8,2'-S-cyclo-adenosine | 16667-76-8

• 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: 8,2'-S-cyclo-adenosine
• 英文别名: 8,2'-thioanhydroadenosine；(6aS)-4-amino-8t-hydroxymethyl-(6ar,9ac)-6a,7,8,9a-tetrahydro-furo[2',3':4,5]thiazolo[3,2-e]purin-7c-ol；8,2'-sulfanediyl-arabino-2'-deoxy-adenosine；(11S,12R,13R,15R)-6-amino-13-(hydroxymethyl)-14-oxa-10-thia-1,3,5,8-tetrazatetracyclo[7.6.0.02,7.011,15]pentadeca-2,4,6,8-tetraen-12-ol
• CAS: 16667-76-8
• 化学式: C₁₀H₁₁N₅O₃S
• 分子量: 281.295
• InChiKey: XNCLSSKPEQWMAM-FJFJXFQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  145
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  8,2'-S-cyclo-adenosine 在 次氯酸叔丁酯 作用下， 以 甲醇 为溶剂， 生成 (6aS)-4-amino-8t-hydroxymethyl-6t-oxo-(6ar,9ac)-6a,7,8,9a-tetrahydro-6H-6λ4-furo[2',3':4,5]thiazolo[3,2-e]purin-7c-ol
  参考文献：
  名称：

  核苷和核苷酸的研究—LXI：嘌呤环核苷23腺嘌呤s-环核苷亚砜的合成

  摘要：

  用以下方法将8,2'-脱水-8-巯基-9-β-d-阿拉伯呋喃糖腺嘌呤，8,3'-脱水-8-巯基-9-β-d-木呋喃糖基腺嘌呤和8,5'-8-巯基腺苷氧化N-溴代琥珀酰亚胺，次氯酸叔丁酯或过甲酸变成它们的8-亚砜。在前两种情况下，亚砜的构型确定为S。在8，5'-环核苷的情况下，获得了S-和R-化合物。记录了这些亚砜的UV，NMR和CD光谱。

  DOI：

  10.1016/0040-4020(76)80019-1
• 作为产物：
  描述：

  N,N,5'-O-tribenzoyl-8,2'-S-cycloadenosine 3'-phosphate 在 氨 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 192.0h， 生成 8,2'-S-cyclo-adenosine
  参考文献：
  名称：

  Polynucleotides. LXI. Synthesis and properties of dinucleoside monophosphates containing 8,2'-S-cycloadenosine and 8,2'-S-cycloinosine residues. Sequence dependency of the stability of the stacking conformation.

  摘要：

  合成了三种含有8,2'-去氧-8-硫-9-β-D-阿拉伯呋喃糖基腺嘌呤(As)及其次黄嘌呤衍生物(Is)的二核苷酸单磷酸盐：AspIs, IspAs和IspIs。通过紫外吸收、圆二色性和氢核磁共振测量对其性质进行检验，并与已知呈左手堆积构象的AspAs的性质进行比较，结果表明所有这些二聚体均呈左手堆积构象，堆积程度的顺序为AspAs≈IspAs>AspIs≈IspIs。这种稳定性的序列依赖性可以用左手堆积中碱基重叠的方式来解释。类似的解释可能也适用于相应天然二聚体右手堆积中的序列依赖性。

  DOI：

  10.1248/cpb.28.3621

文献信息

• New Purine Derivatives as Efficient Preparation of Nucleoside Analogs via Alkylation
  作者：Kirill A. Lukin、Chengxi Yang、John R. Bellettini、B. A. Narayanan

  DOI：10.1080/15257770008035027

  日期：2000.4

  New diazabicycloundecenium and phosphazenium derivatives of purines are introduced for mild and efficient preparation of nucleoside analogs via in situ alkylation. Diazabicycloundecenium salts of purines were obtained directly as a result of an unusual reaction between two corresponding amino compounds.

  引入了新的嘌呤二氮杂双环烯鎓和磷氮烯鎓衍生物，用于通过原位烷基化温和有效地制备核苷类似物。由于两个相应的氨基化合物之间发生异常反应，因此直接获得了嘌呤的二氮杂双环ce盐。
• Studies of Nucleosides and Nucleotides. XXXII. Purine Cyclonucleosides. 3. Synthesis of 2'-Deoxy- and 3'-Deoxyadenosine from Adenosine
  作者：Morio Ikehara、Hiroshi Tada

  DOI：10.1248/cpb.15.94

  日期：——

  5'-O-Acetyl-8-bromo-2', 3'-O-isopropylideneadenosine was obtained either by bromination of 5'-O-acetyl-2', 3'-O-isopropylideneadenosine with N-bromoacetamide or by bromination of 2', 3'-O-isoropylideneadenosine followed by acetylation. 5'-O-Acetyl-8-bromoadenosine, obtained by the formic acid hydrolysis of the isopropylidene group, was tosylated to afford 2'-tosyl-, 3'-tosyl- and 2', 3'-di-O-tosyl-5'-O-acetyl-8-bromoadenosine. Reaction of these tosylates with thiourea followed by deacetylation gave 8, 2'-anhydro-8-mercapto-9-β-D-arabinofuranosyladenine, 8, 3'-anhydro-8-mercapto-9-β-D-xylofuranosyladenine and 8, 2'-anhydro-8-mercapto-3'-O-tosyl-9-β-D-arabinosyladenine, respectively. Desulfurization of 8, 2'-and 8, 3'-anhydro derivatives gave 2'-deoxy- and 3'-deoxyadenosine (Cordycepin).

  5'-O-乙酰基-8-溴-2', 3'-O-异亚丙基腺苷是通过 5'-O-乙酰基-2', 3'-O-异亚丙基腺苷与 N-溴乙酰胺溴化或 2',3'-O-异亚丙基腺苷溴化后乙酰化得到的。5'-O-Acetyl-8-bromoadenosine 由异亚丙基的甲酸水解得到，经对甲苯磺酰化可得到 2'-甲苯磺酰-、3'-甲苯磺酰-和 2'，3'-二-O-甲苯磺酰-5'-O-乙酰基-8-溴腺苷。将这些对甲苯磺酸盐与硫脲反应，然后进行脱乙酰化，分别得到 8，2'-脱水-8-巯基-9-β-D-阿拉伯呋喃糖基腺嘌呤、8，3'-脱水-8-巯基-9-β-D-氧代呋喃糖基腺嘌呤和 8，2'-脱水-8-巯基-3'-O-对甲苯磺酰基-9-β-D-阿拉伯呋喃糖基腺嘌呤。对 8，2'-和 8，3'-脱氢衍生物进行脱硫处理，可得到 2'-脱氧腺苷和 3'-脱氧腺苷（虫草素）。
• Synthesis of Nucleotides from 8,2′-Thioanhydropurine Nucleosides
  作者：Kelvin K. Ogilvie、Lewis A. Slotin

  DOI：10.1139/v73-359

  日期：1973.7.15

  The 5′-mono and diphosphates of the common 8,2′-thioanhydropurine nucleosides have been prepared and studied with 5′-nucleotidase. alkaline phosphatase, and adenylate kinase. Procedures for the preparation of protected anhydronucleosides and their incorporation into dianhydronucleoside monophosphates have been developed. These nucleotides have been found to be completely resistant to spleen and snake

  常见的 8,2'-硫代脱水嘌呤核苷的 5'-单磷酸酯和二磷酸酯已被制备并用 5'-核苷酸酶进行了研究。碱性磷酸酶和腺苷酸激酶。已开发出制备受保护的脱水核苷并将其掺入二脱水核苷单磷酸酯的方法。已发现这些核苷酸对脾脏和蛇毒磷酸二酯酶具有完全抗性，但很容易与雷尼镍一起转化为天然的 2'-脱氧核苷酸。
• Ikehara, Moriko; Uesugi, Seiichi; Shida, Toshio, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 1, p. 189 - 197
  作者：Ikehara, Moriko、Uesugi, Seiichi、Shida, Toshio

  DOI：——

  日期：——
• Polynucleotides. 33. Synthesis and properties of the dinucleoside monophosphates containing adenine S-cyclonucleosides and adenosine. Factors determining the stability and handedness of the stacking conformation in a dinucleoside monophosphate
  作者：Seiichi Uesugi、Junichi Yano、Emi Yano、Morio Ikehara

  DOI：10.1021/ja00449a049

  日期：1977.3