9-(3'-deoxy-β-D-erythro-pentofuranosyl)-2,6-diaminopurine | 3608-57-9

• 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: 9-(3'-deoxy-β-D-erythro-pentofuranosyl)-2,6-diaminopurine
• 英文别名: 9-(3-deoxy-β-D-erythro-pentofuranosyl)-2,6-diaminopurine；2-amino-3'-deoxy-adenosine；Adenosine, 2-amino-3'-deoxy-；(2R,3R,5S)-2-(2,6-diaminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-ol
• CAS: 3608-57-9
• 化学式: C₁₀H₁₄N₆O₃
• 分子量: 266.26
• InChiKey: ALUXLVWCGFWJMC-OBXARNEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  19
• 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：
  145
• 氢给体数：
  4
• 氢受体数：
  8

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  9-(3'-deoxy-β-D-erythro-pentofuranosyl)-2,6-diaminopurine 在 HF*HBF₄ 、 sodium nitrite 作用下， 生成 2-氟-3-脱氧腺苷酸
  参考文献：
  名称：

  Chemo-enzymatic Synthesis of 3-Deoxy-β-D-ribofuranosyl Purines and Study of Their Biological Properties

  摘要：

  9-(3-Deoxy-beta-D-erythro-pentofuranosyl)-2,6-diiminopurine (2) was synthesized by an enzymatic transglycosylation of 2,6-diaminopurine using 3'-deoxycytidine (1) as a donor of the sugar moiety. Nucleoside 2 was transformed to 3'-deoxy guanosine (3), 9-(3-deoxy-beta-D-erythro-pentofuranosyl)-2-amino-6-oxopurine (3'-deoxyisoguanosine; 4), and 9-(3-deoxy-beta-D-erythro-pentofuranosyl)-2-fluoroadenine (5). Compounds 2-5 were evaluated for their anti-HIV activity.

  DOI：

  10.1081/ncn-120022626
• 作为产物：
  描述：

  2-氨基腺嘌呤核苷 在 Dowex 1 x 2 (OH^-) resin 、 2-乙酰氧基异丁酰溴 、 水 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 73.0h， 生成 9-(3'-deoxy-β-D-erythro-pentofuranosyl)-2,6-diaminopurine
  参考文献：
  名称：

  通过 2-氨基腺苷的转化和腺苷脱氨酶的酶促脱氨作用从鸟苷合成糖修饰的 2,6-二氨基嘌呤和鸟嘌呤核苷

  摘要：

  在乙腈中用 α-乙酰氧基异丁酰溴处理 2,6-二氨基嘌呤核苷（2-氨基腺苷）得到反式 2',3'-溴醇乙酸酯的混合物 2。用锌-铜对处理 2 实现还原消除，脱保护得到2,6-diamino-9-(2,3-dideoxy-β-D-erythro-pent-2-enofuranosyl)purine (3a)。在甲醇中用 Dowex 1 × 2 (OH-) 树脂处理 2 得到 2',3'-脱水衍生物 4。甲硅烷基自由基介导的 2 氢解和脱保护得到 2'-脱氧 6a 和 3'-脱氧 7a 核苷. 用三氟甲磺酰氯 - 4-（二甲氨基）吡啶处理 3',5'-O-（四异丙基二硅氧烷基）衍生物 (5a) 得到 2'-三氟甲磺酸酯 5c。用叠氮化锂-二甲基甲酰胺置换并脱保护得到阿拉伯 2'-叠氮衍生物 8a，将其还原为 2，6-diamino-9-(2-amino-2-deoxy-β-D-arabinofuranosyl)purine

  DOI：

  10.1139/v97-092

文献信息

• Chemo-Enzymatic Synthesis of 3-Deoxy-β-D-ribofuranosyl Purines
  作者：Vladimir N. Barai、Anatoli I. Zinchenko、Ludmilla A. Eroshevskaya、Elena V. Zhernosek、Erik De Clercq、Igor A. Mikhailopulo

  DOI：10.1002/1522-2675(200207)85:7<1893::aid-hlca1893>3.0.co;2-p

  日期：2002.7

  formation of uracil (4) and 3-deoxy-α-D-erythro-pentofuranose-1-O-phosphate (5), and iii) coupling of the latter with 2 catalyzed by whole cell (E. coli BMT-4D/1A) purine nucleoside phosphorylase (PNPase). Deamination of 6 by adenosine deaminase (ADase) gave 3′-deoxyguanosine (7). Treatment of 6 with NaNO2 afforded 9-(3-deoxy-β-D-erythro-pentofuranosyl)-2-amino-6-oxopurine (3′-deoxyisoguanosine; 8). Schiemann

  9-(3-Deoxy-β-D-erythro-pentofuranosyl)-2,6-diaminopurine (6) 通过 2,6-diaminopurine (2) 与 3'-deoxycytidine (1) 作为供体的酶促转糖基化合成3-脱氧-D-赤型呋喃糖部分。这种转化包括 i) 在全细胞 (E.coli BM-11) 胞苷脱氨酶 (CDase) 的作用下 1 到 3'-脱氧尿苷 (3) 的脱氨基作用，ii) 尿苷磷酸化酶 (UPase) 对 3 的磷酸分解，从而产生导致形成尿嘧啶 (4) 和 3-deoxy-α-D-erythro-pentofuranose-1-O-phosphate (5)，以及 iii) 后者与 2 在全细胞催化下偶联（大肠杆菌 BMT- 4D/1A) 嘌呤核苷磷酸化酶 (PNPase)。腺苷脱氨酶 (ADase) 对 6 进行脱氨基作用得到 3'-脱氧鸟苷
• METHOD FOR THE PREPARATION OF 2-HALO-2'-DEOXYADENOSINE COMPOUNDS FROM 2'-DEOXYGUANOSINE
  申请人：Robins Morris J.

  公开号：US20090270604A1

  公开（公告）日：2009-10-29

  The present invention is a method for preparing 2-halo-6-aminopurines, and more specifically for preparing the clinical agent cladribine (2-chloro-2′-deoxyadenosine, CldAdo, 4), a drug of choice against hairy-cell leukemia and other neoplasms, from 2-amino-6-oxopurines, which are readily obtained from the naturally occurring compound 2′-deoxyguanosine. According to the methods of the present invention, the 6-oxo group of a protected 2′-deoxyguanosine (1) is converted to a 6-(substituted oxy) leaving group, or alternatively to a 6-chloro leaving group, the 2-amino group is replaced with a 2-chloro group, the 6-(substituted oxy) leaving group, or alternatively the 6-chloro leaving group, is replaced with a 6-amino group or, alternatively, a 2,6-dichloro substituted compound is selectively replaced with a 6-amino group, and the protecting groups are removed.

  本发明涉及制备2-卤代-6-氨基嘌呤，更具体地说，从2-氨基-6-氧代嘌呤制备临床药物克拉德霉素（2-氯-2'-脱氧腺苷，CldAdo，4），这是针对毛细胞白血病和其他肿瘤的首选药物。2-氨基-6-氧代嘌呤可以从天然存在的2'-脱氧鸟苷中轻松获得。根据本发明的方法，保护的2'-脱氧鸟苷（1）的6-氧代基被转化为6-（取代氧）离去基，或者被转化为6-氯离去基，2-氨基被2-氯代基取代，6-（取代氧）离去基或6-氯离去基被6-氨基取代，或者选择性地用6-氨基取代2,6-二氯取代化合物，并去除保护基。
• Method for the preparation of 2-halo-2'-deoxyadenosine compounds for 2'-deoxyguanosine
  申请人：Robins J. Morris

  公开号：US20070032645A1

  公开（公告）日：2007-02-08

  The present invention is a method for preparing 2-halo-6-aminopurines, and more specifically for preparing the clinical agent cladribine (2-chloro-2′-deoxyadenosine, CldAdo, 4), a drug of choice against hairy-cell leukemia and other neoplasms, from 2-amino-6-oxopurines, which are readily obtained from the naturally occurring compound 2′-deoxyguanosine. According to the methods of the present invention, the 6-oxo group of a protected 2′-deoxyguanosine (1) is converted to a 6-(substituted oxy) leaving group, or alternatively to a 6-chloro leaving group, the 2-amino group is replaced with a 2-chloro group, the 6-(substituted oxy) leaving group, or alternatively the 6-chloro leaving group, is replaced with a 6-amino group or, alternatively, a 2,6-dichloro substituted compound is selectively replaced with a 6-amino group, and the protecting groups are removed.

  本发明涉及一种制备2-卤代-6-氨基嘌呤的方法，更具体地说，是从2-氨基-6-氧代嘌呤制备临床药物克拉德霉素（2-氯-2'-脱氧腺苷，CldAdo，4），这是一种用于治疗毛细胞白血病和其他肿瘤的首选药物。2-氨基-6-氧代嘌呤是从天然存在的2'-脱氧鸟苷中容易得到的。根据本发明的方法，保护的2'-脱氧鸟苷（1）的6-氧代基被转化为6-(取代氧)离去基，或者替代为6-氯离去基，2-氨基被替换为2-氯基，6-(取代氧)离去基或者6-氯离去基被替换为6-氨基或者2,6-二氯取代化合物被选择性地替换为6-氨基，并去除保护基。
• Inhibition of 5-α-Reductase (TYPE-II) Expression by Antisense 3′-Deoxy-(2′-5′) Oligonucleotide Chimeras
  作者：Purshotam Bhan、Anila Bhan、Mikung Hong、John G. Hartwell、June M. Saunders、Glenn D. Hoke

  DOI：10.1080/07328319708006156

  日期：1997.7

  3'-Deoxy-(2'-5') oligonucleotides bind selectively to complementary RNA but not to DNA. 3'-Deoxy-(2'-5') phosphorothioate ODN chimeras embedded with a short stretch of 3'-5' phosphorothioate cassette are potent inhibitors of steroid 5-alpha-reductase expression with significantly less non-specific interactions in cell culture.
• METHOD FOR THE PREPARATION OF 2-HALO-2 -DEOXYADENOSINE COMPOUNDS FROM 2 -DEOXYGUANOSINE
  申请人：Brigham Young University

  公开号：EP1556400B1

  公开（公告）日：2013-05-01