N-(7H-嘌呤-6-基)辛酰胺 | 52854-12-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: N-(7H-嘌呤-6-基)辛酰胺
• 英文名称: N6-octanoyladenine
• 英文别名: N-(7H-purin-6-yl)octanamide
• CAS: 52854-12-3
• 化学式: C₁₃H₁₉N₅O
• 分子量: 261.327
• InChiKey: BCHNDUIHZPOJOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(7H-嘌呤-6-基)辛酰胺 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 2.25h， 生成 α-3'-azido-2',3'-dideoxyadenosine
  参考文献：
  名称：

  大肠杆菌的核苷转运蛋白NupC和NupG：配体结合所必需的特定结构基序。

  摘要：

  测试了一系列46种天然核苷和类似物（主要是基于腺苷的）作为从大肠杆菌中富集的，与H（+）连接的核苷转运蛋白NupC和NupG吸收[U-（14）C]尿苷的抑制剂。这两个在进化上不相关的转运蛋白显示出相似但不同的抑制模式，揭示了对不同核苷及其类似物的不同选择性。核苷与NupG的结合需要在核糖的C-3'和C-5'位置分别存在羟基，而与NupC的结合仅需要C-3'羟基取代基。核糖部分对于结合NupG的重要性更高，与该蛋白质和寡糖之间的进化关系一致：运输者的主要促进者超家族（MFS）的H（+）同向转运蛋白（OHS）亚家族。对于两种蛋白质，C-3'处的天然α-构型和C-1'处的天然β-构型对于配体结合都是必需的。发现腺苷的咪唑环中的N-7和C-6的氨基对于结合并不重要，并且两个转运蛋白都显示出C-6 / N取代的灵活性。N-1和N-3中的一个或两个对腺苷类似物与NupC的结合很重要，但对NupG的结合

  DOI：

  10.1039/b414739a
• 作为产物：
  描述：

  辛酸 在 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 N-(7H-嘌呤-6-基)辛酰胺
  参考文献：
  名称：

  Isolation and synthesis of N-acyladenine and adenosine alkaloids from a southern Australian marine sponge, Phoriospongia sp.

  摘要：

  Chemical fractionation of the southern Australian marine sponge Phoriospongia sp. (CMB-03107) yielded phorioadenine A (1) as a nematocidal agent and the first reported example of a 6-N-acyladenine natural product. The structure of 1 was confirmed by spectroscopic analysis and the chemical synthesis of racemic (1a) and enantiomeric (1b) analogues. HPLC-ESIMS analysis of the crude sponge extract with comparisons to the synthetic 6-N-acyladenosine 2a provided evidence that the biosynthetically related adenosine, phorioadenosine A (2), was present as a trace co-metabolite. The rare starfish metabolite asterubine (3) was also isolated as a co-metabolite, and its structure confirmed by spectroscopic analysis and chemical synthesis. Biological investigations confirmed that natural products 1-3 and synthetic analogues la-e and 2a were not cytotoxic to multiple mammalian cancer cell lines, or Gram-positive or -negative bacteria. Nematocidal activity (inhibition of larval development of Haemonchus contortus) detected in the Phoriospongia sp. extract was attributed to 1 (LD99 31 mu g/mL), with preliminary structure-activity relationship investigations confirming the importance of the N-acyl side chain. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.08.116

文献信息

• Efficient and improved synthesis of triazole-linked DNA (TLDNA) oligomers
  作者：Tomoko Fujino、Naomi Yamazaki、Ai Hasome、Kenta Endo、Hiroyuki Isobe

  DOI：10.1016/j.tetlet.2011.12.026

  日期：2012.2

  A method for the synthesis of triazole-linked DNA oligomers has been revisited to incorporate a reliable protective group and linker for solid-phase synthesis. The new solid-phase synthesis allowed the preparation of oligomers with the efficiency of elongation reaching over 90%.

  已经重新考虑了合成三唑连接的DNA低聚物的方法，以结合可靠的保护基和用于固相合成的接头。新的固相合成方法可以制备低聚物，其延伸效率达到90％以上。
• Efficient synthesis of 2′-C-α-aminomethyl-2′-deoxynucleosides
  作者：Nan-Sheng Li、Joseph A. Piccirilli

  DOI：10.1039/c2cc34556k

  日期：——

  Starting from methyl 3,5-di-O-benzyl-2-keto-alpha-D-ribofuranoside, a convergent, six-step synthesis is developed to give efficiently all four 2'-C-alpha-aminomethyl-2'-deoxynucleosides (U, C, A, G) in 38%, 42%, 12%, 12% yield, respectively. Convergence is achieved by the glycosylation of persilylated nucleobases with methyl 2-alpha-phthalimidomethyl ribofuranoside.

  从甲基3,5-二-O-苄基-2-酮基的α-d呋喃核糖苷，会聚开始，六步合成进行显影，得到有效地所有四个2'-C-α-氨基甲基-2'-脱氧核苷（U，C，A，G）在38％，42％，分别为12％，产率12％。收敛通过全硅烷化的核碱基的糖基化与甲基2-α-苯二甲酰呋喃核糖苷实现。
• Process for recovery of the desired cis-1,3-oxathiolane nucleosides from their undesired trans-isomers
  申请人：——

  公开号：US20030013880A1

  公开（公告）日：2003-01-16

  A process for the preparation of 1,3-oxathiolane nucleoside analogues in predominantly the cis-form, from mixture of cis-/trans-1,3-oxathiolane nucleosides or their protected derivatives thereof, comprising: (i) treatment of the cis-/trans-1,3-oxathiolane nucleosides (or protected derivatives thereof) with a pyrimidine base (or it derivatives thereof) and an acid, (ii) adding a suitable acid to the obtained cis-/trans-mixture of isomers, (iii) selective crystallization of the desired cis-isomer salt from a solvent or combination of solvents, and (iv) treatment of the predominantly cis-isomer salt with a suitable base to offer the free 1,3-oxathiolane nucleosides, and thereafter optionally repeating steps (i) to (iv) inclusive.

  一种制备1,3-氧硫环己烷核苷类似物的方法，其主要为顺式形式，从顺/反-1,3-氧硫环己烷核苷或其受保护衍生物混合物中制备，包括：(i)将顺/反-1,3-氧硫环己烷核苷(或其受保护衍生物)与嘧啶碱基(或其衍生物)和酸处理，(ii)向得到的顺/反异构体混合物中加入适当的酸，(iii)从溶剂或溶剂组合中选择性结晶所需的顺异构体盐，(iv)用适当的碱处理主要为顺异构体盐以提供自由的1,3-氧硫环己烷核苷，然后可选地重复步骤(i)至(iv)。
• Therapeutic nucleosides
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0217580A2

  公开（公告）日：1987-04-08

  The present invention relates to certain novel 3'- azidonucleosides and pharmaceutically acceptable derivatives thereof; the use of certain 3'-azidonucleosides, their pharmaceutically acceptable derivatives and therapeutic combinations containing them, in therapy, particularly in the treatment and prophylaxis of gram negative bacterial infections and retroviral infections, especially AIDS; to processes for the preparation of 3'-azidonucleosides; and to formulations containing them.

  本发明涉及某些新型 3'-叠氮核苷及其药学上可接受的衍生物；某些 3'-叠氮核苷、其药学上可接受的衍生物和含有它们的治疗组合物在治疗中的用途，特别是在革兰氏阴性细菌感染和逆转录病毒感染（尤其是艾滋病）的治疗和预防中的用途；3'-叠氮核苷的制备工艺；以及含有它们的制剂。
• Artificial Nucleosides Possessing Metal Binding Sites at the 3‘- and 5‘-Positions of the Deoxyribose Moieties
  作者：Jun-ya Chiba、Kentaro Tanaka、Yukinori Ohshiro、Ryosuke Miyake、Shuichi Hiraoka、Motoo Shiro、Mitsuhiko Shionoya

  DOI：10.1021/jo026026l

  日期：2003.1.1

  This paper describes a convenient synthetic procedure for nucleoside mimics, 1-6, in which the 3',5'-hydroxy groups of natural 2'-deoxythymidine or 2'-deoxyadenosine are replaced by thiol, amine, or alkylthiol groups. Such nucleosides would be built up into a single DNA strand with cooperative participation of metal coordination, where internucleoside linkages are replaced by metal complexation motifs. The X-ray crystal structure and complexation behaviors of 3',5'-dithiothymidine, 1, with Au-I are also reported.