p. 36806 - 36817 (2020/10/27)
Two potential bioactive pyrimidine-5-carbonitrile derivatives have been synthesized and characterized by spectroscopic techniques (1H and 13C-NMR) and the three dimensional structures were elucidated by single crystal X-ray diffraction at low temperature (160 K). In both structures, the molecular conformation is locked by an intramolecular C-H?C interaction involving the cyano and CH of the thiophene and phenyl rings. The intermolecular interactions were analyzed in a qualitative manner based on the Hirshfeld surface and 2D-fingerprint plots. The results suggest that the phenyl and thiophene moieties have an effect on the crystal packing. For instance, the chalcogen bonds are only preferred in the thiophene derivative. However, both structures uses a common N-H?O hydrogen bond motif. Moreover, the structures of 1 and 2 display 1D isostructurality and molecular chains stabilize by intermolecular N-H?O and N-H?N hydrogen bonds. The nature and extent of different non-covalent interactions were further characterized by the topological parameters derived from the quantum theory of atoms-in-molecules approach. This analysis indicates that apart from N-H?O hydrogen bonds, other non-covalent interactions are closed-shell in nature. A strong and linear N-H?O hydrogen bond shows intermediate bonding character between shared and closed-shell interactions. The molecular docking analysis suggests that both compounds display potential inhibitory effect against the dihydrofolate reductase (DHFR) enzyme from humans and Staphylococcus aureus.
Synthesis and cytotoxic activity of novel 4-amino-5-cyano-2-sulfonylpyrimidines
Bunev, Alexander S.,Gasanov, Rovshan E.,Khochenkov, Dmitry A.,Khochenkova, Yulia A.,Machkova, Yulia S.,Stepanova, Eugenia V.
, p. 604 - 606 (2020/10/09)
Novel 4-amino-5-cyano-2-sulfonylpyrimidines were prepared based on three-component cyclization between isothiouronium salts, benzaldehydes and malononitrile, followed by oxidation of the sulfide moiety with Oxone. The cytotoxic activity of the synthesized compounds, as well as the induction of apoptosis, inhibition of the cell cycle and proliferation tests were performed on selected cancer cell lines A431, A549, A375, HCT 116, MCF7, LNCap and SH-SY5Y.
Synthesis and Cytotoxicity of Some Thieno[2,3-d]pyrimidine Derivatives
Saddik, Abdelreheem A.,Kamal El-Dean, Adel M.,El-Sokary, Gamal H.,Hassan, Khairy M.,Abbady, Mohamed S.,Ismail, Ismail A.,Saber, Saber H.
, p. 87 - 93 (2017/01/17)
A series of compounds 5-amino-2-ethylmercapto-4-phenyl-6-subistitutedthieno[2,3-d]pyrimidines (8a–d), 4-chloro-7-ethylmercapto-9-phenylpyrimido[5′,4′:4,5]thieno[3,2-d]triazine (9), and 2-ethylmercapto-8-oxo-4-phenyl-7-(4-chlorophenyl)pyrimido [4′,5′:4,5]thieno[2,3-d]pyrimidine (10) were synthesized and their structures were confirmed by 1H NMR, 13C NMR, and MS. All compounds were evaluated for their IC50 values against three cancer cell lines (MCF-7, HUH-7 and BHK) and WISH cells. The IC50 of compound (8d) was calculated for each cell line. Interestingly, the IC50 for the normal human amnion WISH cell line was much higher (723 μg/mL) than those found for the tumor cell lines BHK (17 μg/mL), HUH-7 (5.8 μg/mL), and MCF-7 (8.3 μg/mL). The proliferation inhibition of normal (WISH) and tumor (BHK, HUH-7, and MCF-7) cells by compound (8d) was investigated using MTT assay, and the IC50 was calculated after 48 h of treatment for each cell line.
