1150615-69-2Relevant articles and documents
Solvatochromic fluorescence behavior of 2-amino-6-hydroxy-4-(3,4- dimethoxyphenyl)-pyrimidine-5-carbonitrile: A sensitive fluorescent probe for detection of pH and water composition in binary aqueous solutions
Suryawanshi, Vishwas D.,Gore, Anil H.,Walekar, Laxman S.,Anbhule, Prashant V.,Patil, Shivajirao R.,Kolekar, Govind B.
, p. 4 - 9 (2013)
A new class of fluorescence sensor for detection of water in organic solvents based on photo-induced electron transfer (PET) of substituted pyrimidine appended with dimethoxyphenyl system has been designed and characterized. The probe 2-amino-6-hydroxy-4-(3,4-dimethoxyphenyl)-pyrimidine-5- carbonitrile AHDPC (I) was synthesized by one step three-component condensation reaction. The solvatochromic fluorescence behavior of AHDPC featuring electron withdrawing CN group, electron donating - OCH3, NH2, OH groups and various π-conjugated backbones in varying polar and non-polar solvents has been investigated. The fluorescence of the compound exhibits red shift from its absorption spectra and correlated with solvent polarity. AHDPC exhibited significant spectral shifts in λem as a function of water composition in binary aqueous solvent systems. The changes are due to the specific interactions of AHDPC by intramolecular hydrogen bonding with water, photoinduced electron transfer as well as general solvent effect. The observed solvatochromic fluorescence characteristic of AHDPC could used as a new probe for micro-environmental polarity changes as well as a sensitive sensor for the determination of water composition in binary aqueous solutions. This study shows that due to the solvent sensitive emission, pyrimidine derivatives are good candidates to be used as fluorescent probes.
Pyrimidinthiones (part I): Utility of 2-thioxopyrimidin-6-(1H)ones as ring transformer in the synthesis of fused bi- and tri-cyclic heterocyclic compounds and their potential biological activities
Salem,Madkour,Marzouk,Azab,Mahmoud
experimental part, p. 2596 - 2614 (2009/08/15)
The pyrimidinethiones have wide biological and pharmaceutical activities, that have attracted considerable interest in recent years especially as antiviral inhibiting production of hepatitis B virus (HBV), and in vitro insulin-mimetic. Activity of the complexes of pyrimidinone derivatives evaluated from 50% inhibitory concentration promoted us to study the transformation of the 2-thioxopyrimidin-6(1H) ones to fused bi- and tri-cyclic heterocyclic compounds having the pyrimidine moieties and screening their biological activity. The reactivity of 2-mercapto-4-aryl-5-cyanopyrimidin-6(1H)ones (1) towards alkylation by different mono and bifunctional halo-organic compounds has been investigated to give S-monoalkylated products 2, 7 and 9; S- and N-dialkylated products 3, 13 and 14. Treatment of 1 and/or 2 with hydrazine hydrate as a nitrogen nucleophile have been investigated to give 4, treatment of 4 with CS2 and sodium nitrite in the presence of acetic acid (0C) produced 1,2,4-triazolopyrimidin-5(1H)one derivatives (5)and tetrazolo[1,5-a]pyrimidin- 5(1H)ones (6), respectively. Also cyclization of 7 and 9 gave [1,3]thiazolo[3,2-a]pyrimidin-5(1H)one and [1,3]thiazolo[3,2-a]pyrimidin-3,5- dione derivatives 8 and 10 respectively, treatment of 10 with aromatic aldehyde produces 11 which reacted with guanidine HCl to give pyrimido[4,5-d]thiazolo[3, 2-a]pyrimidin-6(1H)one derivative 12. Reaction of 14 with o-phenylenediamine was investigated and gave [1,4]quinoxalino[2,3-b][1,3]thiazolo[3,2-a]pyrimidin- 9(1H)one derivative 15.
