875-31-0Relevant academic research and scientific papers
Synthesis and antimicrobial activities of N6-hydroxyagelasine analogs and revision of the structure of ageloximes
Paulsen, Britt,Fredriksen, Kim Alex,Petersen, Dirk,Maes, Louis,Matheeussen, An,Naemi, Ali-Oddin,Scheie, Anne Aamdal,Simm, Roger,Ma, Rui,Wan, Baojie,Franzblau, Scott,Gundersen, Lise-Lotte
, p. 620 - 629 (2019/01/14)
(+)-N6-Hydroxyagelasine D, the enantiomer of the proposed structure of (?)-ageloxime D, as well as N6-hydroxyagelasine analogs were synthesized by selective N-7 alkylation of N6-[tert-butyl(dimethyl)silyloxy]-9-methyl-9H-purin-6-amine in order to install the terpenoid side chain, followed by fluoride mediated removal of the TBDMS-protecting group. N6-Hydroxyagelasine D and the analog carrying a geranylgeranyl side chain displayed profound antimicrobial activities against several pathogenic bacteria and protozoa and inhibited bacterial biofilm formation. However these compounds were also toxic towards mammalian fibroblast cells (MRC-5). The spectral data of N6-hydroxyagelasine D did not match those reported for ageloxime D before. Hence, a revised structure of ageloxime D was proposed. Basic hydrolysis of agelasine D gave (+)-N-[4-amino-6-(methylamino)pyrimidin-5-yl]-N-copalylformamide, a compound with spectral data in full agreement with those reported for (?)-ageloxime D.
A convenient synthesis of new annelated pyrimidines and their biological importance
Wahab Khan,Uddin, Mohammed Kabir,Ali, Morshed,Rahman, Mohammad S.,Rashid, Mohammad Abdur,Chowdhury, Rasheduzzaman
, p. E216-E221 (2014/11/07)
Several bicyclic/tricyclic-fused pyrimidines were synthesized from the reactions of amino esters and bifunctional nucleophiles such as 2-methylthio-thiazoline and 2-methylthio-imidazoline. The synthesized compounds were tested for their in vitro antimicrobial activities that revealed mild to moderate growth inhibitory potentials.
Synthesis and some properties of 6-(ω-aroylbutylthio)purines
Gromov,Skachilova,Aleksandrova,Kochergin
, p. 1225 - 1229 (2007/10/03)
A series of 6-(ω-aroylthio)purines, which have not been described in the literature, has been obtained by the reaction of 6-purinethione with ω-chlorovalerophenone and its substituted derivatives. Some properties of the compounds synthesized have been studied, viz. reaction at the carbonyl group, methylation, and hydrolysis. 1999 KluwerAcademic/Plenum Publishers.
Purines. LXXII. Oxidation of N6-alkyladenines with m-chloroperoxybenzoic acid leading to N6-alkyladenine 1-oxides
Itaya, Taisuke,Ogawa, Kazuo,Takada, Yasutaka,Fujii, Tozo
, p. 967 - 971 (2007/10/03)
Oxidations of N6-methyladenine (8a) and N6-benzyladenine (8b) with m- chloroperoxybenzoic acid (mcpba) in methanol have been found to afford the N(1)-oxides 7a,b in 36% and 35% yields, respectively. The structure of 7b has been established by leading it to N6-methoxyadenine (10) through O- methylation, Dimroth rearrangement, and nonreductive debenzylation. On the other hand, N6,N6-dimethyladenine (16) afforded the N(3)-oxide 17 in 40% yield on treatment with Mcpba in methanol. On the basis of these findings, together with data accumulated for N-oxidations of adenine, N(x)- monosubstituted adenines, and 6-substituted purines, the formation of hydrogen bonding between the 6-amino Nh and the carbonyl oxygen of a peroxycarboxylic acid may account for regioselective N(1)and N(7)-oxidations of adenine and N(x)-monosubstituted adenines.
SYNTHESIS AND SOME PROPERTIES OF 6-β-OXOALKYL(ARALKYL, HETARALKYL, CYCLOALKYL)THIOPURINES
Kochergin, P. M.,Gromov, M. Yu.,Aleksandrova, E. V.,Skachilova, S. Ya.
, p. 1335 - 1339 (2007/10/02)
The reaction of 6-purinethione with α-haloketones has given a series of new 6-β-oxoalkyl(aralkyl, hetaralkyl, cycloalkyl)thiopurines.Their alkylation in position 9 and acid hydrolysis to hypoxanthine and its 9-alkyl derivatives has been studied.The hydrolysis of the acetals of 6-formylmethylthiopurine and the oxidation of 6-(2,3-dihydroxypropyl)thiopurine leads to 6-formylmethylthiopurine, which shows a ring-chain tautomerism and exists in the form of 7-hydroxy-7,8-dihydrothiazolopurine.
Purines. LI. Synthesis and biological activity of hypoxanthine 7-N-oxide and related compounds
Ogawa,Nishii,Nohara,Saito,Itaya,Fujii
, p. 612 - 616 (2007/10/02)
A detailed account is given of the first chemical synthesis of hypoxanthine 7-N-oxide (5), which started from coupling of 6-chloro-5-nitro-4(3H)-pyrimidinone (7) with N-(4-methoxybenzyl)phenacylamine, generated in situ from the hydrochloride (8), and proceeded through cyclization of the resulting phenacylamino pyrimidinone (9) and removal of the 4-methoxybenzyl group. The results of catalytic hydrogenolysis, methylation followed by catalytic hydrogenolysis, and rearrangement under acidic conditions of 5 supported the correctness of the assigned structure. An ultraviolet spectroscopic approach suggested that the neutral species of 5 exists in H2O mainly as the N(7)-OH tautomer (21). In the in vitro bioassay of antileukemic activity against murine L5178Y cells, 5 was weakly cytotoxic, with IC50 of 100 μg/ml. It did not show any antimicrobial activity even at 1000 μg/ml. None of the 9-(4-methoxybenzyl) (11) and O-methyl (12, 13, and 14) derivatives was found to be antileukemic or antimicrobial.
SYNTHESIS OF HYPOXANTHINE 7-OXIDE, A NEW N-OXIDE AT THE 6-OXOPURINE LEVEL
Ogawa, Kazuo,Saito, Tohru,Nohara, Fujio,Nishii, Masahiro,Itaya, Taisuke,Fujii, Tozo
, p. 885 - 888 (2007/10/02)
Hypoxanthine 7-oxide (IV) has been synthesized for the first time from 6-chloro-5-nitro-4(3H)-pyrimidinone (I) through the intermediates II and V; catalytic hydrogenolysis, methylation followed by catalytic hydrogenolysis, and isomerization under acidic conditions of IV supported the correctness of the assigned structure.
