N²-palmytoylguanine | 21047-87-0

• 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: N²-palmytoylguanine
• 英文别名: N2-palmitoylguanine；N-(6-oxo-1,7-dihydropurin-2-yl)hexadecanamide
• CAS: 21047-87-0
• 化学式: C₂₁H₃₅N₅O₂
• 分子量: 389.541
• InChiKey: OFRCCDYYOMSXAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  28
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  99.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N²-palmytoylguanine 在 吡啶 、 ammonium hydroxide 、 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 反应 28.5h， 生成 2'-deoxyguanosine
  参考文献：
  名称：

  L-Thymidine is phosphorylated by herpes simplex virus type 1 thymidine kinase and inhibits viral growth

  摘要：

  We have demonstrated that herpes simplex 1 (HSV1) thymidine kinase (TK) shows no stereospecificity for D- and L-beta-nucleosides. In vitro, L enantiomers are not recognized by human TK, but function as specific substrates for the viral enzyme in the order: L-thymidine (L-T) much greater than 2'-deoxy-L-guanosine (L-dG) > 2'-deoxy-L-uridine (L-dU) > 2'-deoxy-L-cytidine (L-dC) > 2'-deoxy-L-adenosine (L-dA). HSV1 TK phosphorylates both thymidine enantiomers to their corresponding monophosphates with identical efficiency and the K(i) of L-T (2 muM) is almost identical to the K(m) for the natural substrate D-T (2.8 muM). The L enantiomer reduces the incorporation of exogenous [H-3]T into cellular DNA in HeLa TK-/HSV1 TK+ but not in wild-type HeLa cells, without affecting RNA, protein synthesis, cell growth, and viability. L-T markedly reduces HSV1 multiplication in HeLa cells. Our observations could lead to the development of a novel class of antiviral drugs characterized by low toxicity.

  DOI：

  10.1021/jm00100a029
• 作为产物：
  描述：

  棕榈酰氯 、 鸟嘌呤 以 吡啶 为溶剂， 反应 8.0h， 以90%的产率得到N²-palmytoylguanine
  参考文献：
  名称：

  Visser, G. M.; van Westrenen, J.; van Boeckel, C. A. A., Recueil des Travaux Chimiques des Pays-Bas, 1986, vol. 105, p. 528 - 537

  摘要：

  DOI：

文献信息

• Synthesis and Conformational Analysis of 1′- and 3′-Substituted 2-Deoxy-2-fluoro-D-ribofuranosyl Nucleosides
  作者：Grigorii G. Sivets、Elena N. Kalinichenko、Igor A. Mikhailopulo

  DOI：10.1002/hlca.200790191

  日期：2007.9

  with silylated N6-benzoyladenine to afford, after deprotection, 2′,3′-dideoxy-2′,3′-difluoroadenosine (13). Condensation of 1-O-acetyl-3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-ribofuranose (14) with silylated N2-palmitoylguanine gave, after chromatographic separation and deacylation, the N7-β-anomer 17 as the main product, along with 2′-deoxy-2′-fluoroguanosine (15) and its N9-α-anomer 16 in a ratio of ca

  9-（3-X-2,3-dideoxy-2-fluoro- β -D-rifurfuranosyl）adenenes 5（X = N 3）和7（X = NH 2）及其各自的收敛合成描述了使用甲基2-叠氮基-5 - O-苯甲酰基-2，3-二脱氧-2-氟-β -D-呋喃呋喃糖苷（4）作为糖基化剂的α-端基异构体6和8。从两种前体开始，制备甲基5- O-苯甲酰基-2,3-二脱氧-2,3-二氟-β -D-呋喃呋喃糖苷（12），并与甲硅烷基化的N 6偶联。-苯甲酰腺嘌呤在脱保护后得到2'，3'-二脱氧-2'，3'-二氟腺苷（13）。1-缩合ø -乙酰基-3,5-二- ø -苯甲酰基-2-脱氧-2-氟- β -D-呋喃核糖（14）与甲硅烷基化Ñ 2 -palmitoylguanine得到，色谱分离和脱酰，所述后Ñ 7 - β-端基异构体17为主要产物，以及2'-脱氧-2'-氟鸟苷（15）及其N 9 -
• Improved synthesis of 2′-amino-2′-deoxyguanosine and its phosphoramidite
  作者：Qing Dai、Shirshendu K. Deb、James L. Hougland、Joseph A. Piccirilli

  DOI：10.1016/j.bmc.2005.08.050

  日期：2006.2

  2'-Amino-2'-deoxynucleosides and oligonucleotides containing them have proven highly effective for an array of biochemical applications. The guanosine analogue and its phosphoramidite derivatives have been accessed previously from 2'-amino-2'-deoxyuridine by transglycosylation, but with limited overall efficiency and convenience. Using simple modifications of known reaction types, we have developed

  2'-氨基-2'-脱氧核苷和包含它们的寡核苷酸已被证明对一系列生化应用非常有效。鸟苷类似物及其亚磷酰胺衍生物先前已经通过转糖基化从2'-氨基-2'-脱氧尿苷中获得，但是总体效率和便利性有限。使用已知反应类型的简单修饰，我们已经开发了有用的方案，与以前报道的相比，具有更大的便利性，更少的步骤和更高的产率来获得2'-氨基-2'-脱氧鸟苷及其两个亚磷酰胺衍生物。这些亚磷酰胺为将2'-氨基-2'-脱氧鸟苷掺入寡核苷酸中提供了有效的合成子。
• Epimerization during the acetolysis of 3-O-acetyl-5-O-benzoyl-1,2-O-isopropylidene-3-C-methyl-α-d-ribofuranose. Synthesis of 3′-C-methylnucleosides with the β-d-ribo- and α-d-arabino configurations
  作者：Leon N. Beigelman、Galina V. Gurskaya、Elena N. Tsapkina、Sergey N. Mikhailov

  DOI：10.1016/0008-6215(88)84024-2

  日期：1988.10

  Abstract Acetolysis of 3-O-acetyl-5-O-benzoyl-1,2-O-isopropylidene-3-C-methyl-α- d -ribofuranose with a high concentration of acetic acid yielded 1,2,3-tri-O-acetyl-5-O-benzoyl-3-C-methyl- d -arabinofuranose, which was used for the preparation of 3-C-methyl-α- d -arabinofuranosyl nucleosides. 3′-C-Methylribonucleosides were also synthesized starting from 1,2,3-tri-O-acetyl-5-O-benzoyl-3-C-methyl- d

  摘要用高浓度乙酸将3-O-乙酰基-5-O-苯甲酰基-1,2-O-异亚丙基-3-C-甲基-α-d-核呋喃糖进行乙酰化反应可得到1,2,3-tri- O-乙酰基-5-O-苯甲酰基-3-C-甲基-d-呋喃糖，用于制备3-C-甲基-α-d-呋喃糖基核苷。还从1,2,3-三-O-乙酰基-5-O-苯甲酰基-3-C-甲基-d-核呋喃糖开始合成3'-C-甲基核糖核苷。
• Oxypurine nucleosides and their congeners, and acyl derivatives thereof, for improvement of hematopoiesis
  申请人：Pro-Neuron, Inc.

  公开号：US20040235782A1

  公开（公告）日：2004-11-25

  The invention relates to certain oxypurine nucleosides, congeners of such oxypurine nucleosides, and acyl derivatives thereof, and compositions which contain at least one of these compounds. The invention also relates to methods of treating or preventing hematopoietic disorders and modifying hematopoiesis, and treating or preventing inflammatory diseases and bacterial infections by administering a compound or composition of the present invention to an animal.

  本发明涉及某些氧杂嘌呤核苷、这些氧杂嘌呤核苷的同系物和酰基衍生物，以及至少含有这些化合物之一的组合物。本发明还涉及通过向动物施用本发明的化合物或组合物来治疗或预防造血障碍和调节造血以及治疗或预防炎症性疾病和细菌感染的方法。
• Use of 3'-fluro-3' deoxythymidine for the manufacture of a medicament for the treatment of virus infections
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：EP0286825A2

  公开（公告）日：1988-10-19

  A method of treating viral diseases in a human subject is disclosed. The method involves applying effective amounts of the compound: wherein X is an azido group, a methoxy radical or a fluorine atom and B is thymine, uracil, guanine, cytosine, purine or hypoxanthine if X is methoxy or fluorine, and B is guanine, purine or hypoxanthine if X is azido or a pharmaceutically acceptable salt thereof. Also disclosed are compositions and compounds useful in the method.

  本发明公开了一种治疗人类病毒性疾病的方法。该方法包括应用有效量的化合物： 其中 X 是叠氮基、甲氧基或氟原子，如果 X 是甲氧基或氟原子，则 B 是胸腺嘧啶、尿嘧啶、鸟嘌呤、胞嘧啶、嘌呤或次黄嘌呤；如果 X 是叠氮基，则 B 是鸟嘌呤、嘌呤或次黄嘌呤或其药学上可接受的盐。还公开了用于该方法的组合物和化合物。