• Title/Summary/Keyword: pyrimidines

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Synthesis of Imidazo[1,2-a]pyridines and Pyrido[1,2-a]pyrimidines in Water and their SNAr Cyclizations

  • Chanu, Langpoklakpam Gellina;Singh, Thokchom Prasanta;Jang, Yong Ju;Yoon, Yong-Jin;Singh, Okram Mukherjee;Lee, Sang-Gyeong
    • Bulletin of the Korean Chemical Society
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    • v.35 no.4
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    • pp.994-1000
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    • 2014
  • Synthesis of tetrahydroimidazo[1,2-a]pyridines and tetrahydropyrido[1,2-a] pyrimidines by a one-pot and three component reaction of ${\alpha}$-oxoketenedithioacetals, diamines and DMAD in water has been described. Different routes for accessing the desired compounds were examined and a few specially designed-substrates have been utilized further to afford the new imidazo and pyrido fused [1,8] naphthyridine tetracyclic compound by $S_NAr$ intramolecular cyclization.

Facile Synthesis of New Pyrazolopyrimidine Derivatives of Potential Biosignificant Interest

  • Aly, Aly A.;El-Karim, Iman A. Gad
    • Journal of the Korean Chemical Society
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    • v.55 no.5
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    • pp.781-786
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    • 2011
  • An easy and efficient route for the synthesis of some imidazo[1,2-c]pyrazolo[4,3-e]pyrimidines 3-6, imidazo[1,2-c]pyrazolo[4,3-e]triazine 8, pyrazolo[4,3-e]triazolo[1,5-c]pyrimidines 12-15 and pyrazolo-[3',4':4,5]pyrimido[1,6-b]triazines 16, 17 was described through the reaction of readily available 5-aminopyrazole-4-carbonitrile 1 with different reagents. The in vitro antimicrobial activity of some synthesized compounds was examined. Most of the tested compounds proved to be active as antibacterial and antifungal agents.

Diversification of 4,5-disubstituted Pyrrolo[3,2-d]-pyrimidines by Microwave Assisted Metal Catalyzed Reaction (마이크로파와 금속 촉매를 이용한 Pyrrolo[3,2-d]-pyrimidine 유도체의 다양화)

  • Jeong Seob, Byeon;Eul Kgun, Yum;Yeong-Joon, Kim
    • Journal of the Korean Chemical Society
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    • v.66 no.6
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    • pp.442-450
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    • 2022
  • Diverse pyrrolo[3,2-d]pyrimidines that are expected to exhibit bioactivity were synthesized through O-arylation and Suzuki coupling reactions. Microwave-assisted O-arylation was successfully performed using a Cu metal catalyst, so that 4 position of pyrrolo[3,2-d]pyrimidine could be substituted with phenol group. In addition, 4-aryl substituted pyrrolo[3,2-d]pyrimidines were synthesized with good to excellent yields by microwave-assisted Suzuki coupling reaction using a Pd metal catalyst. By using microwaves as reaction conditions for diversification of derivatives, it was possible to dramatically overcome the disadvantages of traditional heat reactions of long reaction times and heat transfer efficiency problems. The result of this study can be used to be diversify pyrrolo[3,2-d]pyrimidine derivatives, which are expected to play an important role in the drug discovery research.

In vitro Selection of the 2'-Fluoro-2'-Deoxyribonucleotide Decoy RNA Inhibitor of Myasthenic Autoantibodies

  • Seo, Hwa-Seon;Lee, Seong-Wook
    • Journal of Microbiology and Biotechnology
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    • v.10 no.5
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    • pp.707-713
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    • 2000
  • Myasthenia gravis (MG) is caused mainly by autoantibodies directed against acetylcholine receptors located in the postsynaptic muscle cell membrane. Using in vitro selection techniques, we isolated an RNA containing 2'-fluoro pyrimidines that can specifically and avidly ($K_d$ ~25 nM) bind rat monoclonal antibody called mAb198, which recognizes the main immunogenic region on the acetylcholine receptors. This RNA can act as a very effective decoy and block mAb198 binding to the receptors in vitro. Furthermore, this RNA decoy can prevent the antigenic modulation of the acetylcholine receptor caused by mAb198 in human muscle cell cultures with and $IC_{50} $of approximately $2.4{\mu}M$. These results indicate that the RNA selected in this study is a more potent decly inhibitor of myashthenic antibodies than the previously identified RNA with 2'-amino pyrimidines [11]. Moreover, this RNA cross-reacts with autoantibodies from patients with MG and can protect human cells from the effects of these antibodies. These observations have important implications for developing an antigen-specific treatment of autoimmune diseases including MG, which is based on decoy RNAs selected in vitro.

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A Novel Synthesis of 3,9-Dialkyl and 8-Aryl-3,9-dimethylxanthines

  • Youssif, Shaker;El-Kafrawy, Azza;Bayoumy, Besheer;El-Bahaie, Said
    • Bulletin of the Korean Chemical Society
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    • v.23 no.3
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    • pp.374-380
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    • 2002
  • Several compounds of 3,9-dialkylxanthines were prepared from 1-methyl-6-chlorouracil via nucleophillic reactions with different aliphatic amines, followed by nitrosation, reduction, formaylation and finally dehydrocyclization. On the other hands, a series of 8-aryl-3,9-dimethylxanthines were synthesized by dehydrocyclization of 5-arylamido-1-methyl-6-methylaminouracils either by fussion or oxidation of 5-arylidine-amino-1-methyl-6-methylaminouracils using sodium periodate. Phosphoryl chloride was found to be uneffective reagent for dehydrocyclization that, gave another products from 1,3-oxazolo[5,4-d] pyrimidines.

Reactions with Heterocyclic Amidines $(Vl)^1$: Synthesis of some new sym. and assym. pyrazolotriazines and pyrazolo[4,5-e]pyrimidine derivatives

  • Ali Elagamey, Abdel Ghani
    • Archives of Pharmacal Research
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    • v.10 no.3
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    • pp.173-178
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    • 1987
  • Several new pyrazolo [1, 5-a]-S-triazine, pyrazolo [4, 5, -elpyrimidine, pyrazolo [1, 5-a] pyrimidine derivatives were synthesized via condensation of 3-antipyrinyl-5-amino-pyrazole (2) with $\beta$$-bifunctional reagents. The azo analogues of pyrazolo [1, 5-a] pyrimidines ; i. e. pyrazolo [5, 1, c]-as-triazine and pyrazolo[5, 1, -c]-as-benzotriazine were synthesized by coupling of diazotized 2-with agents containing active hydrogen.

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Synthesis of 5-Fluorouracil by Ring Transformation of s-Triazine (s-Triazine의 Ring Transformation에 의한 5-FU의 합성)

  • 정원근;정진현
    • YAKHAK HOEJI
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    • v.26 no.1
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    • pp.25-27
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    • 1982
  • We had reported that s-triazine can readily be converted into the corresponding 5-substituted pyrimide. In order to develop new synthetic method of 5-fluorouracil, we tried to replace eliminating fragment, 1, 3-dimethylurea, by fluoroacetamide, which was expected to undergo nucleophilic attack by proton extraction of both .alpha.-hydrogen and aminohydrogen by lithium diisopropylamide (LDA). We found that 5-fluorouracil could be transformed from s-triazine under strong base condition like LDA as well as other 5-substituted pyrimidines.

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