• Bulletin of the Korean Chemical Society
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• 제25권7호
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• pp.991-996
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• 2004

New series of 6-(arylthio)uracils, 6-(4-substituted-1-piperazinyl)uracils, 2,4,5-trioxo-1H,3H-benzothiopyrano[2,3-d]pyrimidine and 5-aryl-2,4-dioxo-1H,3H-pyrimido[5,4-f]benzo[1,4]thiazepines have been prepared and screened for their in vitro activity against herpes simplex-1 virus (HSV-1) and human immunodeficiency virus-1 (HIV-1). The in vitro cytotoxic activity was also evaluated. The results of biological testing revealed that compound 5b showed marginal activity against HSV-1, while compounds 5b and 5f exhibited marginal activity against HIV-1. The rest of the tested compounds were found devoid of antiviral activity against both HSV-1 and HIV-1.

• 한국응용과학기술학회지
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• 제26권1호
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• pp.29-37
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• 2009

This study is focused on the synthesis of urea and amide derivatives particularly, since the amide moiety is an essential binding group at the binding site. Urea derivatives 3-7 and 13-14 were obtained by reaction of 2-aminopyrimidines and other amines with diverse isocyanates in pyridine as a solvent under reflux. The urea derivatives were obtained in low yield because of the highly electron deficient nature of the amino group of the 2-aminopyrimidine. Amide derivatives 8-10 were obtained in moderate yields by reaction of compound 1 with aryl chloride derivatives. Also, arylamine 11 was synthesized by Buchwald-Hartwig amination in moderate yields. Most of the compound did not show good activity against A375P melanoma cells, compared with Sorafenib as control compound.

• Natural Product Sciences
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• 제21권1호
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• pp.25-29
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• 2015

In a continuation of our studies to discover bioactive secondary metabolites from marine sources, we further investigated samples from a tryptamine and phenyl-alkane producing sponge, which resulted in the isolation of four uncommon small molecules and five nucleosides. Their structures were determined to be 7,8-dihydroimidazo[1,5-c]pyrimidin-5(6H)-one (1), 5-chlorocavernicolin (2), maleimide-5-oxime (3), 3-methylmaleimide-5-oxime (4), uridine (5), 2'-deoxyuridine (6), thymidine (7), adenine (8), and adenosine (9) by spectroscopic analyses. The isolated compounds were evaluated for inhibitory activity against soluble epoxide hydrolase (sEH) as well as the Wnt/${\beta}$-catenine signaling pathway.

• Archives of Pharmacal Research
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• 제25권6호
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• pp.790-794
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• 2002

A series of novel exomethylene cyclopropyl nucleosides have been synthesized starting from Feist's acid. Classical nucleophilic substitution conditions ($K_2CO_3$, 18-crown-6) of the tosylate 2 as well as Mitsunobu reaction (DEAD, $PPh_3$) of alcohol 1 with pyrimidine bases afforded a series of novel cyclopropyl nucleosides. Compound 4b displayed moderate anti-HBV activity without any cytotoxicity up to $100{\;}{\mu}M$.

• Archives of Pharmacal Research
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• 제28권11호
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• pp.1205-1212
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• 2005

2-Thiouracil-5-sulphonic acid N-(4-acetylphenyl) Amide (1) was reacted with a series of aromatic aldehydes giving chalcones 2 (Claisen-Schemidt reaction), some of these chalcones were reacted with urea and thiourea giving pyrimidine-2-one and pyrimidine-2 thione derivatives respectively of the type 3a,b and 4a,b. In addition many chalcones were reacted with hydroxylamine hydrochloride giving isoxazoline derivatives 5a,b. They could also reacted with phenylhydrazine to give pyrazoline derivatives 5a,b, chalcones also were reacted withethylcyano acetate and/or malononitryl in pyridine giving pyran derivatives 7a,c and 8a,c. In another pathway chalcones were epoxidised by $H_{2}O_{2}$ giving epoxides 9a,c which in turn were reacted with phenylhydrazine giving 4-hydroxypyrazoline derivatives 10a,c. In another reaction chalcones were reacted with ethylcyanoacetate in presence of amm.acetate giving pyridone derivatives 11a,d which could be prepared also in exellent yield from compound 1 by its reaction with certain aromatic aldehydes and ethylcyanoacetate in presence of ammonium acetate. Finally, compound 1 was reacted with semicarbazide giving semicarbazone intermediate 12 which in turn was reacted with thionyl chloride giving thiadiazole derivative 13. The biological effects of some of the new synthesized compounds were also investigated.

• 생명과학회지
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• 제21권10호
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• pp.1370-1376
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• 2011

고세균 Sulfolobus acidocaldarius의 기능유전체학 연구를 위하여 피리미딘 생합성 유전자군의 pyrEF 유전자에 근거한 피리미딘 영양요구주를 구축하였다. 원균주는 정상적인 pyrEF 존재하에서 5-fluoroorotic acid를 첨가하면 성장이 불가능하나 피리미딘 영양요구주는 성장이 가능한 원리를 활용하였다. 자외선을 이용하여 얻어진 5-FOA 첨가에 저항성을 갖는 돌연변이주를 얻었으며, 두 돌연변이주 KH1U와 KH2U는 각각 pyrE 유전자 부분의 점돌연변이와 삽입돌연변이를 갖는 돌연변이주임을 알 수 있었다. 이 두 돌연변이 균주는 5-FOA의 첨가에 의하여 이 세포를 사멸시킬 수 있는 능력이 사라짐을 확인하였다. 정상적인 pyrEF 유전자를 갖는 Sulfolobus-E. coli 플라스미드를 이용하여 보완실험을 수행한 결과 KH2U 돌연변이주는 다시 5-FOA에 대한 저항성을 잃어버렸으며, 배지내에 피리미딘의 첨가가 없어도 생존할 수 있는 능력을 보여주는 원균주와 같은 표현형으로 회귀함을 확인하였다. 이 연구는 차후 고세균 Sulfolobus acidocaldarius의 유전자 불활성화를 통한 유전학연구에 효율적인 도구로 사용되기에 유용한 연구로 생각된다.

• 약학회지
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• 제50권2호
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• pp.65-69
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• 2006

Novel 4'-hydroxymethyl branched thioapiosyl nucleosides were synthesized in this study. The introduction of hydroxymethyl group in the 4'-position was accomplished by a [3,3]-sigmatropic rearrangement. Thioapiosyl sugar moiety was constructed by sequential ozonolysis, reduction and cyclization. The pyrimidine nucleosidic bases (uracil, 5-fluorouracil, 5-iodouracil, 5-chlorouracil, 5-bromouracil) were efficiently coupled by Vorbruggen glycosyl condensation procedure (per-silyated base and TMSOTf). The antiviral activities of the synthesised compounds were evaluated against the HIV-1, HSV-1, HSV-2 and EMCV 5-Iodouracil 18 showed weak antiviral activity against HSV-1 $(EC_{50}=30.7{\mu}M)$.

• Asian-Australasian Journal of Animal Sciences
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• 제1권4호
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• pp.219-222
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• 1988

Degradation of deoxyribonucleic acid(DNA) and ribonucleic acid(RNA) by cell-free extract of mixed rumen protozoa of buffalo rumen was investigated. DNA was observed to be degraded rapidly during an initial incubation period of 2 hr with simultaneous appearance of degradation products. RNA on the other hand recorded a rapid degradation during an initial incubation period of 1 hr. RNA degradation products appeared upto an incubation period of 2 hr. DNA was observed to degrade into oligo- and mononucleotides. pyrimidine nucleosides, purine nucleoside adenosine and bases xanthine, hypoxanthine and thymine. Degradation products of RNA comprised of pyrimidine nucleosides, purine nucleoside, adenosine and bases xanthine, hypoxanthine and uracil besides oligo- and mononucleotides.

• Bulletin of the Korean Chemical Society
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• 제35권12호
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• pp.3502-3508
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• 2014

The first synthetic route to 5'-norcarbocyclic C-nucleoside [7-oxa-7,9-dideazadenosine (furo[3,2-d]pyrimidine) and 9-deazaadenosine (pyrrolo[3,2-d]pyrimidine)] phosphonic acids from commercially available 1,3-dihydroxy cyclopentane was described. The key C-C bond formation from sugar to base precursor was performed using Knoevenagel-type condensation from a ketone derivative. Synthesized C-nucleoside phosphonic acids were tested for anti-HIV activity as well as anti-leukemic activity. Compound 26 showed significant anti-leukemic activity.

• Bulletin of the Korean Chemical Society
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• 제2권3호
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• pp.112-114
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• 1981

The photocycloaddition reaction of 8-methoxypsoralen with purine and/or pyrimidine bases is studied as a model for the charge transfer interactions of psoralens with DNA bases by the FMO method. The results indicate that, in the case of the molecular complex formation between psoralens and purine and/or pyrimidine bases, the most probable photocycloaddition should occur in the following order: Thy (5,6)<>(3,4) 8-MOP, Cyt(5,6)<>(3,4)8-MOP, Ade (7,8)<>(3,4)8-MOP, Gua(7,8)<>(3,4)8-MOP. The theoretical results for the photocycloaddition reaction are also correlated with the experimental results. The photoadducts between 8-methoxypsoralen and adenine are likely to be C4-cycloadducts through the cycloaddition of 3,4-pyrone double bond of 8-methoxypsoralen to 7,8-double bond of adenine.