6-chloropurine-2'-deoxyriboside | 4594-45-0

• 物质功能分类: 生物化工 - 核苷类药物 - 脱氧核苷酸及其类似物
• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 6-chloropurine-2'-deoxyriboside
• 英文别名: 6-chloropurine deoxyriboside；6-chloro-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine；6-chloro-2'-deoxypurine riboside；9-(2'-deoxyribosyl)-6-chloropurine；6-chloropurinyl 2'-deoxyriboside；(2R,3S,5R)-5-(6-chloro-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol；6-chloropurine-9-2′-deoxyriboside；6-chloropurine-2′-deoxyriboside；6-chloropurine-2’-deoxyribose；6-chloropurine-2′-deoxyribose；1-(6-chloro-purin-9-yl)-β-D-threo-1,2-dideoxy-pentofuranose；6-chloropurine-2′-deoxy-9-β-D-riboside；6-chloropurine-2′-deoxyribonucleoside；6ClPdR；(2R,3S,5R)-5-(6-chloropurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 4594-45-0
• 化学式: C₁₀H₁₁ClN₄O₃
• 分子量: 270.675
• InChiKey: PGEULCIODBNODW-RRKCRQDMSA-N

物化性质

• 沸点：
  568.0±60.0 °C(Predicted)
• 密度：
  1.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.3
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险品标志：
  T
• 安全说明：
  S22,S26,S36,S45
• 危险类别码：
  R23/24/25,R36/37/38
• WGK Germany：
  3
• 海关编码：
  2934999090
• 储存条件：
  -20°C

反应信息

• 作为反应物：
  描述：

  6-chloropurine-2'-deoxyriboside 以 盐酸 、 水 为溶剂， 生成 6-氯嘌呤
  参考文献：
  名称：

  6-取代的9-（2-脱氧-β-d-异戊-呋喃呋喃糖基）嘌呤及其9-（1-烷氧乙基）对应部分的酸性水解：动力学和机理。1个

  摘要：

  已经在不同浓度的氧离子下测量了几种6-取代的9-（2-脱氧-β-D-赤-戊呋喃糖基）嘌呤和9-（1-烷氧基乙基）嘌呤的水解速率常数。解释了改变烷氧基极性性质对未取代的9-（1-烷氧基乙基）嘌呤水解的影响，这表明该反应是通过质子化碱部分的限速离去并伴随形成一个烷氧基乙基氧碳鎓离子。通过比较6-取代基对这些化合物及其9-（1-烷氧基乙基）反应剂的反应性的影响，将相同的机理应用于9-（2-脱氧-β-D-赤-戊呋喃糖基）嘌呤的水解。 -部分。当2'-脱氧腺苷水解后进行1 H NMR光谱。

  DOI：

  10.1016/s0040-4020(01)90052-3
• 作为产物：
  描述：

  2'-脱氧肌苷 在 氯化亚砜 、 碳酸氢钠 、 三氟乙酸酐 作用下， 生成 6-chloropurine-2'-deoxyriboside
  参考文献：
  名称：

  Synthesis of 1,N⁶-Ethano-2‘-deoxyadenosine, a Metabolic Product of 1,3-Bis(2-chloroethyl)nitrosourea, and Its Incorporation into Oligomeric DNA

  摘要：

  1,N-6-Ethano-2'-deoxyadenosine (1) is one of the adducts formed during DNA reaction with the antitumor agent, 1,3-bis(2-chloroethyl)nitrosourea (BCNU), and was synthesized and incorporated into a site-specific deoxyoligonucleotide for the first time. The product 6-chloropurine-2'-deoxyriboside (11) was prepared in high yield by the reaction of 2'-deoxyinosine (6) with SOCl2, which then was derivatized to give compound 12 using tert-butyldimethylsilyl chloride, which was then reacted with 2-hydroxyethylamine to produce compound 13 in 86% yield. Reaction of 13 with (PhO)(8)P+MeI- in DMF gave the cyclized 1,N-6-ethano derivative 10 in 67% yield. Desilylation of 10 with triethylamine trihydrofluoride in THF gave 1,N-6-ethano-dA (1) in 91% yield. Tritylation of compound 1 with DMT+BF4- gave the 5'-O-DMT product 14 in 62% yield, which then was phosphitylated with 2-cyanoethyl N,N-diisopropylchlorophosphoramidite, which yielded a 1:1 mixture of the diastereoisomers 15 in 71% yield. This fully protected compound 15 was incorporated site-specifically into a 25-mer oligonucleotide. The coupling efficiency of ethano-dA phosphoramidite was 93%. Enzymatic hydrolysis and analysis by HPLC confirmed the incorporation of ethano-dA and base composition of the DNA oligomer. The latter is now under investigation for its biochemical and physical properties.

  DOI：

  10.1021/jo980170i

文献信息

• Exocyclic Deoxyadenosine Adducts of 1,2,3,4-Diepoxybutane: Synthesis, Structural Elucidation, and Mechanistic Studies
  作者：Uthpala Seneviratne、Sergey Antsypovich、Melissa Goggin、Danae Quirk Dorr、Rebecca Guza、Adam Moser、Carrie Thompson、Darrin M. York、Natalia Tretyakova

  DOI：10.1021/tx900312e

  日期：2010.1.18

  guanine within DNA, DEB induces a large number of A → T transversions, suggesting that it forms strongly mispairing lesions at adenine nucleobases. We now report the discovery of three potentially mispairing exocyclic adenine lesions of DEB: N6,N6-(2,3-dihydroxybutan-1,4-diyl)-2′-deoxyadenosine (compound 2), 1,N6-(2-hydroxy-3-hydroxymethylpropan-1,3-diyl)-2′-deoxyadenosine (compound 3), and 1,N6-(1

  1,2,3,4-二环氧丁烷 (DEB) 被认为是 1,3-丁二烯的最终致癌代谢物，1,3-丁二烯是城市空气中存在的一种重要的工业化学品和环境污染物。虽然它优先修饰 DNA 中的鸟嘌呤，但 DEB 会诱导大量 A → T 颠换，表明它在腺嘌呤核碱基处形成强烈的错配损伤。我们现在报告了 DEB 的三个潜在错配环外腺嘌呤病变的发现：N 6 , N 6 -(2,3-dihydroxybutan-1,4-diyl)-2'-deoxyadenosine (compound 2 ), 1, N 6 -( 2-hydroxy-3-hydroxymethylpropan-1,3-diyl)-2'-deoxyadenosine (compound 3 ), and 1, N 6-(1-羟甲基-2-羟基丙烷-1,3-二基)-2'-脱氧腺苷(化合物4 )。新型 DEB-dA 加合物的结构和立体化学由紫外和核磁共振
• Generation of 2′-Deoxyadenosine <i>N</i>⁶-Aminyl Radicals from the Photolysis of Phenylhydrazone Derivatives
  作者：Vandana Kuttappan-Nair、Francois Samson-Thibault、J. Richard Wagner

  DOI：10.1021/tx900268r

  日期：2010.1.18

  one-electron oxidation of adenine derivatives. Aminyl radicals are also generated in the decomposition of adenine chloramines upon reaction of hypochlorite. Here, we report the photochemistry of modified 2′-deoxyadenosine (dAdo) containing photoactive hydrazone substituents as a model to investigate the chemistry of dAdo N6-aminyl radicals. Derivatives of dAdo containing a phenylhydrazone moiety at N6

  以氮为中心的自由基是通过添加羟基自由基和腺嘌呤衍生物的单电子氧化产生的主要物种。在次氯酸盐反应时，腺嘌呤氯胺的分解过程中也会产生氨基自由基。在这里，我们报告包含光活性hydr取代基的2'-脱氧腺苷（dAdo）的光化学作为模型，以研究dAdo N 6-氨基自由基的化学性质。在N6处含有苯hydr部分的dAdo衍生物显示300至400 nm之间的紫外线吸收。在存在氢供体（即谷胱甘肽）的情况下进行紫外光解后，形成了两种主要产物，即dAdo和苯甲醛，表明有效的均质裂解为dAdo N 6-氨基烷基和亚苄基亚氨基。在摩尔过量的未修饰dAdo的存在下，将dAdo N 6-苯photo光解以模拟在DNA中发生的反应，并通过高效液相色谱，质谱和核磁共振来鉴定主要的光产物。2-（亚苄基氨基）-2'-脱氧腺苷的形成以及更广泛的氧化产物可以通过初始dAdo N 6-氨基和亚苄基亚氨基的重组来解释。2'-脱氧肌苷的形成可以通过dAdo
• [EN] NUCLEOSIDE AND NUCLEOTIDE ANALOGUES AS CD73 INHIBITORS AND THERAPEUTIC USES THEREOF<br/>[FR] ANALOGUES DE NUCLÉOSIDES ET DE NUCLÉOTIDES EN TANT QU'INHIBITEURS DE CD73 ET UTILISATIONS THÉRAPEUTIQUES ASSOCIÉES
  申请人：ETERNITY BIOSCIENCE INC

  公开号：WO2018208727A1

  公开（公告）日：2018-11-15

  Nucleoside and nucleotide compounds and analogues, and pharmaceutically acceptable compositions thereof, as inhibitors of CD73 for the treatment of diseases or disorders associated with CD73 activities, especially cancers, and methods of preparing these compounds are disclosed.

  核苷和核苷酸化合物及其类似物，以及药学上可接受的组合物，作为CD73抑制剂用于治疗与CD73活性相关的疾病或障碍，尤其是癌症，以及制备这些化合物的方法被公开。
• Synthesis of 2-Deoxy-β-D-ribonucleosides and 2,3-Dideoxy-β-D-pentofuranosides on Immobilized Bacterial Cells
  作者：Ivan Votruba、Antonín Holý、Hana Dvořáková、Jaroslav Günter、Dana Hocková、Hubert Hřebabecký、Tomas Cihlar、Milena Masojídková

  DOI：10.1135/cccc19942303

  日期：——

  Alginate gel-entrapped cells of auxotrophic thymine-dependent strain of E. coli catalyze the transfer of 2-deoxy-D-ribofuranosyl moiety of 2'-deoxyuridine to purine and pyrimidine bases as well as their aza and deaza analogs. All experiments invariably gave β-anomers; in most cases, the reaction was regiospecific, affording N⁹-isomers in the purine and N¹-isomers in the pyrimidine series. Also a 2,3-dideoxynucleoside can serve as donor of the glycosyl moiety. The acceptor activity of purine bases depends only little on substitution, the only condition being the presence of N⁷-nitrogen atom. On the other hand, in the pyrimidine series the activity is limited to only a narrow choice of mostly short 5-alkyl and 5-halogeno uracil derivatives. Heterocyclic bases containing amino groups are deaminated; this can be avoided by conversion of the base to the corresponding N-dimethylaminomethylene derivative which is then ammonolyzed. The method was verified by isolation of 9-(2-deoxy-β-D-ribofuranosyl) derivatives of adenine, guanine, 2-chloroadenine, 6-methylpurine, 8-azaadenine, 8-azaguanine, 1-deazaadenine, 3-deazaadenine, 1-(2-deoxy-β-D-ribofuranosyl) derivatives of 5-ethyluracil, 5-fluorouracil, and 9-(2,3-dideoxy-β-D-pentofuranosyl)hypoxanthine, 9-(2,3-dideoxy-β-D-pentofuranosyl)-6-methylpurine, and other nucleosides.

  藻酸盐凝胶包埋的辅助胸腺嘧啶依赖菌株大肠杆菌细胞催化2'-脱氧尿嘧啶的2-脱氧-D-核糖呋喃基团转移到嘌呤和嘧啶碱基以及它们的氮杂和去氮类似物。所有实验都不可避免地产生β-异构体；在大多数情况下，反应是区域特异性的，产生嘌呤中的N⁹-异构体和嘧啶系列中的N¹-异构体。此外，2,3-二脱氧核苷酸可以作为糖基团的供体。嘌呤碱基的受体活性仅在取代上有少许影响，唯一的条件是存在N⁷-氮原子。另一方面，在嘧啶系列中，活性仅限于大多数短链5-烷基和5-卤代尿嘧啶衍生物的狭窄选择。含氨基的杂环碱基会发生脱氨作用；可以通过将碱基转化为相应的N-二甲氨基甲烯基衍生物来避免这种情况，然后进行氨解作用。该方法通过分离腺嘌呤、鸟嘌呤、2-氯腺嘌呤、6-甲基嘌呤、8-氮杂腺嘌呤、8-氮杂鸟嘌呤、1-去氮腺嘌呤、3-去氮腺嘌呤的9-(2-脱氧-β-D-核糖呋喃基)衍生物，5-乙基尿嘧啶、5-氟尿嘧啶的1-(2-脱氧-β-D-核糖呋喃基)衍生物，以及9-(2,3-二脱氧-β-D-戊呋喃基)缺氧嘌呤、9-(2,3-二脱氧-β-D-戊呋喃基)-6-甲基嘌呤和其他核苷酸的验证。
• OLIGONUCLEOTIDE HAVING NON-NATURAL NUCLEOTIDE AT 5'-TERMINAL THEREOF
  申请人：Kyowa Hakko Kirin Co., Ltd.

  公开号：US20170354673A1

  公开（公告）日：2017-12-14

  An oligonucleotide having a nucleotide residue or a nucleoside residue represented by formula (I) wherein X 1 is an oxygen atom or the like, R 1 is formula (IIA) (wherein R 5A is halogen or the like, and R 6A is a hydrogen atom or the like), formula (IVA) (wherein Y 3A is a nitrogen atom or the like, and Y 4A is CH or the like), or the like, R 2 is a hydrogen atom, hydroxy, halogen, or optionally substituted lower alkoxy, and R 3 is a hydrogen atom or the like, or formula (VI) (wherein n2 is 1, 2 or 3)} at the 5′ end thereof, wherein the nucleotide residue or the nucleoside residue binds to an adjacent nucleotide residue through the oxygen atom at position 3, is provided.

  具有由式(I)表示的核苷酸残基或核苷酸残基的寡核苷酸其中X1是氧原子或类似物，R1是式(IIA)（其中R5A是卤素或类似物，而R6A是氢原子或类似物），式(IVA)（其中Y3A是氮原子或类似物，而Y4A是CH或类似物），或类似物，R2是氢原子，羟基，卤素，或可选择地取代的较低烷氧基，而R3是氢原子或类似物，或式(VI)（其中n2为1、2或3）}在其5'端，其中核苷酸残基或核苷酸残基通过位于位置3的氧原子与相邻核苷酸残基结合。