6-(decyloxy)-9H-purine

• 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: 6-(decyloxy)-9H-purine
• 英文别名: 6-Decyloxypurine；6-decoxy-7H-purine
• 化学式: C₁₅H₂₄N₄O
• 分子量: 276.382
• InChiKey: QFQOOHCGTPAGJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  63.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2',3'-二脱氧胸苷 、 6-(decyloxy)-9H-purine 在 对硝基苯酚 、 potassium phosphate buffer containing 0.004percent potassium azide (buffer A) 、 TPase 作用下， 反应 24.0h， 以19%的产率得到6-(decyloxy)-9-<(2R,5S)-tetrahydro-5-(hydroxymethyl)-2-furyl>-9H-purine
  参考文献：
  名称：

  Novel 6-alkoxypurine 2',3'-dideoxynucleosides as inhibitors of the cytopathic effect of the human immunodeficiency virus

  摘要：

  Twenty-one 6-alkoxypurine 2',3'-dideoxynucleosides were enzymatically synthesized with nucleoside phosphorylases purified from E. coli. Eighteen analogs exhibited anti-HIV-1 activity in MT4 cells. Two analogs,6-(hexyloxy)-(17) and 6-(heptyloxy)-(18) purine 2',3'-dideoxynucleoside, were as potent as 2',3'-dideoxyinosine (ddI, didanosine, Videx). Although the antiviral activities of 17 and 18 were equivalent, 18 was more cytotoxic. Analogs containing less than four carbons in the 6-alkoxypurine substituent exhibited weak anti-HIV-1 activity. Analogs containing more than seven carbons in the 6-alkoxypurine substituent were too cytotoxic to be effectively evaluated for antiviral activity. Several 6-alkoxypurine 2',3'-dideoxynucleosides were evaluated for substrate activity with calf intestinal adenosine deaminase (ADA). Increasing the carbon chain length of the 6-alkoxypurine substituent decreased the rate of dealkoxylation. The best substrate in this series was 6-methoxypurine 2',3'-dideoxynucleoside (1); however, the rate of dealkoxylation of 100 muM 1 was 0.17 % of the rate of deamination of 100 muM 2',3'-dideoxyadenosine. Compound 17, the most potent anti-HIV-1 analog, was not a substrate for ADA. EHNA (erythro-9-(2-hydroxy-3-nonyl) adenine), a potent inhibitor of ADA, had little effect on the antiviral activities of 17 and ddI. In contrast, coformycin, a potent inhibitor of both ADA and AMP deaminase, dramatically decreased the antiviral activity of 17, but not the antiviral activity of ddI. Thus, AMP deaminase appeared to be involved in the anabolism of 17. The pharmacokinetic profile of 17, the most promising analog in this series, was determined in the rat. At least seventeen metabolites of 17, including ddI, were detected in plasma samples. This analog also had poor oral bioavailability.

  DOI：

  10.1021/jm00055a009
• 作为产物：
  描述：

  癸醇 、 6-氯嘌呤 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以5.25 g的产率得到6-(decyloxy)-9H-purine
  参考文献：
  名称：

  Novel 6-alkoxypurine 2',3'-dideoxynucleosides as inhibitors of the cytopathic effect of the human immunodeficiency virus

  摘要：

  Twenty-one 6-alkoxypurine 2',3'-dideoxynucleosides were enzymatically synthesized with nucleoside phosphorylases purified from E. coli. Eighteen analogs exhibited anti-HIV-1 activity in MT4 cells. Two analogs,6-(hexyloxy)-(17) and 6-(heptyloxy)-(18) purine 2',3'-dideoxynucleoside, were as potent as 2',3'-dideoxyinosine (ddI, didanosine, Videx). Although the antiviral activities of 17 and 18 were equivalent, 18 was more cytotoxic. Analogs containing less than four carbons in the 6-alkoxypurine substituent exhibited weak anti-HIV-1 activity. Analogs containing more than seven carbons in the 6-alkoxypurine substituent were too cytotoxic to be effectively evaluated for antiviral activity. Several 6-alkoxypurine 2',3'-dideoxynucleosides were evaluated for substrate activity with calf intestinal adenosine deaminase (ADA). Increasing the carbon chain length of the 6-alkoxypurine substituent decreased the rate of dealkoxylation. The best substrate in this series was 6-methoxypurine 2',3'-dideoxynucleoside (1); however, the rate of dealkoxylation of 100 muM 1 was 0.17 % of the rate of deamination of 100 muM 2',3'-dideoxyadenosine. Compound 17, the most potent anti-HIV-1 analog, was not a substrate for ADA. EHNA (erythro-9-(2-hydroxy-3-nonyl) adenine), a potent inhibitor of ADA, had little effect on the antiviral activities of 17 and ddI. In contrast, coformycin, a potent inhibitor of both ADA and AMP deaminase, dramatically decreased the antiviral activity of 17, but not the antiviral activity of ddI. Thus, AMP deaminase appeared to be involved in the anabolism of 17. The pharmacokinetic profile of 17, the most promising analog in this series, was determined in the rat. At least seventeen metabolites of 17, including ddI, were detected in plasma samples. This analog also had poor oral bioavailability.

  DOI：

  10.1021/jm00055a009

文献信息

• COLOR PHOTOGRAPHIC ELEMENT CONTAINING NITROGEN HETEROCYCLE DERIVATIVE AND INHIBITOR RELEASING COUPLER
  申请人：——

  公开号：US20010010895A1

  公开（公告）日：2001-08-02

  Disclosed is a color photographic element comprising: a) a first light sensitive silver halide emulsion layer containing a compound with an aromatic bicyclic nitrogen nucleus of which at least one ring is six-membered and with two nitrogen ring atoms in each ring and with at least one N—H bond provided that the ClogP for the compound is at least 2.0 and less than 7.2; and (b) a second light sensitive silver halide emulsion layer, having a spectral sensitivity different from that of the first light sensitive silver halide emulsion layer, containing a compound of Formula III: COUP—(TIME) j —INH  III wherein: COUP is a coupler parent group capable of forming a dye upon reaction with an oxidized developer; TIME is a timing group and j is 0,1 or 2; and INH is a mild silver development inhibitor fragment. The invention provides improved color reproduction.

  本发明涉及一种彩色感光元素，包括：a）第一种感光银卤化物乳剂层，含有一种芳香双环氮核化合物，其中至少一个环是六元环，每个环中有两个氮环原子，并且至少有一条N-H键，该化合物的ClogP值为至少2.0且小于7.2；和b）第二种感光银卤化物乳剂层，其光谱灵敏度与第一种感光银卤化物乳剂层不同，含有公式III的化合物：COUP-(TIME)j-INH III其中：COUP是能够与氧化显影剂反应形成染料的偶联剂母体；TIME是一个计时基团，j为0、1或2；INH是一种温和的银显影抑制剂片段。本发明提供了改进的彩色再现性。
• Color photographic element containing nitrogen heterocycle derivative and inhibitor releasing coupler
  申请人：Eastman Kodak Company

  公开号：US06309811B2

  公开（公告）日：2001-10-30

  Disclosed is a color photographic element comprising: a) a first light sensitive silver halide emulsion layer containing a compound with an aromatic bicyclic nitrogen nucleus of which at least one ring is six-membered and with two nitrogen ring atoms in each ring and with at least one N—H bond provided that the ClogP for the compound is at least 2.0 and less than 7.2; and (b) a second light sensitive silver halide emulsion layer, having a spectral sensitivity different from that of the first light sensitive silver halide emulsion layer, containing a compound of Formula III: COUP-(TIME)j-INH  III  wherein: COUP is a coupler parent group capable of forming a dye upon reaction with an oxidized developer; TIME is a timing group and j is 0,1 or 2; and INH is a mild silver development inhibitor fragment. The invention provides improved color reproduction.

  本发明公开了一种彩色感光元件，包括： a）第一感光性银卤化物乳剂层，其中包含一种具有芳香族双环氮核的化合物，其中至少一个环为六元环，每个环中有两个氮环原子，并且至少有一条N-H键，该化合物的ClogP为至少2.0且小于7.2；以及 b）第二感光性银卤化物乳剂层，其光谱灵敏度不同于第一感光性银卤化物乳剂层，其中包含公式III的化合物： COUP-(TIME)j-INH  III 其中： COUP是能够与氧化的显影剂反应形成染料的偶联剂母体基团； TIME是计时基团，j为0、1或2； INH是轻微的银显影抑制剂片段。 本发明提供了改进的彩色再现性能。
• 6-Oxo and 6-thio purine analogs as antimycobacterial agents
  作者：Ashish K. Pathak、Vibha Pathak、Lainne E. Seitz、William J. Suling、Robert C. Reynolds

  DOI：10.1016/j.bmc.2013.01.054

  日期：2013.4

  6-Oxo and 6-thio analogs of purine were prepared based on the initial activity screening of a small, diverse purine library against Mycobacterium tuberculosis (Mtb). Certain 6-oxo and 6-thio-substituted purine analogs described herein showed moderate to good inhibitory activity. N-9-substitution apparently enhances the anti-mycobacterial activity in the purine series described herein. Several 2-amino and 2-chloro purine analogs were also synthesized that showed moderate inhibitory activity against Mtb. (C) 2013 Elsevier Ltd. All rights reserved.