- Eucalyptol as bio-based solvent for Migita–Kosugi–Stille coupling reaction on O,S,N-heterocycle
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We report herein an investigation on the use of eucalyptol as new solvent for organic transformations applied to the Migita-Kosugi-Stille palladium-catalyzed cross-coupling reaction. Heterocycles containing oxygen, sulfur and nitrogen were chosen as starting materials. Eucalyptol turned out to be a viable sustainable alternative to common solvents for this reaction.
- Campos, Joana F.,Berteina-Raboin, Sabine
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- Method for catalytically synthesizing 7-denitrified purine compound by using iron coordination compound
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The invention relates to a method for catalytically synthesizing a 7-denitrogenated purine compound by using an iron coordination compound. The method comprises the following steps: in the presence of an alkali, taking 7-denitrogenated purine and halogenated hydrocarbon as raw materials, taking an iron coordination compound containing an ortho-carborane benzoxazole structure as a catalyst, and reacting at room temperature to obtain the 6-substituted 7-denitrogenated purine compound. Compared with the prior art, the method has the advantages that the iron coordination compound containing the ortho-carborane benzoxazole structure is utilized to catalytically synthesize the 6-substituted 7-deazapurine compound, so that the compound is prepared by a one-pot method at room temperature, the use equivalent of the catalyst is low, the reaction condition is mild, the raw materials are cheap and easy to obtain, the substrate universality is high, and the yield is high.
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Paragraph 0043-0047
(2021/10/27)
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- NOVEL 6-SUBSTITUTED 7-DEAZAPURINES AND CORRESPONDING NUCLEOSIDES AS MEDICAMENTS
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The present invention relates to the synthesis of 6-substituted 7-deazapurines and their corresponding nucleosides by coupling aryl or alkyl Grignard reagents with halogenated purine nucleosides in the presence of iron or an iron/copper mixture such as Fe(acac)3/Cul. The present invention also relates to pharmaceutical compositions comprising said compounds and the use of said pharmaceutical compositions to treat or prevent viral infections.
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Page/Page column 25-26; 47; 51; 52
(2021/08/27)
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- 6-Methyl-7-Aryl-7-Deazapurine Nucleosides as Anti-Trypanosoma cruzi Agents: Structure-Activity Relationship and in vivo Efficacy
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Chagas disease is a tropical infectious disease resulting in progressive organ-damage and currently lacks efficient treatment and vaccine options. The causative pathogen, Trypanosoma cruzi, requires uptake and processing of preformed purines from the host because it cannot synthesize these de novo, instigating the evaluation of modified purine nucleosides as potential trypanocides. By modifying the pyrimidine part of a previously identified 7-aryl-7-deazapurine nucleoside, we found that substitution of a 6-methyl for a 6-amino group allows retaining T. cruzi amastigote growth inhibitory activity but confers improved selectivity towards mammalian cells. By keeping the 6-methyl group unaltered, and introducing different 7-aryl groups, we identified several analogues with sub-micromolar antitrypanosomal activity. The 7-(4-chlorophenyl) analogue 14, which was stable in microsomes, was evaluated in an acute mouse model. Oral administration of 25 mg/kg b.i.d. suppressed peak parasitemia and protected mice from infection-related mortality, gave similar reductions as the reference drug of blood parasite loads determined by qPCR, but as benznidazole failed to induce sterile cure in the short time period of drug exposure (5 days).
- Lin, Cai,Ferreira de Almeida Fiuza, Ludmila,Cardoso Santos, Camila,Ferreira Nunes, Daniela,Cruz Moreira, Otacílio,Bouton, Jakob,Karalic, Izet,Maes, Louis,Caljon, Guy,Hulpia, Fabian,de Nazaré C. Soeiro, Maria,Van Calenbergh, Serge
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p. 2231 - 2253
(2021/05/18)
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- Synthesis and biological evaluation of selected 7H-pyrrolo[2,3-d]pyrimidine derivatives as novel CDK9/CyclinT and Haspin inhibitors
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Protein kinases, including CDK9/CyclinT and Haspin, are regarded as potential drug targets in cancer therapy. Findings from a previous study suggested 7-azaindole as a privileged scaffold for producing inhibitors of CDK9/CyclinT and Haspin. Inspired by these findings, the current study synthesised and evaluated thirteen (13) C6-substituted 7-azaindole and twenty (20) C4-substituted structurally related 7H-pyrrolo[2,3-d]pyrimidine derivatives against a panel of protein kinases, including CDK9/CyclinT and Haspin. Eleven of the 7H-pyrrolo[2,3-d]pyrimidine derivatives exhibited activity toward CDK9/CyclinT, while 4 of compounds had activity against Haspin. The best CDK9/CyclinT (IC50 of 0.38 μM) and Haspin (IC50 of 0.11 μM) activities were achieved by compounds 7d and 7f, respectively. Hence, these compounds may be valuable starting points for development of new anti-cancer drugs.
- Baratte, Blandine,Beteck, Richard M.,Jesumoroti, Omobolanle J.,Legoabe, Lesetja J.,Pieterse, Lianie,Robert, Thomas,Ruchaud, Sandrine,Bach, Stéphane
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- Iron/Copper Co-Catalyzed Cross-Coupling Reaction for the Synthesis of 6-Substituted 7-Deazapurines and the Corresponding Nucleosides
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An efficient access to 6-substituted 7-deazapurine and the corresponding nucleosides by coupling aryl or alkyl Grignard reagents and halogenated purine nucleosides in the presence of Fe(acac)3/CuI is described. A series of 6-substituted 7-deazapurines and the corresponding nucleosides were obtained in medium to good yields. For the synthesis of modified nucleosides that will be the subject of biological testing, we propose to use iron-catalyzed instead of palladium-catalyzed reaction. The synthesized compounds were tested for their antiproliferative activity. The cytotoxicity study of compounds 11a-q shows that by modifying the 6-position of 7-deazapurine ribonucleosides, the compounds may become selective for certain cancer cell lines.
- Daelemans, Dirk,Herdewijn, Piet,Li, Qingfeng,Persoons, Leentje
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- Direct C-H sulfenylation of purines and deazapurines
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A general method for Cu-catalyzed C-H sulfenylation of purines, 7-deaza- and 9-deazapurines with aryl- or alkyldisulfides has been developed. In purines, the reaction occurs at position 8, in 7-deazapurines at position 7 and in 9-deazapurines at position 9, leading to new interesting arylsulfanyl derivatives of purine or deazapurine bases. The resulting 8-arylsulfanylpurines undergo Liebesking-Srogl coupling with arylstannanes or boronic acids, whereas the (arylsulfanyl)deazapurines are not reactive under these conditions.
- Kle?ka, Martin,Pohl, Radek,?ejka, Jan,Hocek, Michal
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supporting information
p. 5189 - 5193
(2013/08/23)
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- PYRROLOPYRIMIDINES AS JANUS KINASE INHIBITORS
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The instant invention provides compounds of formula I which are JAK3 inhibitors. Specifically, the compounds of formula I are pyrrolo[2,3-d]pyrimidine derivative compounds. The instant invention also provides methods of treating JAK-mediated diseases such
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Page/Page column 175-176
(2013/06/27)
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- PYRROLO[2,3-D]PYRIMIDINE DERIVATIVES AS CGRP RECEPTOR ANTAGONISTS
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The present invention relates to novel compounds that are CGRP receptor antagonists, processes for their preparation, to compositions containing them and to their use in the treatment of migraine, headache, and cluster headache.
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Page/Page column 33
(2009/07/25)
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