9-Trimethylsilanyl-9H-purin-6-ylamine | 130372-34-8

• 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: 9-Trimethylsilanyl-9H-purin-6-ylamine
• 英文别名: 9-Trimethylsilyl-adenine；9-trimethylsilylpurin-6-amine
• CAS: 130372-34-8
• 化学式: C₈H₁₃N₅Si
• 分子量: 207.31
• InChiKey: KFQOBCCGANICSN-UHFFFAOYSA-N

物化性质

• 沸点：
  337.7±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-Trimethylsilanyl-9H-purin-6-ylamine 在 三氟甲磺酸三甲基硅酯 、 氨 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 68.0h， 生成 9-(2-deoxy-2-fluoro-α-D-arabinofuranosyl)adenine
  参考文献：
  名称：

  Striking Ability of Adenosine-2′(3′)-deoxy-3′(2′)-triphosphates and Related Analogues to Replace ATP as Phosphate Donor for All Four Human, and theDrosophila Melanogaster, Deoxyribonucleoside Kinases

  摘要：

  In extension of an earlier report, six non-conventional analogues of ATP, three adenosine-2'-triphosphates (3'-deoxy, 3'-deoxy-3'-fluoro- and 3'-deoxy-3'-fluoroxylo-), and three adenosine-3'-triphosphates (2'-deoxy-, 2'-deoxy-2'-fluoro- and 2'-deoxy-2'-fluoroara-), were compared with ATP as potential phosphate donors for human deoxycytidine kinase (dCK), cytosolic thymidine kinase (TK1), mitochondrial TK2, deoxyguanosine kinase (dGK), and the deoxyribonucleoside kinase (dNK) from Drosophila melanogaster. With one group of enzymes, comprising TK1, TK2, dNK and dCK (with dAdo as acceptor), only 3'-deoxyadenosine-2'-triphosphate was an effective donor (5-60% that for ATP), and the other five analogues much less so, or inactive. With a second set, including dCK (dCyd, but not dAdo, as acceptor) and dGK (dGuo as acceptor), known to share high sequence similarity (approximate to 45% sequence identity), all six analogues were good to excellent donors (13-119% that for ATP). With dCK and ATP1, products were shown to be 5'-phosphates. With dCK, donor properties of the analogues were dependent on the nature of the acceptor, as with natural 5'-triphosphate donors. With dCK (dCyd as acceptor), K-m and V-max for the two 2'(3)deoxyadenosine-3'(2')-triphosphates are similar to those for ATP. With dGK, K-m values are higher than for ATP, while V-max values are comparable. Kinetic studies further demonstrated Michaelis-Menten (non-cooperative) or cooperative kinetics, dependent on the enzyme employed and the nature of the donor. The physiological significance, if any, of the foregoing remains to be elucidated. The overall results are, on the other hand, highly relevant to studies on the modes of interaction of nucleoside kinases with donors and acceptors; and, in particular, to interpretations of the recently reported crystal structures of dGK with bound ATP, of dNK with bound dCyd, and associated modeling studies.

  DOI：

  10.1081/ncn-120019510
• 作为产物：
  描述：

  腺嘌呤 、 六甲基二硅氮烷 在 silica sulfuric acid 作用下， 生成 9-Trimethylsilanyl-9H-purin-6-ylamine
  参考文献：
  名称：

  核碱基/四唑杂化化合物的合成和生物学评估：一类新的3型磷酸二酯酶（PDE3）抑制剂。

  摘要：

  受西洛他唑，选择性磷酸二酯酶3A（PDE3A）抑制剂的化学结构的刺激，设计并成功合成了几种新型核碱基（尿嘧啶，6-氮杂尿嘧啶，2-硫嘧啶，腺嘌呤，鸟嘌呤，茶碱和可可碱）和四唑的杂合化合物。研究了它们对PDE3A的抑制作用以及对HeLa和MCF-7癌细胞系的细胞毒性。所得结果表明合成化合物的抑制作用与其细胞毒性之间呈线性关系。在某些情况下，合成化合物对PDE3A的抑制作用高于西洛他唑。此外，与标准抗癌药甲氨蝶呤相比，一些合成的化合物对HeLa和MCF-7癌细胞具有更高的细胞毒性。

  DOI：

  10.1016/j.bmc.2020.115540

文献信息

• Synthesis and Evaluation of 2′-Deoxy-2′-Spirodiflurocyclopropyl Nucleoside Analogs
  作者：Xiao Liu、Xueliang Xia、Chenghai Sun、Cai Lin、Yiqian Zhou、Muzammal Hussain、Fei Tang、Lu Liu、Xue Li、Jiancun Zhang

  DOI：10.1080/15257770.2016.1202965

  日期：2016.9

  propany-lnucleoside analogs has been achieved from α-d-glucose in several steps. The key step in the synthesis was the introduction of the difluorocyclopropane through a difluorocarbene type reaction at the 2′-position. Then, a series of novel 2′-deoxy-2′-spirodifluorocyclopropanyl nucleoside analogs were synthesized using the Vorbrüggen method. All the synthesized nucleosides were characterized and

  由α- d-葡萄糖分几步完成了2'-脱氧-2'-siprodifluorocyclopropany-l核苷类似物的制备。合成中的关键步骤是通过在2'-位的二氟卡宾型反应引入二氟环丙烷。然后，使用Vorbrüggen方法合成了一系列新颖的2'-脱氧2'-螺二氟环丙烷基核苷类似物。对所有合成的核苷进行表征，然后在体外对丙型肝炎和甲型流感病毒株进行评估。
• A Concise Synthesis of 4‘-Fluoro Nucleosides
  作者：Seongmin Lee、Chayasith Uttamapinant、Gregory L. Verdine

  DOI：10.1021/ol702222z

  日期：2007.11.1

  Various 4'-F nucleosides have been prepared in only two to three steps via sequential bromination and fluorination of ribofuranoses or nucleosides.

  通过呋喃核糖或核苷的连续溴化和氟化，仅用两到三个步骤即可制备各种 4'-F 核苷。
• A Stereoselective Approach to β-<scp>l</scp>-Arabino Nucleoside Analogues: Synthesis and Cyclization of Acyclic 1′,2′-<i>syn</i><i>N</i>,<i>O</i>-Acetals
  作者：Starr Dostie、Michel Prévost、Yvan Guindon

  DOI：10.1021/jo3012754

  日期：2012.9.7

  Reported herein is a novel and versatile strategy for the stereoselective synthesis of unnatural β-l-arabinofuranosyl nucleoside analogues from acyclic N,OTMS-acetals bearing pyrimidine and purine bases. These unusual acetals undergo a C1′ to C4′ cyclization where the OTMS of the acetal serves as the nucleophile to generate 2′-oxynucleosides with complete retention of configuration at the C1′ acetal

  本文报道的是的立体选择性合成的新颖和通用的策略不自然β-升-arabinofuranosyl核苷类似物从非环状Ñ，OTMS -acetals轴承嘧啶和嘌呤碱基。这些不寻常的缩醛经过C1'至C4'环化，其中缩醛的OTMS充当亲核试剂，生成2'-氧核苷，并完全保留了C1'缩醛中心的构型。Ñ，OTMS被非对映选择性甲硅烷基化由核碱基的添加在MgBr的存在下获得到非环状polyalkoxyaldehydes -acetals 2 ·OET 2。该策略报告是通过提供不自然的立体选择性访问寻址重要的合成挑战升核苷从容易访问的池起始d -sugars和，重要的是，通过允许在空间上具有挑战性的1'，2'-的形成CIS核苷。从易于获得的D-木糖以7-8个步骤合成了各种各样的核苷类似物。
• Synthesis of 2′-C-α-Methyl-2′,3′-dideoxynucleosides
  作者：Indrajit Giri、Pascal J. Bolon、Chung K. Chu

  DOI：10.1080/07328319608002379

  日期：1996.1

  A general method for the synthesis of 2'-C-alpha-methyl-2',3'-dideoxynucleosides is presented. Stereofacial selectivity of the 2-C-methylation reaction of gamma-lactone has been investigated, in which the presence of a bulky group at the 5-hydroxymethyl produced the alpha-isomer as a major product. During glycosylation, the alpha-methyl group directed the formation of nucleosides in favor of the beta-isomer. This methodology is applied to the synthesis of some new pyrimidine and purine nucleosides.
• Azymah, Muhammad; Chavis, Claude; Lucas, Marc, Journal of the Chemical Society. Perkin transactions I, 1991, # 6, p. 1561 - 1563
  作者：Azymah, Muhammad、Chavis, Claude、Lucas, Marc、Imbach, Jean-Louis

  DOI：——

  日期：——