• Title/Summary/Keyword: Pyrimidine

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A New Synthesis of a Chiral Ester Containing Phenylpyrimidine Rinf as Liquid Crystal Dopant

  • 박정호;이용섭;정선호;박호군
    • Bulletin of the Korean Chemical Society
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    • v.16 no.6
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    • pp.489-492
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    • 1995
  • A new synthetic route to chiral liquid crystal dopant, 4-[2-(7S-methylnonanyl)oxy-5-pyrimidinyl]phenyl(2S,3S)-2-chloro-3-methylpentanoate (1), starting from 4-nitrophenylacetic acid is described. The key intermediate methylthiopyrimidine compound (8) has been synthesized from 4-nitrophenylacetic acid by Vilsmyer-Haack reaction followed by the formation of pyrimidine ring, and then converted to chiral ester (1) by the replacement of nitro group by (2S,3S)-2-chloro-3-methylpentanoic acid 2 through the formation of diazonium salt.

Synthesis of Acyclic Nucleosides of 2-Thio-Pyrimidines and -Purines Using a New Coupling Agent of Lithium Bromide

  • Kim, Joong-Young;Kim, Yong-Hae
    • Bulletin of the Korean Chemical Society
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    • v.9 no.5
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    • pp.295-298
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    • 1988
  • Acyclic nucleosides, 1-[[1,3-bis(benzyloxy)-2-propoxy]methyl]-2-thiopyrimidine, 9-[[1,3-bis(benzyloxy)-2-propoxy]methyl]-6-amino -2-thiopurine, 1-(2-acetoxyethoxymethyl)-2-thiopyrimidine, and 9-[[1,3-bis(benzyloxy)-2-propoxy]methyl]-6-amino -2-thiopurine have been synthesized by coupling pyrimidine and purine bases with acyclic acetates using a new coupling reagent of lithium bromide in the presence of trifluoro acetic acid in acetonitrile.

Synthesis and Biological Evaluation of Pyrimidine Nucleosides Fused with 3′,4′- Tetrahydrofuran Ring

  • Kim, Myong-Jung;Chung, Soon-Yong;Liang, Cheng-Wu;Chun, Moon-Woo
    • Proceedings of the PSK Conference
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    • 2002.10a
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    • pp.363.2-363.2
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    • 2002
  • A number of 2',3'-deoxynucleosides have been discovered to possess significant antiviral activity against HIV-1 and other viruses. Since it has been suggested that proper conformation of the dideoxynucleosides in terms of ring puckering of the five-membered sugar moiety is required for them to exhibit antiviral activity a number of nucleoside analogues to fix sugar-ring puckering have been synthesize and evaluated for antiviral activity. (omitted)

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Synthesis and Biological Activities of New Substituted Indoles

  • Hishmat, Orchidee H.;Nakkady, Sally S.;El Shabrawy, Osama A.;Mahmoud, Sawsan S.
    • Archives of Pharmacal Research
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    • v.15 no.1
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    • pp.104-108
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    • 1992
  • 2, 3-Diphenyl-6-formyl-5-methoxyindole reacts with ethyl cyano acetate to yield the arylidene derivative which forms with urea and thiourea the corresponding pyrimidine derivatives. The arylidene derivatives react with hydrazines and with active methylenes to form the respective pyrazole derivatives and the $\alpha, \;\beta$-disubstituted acrylonitriles. Seven new compounds were tested for their effects on the arterial blood pressure of rats and analgesic activity.

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Control and Mechanism of Tumor Promotion in UV-Carcinogenesis

  • Ueda, Masato;Budiyanto, Arief;Ashida, Masashi;Bito, Toshinori;Ichihashi, Masamitsu
    • Journal of Photoscience
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    • v.9 no.2
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    • pp.221-224
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    • 2002
  • Carcinogenesis can be theoretically divided to intiation step and promotion step. Intiation associates with genetic alterations including p53 tumor suppressor gene and ras oncogene. Promotion involves in clonal expansion of of an initiated cell by epigenetic mechanism, mainly through signal transduction and gene expression. Ultraviolet light (UV) acts as both initiator and promoter. Initiation is closely related with DNA damage induced by UV, including cyclobutane pyrimidine dimers, (6-4) photoproducts and 8-hydroxy-2'-deoxyguanosine. Cyclobutane pyrimidine dimers and (6-4) photoproducts are directly induced by UV, while 8-hydroxy-2'-deoxyguanosine is induced indirectly by the reactive oxygen species. Because initiation is an irreversal genetic event, while promotion is a reversal and epigenetic event, to know the molecular mechanisms of tumor promotion in UV-carcinogenesis is crucial to develop preventive medicine and suppress UV-carcinogenesis. Because ROS is also involved in signal transduction of the cell, anti-oxidant could be the good candidate of anti-promoting agent. Here, we describe the suppressive effect of UV-carcinogenesis by various anti-oxidant including olive oil. In addition, we discuss about the mechanism of UVB-induced expression of cyclooxygenase-2, which might be a representative molecule involved in promotion of UV-carcinogenesis.

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Differences in the Amino Acid Sequences of CPD Photolyases of UV-sensitive and UV-resistant Rice Cultivars

  • Teranishi, Mika;Hidema, Jun;Fujino, Takana;Hirouchi, Tokuhisa;Yamamoto, Kazuo;Kumagai, Tadashi
    • Journal of Photoscience
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    • v.9 no.2
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    • pp.329-331
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    • 2002
  • There is a difference in the inhibitory effects to supplemental UVB (wavelengths 280 to 320 nm) among Japanese rice (Oryza sativa L.), the cultivar Norin I is less resistant while the cultivar Sasanishiki is resistant. UVB induces photodamage in DNA. Cyclobutane pyrimidine dimer (CPD) is a major UV-induced DNA lesion. Photorepair, which is mediated by photolyase, is the major pathway in plants for repairing CPD. We have analyzed CPD induction and repair in Sasanishiki and its close relative Norin I using alkaline agarose gel electrophoresis. Norin I is deficient in CPD photoreactivation and excision, thus UV sensitivity correlates with deficient dimer repair [I]. The photorepair deficiency in Norin I results from a functionally altered photolyase with a photoflash analysis [2]. In this paper, we examined the UVB-sensitivity of several other UV-sensitive and -resistant cultivars and found that the CPD photolyase activity was deficient in UV-sensitive ones. It was also evident that there was a variation in the deduced amino acid sequences of CPD photolyases of the UV-sensitive and -resistant cultivars, whereas each deduced amino acid sequence of the UV-sensitive cultivars and of the UV-resistant ones was the same. These results suggest that the difference in the CPD photolyases of UV-sensitive and -resistant rice might be due to the structural alteration of CPD photolyase.

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Long-term Clinical Course of a Korean Girl with β-ureidopropionase Deficiency (β-ureidopropionase 결핍증의 장기간의 임상경과 1례)

  • Song, Woo Sun;Park, Youngjin;Lee, Jun Hwa
    • Journal of The Korean Society of Inherited Metabolic disease
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    • v.17 no.1
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    • pp.18-23
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    • 2017
  • ${\beta}$-ureidopropionase deficiency (${\beta}$-UPD; OMIM # 613161) is a rare autosomal recessive inborn error of pyrimidine metabolism caused by mutations in the UPB1 gene and approximately 30 cases have been reported in the world. The clinical features of patients with ${\beta}$-UPD have been reported to vary from asymptomatic to severe developmental delays. However, the long-term clinical courses of patients with ${\beta}$-UPD have not yet been reported. A Korean girl was diagnosed with ${\beta}$-UPD at the age of 8 years and 10 months by targeted next-generation sequencing which was subsequently confirmed by Sanger sequencing. She had many clinical features such as poor oral feeding, failure to thrive, global developmental delay, microcephaly, frequent infection, and intractable epilepsy. She died suddenly of an unknown cause at the age of 11 years and 5 months. Here we report the long-term (i.e. lifelong) clinical aspects of a Korean patient with ${\beta}$-UPD.

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Physico-chemical Characteristics of the Inhibitory Substance on the Germination of Mung Bean (녹두 발아 조해물질(阻害物質)의 이화학적(理化學的) 성질(性質))

  • Kim, Kwang-Hyeon
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.14 no.1
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    • pp.57-60
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    • 1985
  • The inhibitory substance on the growth of mung bean seedling was amorphous crystal that had a single spot on silica gel thin layer chromatography under ultra-violet irradiation in dark room. The Rf value was 0.85 in n-butanol-acetic acid-formic acid-water(15 : 12 : 3 : 10) system, and 0.92 in n-butanol-acetic acid-water(4 : 1 : 5) system, respectively. Biochemical reaction of the inhibitor was negative to $FeCl_3$, pyrimidine, ninhydrine, folin, fehling, Salkowski and Ehrlich reaction, but the inhibitor had a blue fluorescence from irradiation of ultra-violet rays and had maximum absorption at 252nm on UV spectrum. On IR spectrum, the Peaks of the inhibitor appeared at $3300{\sim}3500,\;2900{\sim}3000,\;1600{\sim}1700,\;and\;1400cm^{(-1)}$. The strain tested was identified to be similar Streptomyces iuteogriseus by morphorogical and physiological characteristics.

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Inhibition of Acetolactate Synthase from Pea by Pyrimidine Derivatives (Pyrimidine 유도체에 의한 완두 Acetolactate Synthase의 저해에 관한 연구)

  • Joo, Young A;Kim, Dae Whang;Chang, Soo Ik;Choi, Jung Do
    • Journal of the Korean Chemical Society
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    • v.41 no.6
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    • pp.304-312
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    • 1997
  • Acetolactate synthase(ALS) is the common enzyme in the biosynthetic of valine, leucine, and isoleucine, and is the target of several classes of structually unrelated herbicides, including sulfonylureas, imidazolinones, and triazolopyrimidines. In an effort to develop new and desirable herbicides, we have synthesized 4,6-dimethoxypyrimidine derivatives, and examined their inhibitory activities on pea ALS. The most active compound was found to be K11570 and $IC_{50}$ value for K11570 was 0.2 ${\mu}M.$ The inhibition of pea ALS by K11570 was biphasic, showing increased inhibition with incubation time. The K11570 showed mixed-type inhibition with respect to substrate pyruvate. Dual inhibition analysis of K11570 versus sufonylurea herbicide Ally and feedback inhibitor leucine revealed that three inhibitors were competitive for binding to ALS. The arginine modified enzyme showed decreased inhibition by K11570, sufonylurea Ally, and leucine, in constrast to, tryptophan modification did not affect on the sensitivity of ALS to the inhibitors.

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Synthesis and Characterization of Palladium (IV) Complexes with Guanine, Adenine, and Uracil Base (Guanine, Adenine 및 Uracil 염기를 갖는 팔라듐 (IV) 착물의 합성과 그 성질)

  • Oh Sang Oh;Chung Duck Young;Kim Hee Seon
    • Journal of the Korean Chemical Society
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    • v.36 no.5
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    • pp.679-684
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    • 1992
  • New Pd(IV) complexes have been prepared through the reactions of $trans-[Pd(en)_2Cl_2](ClO_4)_2 $(en = ethylenediamine) with Guanine, Adenine, or Uracil anion as purine and pyrimidine base. We identified the ratio of central metal versus ligands by $C{\cdot}H{\cdot}N$ elemental analysis and proposed the coordinating site of the base by infrared spectrum, $^1H-NMR,\; and\; ^{13}C$-NMR spectrum. Guanine or Adenine ligand coordinated at N7 site and an en ligand exchanged for $ClO_4^-$ counter ions of the starting material . As these results, the complexes showed the formula $[Pd(en)L_2(ClO_4)_2](ClO_4)_2{\cdot}(en)$, (L = Guanine, Adenine). But in the Uracil complex no exchange of the en ligand and $ClO_4^-$ occured and Uracil anion preferred the N1 to N3 as coordinating site, the complex $[Pd(en)_2(Urac)_2](ClO_4)_2(Urac = Uracil anion).$

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