6-N-己基氨基嘌呤 | 14333-96-1

• 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: 6-N-己基氨基嘌呤
• 英文名称: N⁶-n-hexyladenine
• 英文别名: N-hexyl-9H-purin-6-amine；6-hexylaminopurine；hexyl-(7(9)H-purin-6-yl)-amine；N(6)-hexyl-adenine；N-hexyl-1H-adenine；6-Hexylamino-9H-purine；6-n-Hexylaminopurine；N-hexyl-7H-purin-6-amine
• CAS: 14333-96-1
• 化学式: C₁₁H₁₇N₅
• mdl: MFCD00047150
• 分子量: 219.289
• InChiKey: SSVCRPKUKBLUMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.545
• 拓扑面积：
  66.5
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• WGK Germany：
  3
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  6-N-己基氨基嘌呤 、 Pent-4-enyl 2',3',5'-tri-O-benzoyl-β-D-erythro-pentofuranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 4 A molecular sieve 作用下， 以 乙腈 为溶剂， 反应 0.67h， 以70%的产率得到N⁶-Hexyl-2',3',5'-tri-O-benzoyladenosine
  参考文献：
  名称：

  Pentenyl ribosides: new reagents for purine nucleoside synthesis

  摘要：

  Protected pent-4-enyl ribosides and deoxyribosides were synthesized as reagents for the preparation of nucleosides and deoxynucleosides. Reaction of pent-4-enyl 2',3',5'-tri-O-benzoyl-D-erythro-pentofuranoside with five nucleobases in the presence of N-iodosuccinimide/trifluoromethanesulfonic acid (NIS/TfOH) produced the N-9-beta-nucleosides in 50-70% yields. Pent-4-enyl-2-deoxy-3',5'-di-O-p-toluyl-alpha-D-erythro-pentofuranoside coupled with 6-chloropurine in the presence of iodonium dicollidine perchlorate (IDCP) to produce a mixture of deoxynucleoside isomers (N-9, N-7, alpha,beta) in 91% yield. Under the same conditions, coupling of 6-chloropurine with pent-4-enyl 2'-deoxy-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-D-erythro-pentofuranoside produced only N-9alpha and N-9beta products in 40% total yield. The N-9beta nucleoside was the only product of the reaction of 6-chloropurine with pent-4-enyl 2'-O-benzoyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-D-erythro-pentofuranoside in the presence of NIS/TfOH. Pent-4-enyl ribosides appear to be useful reagents for the synthesis of ribo- and deoxyribonucleosides under mild (NIS/TfOH) or neutral (IDCP) conditions.

  DOI：

  10.1021/jo00077a057
• 作为产物：
  描述：

  C₁₁H₁₅N₅ 在 dimethyl sulfide borane 、 盐酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲醇 、 水 为溶剂， 反应 12.0h， 生成 6-N-己基氨基嘌呤
  参考文献：
  名称：

  N（6）-和N（4）-取代的腺嘌呤和胞嘧啶及其2'-脱氧核糖苷的便捷合成方法。

  摘要：

  开发了一种便捷高效的合成腺嘌呤和胞嘧啶的N 6-和N 4-取代衍生物及其2'-脱氧核糖苷的方法。未保护的核碱基（腺嘌呤，胞嘧啶）或未保护的2'-脱氧核糖苷与芳基或烷基醛的反应可生成相应的席夫碱，这些席夫碱可被还原为目标标题化合物，且总收率高。在芳基醛的情况下，亚胺衍生物在甲醇中的甲醇盐存在下获得，并用硼氢化钠还原。与烷基醛的相应反应需要使用乙酸和硼烷二甲基硫醚络合物。

  DOI：

  10.1080/15257770.2012.742198

文献信息

• Lewis Acid-Catalyzed Generation of CC and CN Bonds on π-Deficient Heterocyclic Substrates
  作者：Matteo Staderini、Maria Laura Bolognesi、J. Carlos Menéndez

  DOI：10.1002/adsc.201400674

  日期：2015.1.12

  to the efficient and completely regioselective generation of aromatic CC and CN bonds. The method is simple, rapid, general and inexpensive, and can be performed without the use of dried solvents. Most of the synthetized compounds are new and in many cases the work‐up required only filtration. Furthermore, this is the first example of the use of a Lewis acid as a catalyst for heteroarylation, vinylation

  在催化量的三氯化铟的存在下，对一系列卤化的氮杂环和不同种类的亲核试剂进行聚焦微波辐照可有效且完全区域选择性地生成芳族CC和CN键。该方法简单，快速，通用且廉价，并且可以在不使用干燥溶剂的情况下进行。大多数合成的化合物都是新化合物，在许多情况下，仅需过滤即可进行后处理。此外，这是使用路易斯酸作为催化剂在π缺陷杂环底物上进行杂芳基化，乙烯基化和胺化反应的第一个例子。
• Method for treating disease or condition susceptible to amelioration by AMPK activators and compounds of formula which are useful to activate AMP-activated protein kinase (AMPK)
  申请人：CHEN Han-Min

  公开号：US20140303112A1

  公开（公告）日：2014-10-09

  The present invention relates to a method for treating disease or condition susceptible to amelioration by AMPK activators and compounds of formula which are useful to activate AMP-activated protein kinase (AMPK) and the use of the compounds in the prevention or treatment of disease, including pre-diabetes, type 2 diabetes, syndrome X, metabolic syndrome and obesity.

  本发明涉及一种治疗疾病或病情的方法，该疾病或病情容易通过AMPK激活剂和公式化合物得到改善，这些化合物有助于激活AMP激活蛋白激酶（AMPK），并将这些化合物用于预防或治疗疾病，包括糖尿病前期、2型糖尿病、X综合症、代谢综合征和肥胖症。
• 2',3'-dideoxy-3'-fluoro-purine ribonucleosides
  申请人：Glaxo Wellcome Inc.

  公开号：US05663154A1

  公开（公告）日：1997-09-02

  2',3'-Dideoxy-3'-fluoro-(B-D-ribofuranosyl) purine nucleosides possessing the ability to inhibit hepatitis B and HIV viral infections.

  2',3'-二脱氧-3'-氟-(B-D-核糖呋喃基) 嘌呤核苷具有抑制乙型肝炎和HIV病毒感染的能力。
• [EN] METHOD AND COMPOSITION FOR AMELIORATING THE ADVERSE EFFECTS OF AGING
  申请人：SENETEK, PLC

  公开号：WO1992020341A1

  公开（公告）日：1992-11-26

  (EN) 6-(substituted amino)purine cytokinins, including kinetin, have been discovered to ameliorate the adverse effects of aging on mammalian cells, by slowing or reversing the morphological changes that normally accompany aging of such cells, without significantly increasing the growth rate or total proliferative capacity of such cells. Thus, method are provided for countering the adverse effects of aging on cells in culture and in vivo which comprise administering to said cells an adverse-age-effect-ameliorative amount of kinetin or another 6-(substituted amino)purine cytokinin. Compositions for carrying out the methods are also provided. Among the preferred applications of the invention are the preservation of the health of mammalian cells in culture and, by application to human skin of kinetin-containing lotions, ointments or creams, the health and youthful appearance of skin.(FR) On a découvert que des cytokinines de purine (à substitution amino)-6, y compris la kinétine, améliorent les effets fâcheux du vieillissement sur les cellules de mammifères, en ralentissant ou en inversant les modifications morphologiques qui accompagent normalement le vieillissement de ce type de cellules, sans augmenter significativement la vitesse de croissnce ou la capacité de prolifération totale de ces cellules. Cette invention concerne donc des procédés utilisés pour contrecarrer les effets fâcheux du vieillissement sur des cellules cultivées et sur des cellules in vivo, consistant à administrer à ces cellules une quantité améliorant les effets fâcheux du vieillissement, de kinétine ou d'une autre cytokinine de purine (à substitution amino)-6. Des compositions permettant de mettre en application les procédés sont également présentées. Parmi les applications préférées de l'invention, on peut citer la conservation de la santé de cellules de mammifères cultivées et, l'aspect sain et jeune de la peau lorsqu'on applique sur la peau d'une personne des lotions, des onguents ou des crèmes contenant de la kinétine.

  6-（取代氨基）嘌呤细胞因子（包括亲脂素）已被发现能够改善哺乳动物细胞衰老的不利影响，通过减缓或逆转通常伴随细胞衰老的形态变化，而不会显著增加细胞的生长速率或总增殖能力。因此，为应对细胞在培养和体内的衰老不利影响提供了方法，具体包括向细胞中输注缓解衰老不利影响的亲脂素或另一类6-（取代氨基）嘌呤细胞因子的去不利作用量的数量。还提供了执行上述方法的成分。 preferred发明的应用包括维护哺乳动物细胞的健康（在细胞培养中），以及通过亲脂素包含的乳液、药膏或霜来维护皮肤的健康和青春状态。
• Ruthenium(III) complexes with modified nucleobases: N6-Substituted adenines
  作者：Juan J. Fiol、Angel García-Raso、Francisca M. Albertí、Andrés Tasada、Miquel Barceló-Oliver、Angel Terrón、María J. Prieto、Virtudes Moreno、Elies Molins

  DOI：10.1016/j.poly.2008.06.013

  日期：2008.9

  New chlorido-dimethylsulfoxide-ruthenium(III) complexes with different N-6-substituted adenines have been prepared and characterized. Three ruthenium complexes have been structurally characterized by X-ray diffraction crystallography: [(RuCl4)-Cl-III(DMSO)[H-(N-6-pentyladenine)]] (1), [(RuCl4)-Cl-III(DMSO)[H-(N-6-hexyladenine)]] (2) and [(RuCl4)-Cl-III(DMSO)[H-(N-6,N-6-dibutyladenine)]] (3). In all cases ruthenium ion show octahedral geometry coordinated to four chlorido ligands and one S coordinated sulfoxide (DMSO). The coordination sphere is completed by an adenine moiety coordinated to Ru(III) via N(9) and protonated at N(3). Other similar complexes have been obtained with N-6-propyladenine, [(RuCl4)-Cl-III(DMSO)[H-(N-6-propyladenine)]] - 0.5EtOH (4) and N-6-benzylaminopurine (BAP) [(RuCl4)-Cl-III(DMSO)[H-(BAP)]]center dot 0.5H(2)O (5) which have been spectroscopically characterized. Otherwise, in. different reaction conditions, we have obtained an out sphere complex of Ru(II), [H-(BAP)][(RuCl3)-Cl-II(DMSO)(3)] (6), with identical complex unit than the structurally solved [H-(creat)][(RuCl3)-Cl-II(DMSO)(3)] (7) which was included for comparison purposes. Preliminary electrophoretic mobility and atomic force microscopy (AFM) studies of the interaction between Ru(III) compounds and plasmidic DNA pBR322 have been performed. These results show different morphological changes in plasmidic DNA forms. (C) 2008 Elsevier Ltd. All rights reserved.