(2S,3R)-3-(6-aminopurin-9-yl)nonane-2,9-diol | 159722-90-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (2S,3R)-3-(6-aminopurin-9-yl)nonane-2,9-diol
• 英文别名: 9-[2(S),9-dihydroxy-3(R)-nonyl]adenine；1,8-Nonanediol, 7-(6-amino-9H-purin-9-yl)-, (7R,8S)-；(7R,8S)-7-(6-aminopurin-9-yl)nonane-1,8-diol
• CAS: 159722-90-4
• 化学式: C₁₄H₂₃N₅O₂
• 分子量: 293.369
• InChiKey: JPMVIXUFWCZSGS-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  magnesium,pent-1-ene,bromide 在 吡啶 、 盐酸 、 palladium dihydroxide 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 sodium azide 、 硼烷四氢呋喃络合物 、 dilithium tetrachlorocuprate 、 三正丁胺 、 氨 、 双氧水 、 环己烯 作用下， 以 乙醚 、 乙醇 、 戊醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 126.75h， 生成 (2S,3R)-3-(6-aminopurin-9-yl)nonane-2,9-diol
  参考文献：
  名称：

  Adenosine Deaminase Inhibitors. Synthesis and Biological Evaluation of Putative Metabolites of (+)-erythro-9-(2S-Hydroxy-3R-nonyl)adenine

  摘要：

  The synthesis and biological evaluation of three chain-hydroxylated (+)-erythro-9-(2S-hydroxy-3R-nonyl)adenine [(+)-EHNA] derivatives are reported. Hydroxy groups at positions 9', 8', and 8',9' (12, 25, and 16) were introduced by either epoxidation or hydroboration of a terminal olefinic intermediate. Affinities for calf intestinal adenosine deaminase (ADA) were determined from the steady-state inhibition of adenosine deamination. K-i values of 0.82, 3.8, 6.4, and 15.8 nM were estimated for (+)-EHNA, 9'-hydroxy-(+)-EHNA (12), 8'-hydroxy-(+)-EHNA (25), and 8',9'-dihydroxy-(+)-EHNA (16), respectively, by assuming a single class of binding sites. However, the data for all inhibitors conformed more closely to the kinetics of a heterogeneous system with different affinities for two or more binding sites. The fairly high potencies of 12 and 25 suggest that other substitutions at the terminal position of the nonyl chain could yield useful ADA inhibitors.

  DOI：

  10.1021/jm00048a020

文献信息

• [EN] HYDROXYNONYLADENINE ANALOGS WITH ENHANCED LIPOPHILIC AND ANTI-ISCHEMIC TRAITS<br/>[FR] ANALOGUES D'ERYTHRO-HYDROXYNONYLADENINE A PROPRIETES LIPOPHILES ET ANTI-ISCHEMIQUES RENFORCEES
  申请人：CYPROS PHARMACEUTICAL CORPORATION

  公开号：WO1997028803A1

  公开（公告）日：1997-08-14

  (EN) Analogs of erythro-hydroxynonyladenine (EHNA) are disclosed which have been modified by bonding various types of moieties to the #8 or #9 carbon atoms in the 'side chain' portion of the molecule. The compounds inhibit the intracellular enzymatic activity of adenosine deaminase and are therapeutically effective in reducing hypoxic and ischemic damage in heart and brain tissue.(FR) Analogues d'érythro-hydroxynonyladénine (EHNA) qui ont été modifiés par la liaison de divers types de fractions aux atomes de carbone en position 8 ou 9 dans la partie chaîne latérale de la molécule. Ces composés inhibent l'activité enzymatique intracellulaire de l'adénosine désaminase et réduisent efficacement, sur le plan thérapeutique, les lésions ischémiques et hypoxiques des tissus du coeur et du cerveau.

  （中文翻译）披露了已经通过将各种类型的基团连接到分子的“侧链”部分的＃8或＃9碳原子上而改性的erythro-hydroxynonyladenine（EHNA）的类似物。这些化合物抑制腺苷脱氨酶的细胞内酶活性，并在治疗上有效减少心脏和脑组织的缺氧和缺血损伤。
• HYDROXYNONYLADENINE ANALOGS WITH ENHANCED LIPOPHILIC AND ANTI-ISCHEMIC TRAITS
  申请人：Cypros Pharmaceutical Corporation

  公开号：EP0871449A1

  公开（公告）日：1998-10-21
• EP0871449A4
  申请人：——

  公开号：EP0871449A4

  公开（公告）日：1998-10-21
• US5491146A
  申请人：——

  公开号：US5491146A

  公开（公告）日：1996-02-13
• Adenosine Deaminase Inhibitors. Synthesis and Biological Evaluation of Putative Metabolites of (+)-erythro-9-(2S-Hydroxy-3R-nonyl)adenine
  作者：Chandra Vargeese、Mallela S. P. Sarma、Palle V. P. Pragnacharyulu、Elie Abushanab、Shih-Ying Li、Johanna D. Stoeckler

  DOI：10.1021/jm00048a020

  日期：1994.10

  The synthesis and biological evaluation of three chain-hydroxylated (+)-erythro-9-(2S-hydroxy-3R-nonyl)adenine [(+)-EHNA] derivatives are reported. Hydroxy groups at positions 9', 8', and 8',9' (12, 25, and 16) were introduced by either epoxidation or hydroboration of a terminal olefinic intermediate. Affinities for calf intestinal adenosine deaminase (ADA) were determined from the steady-state inhibition of adenosine deamination. K-i values of 0.82, 3.8, 6.4, and 15.8 nM were estimated for (+)-EHNA, 9'-hydroxy-(+)-EHNA (12), 8'-hydroxy-(+)-EHNA (25), and 8',9'-dihydroxy-(+)-EHNA (16), respectively, by assuming a single class of binding sites. However, the data for all inhibitors conformed more closely to the kinetics of a heterogeneous system with different affinities for two or more binding sites. The fairly high potencies of 12 and 25 suggest that other substitutions at the terminal position of the nonyl chain could yield useful ADA inhibitors.