CAS: 1122-44-7; 4-Amino-5-Iodopyrimidin-2(1H)-One

该化合物是一种杂交有机化合物,其特点是具有包括一个氨基氨基和碘替代体在内的青米丁环状结构,其中含有一个氨基氨基氨基组和碘原子,其存在有助于其在药用化学中的再活性和潜在应用.该化合物一般在室温下是固体,由于氨基甘油组的存在,极地溶剂的处理和处置可能具有中等溶解性,因为该组可以从事氢结合.其分子结构表明潜在的生物活动,使其对药物开发感兴趣,特别是在抗病毒或抗癌剂领域.碘原子还可增强该化合物的脂性,影响其药性能特性.与许多卤化化合物一样,由于潜在的环境和健康影响,应注意其处理和处置.

结构式图片

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71-30-7 2022-85-7 2240-25-7

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CAS号71-30-7 胞嘧啶 | CAS号83966-92-1 5-iodo-N,N-bis(...

合成工艺路线路线简述

    胞嘧啶置于碘,Potassium Hydroxide体系中,用 水 用作溶剂,化学反应生成5-碘胞核嘧啶
    参考文献:未溶剂化和 Dmso 溶剂化形式的含卤素核碱基衍生物的 X 射线晶体结构
    标题:未溶剂化和 Dmso 溶剂化形式的含卤素核碱基衍生物的 X 射线晶体结构
    摘要:据报道,一系列卤化核碱基衍生物 1-4 在从 Dmso 结晶时产生无溶剂 (2) 和 Dmso 溶剂化晶体 (1,3,4),其中一个 (4) 含有额外的水分子.参考有关化合物的先前结果描述和比较讨论了分子和晶体结构.1的分子是平面的,2和3的分子关于杂环和核糖残基的共同c2'-内构象显示syn对齐,而4也是syn对齐但糖构象中的c4'-Exo.堆积结构揭示了通过氢键网络产生的典型聚集.这些涉及核碱基和核糖单元以及溶剂分子之间的常规 N-h...n,N-h...o 和 O-h...o 相互作用,
    Doi:10.1007/s11224-009-9570-5

    专利信息


    专利号:US-9884885-B2
    优先权日:2009-05-18
    标题:Synthesis of labile base protected-modified deoxy and modified ribo nucleosides, corresponding phosphoramidites and supports and their use in high purity oligonucleotide synthesis
    发明人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P
    权利人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P; CHEMGENES CORP
    摘要:This invention relates to novel method of synthesis of RNA utilizing N-2-acetyl protected guanine as nucleoside base, nucleosides, succinates, phosphoramidites, corresponding solid supports that are suitable for oligo deoxy nucleosides and RNA oligonucleotide synthesis. Our discovery using N-acetyl protected guanine as nucleoside base protecting group, which is significantly faster base labile protecting group, yet significantly more stable than commonly utilized-2-isobutyryl guanosine is a novel approach to obtain highest purity oligonucleotides. This approach is designed to lead to very high purity and very clean oligonucleotide, after efficient removal of the protecting groups, including acetyl group from guanine and to produce high purity therapeutic grade DNA oligonucleotides, RNA oligonucleotides, diagnostic DNA, diagnostic RNA for microarray platform. The deprotection of acetyl protecting groups of the natural deoxy and ribonucleosides occurs under substantially reduced time in contact with mild deprotection conditions such as mild bases, secondary amines for removal of such groups under such conditions would allows synthesis of various DNA and RNA of highest purity for diagnostics and therapeutic application. This approach is designed to lead to high purity large scale therapeutic grade oligonucleotide chimeras which consist of fluoro sugar modification in conjunction with deoxy nucleosides, ribonucleosides, modified base and modified sugar nucleosides. This approach is further designed to use acetyl guanine protecting group when other bases are sensitive nucleoside, and for use in oligo peptide synthesis and for support bound oligo nucleotides.

    专利号:US-8981076-B2
    优先权日:2008-11-29
    标 题 :Synthesis of N-FMOC protected deoxy nucleosides, ribo nucleosides, modified deoxy and ribo nucleosides, and phosphoramidites, and their use in oligonucleotide synthesis
    发明人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P
    权利人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P; CHEMGENES CORP
    摘要:This invention relates to synthesis of novel -N-FMOC protected nucleosides, succinates, phosphoramidites, corresponding solid supports that are suitable for oligo deoxy nucleosides and RNA oligonucleotide synthesis. Our discovery using N-FMOC as nucleoside base protecting group, which is highly base labile protecting group is a novel approach to obtain highest purity oligonucleotides. This approach is designed to lead to very high purity and very clean oligonucleotide, after efficient removal of the protecting groups and to produce high purity therapeutic grade DNA oligonucleotides, RNA oligonucleotides, diagnostic DNA, diagnostic RNA for microarray platform. The deprotection of FMOC protecting groups of the natural deoxy and ribonucleosides occurs under very mild deprotection conditions such as mild bases, secondary and tertiary amines for removal of such groups under such conditions would allows synthesis of various DNA and RNA of highest purity for diagnostics and therapeutic application. This approach is further designed to use FMOC protecting group on various base sensitive nucleoside, and for use in oligo peptide synthesis and for support bound oligo nucleotides. DNA oligonucleotides containing 3′-end dA at the 3′-terminal will be produced using the FMOC-dA-supports would lead to much reduced M−1 deletion sequences, and thereby high purity.

    专利号:US-10253153-B2
    优先权日:2015-04-24
    标题 :Linker and support for solid phase synthesis of nucleic acid, and production method of nucleic acid using said support
    发明人:MAETA ERI; MORI KENJIRO; HORIE SHOHEI; ITO TAKAHIKO; SAITO SHOICHIRO; NAGAO RYUHEI
    权利人:NITTO DENKO CORP
    摘要:The present invention provides a linker for solid phase synthesis of nucleic acid, which consists of a compound represented by the formula (I) or the formula (II), a support for solid phase synthesis of nucleic acid, which has a structure represented by the formula (III), and a production method of a nucleic acid, which uses the support: n nwherein each symbol is as defined in the SPECIFICATION.

    专利号:WO-2023039068-A1
    优先权日:2021-09-08
    标题:Compositions and methods for synthesis of peptide nucleic acid intermediates
    发明人:COULL JAMES M; GILDEA BRIAN D
    权利人:NEUBASE THERAPEUTICS INC
    摘要:The present disclosure provides intermediates for the synthesis of peptide nucleic acid (PNA) backbones and monomers, such as cyclic intermediates, and methods of making the same.

    专利号:WO-2024185775-A1
    优先权日:2023-03-06
    标 题:Long-chain alkenyloxy–substituted benzoyl derivative and oligonucleotide synthesis method using same
    发明人:OKADA YOHEI; INANAGA KAZATO; SHOJI Yukiya; MIZUFUNE HIDEYA; SUDO TATSUYA; ADACHI Sota; HOSOI Kazushi
    权利人:SPERA PHARMA INC; TOKYO UNIV OF AGRICULTURE AND TECHNOLOGY
    摘要:The purpose of the present invention is to provide a novel pseudo–solid phase protecting group that can be used in liquid-phase oligonucleotide synthesis. The purpose of the present invention is also to provide an oligonucleotide synthesis method that uses a novel pseudo–solid phase protecting group. The present invention provides a compound represented by formula (1) (in which R represents a C14–60 alkenyl group, n represents 2 or 3, m represents 0 or 1, p represents 1 or 2, X represents C, N, O, or S, Y represents a single bond or B(CH 2 ) t * or may form a ring with X, and Z represents a single bond or (CH 2 ) s (s being an integer from 1 to 5)). The present invention also provides an oligonucleotide production method that uses the compound.

    专利号:WO-2024163733-A1
    优先权日:2023-02-01
    标题:Electrochemical synthesis with redox stable nucleotides
    发明人:WU TIANDI; LACKEY JEREMY; LIN YANYOU; PITSCH STEFAN
    权利人:TWIST BIOSCIENCE CORP
    摘要:Provided herein are compositions, devices, systems and methods for constructing and storing polynucleotides encoding information with redox resistant bases. The compositions, devices, systems, and methods described herein provide for storage or synthesis of a library comprising a plurality of polynucleotides with one or more redox resistance bases. Further provided herein are methods to increase DNA synthesis yield and fidelity.
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    主要参考文献

    [参考文献]: E Ferrer, Et Al. Preparation And Properties Of Oligodeoxynucleotides Containing 5-Iodouracil And 5-Bromo- And 5-Iodocytosine. Bioconjug Chem. 1997 Sep-Oct;8(5):757-61.
    [参考文献]: Jesse J Chen, Et Al. Enzymatic Primer-Extension With Glycerol-Nucleoside Triphosphates On Dna Templates. Plos One. 2009;4(3):E4949.
    [参考文献]: Mari Nonaka, Et Al. Mouse Rs21-C6 Is A Mammalian 2'-Deoxycytidine 5'-Triphosphate Pyrophosphohydrolase That Prefers 5-Iodocytosine. Febs J. 2009 Mar;276(6):1654-66.
    [参考文献]: R H E Hudson, Et Al. A Direct Synthesis Of Pyrrolocytosine From 5-Iodocytosine. Nucleosides Nucleotides Nucleic Acids. 2005;24(5-7):581-4.
    [参考文献]: R H E Hudson, Et Al. Nucleobase Modified Peptide Nucleic Acid. Nucleosides Nucleotides Nucleic Acids. 2003 May-Aug;22(5-8):1029-33.

    合成参考文献


    参考文献:10.1021/bi015687u
    摘要:Pieper U, Groll DH, Wünsch S, Gast FU, Speck C, Mücke N, Pingoud A. The GTP-dependent restriction enzyme McrBC from Escherichia coli forms high-molecular mass complexes with DNA and produces a cleavage pattern with a characteristic 10-base pair repeat. Biochemistry. 2002 Apr 23;41(16):5245–54. doi: 10.1021/bi015687u.
    参考文献:10.1111/j.1751-1097.1992.tb09595.x
    摘要:Rahn RO. Photochemistry of halogen pyrimidines: iodine release studies. Photochem Photobiol. 1992 Jul;56(1):9–15. doi: 10.1111/j.1751-1097.1992.tb09595.x.
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