用1,3 - 二溴 - 5,5 - 二甲基乙内酰脲对嘧啶的C - 5和嘌呤核苷的C - 8进行溴化反应。
Bromination at C-5 of Pyrimidine and C-8 of Purine Nucleosides with 1,3-Dibromo-5,5-dimethylhydantoin.
作者信息
Rayala Ramanjaneyulu, Wnuk Stanislaw F
机构信息
Department of Chemistry & Biochemistry, Florida International University, Miami, FL 33199, USA.
出版信息
Tetrahedron Lett. 2012 Jun 27;53(26):3333-3336. doi: 10.1016/j.tetlet.2012.04.081. Epub 2012 Apr 24.
Abstract
Treatment of the protected and unprotected nucleosides with 1,3-dibromo-5,5- dimethylhydantoin in aprotic solvents such as CH(2)Cl(2), CH(3)CN, or DMF effected smooth bromination of uridine and cytidine derivatives at C-5 of pyrimidine rings as well as adenosine and guanosine derivatives at C-8 of purine rings. Addition of Lewis acids such as trimethylsilyl trifluoromethanesulfonate enhanced efficiency of bromination.
摘要
在二氯甲烷、乙腈或N,N -二甲基甲酰胺等非质子溶剂中，用1,3 -二溴- 5,5 -二甲基海因处理受保护和未受保护的核苷，可使嘧啶环C-5位的尿苷和胞苷衍生物以及嘌呤环C-8位的腺苷和鸟苷衍生物顺利发生溴化反应。添加三甲基甲硅烷基三氟甲磺酸酯等路易斯酸可提高溴化效率。
相似文献
1
Bromination at C-5 of Pyrimidine and C-8 of Purine Nucleosides with 1,3-Dibromo-5,5-dimethylhydantoin.用1,3 - 二溴 - 5,5 - 二甲基乙内酰脲对嘧啶的C - 5和嘌呤核苷的C - 8进行溴化反应。
Tetrahedron Lett. 2012 Jun 27;53(26):3333-3336. doi: 10.1016/j.tetlet.2012.04.081. Epub 2012 Apr 24.
2
An efficient and facile methodology for bromination of pyrimidine and purine nucleosides with sodium monobromoisocyanurate (SMBI).一种高效、简便的方法，用于用单溴代异氰尿酸钠（SMBI）溴化嘧啶和嘌呤核苷。
Molecules. 2013 Oct 15;18(10):12740-50. doi: 10.3390/molecules181012740.
3
Reactions of Trimethylsilyl Fluorosulfonyldifluoroacetate with Purine and Pyrimidine Nucleosides.三甲基甲硅烷基氟磺酰基二氟乙酸酯与嘌呤和嘧啶核苷的反应
J Fluor Chem. 2009 Mar 1;130(3):321-328. doi: 10.1016/j.jfluchem.2008.12.004.
4
Lewis acid catalyzed benzylic bromination.路易斯酸催化的苄基溴化反应。
Chem Asian J. 2008 Sep 1;3(8-9):1581-4. doi: 10.1002/asia.200800087.
5
Facile Access to Bromonucleosides Using Sodium Monobromoisocyanurate (SMBI).使用一溴异氰尿酸钠（SMBI）简便合成溴代核苷。
Curr Protoc Nucleic Acid Chem. 2017 Mar 2;68:1.39.1-1.39.9. doi: 10.1002/cpnc.24.
6
Trimethylsilyl trifluoromethanesulfonate-promoted reductive 2'-O-arylmethylation of ribonucleoside derivatives.三甲基甲硅烷基三氟甲磺酸酯促进的核糖核苷衍生物的还原性2'-O-芳基甲基化反应。
Nucleosides Nucleotides Nucleic Acids. 2011 Jun;30(6):446-56. doi: 10.1080/15257770.2011.592171.
7
8
A molecular orbital investigation of the dipole moments of the syn and anti conformers of purine and pyrimidine nucleosides.
Biochem Biophys Res Commun. 1972 Jan 14;46(1):125-9. doi: 10.1016/0006-291x(72)90639-0.
9
Halogenation of 6-O-cyclouracil nucleosides.6 - O - 环尿嘧啶核苷的卤化反应。
Nucleic Acids Symp Ser. 1980(8):s45-7.
10
Two nucleoside uptake systems in Lactococcus lactis: competition between purine nucleosides and cytidine allows for modulation of intracellular nucleotide pools.乳酸乳球菌中的两种核苷摄取系统：嘌呤核苷与胞苷之间的竞争可调节细胞内核苷酸池。
J Bacteriol. 2003 Mar;185(5):1503-8. doi: 10.1128/JB.185.5.1503-1508.2003.
引用本文的文献
1
Non-Canonical Helical Structure of Nucleic Acids Containing Base-Modified Nucleotides.含碱基修饰核苷酸的核酸的非经典螺旋结构。
Int J Mol Sci. 2021 Sep 2;22(17):9552. doi: 10.3390/ijms22179552.
2
Electrochemical Umpolung of Bromide: Transition-Metal-Free Bromination of Indole C⁻H Bond.电化学反转溴代反应：吲哚 C-H 键的无过渡金属溴化反应。
Molecules. 2019 Feb 15;24(4):696. doi: 10.3390/molecules24040696.
3
N-Heterocyclic Carbenes Derived from Guanosine: Synthesis and Evidences of Their Antiproliferative Activity.源自鸟苷的氮杂环卡宾：其抗增殖活性的合成与证据
ACS Omega. 2018 Nov 30;3(11):15653-15656. doi: 10.1021/acsomega.8b02387. Epub 2018 Nov 16.
4
Synthesis of 8-(1,2,3-triazol-1-yl)-7-deazapurine nucleosides by azide-alkyne click reactions and direct C-H bond functionalization.通过叠氮化物-炔烃点击反应和直接C-H键官能化合成8-(1,2,3-三唑-1-基)-7-脱氮嘌呤核苷。
Tetrahedron Lett. 2016 Sep 28;57(39):4364-4367. doi: 10.1016/j.tetlet.2016.08.053. Epub 2016 Aug 19.
5
Studies toward the oxidative and reductive activation of C-S bonds in 2'--aryl-2'-thiouridine derivatives.关于2'-芳基-2'-硫代尿苷衍生物中碳-硫键氧化和还原活化的研究。
Tetrahedron. 2016 Apr 21;72(16):1969-1977. doi: 10.1016/j.tet.2016.02.063.
6
Strain Promoted Click Chemistry of 2- or 8-Azidopurine and 5-Azidopyrimidine Nucleosides and 8-Azidoadenosine Triphosphate with Cyclooctynes. Application to Living Cell Fluorescent Imaging.2-或8-叠氮嘌呤、5-叠氮嘧啶核苷以及8-叠氮三磷酸腺苷与环辛炔的应变促进点击化学。在活细胞荧光成像中的应用。
Bioconjug Chem. 2015 Aug 19;26(8):1519-32. doi: 10.1021/acs.bioconjchem.5b00300. Epub 2015 Jul 2.
7
Salvadenosine, a 5'-deoxy-5'-(methylthio) nucleoside from the Bahamian tunicate Didemnum sp.萨尔瓦地腺苷，一种来自巴哈马被囊动物Didemnum sp.的5'-脱氧-5'-(甲硫基)核苷。
J Org Chem. 2014 Nov 7;79(21):9992-7. doi: 10.1021/jo501486p. Epub 2014 Oct 20.
8
Palladium-catalyzed direct arylation of 5-halouracils and 5-halouracil nucleosides with arenes and heteroarenes promoted by TBAF.钯催化的 5-卤尿嘧啶和 5-卤尿嘧啶核苷与芳烃和杂芳烃的直接芳基化反应，由 TBAF 促进。
J Org Chem. 2014 May 2;79(9):4094-103. doi: 10.1021/jo500602p. Epub 2014 Apr 23.
本文引用的文献
1
Lewis acid catalyzed benzylic bromination.路易斯酸催化的苄基溴化反应。
Chem Asian J. 2008 Sep 1;3(8-9):1581-4. doi: 10.1002/asia.200800087.
2
PURINE NUCLEOSIDES. IX. THE SYNTHESIS OF 9-BETA-D-RIBOFURANOSYL URIC ACID AND OTHER RELATED 8-SUBSTITUTED PURINE RIBONUCLEOSIDES.嘌呤核苷。IX. 9-β-D-呋喃核糖基尿酸及其他相关8-取代嘌呤核糖核苷的合成。
J Am Chem Soc. 1965 Apr 20;87:1772-6. doi: 10.1021/ja01086a028.
3
Palladium-assisted routes to nucleosides.钯辅助的核苷合成路线。
Chem Rev. 2003 May;103(5):1875-916. doi: 10.1021/cr010374q.
4
A novel nitration product formed during the reaction of peroxynitrite with 2',3',5'-tri-O-acetyl-7,8-dihydro-8-oxoguanosine: N-nitro-N'-[1-(2,3,5-tri-O-acetyl-beta-D-erythro-pentofuranosyl)- 2, 4-dioxoimidazolidin-5-ylidene]guanidine.一种过氧亚硝酸根与2',3',5'-三-O-乙酰基-7,8-二氢-8-氧代鸟苷反应过程中形成的新型硝化产物：N-硝基-N'-[1-(2,3,5-三-O-乙酰基-β-D-赤藓糖基)-2,4-二氧代咪唑烷-5-亚基]胍。
Chem Res Toxicol. 2000 May;13(5):390-6. doi: 10.1021/tx0000318.
5
Potent and selective inhibition of varicella-zoster virus (VZV) by nucleoside analogues with an unusual bicyclic base.具有独特双环碱基的核苷类似物对水痘带状疱疹病毒（VZV）的强效选择性抑制作用
J Med Chem. 1999 Nov 4;42(22):4479-84. doi: 10.1021/jm990346o.
6
Nucleic acid related compounds. 40. Synthesis and biological activities of 5-alkynyluracil nucleosides.核酸相关化合物。40. 5-炔基尿嘧啶核苷的合成及生物活性
J Med Chem. 1983 May;26(5):661-6. doi: 10.1021/jm00359a008.
7
Bromination of nucleosides.核苷的溴化反应。
Experientia. 1970;26(2):220. doi: 10.1007/BF01895597.
8
Purine and 8-substituted purine arabinofuranosyl and ribofuranosyl nucleoside derivatives as potential inducers of the differentiation of the Friend erythroleukemia.嘌呤及8-取代嘌呤阿拉伯呋喃糖基和核糖呋喃糖基核苷衍生物作为Friend红白血病分化的潜在诱导剂。
J Med Chem. 1985 Oct;28(10):1481-5. doi: 10.1021/jm00148a018.
9
8-Substituted guanosine and 2'-deoxyguanosine derivatives as potential inducers of the differentiation of Friend erythroleukemia cells.8-取代鸟苷和2'-脱氧鸟苷衍生物作为Friend红白血病细胞分化的潜在诱导剂。
J Med Chem. 1985 Sep;28(9):1194-8. doi: 10.1021/jm00147a012.
10
Synthesis and tumor uptake of 5-82Br- and 5-131I-labeled 5-halo-1-(2-fluoro-2-deoxy-beta-D-ribofuranosyl)uracils.5-82Br-和5-131I标记的5-卤代-1-(2-氟-2-脱氧-β-D-呋喃核糖基)尿嘧啶的合成及其在肿瘤中的摄取
J Med Chem. 1989 Jun;32(6):1289-94. doi: 10.1021/jm00126a024.
Zotero 插件