CAS: 123402-21-1; 2-Amino-9-((2R,3S,4S,5R)-4-Fluoro-3-Hydroxy-5-(Hydroxymethyl)Tetrahydrofuran-2-yl)-1H-Purin-6(9H)-One

该化合物是一种氟化核素类比,其特点是在环的3'位置上替换氟原子,这种改变通过抵抗酶降解,使其对生化化学和药理研究具有价值,增强了代谢稳定性.复合物具有潜在的抗病毒和抗癌特性,因为它能够干扰核酸合成.它与天然核素相近,因此它能够作为病毒聚合酶和其他核酸处理酶的基质或抑制剂.氟替代剂进一步提高其亲脂性,促进细胞吸收.研究人员利用这种类似物研究核素代谢并开发新型治疗剂.

结构式图片

上下游产品

2-N-Acetyl-6-O-((4-Nitrophenyl)Ethyl)Guanosine
2-N-Acetyl-6-O-((4-Nitrophenyl)Ethyl)-9-(2,5-Di-O-Trityl-3.Deoxy-3 Fluoro-β-D-Ribofuranosyl)Guanine 144588-25-0
N-[9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(Trityloxymethyl)Oxolan-2-Yl]-6-[2-(4-Nitrophenyl)Ethoxy]Purin-2-Yl]Acetamide 144588-12-5

合成工艺路线路线简述

  • 合成目标产物 3Fluoro-3Deoxyguanosine 主要起始原料 α-D-Ribofuranoside, Methyl 3-Deoxy-3-Fluoro-5-O-(Phenylmethyl)-, 2-Benzoate
  • (文献来源)合成步骤主要原料 α-D-Ribofuranoside, Methyl 3-Deoxy-3-Fluoro-5-O-(Phenylmethyl)-, 2-Benzoate
Methyl 2,3-Anhydro-5-O-Benzyl-α-D-Lyxofuranoside置于palladium On Activated Charcoal 吡啶,二苯并-18-冠醚-6,Potassium Hydrogen Bifluoride,硫酸,氨,氢气,Tmsotf,Sodium Fluoride,溶剂黄146体系中,用 甲醇,乙醇,乙二醇,二甲基亚砜,1,2-二氯乙烷 用作溶剂,化学反应 192.5H,反应生成3-氟-3-脱氧鸟苷
参考文献:天然杂环碱基的3'-脱氧-3'-氟-和2'-叠氮基3'-氟-2',3'-二脱氧-D-呋喃呋喃糖苷的合成及其抗病毒和细胞抑制特性.
标题:天然杂环碱基的3'-脱氧-3'-氟-和2'-叠氮基3'-氟-2',3'-二脱氧-D-呋喃呋喃糖苷的合成及其抗病毒和细胞抑制特性.
摘要:已使用通用碳水化合物前体合成了一系列天然杂环碱的3'-脱氧3'-氟和2'-叠氮基2',3'-二脱氧3'-氟-D-呋喃核糖苷,即1-O-乙酰基-2,5-二-O-苯甲酰基-3-脱氧-3-氟-D-呋喃核糖和甲基2-叠氮基-5-O-苯甲酰基-2,3-二脱氧-3-氟-β-D-核呋喃糖苷.分别针对多种肿瘤细胞系和dna / Rna病毒评估了该化合物的细胞抑制活性和抗病毒活性.从细胞抑制活性和抗病毒活性的观点来看,作为最活性的化合物出现了3'-脱氧-3'-氟腺苷.它以0.2-2微克/ Ml的浓度抑制某些肿瘤细胞系(例如鼠白血病l1210和人t淋巴细胞mt-4)的增殖,
Doi:10.1021/jm00111A040

海关参考信息

专利信息


专利号:WO-2025037891-A1
优先权日:2023-08-14
标题:Oligonucleotide for 5'-capped rna synthesis
发明人:KIM KYUNGJIN; KIM UK-IL; KIM DAYOUNG; CHOI KANG HYUN; KIM JI SU
权利人:ST PHARM CO LTD
摘要:The present invention relates to a novel oligonucleotide primer used for the synthesis of 5'-capped RNA. The novel oligonucleotide primer for RNA capping, represented by chemical formula 1 in the present invention, can be usefully utilized in the fields of nucleic acid therapeutic agents or vaccines.

专利号:US-11685761-B2
优先权日:2017-12-20
标 题:Cyclic di-nucleotide compounds as sting agonists
发明人:ANDRESEN BRIAN M; BENNETT FRANK; CHANG WONSUK; CHILDERS MATTHEW LLOYD; CUMMING JARED N; LIM JONGWON; LU MIN; TROTTER BENJAMIN WESLEY; WU WEN-LIAN
权利人:MERCK SHARP & DOHME; ANDRESEN BRIAN M; BENNETT FRANK; CHANG WONSUK; CHILDERS MATTHEW LLOYD; CUMMING JARED N; LIM JONGWON; LU MIN; TROTTER BENJAMIN WESLEY; WU WEN LIAN; MERCK SHARP & DOHME LLC
摘要:A class of polycyclic compounds of general formula (I), wherein Base1, Base2, Y, Za, Xa, Xa1, Xb, Xb1, Xc, Xc1, Xd, Xd1, R1, R1a, R2, R2a, R3, R4, R4a, R5, R6, R6a, R7, R7a, R8, R8a, and R9 are defined herein, that may be useful as inductors of type I interferon production, specifically as STING active agents, are provided. Also provided are processes for the synthesis and use of compounds.

专利号:US-10766919-B2
优先权日:2015-08-13
标 题 :Cyclic di-nucleotide compounds as sting agonists
发明人:ALTMAN MICHAEL D; ANDRESEN BRIAN; CHANG WONSUK; CHILDERS MATTHEW LLOYD; CUMMING JARED N; HAIDLE ANDREW MARC; HENDERSON TIMOTHY J; JEWELL JAMES P; LIANG RUI; LIM JONGWON; LIU HONG; LU MIN; NORTHRUP ALAN B; OTTE RYAN D; SIU TONY; TROTTER BENJAMIN WESLEY; TRUONG QUANG T; WALSH SHAWN P; ZHAO KAKE
权利人:MERCK SHARP & DOHME
摘要:A class of polycyclic compounds of general formula (I), of general formula (I′), or of general formula (I″), wherein Base 1 , Base 2 , Y, Y a , X a , X a1 , X b , X b1 , X c , X c1 , X d , X d1 , R 1 , R 1a , R 2 , R 2a , R 3 , R 4 , R 4a , R 5 , R 6 , R 6a , R 7 , R 7a , R 8 , and R 8a are defined herein, that may be useful as inductors of type I interferon production, specifically as STING active agents, are provided. Also provided are processes for the synthesis and use of compounds.

专利号:US-11453697-B1
优先权日:2015-08-13
标题 :Cyclic di-nucleotide compounds as sting agonists
发明人:ALTMAN MICHAEL D; ANDRESEN BRIAN; CHANG WONSUK; CUMMING JARED N; OTTE RYAN D; TROTTER BENJAMIN WESLEY
权利人:MERCK SHARP & DOHME; MERCK SHARP & DOHME LLC
摘要:A class of polycyclic compounds of general formula (I), of general formula (I′), or of general formula (I″), wherein Base 1 , Base 2 , Y, Y a , X a , X a1 , X b , X b1 , X c , X c1 , X d , X d1 , R 1 , R 1a , R 2 , R 2a , R 3 , R 4 , R 4a , R 5 , R 6 , R 6a , R 7 , R 7a , R 8 , and R 8a are defined herein, that may be useful as inductors of type I interferon production, specifically as STING active agents, are provided. Also provided are processes for the synthesis and use of compounds.

专利号:US-11466047-B2
优先权日:2017-05-12
标 题 :Cyclic di-nucleotide compounds as sting agonists
发明人:WU WEN-LIAN; LIM JONGWON; CUMMING JARED N; TROTTER BENJAMIN WESLEY; CHANG WONSUK
权利人:MERCK SHARP & DOHME; WU WEN LIAN; LIM JONGWON; CUMMING JARED N; TROTTER BENJAMIN WESLEY; CHANG WONSUK; MERCK SHARP & DOHME LLC
摘要:A class of polycyclic compounds of general formula (I), wherein Base1, Base2, Y, Ya, Xa, Xa1, Xb, Xb1, Xc, Xc1, Xd, Xd1, R1, R1a, R2, R2a, R3, R4, R4a, R5, R6, R6a, R7, R7a, R8, R8a, and R9 are defined herein, that may be useful as inductors of type I interferon production, specifically as STING active agents, are provided. Also provided are processes for the synthesis and use of compounds.
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合成参考文献


参考文献:10.1021/jm030424e
摘要:Eldrup AB, Allerson CR, Bennett CF, Bera S, Bhat B, Bhat N, Bosserman MR, Brooks J, Burlein C, Carroll SS, Cook PD, Getty KL, MacCoss M, McMasters DR, Olsen DB, Prakash TP, Prhavc M, Song Q, Tomassini JE, Xia J. Structure-activity relationship of purine ribonucleosides for inhibition of hepatitis C virus RNA-dependent RNA polymerase. J Med Chem. 2004 Apr 22;47(9):2283–95. doi: 10.1021/jm030424e.
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