2',3'-Di-O-acetyl-5'-S-(fluoromethyl)-5'-thioadenosine | 119771-18-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 2',3'-Di-O-acetyl-5'-S-(fluoromethyl)-5'-thioadenosine
• 英文别名: [(2S,3S,4R,5R)-4-acetyloxy-5-(6-aminopurin-9-yl)-2-(fluoromethylsulfanylmethyl)oxolan-3-yl] acetate
• CAS: 119771-18-5
• 化学式: C₁₅H₁₈FN₅O₅S
• 分子量: 399.403
• InChiKey: MHKHANOAWVIKDF-SDBHATRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  157
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2',3'-Di-O-acetyl-5'-S-(fluoromethyl)-5'-thioadenosine 生成 5'-Deoxy-5'-fluoro-5'-(methylthio)adenosine
  参考文献：
  名称：

  ROBINS, MORRIS J.;WNUK, STANISLAW F., TETRAHEDRON LETT., 29,(1988) N 45, C. 5729-5732

  摘要：

  DOI：
• 作为产物：
  描述：

  5'-氯-5'-脱氧腺苷 在 吡啶 、 diethylaminosulfur trichloride 、 三氯化锑 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2',3'-Di-O-acetyl-5'-S-(fluoromethyl)-5'-thioadenosine
  参考文献：
  名称：

  Fluorination at C5′ of nucleosides. Synthesis of the new class of 5′-fluoro-5′-S-aryl (alkyl) thionucleosides from adenosine.

  摘要：

  DOI：

  10.1016/s0040-4039(00)82174-7

文献信息

• Synthesis of fluorinated derivatives of methionine and 5′-deoxy-5′-(methylthio)-adenosine using the mccarthy transformation of sulfoxides to α-fluoro thioethers
  作者：Janice R. Sufrin、Arthur J. Spiess、Vitauts Alks

  DOI：10.1016/s0022-1139(00)80377-2

  日期：1990.8

  trifluoride (DAST) or dimethylaminosulfur trifluoride (meDAST) yielded N-acetyl-S-(monofluoromethyl)homocysteine methyl ester as the sole fluorinated product. In contrast, treatment of 2′,3′-di-O-acetyl-5′-(methylthio)adenosine sulfoxide with DAST or meDAST unexpectedly produced three novel fluorinated products.

  用二乙基氨基三氟化硫（DAST）或二甲基氨基三氟化硫（meDAST）处理N-乙酰甲硫氨酸亚砜甲酯，得到的N-乙酰基-S-（单氟甲基）高半胱氨酸甲酯是唯一的氟化产物。相反，用DAST或meDAST处理2'，3'-二-O-乙酰基-5'-（甲硫基）腺苷亚砜意外地产生了三种新颖的氟化产物。
• Synthesis and antiproliferative effects of novel 5'-fluorinated analogs of 5'-deoxy-5'-(methylthio)adenosine
  作者：Janice R. Sufrin、Arthur J. Spiess、Debora L. Kramer、Paul R. Libby、Carl W. Porter

  DOI：10.1021/jm00125a012

  日期：1989.5

  5'-Deoxy-5'-[(monofluoromethyl)thio]adenosine (9) and 5'-deoxy-5'-fluoro-5'-(methylthio)adenosine (10), two novel analogues of 5'-deoxy-5'-(methylthio)adenosine (MTA), have been synthesized and evaluated for their substrate and inhibitory activities toward MTA phosphorylase and for their biological effects in L1210 (MTA phosphorylase deficient) and L5178Y (MTA phosphorylase containing) murine leukemia

  5'-脱氧-5'-[（单氟甲基）硫代]腺苷（9）和5'-脱氧-5'-氟-5'-（甲硫基）腺苷（10），这是5'-脱氧-5的两个新类似物已经合成了'-（甲硫基）腺苷（MTA）并评估了它们对MTA磷酸化酶的底物和抑制活性，以及​​它们在L1210（MTA磷酸化酶缺陷）和L5178Y（含MTA磷酸化酶）鼠白血病细胞系中的生物学作用。化合物9是一种有效的MTA磷酸化酶竞争性抑制剂，Ki值为3.3 microM，并且还是一种底物，其活性约为MTA的53％。化合物10对磷酸化酶的抑制作用明显较小，Ki值为141 microM。其底物活性的缺乏归因于快速的非酶降解。在L1210和L5178Y细胞中，9的50％生长抑制浓度（48 h）分别为300和200 microM。对于10，这些各自的值为2和0.7 microM。这些系统中9的初始特征表明，它与MTA的不同之处在于它不充当多胺生物合成途径的产物调节剂。
• Fluorination of 5′-deoxy-5′-(methylthio)adenosine with xenon difluoride provides an expedient synthesis of (fluoromethylthio)adenosine
  作者：Georges Guillerm、Marie Gâtel

  DOI：10.1039/p19940000153

  日期：——

  Fluorination of 5′-deoxy-5′-(fluoromethylthio)adenosine derivatives with xenon difluoride at –60 °C in dichloromethane occurs exclusively at the methylthio position to provide a simple and efficient preparation of 5′-deoxy-5′-(fluoromethylthio)adenosine.

  在–60°C的二氯甲烷中，氟化二氟氙对5'-脱氧-5'-（氟甲硫基）腺苷衍生物的氟化仅在甲硫基位置发生，以提供简单有效的5'-脱氧-5'-（氟甲硫基）制备方法腺苷。
• Nucleic acid related compounds. 79. Efficient conversions of thioethers to .alpha.-fluoro thioethers with DAST or DAST/antimony(III) chloride
  作者：Morris J. Robins、Stanislaw F. Wnuk

  DOI：10.1021/jo00067a009

  日期：1993.7

  Dialkyl or alkyl aryl thioethers, including nucleoside thioethers, undergo virtually quantitative conversion to alpha-fluoro thioethers with (diethylamino)sulfur trifluoride (DAST) in dichloromethane at ambient temperature. Antimony(III) chloride catalyzes the process.
• Nucleic Acid Related Compounds. 80. Synthesis of 5'-S-(Alkyl and aryl)-5'-fluoro-5'-thioadenosines with Xenon Difluoride or (Diethylamido)sulfur Trifluoride, Hydrolysis in Aqueous Buffer, and Inhibition of S-Adenosyl-L-homocysteine hydrolase by derived "Adenosine 5'-Aldehyde" Species
  作者：Morris J. Robins、Stanislaw F. Wnuk、Khairuzzaman B. Mullah、N. Kent Dalley、Chong-Sheng Yuan、Younha Lee、Ronald T. Borchardt

  DOI：10.1021/jo00082a010

  日期：1994.2

  Treatment of 5/-S-(alkyl and aryl)-5'-thioadenosine derivatives 2 with XeF2, or the corresponding sulfoxides 3 with DAST/SbCl3, gave diastereomeric 5'-fluoro compounds which were deprotected to give the 5'-S-(alkyl and aryl)-5'-fluoro-5'-thioadenosine analogues 5. Stereochemistry was established by X-ray crystallography, and F-19 NMR chemical shifts were definitive for configurationally-related 5'-fluoro diastereomers. Sulfoxidation and thermolysis afforded the fluoromethylene analogues with retained relative configuration. The nucleoside 5'-alpha-fluoro thioethers 5 underwent spontaneous hydrolysis in aqueous buffer to give derived ''adenosine 5'-aldehyde'' species which caused potent time-dependent inactivation of S-adenosyl-L-homocysteine hydrolase.