CAS: 892-48-8; 5'-Chloro-5'-Deoxyadenosine

该化合物是一种核糖类比,其特点是在5岁脱氧核糖的位置上存在氯原子,取代典型的代代氨氨酸中发现的氢氧基组,这种改变具有独特的生化特性,使其在各个领域,包括医药化学和分子生物学中都引起兴趣,该化合物以其潜在的抗病毒和抗癌活动而著称,因为它可能干扰核酸合成和细胞过程,其结构包括一个与脱氧制冷糖相连的纯基(九分之九),该净基因氯替代品而进一步改变.氯原子的存在可影响化合物的溶性,稳定性和与生物目标的互动.5欧元-克罗罗诺-5欧元-脱氧基新陈代谢和治疗应用中核糖类似作用机制经常用于研究.与许多核糖模拟一样,仔细考虑其药理学和毒性对于临床环境的潜在用途至关重要.

英文名称5'-Chloro-5'-Deoxyadenosine
中文名称5'-氯-5'-脱氧腺苷
IUPAC名称(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-(chloromethyl)tetrahydrofuran-3,4-diol
其它别名(2R,3R,4S,5S)-2-(6-氨基-9H-嘌呤-9-基)-5-(氯甲基)四氢呋喃-3,4-二醇; Adenosine, 5'-Chloro-5'-Deoxy-
CAS编号892-48-8
MFCD编号:MFCD00049038
分子式:C10H12ClN5O3
分子量:285.69
产品CID: 1913708
产品分类有机原料→生命科学→核苷&核苷酸→其他保护性核苷

相似结构搜索
InChIKey: IYSNPOMTKFZDHZ-KQYNXXCUSA-N
InChI=1S/C10H12ClN5O3/c11-1-4-6(17)7(18)10(19-4)16-3-15-5-8(12)13-2-14-9(5)16/h2-4,6-7,10,17-18H,1H2,(H2,12,13,14)/t4-,6-,7-,10-/m1/s1…
计算化学: 氢键受体数8.0氢键供体数3.0可旋转键数2.0

相似化合物

58-61-7 5536-17-4 3080-29-3

物理性质

熔点187 °C
沸点645.6±65.0 °C at 760 mmHg
闪点344.2 °C
密度2.03±0.1 g/cm3(预测)
pKa:13.03±0.70(预测)
PSA:119.31
LogP:-0.7335
折射率1.87
蒸汽压1.5E-17 mmHg at 25 °C
溶解性DMSO (Slightly), Water (Slightly, Heated)
外观形态类白色至浅米色固体
储存条件置于阴暗处,密封干燥,2-8°C
产品应用该化合物是5'DEXY-5'(甲基硫磷)乙酰胺合成的中间体,是研究5'M-甲基乙酰乙烯磷酸盐(MTAP, EC 2.4.2.28)的特性和动能的基底,该物质是肿瘤抑制或基因表达的酶,支持S-DENOSYLMETHIONINE(ADOMET)和甲基苯磷酸甲胺的挽救途径.

MSDS等安全信息

GHS符号GHS07
警示词Warning
危险描述H302-H315-H319-H335
防范说明P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
WGK Germany3

上下游产品

5'-chloro-5'-deoxy-2',3'-O-sulfinyladenosine 5'-chloro-5'-deoxy-2',3'-O-sulphinyladenosine hydr°Chloride 9-((3aR,4R,6S,6aS)-6-(chloromethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-amine adenosine 5'-S-phenyl-5'-thioadenosine 5'-S-(4-Chlorophenyl)-5'-thioadenosine 5'-S-(4-methoxyphenyl)-5'-thioadenosine 5'-Deoxy-5'-methylthioadenosine

合成工艺路线路线简述

662131-88-6 = 892-48-8
反应条件:1.1 Reagents: Ammonium Hydroxide Solvents: Methanol; 1 H,Rt
标题:Potent Sars-Cov-2 Mrna Cap Methyltransferase Inhibitors By Bioisosteric Replacement Of Methionine In Sam Cosubstrate
作者:Bobileva,Olga; Bobrovs,Raitis; Kanepe,Iveta; Patetko,Liene; Kalnins,Gints; Et Al
参考文献:Acs Medicinal Chemistry Letters 日期:2021 卷标:12(7) 页码:1102-1107]

58-61-7 = 892-48-8
反应条件:1.1 Reagents: Pyridine,Thionyl Chloride Solvents: Acetonitrile; 0 °C; 3 H,0 °C; 0 °C -> Rt; 16 H,Rt1.2 Reagents: Ammonium Hydroxide Solvents: Methanol,Water; 30 Min,Rt
标题:S-Adenosyl Methionine Cofactor Modifications Enhance The Biocatalytic Repertoire Of Small Molecule C-Alkylation
作者:Mckean,Iain J. W.; Sadler,Joanna C.; Cuetos,Anibal; Frese,Amina; Humphreys,Luke D.; Et Al
参考文献:Angewandte Chemie 日期:2019 卷标:58(49) 页码:17583-17588]

58-61-7 = 892-48-8
反应条件:1.1 Reagents: Pyridine,Thionyl Chloride Solvents: Acetonitrile; 4 H,0 °C; Overnight,Rt1.2 Reagents: Ammonia Solvents: Water; Rt
标题:Convenient Preparation Of Pinometostat And Related 5'-Deoxy-5'-Amino Adenosine Derivatives As Well As Their Activity Against Dot1L
作者:Liu,Tongchao; Ren,Huanming; Li,Cong; Chen,Guohua; Cheng,Maosheng; Et Al
参考文献:Tetrahedron Letters 日期:2018 卷标:59(4) 页码:415-417]

58-61-7 = 892-48-8
反应条件:1.1 Reagents: Pyridine,Thionyl Chloride Solvents: Acetonitrile; 5 Min,0 °C; 3 H,0 °C; 0 °C -> 22 °C; 16 H,22 °C1.2 Reagents: Ammonia Solvents: Water; 30 Min,22 °C
标题:Structural And Functional Basis Of C-Methylation Of Coumarin Scaffolds By Novo
作者:Sadler,Joanna C.; Chung,Chun-Wa H.; Mosley,Julie E.; Burley,Glenn A.; Humphreys,Luke D.
参考文献:Acs Chemical Biology 日期:2017 卷标:12(2) 页码:374-379]

58-61-7 = 892-48-8
反应条件:1.1 Reagents: Pyridine,Thionyl Chloride Solvents: Acetonitrile; 5 Min,0 °C; 3 H,0 °C; 0 °C -> 22 °C; 16 H,22 °C1.2 Reagents: Ammonia Solvents: Water; 30 Min,22 °C
标题:A Tandem Enzymatic Sp2-C-Methylation Process: Coupling In Situ S-Adenosyl-L-Methionine Formation With Methyl Transfer
作者:Sadler,Joanna C.; Humphreys,Luke D.; Snajdrova,Radka; Burley,Glenn A.
参考文献:Chembiochem 日期:2017 卷标:18(11) 页码:992-995]

58-61-7 = 892-48-8
反应条件:1.1 Reagents: Pyridine,Thionyl Chloride Solvents: Acetonitrile; 0 °C; 4 H,0 °C; Overnight,Rt1.2 Reagents: Ammonia Solvents: Methanol,Water; 30 Min,Rt
标题:Modification Of The Length And Structure Of The Linker Of N6-Benzyladenosine Modulates Its Selective Antiviral Activity Against Enterovirus 71
作者:Drenichev,Mikhail S.; Oslovsky,Vladimir E.; Sun,Liang; Tijsma,Aloys; Kurochkin,Nikolay N.; Et Al
参考文献:European Journal Of Medicinal Chemistry 日期:2016 卷标:111 页码:84-94]

58-61-7 = 892-48-8
反应条件:1.1 Reagents: Pyridine,Thionyl Chloride Solvents: Acetonitrile; 0 °C; 4 H,5 °C; Overnight,5 °C -> Rt1.2 Reagents: Ammonia Solvents: Methanol,Water; 30 Min,Rt
标题:Directed Evolution Of A Fluorinase For Improved Fluorination Efficiency With A Non-Native Substrate
作者:Sun,Huihua; Yeo,Wan Lin; Lim,Yee Hwee; Chew,Xinying; Smith,Derek John; Et Al
参考文献:Angewandte Chemie 日期:2016 卷标:55(46) 页码:14277-14280]

58-61-7 = 892-48-8
反应条件:1.1 Reagents: Thionyl Chloride Solvents: Acetonitrile,Pyridine; 0 °C; 4 H,5 °C; Overnight,5 °C -> Rt1.2 Reagents: Ammonium Hydroxide Solvents: Methanol,Water; 30 Min,Rt
标题:Discovery Of A Dual Prmt5-Prmt7 Inhibitor
作者:Smil,David; Eram,Mohammad S.; Li,Fengling; Kennedy,Steven; Szewczyk,Magdalena M.; Et Al
参考文献:Acs Medicinal Chemistry Letters 日期:2015 卷标:6(4) 页码:408-412]

58-61-7 = 892-48-8
反应条件:1.1 Reagents: Pyridine,Thionyl Chloride Solvents: Acetonitrile; 0 - 5 °C; 3 H,0 °C; Overnight,0 °C; 0 °C -> Rt1.2 Reagents: Sodium Bicarbonate Solvents: Water; Ph 5 - 6,Rt1.3 Reagents: Ammonium Hydroxide Solvents: Methanol,Water; 1 H,Rt
标题:Synthesis And Characterization Of Se-Adenosyl-L-Selenohomocysteine Selenoxide
作者:Duclos,Richard I. Jr.; Cleary,Dillon C.; Catcott,Kalli C.; Zhou,Zhaohui Sunny
参考文献:Journal Of Sulfur Chemistry 日期:2015 卷标:36(2) 页码:135-144

腺苷置于吡啶,氯化亚砜,Ammonium Hydroxide体系中,用乙腈,甲醇,水作为反应溶剂,化学反应 0.5H,以60%的收率获得产物5'-氯-5'-脱氧腺苷
参考文献:N 6-苄基腺苷连接子的长度和结构的改变调节其针对肠道病毒的选择性抗病毒活性71
标题:N 6-苄基腺苷连接子的长度和结构的改变调节其针对肠道病毒的选择性抗病毒活性71
摘要:最近,我们证明了n 6-异戊烯基腺苷,一种细胞分裂素核苷,对人肠病毒71的复制具有有效的选择性抗病毒作用.本研究致力于另一种天然化合物n 6-苄基腺苷的结构优化.我们主要研究腺嘌呤和苯环之间连接基的大小和性质,以及d-核糖残基的必要性.制备了30多种n 6-苄基腺苷类似物,并评估了它们的抗病毒特性.两种主要的制备方法:N 6-乙酰基-2',3',5'-Tri-O-乙酰基腺苷可以在碱促进条件下通过烷基卤或在mitsunobu反应中通过醇进行区域选择性烷基化.在室温下用4 M Prnh 2在meoh中的溶液脱酰1天后,以高总收率获得所需产物.对结构-活性关系的分析清楚地表明,连接子的最佳尺寸限于2或3个原子(化合物4-7).2'-脱氧腺苷衍生物没有引起任何抑制或细胞毒性作用,而5'-脱氧核苷仍然诱导了某些细胞保护性抗病毒活性.基于这些观察,可以假设除了可能的5'-三磷酸化继之以对rna合
DOI:10.1016/j.Ejmech.2016.01.036

海关参考信息

2905122000-异丙醇
2905310000-1,2-乙二醇
2905320000-1,2-丙二醇
2905399001-1,3-丙二醇
💡 提示：海关信息按照顺序优先匹配，如需确认的海关信息，请参考相关资料。
详情请参考：📖 海关编码查询和海关进出口税则

专利信息

专利号:US-2003181713-A1
优先权日:2002-03-04
标题:Processes for the synthesis of chloroadenosine and methylthioadenosine
发明人：SRIRANGAM JAYARAM KASTURI; SAENZ JAMES EDWARD
摘要:An in situ process for preparing chloroadenosine is described, wherein adenosine in a non-aqueous solvent is reacted with a thionyl chloride and a pyridine to form a reaction solution; the non-aqueous solvent is exchanged with a lower alcohol, and a base is added to the reaction solution; and the resulting chloroadenosine is filtered, washed and dried. Additionally, a two-step process for the synthesis of methylthioadenosine using the chloroadenosine prepared in situ is described.

专利号:US-2020239921-A1
优先权日:2016-02-03
标题 :Chemoenzymatic synthesis of s-nucleosyl amino acids (sna), analogs of s-adenosyl-l-methionine and s-adenosyl-l- homocysteine and uses thereof
发明人：BURGOS EMMANUEL SEBASTIEN; SHECHTER DAVID
权利人:ALBERT EINSTEIN COLLEGE MEDICINE
摘要:Disclosed are methods for chemoenzymatic synthesis of S-Nucleosyl Amino acid probes (SNA), analogs of S-adeno-syl-L-methionine and S-adenosyl-L-homo-cysteine, analogs synthesized by the methods, and uses thereof.

专利号:WO-2022189846-A1
优先权日:2021-03-10
标题:NOVEL ADENOSYLMERCAPTANE DERIVATIVES AS VIRAL mRNA CAP METHYLTRANSFERASE INHIBITORS
发明人：BOBILEVA OLGA; BOBROVS RAITIS; KANEPE IVETA; KALNINS GINTS; SISOVS MIHAILS; BULA ANNA LINA; JIRGENSONS AIGARS; TARS KASPARS; JAUDZEMS KRISTAPS
权利人:LATVIAN INST ORGANIC SYNTHESIS
摘要:The present invention relates to medicine, and in particular to the treatment of viral infections, more particularly to inhibitors of viral mRNA cap methyltransf erases (MTases). Even more particularly, the invention relates to adenosylmercaptane derivatives and pharmaceutical compositions thereof and their use as inhibitors for viral mRNA cap methyltransferases.

专利号:WO-2017136194-A1
优先权日:2016-02-03
标题:Chemoenzymatic synthesis of s-nucleosyl amino acids (sna), analogs of s-adenosyl-l-methionine and s-adenosyl-l-homocysteine and uses thereof

专利号:EP-1483279-A1
优先权日:2002-03-04
标题:Processes for the synthesis of 5'-deoxy-5'-chloroadenosine and 5'-deoxy-5'-methylthioadenosine

专利号:CA-2477729-A1
优先权日:2002-03-04
标题 :Processes for the synthesis of 5'-deoxy-5' chloroadenosine and 5'-deoxy-5'methylthioadenosine