(2R,3S,4S,5R)-2-(benzoyloxymethyl)-5-(4-thioxo-3,4-dihydrothieno[3,4-b]pyrimidin-7-yl)tertahydrofuran-3,4-diyl dibenzoate | 152615-87-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,5R)-2-(benzoyloxymethyl)-5-(4-thioxo-3,4-dihydrothieno[3,4-b]pyrimidin-7-yl)tertahydrofuran-3,4-diyl dibenzoate
• 英文别名: 7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)thieno<3,4-d>pyrimidine-4(3H)-thione；7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)thieno[3,4-d]pyrimidine-4(3H)-thione；[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(4-sulfanylidene-1H-thieno[3,4-d]pyrimidin-7-yl)oxolan-2-yl]methyl benzoate
• CAS: 152615-87-7
• 化学式: C₃₂H₂₄N₂O₇S₂
• 分子量: 612.684
• InChiKey: WHXJSQWQJUYMRV-MIRJVGOZSA-N

物化性质

• 沸点：
  763.8±70.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  43
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  173
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R)-2-(benzoyloxymethyl)-5-(4-thioxo-3,4-dihydrothieno[3,4-b]pyrimidin-7-yl)tertahydrofuran-3,4-diyl dibenzoate 在 sodium hydroxide 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 4-(methylthio)-7-β-D-ribofuranosylthieno<3,4-d>pyrimidine
  参考文献：
  名称：

  一些新的噻吩并[3,4- d ]嘧啶及其C-核苷的合成

  摘要：

  描述了几种新的噻吩并[3,4- d ]嘧啶C-核苷5-8的合成。通过将糖15与甲基4-（甲酰基氨基）噻吩-3缩合，可以以显着提高的收率获得作为已知的5-核糖基化的4-（甲酰胺基氨基）噻吩-3-羧酸甲酯关键中间体20的混合物。在氯化锡存在下，在60°C的硝基甲烷中将羧酸19羧酸酯化。尝试以制备C-7核糖基化化合物21由双环基的直接缩合β 10与15给出而不是N-1核糖基化的核苷16。描述了相应的和以前未知的噻吩并[3,4- d ]嘧啶碱12和13的合成，以及对4-甲硫基衍生物12的稳定性研究。初步的生物学研究表明，腺苷类似物7是几种哺乳动物肿瘤细胞系的有效生长抑制剂。

  DOI：

  10.1002/jhet.5570300240
• 作为产物：
  描述：

  3-氨基噻吩-4-羧酸甲酯盐酸盐 在 盐酸 、 tetraphosphorus decasulfide 、 sodium acetate 、 四氯化锡 、 三乙胺 作用下， 以 吡啶 、 甲醇 、 硝基甲烷 、 乙醇 、 氯仿 、 水 为溶剂， 反应 36.67h， 生成 (2R,3S,4S,5R)-2-(benzoyloxymethyl)-5-(4-thioxo-3,4-dihydrothieno[3,4-b]pyrimidin-7-yl)tertahydrofuran-3,4-diyl dibenzoate
  参考文献：
  名称：

  Emissive RNA Alphabet

  摘要：

  A fluorescent ribonucleoside alphabet consisting of highly emissive purine ((th)A, (th)G) and pyrimidine (U-th, C-th) analogues, all derived from thieno[3,4-d]pyrimidine as the heterocyclic nucleus, is described. Structural and biophysical analyses demonstrated that the emissive analogues are faithful isomorphic nucleoside surrogates. Photophysical analysis established that the nucleosides offer highly desirable qualities, including visible emission, high quantum yield, and responsiveness to environmental perturbations, traits entirely lacking in their native counterparts.

  DOI：

  10.1021/ja206095a

文献信息

• Enzymatic Interconversion of Isomorphic Fluorescent Nucleosides: Adenosine Deaminase Transforms an Adenosine Analogue into an Inosine Analogue
  作者：Renatus W. Sinkeldam、Lisa S. McCoy、Dongwon Shin、Yitzhak Tor

  DOI：10.1002/anie.201307064

  日期：2013.12.23

  Adenosine deaminase (ADA), a major enzyme involved in purine metabolism, converts an isomorphic fluorescent analogue of adenosine (thA) into an isomorphic inosine analogue (thI), which possesses distinct spectral features, allowing one to monitor the enzyme‐catalyzed reaction and its inhibition in real time. The utility of this sensitive fluorescence‐monitored transformation for the high‐throughput

  腺苷脱氨酶(ADA) 是一种参与嘌呤代谢的主要酶，可将腺苷 ( th A) 的同构荧光类似物 ( th A) 转化为同构肌苷类似物 ( th I)，该类似物具有独特的光谱特征，可用于监测酶催化反应并实时抑制。证明了这种灵敏的荧光监测转换在 ADA 抑制剂的高通量检测和分析中的实用性。
• Azetidines‐Containing Fluorescent Purine Analogs: Synthesis and Photophysical Properties
  作者：Kaivin Hadidi、Yitzhak Tor

  DOI：10.1002/chem.202200765

  日期：2022.5.25

  Analogues of N,N-dimethyladenine exploiting both thieno-and isothiazolo-pyrimidine cores were modified with 3-subsituted azetidines to yield visibly emissive and responsive fluorophores. Ribosylation of the difluoroazetidino-modified nucleobase yielded an emissive nucleoside that displayed a substantially lower emission quantum yield in water, compared to the precursor nucleobase. The impact of the

  利用噻吩并和异噻唑并嘧啶核的N , N-二甲基腺嘌呤的类似物用 3-取代的氮杂环丁烷进行修饰，以产生明显的发射性和响应性荧光团。与前体核碱基相比，二氟氮杂环丁基修饰的核碱基的核糖基化产生了一种发射核苷，其在水中的发射量子产率显着降低。分析了糖部分对荧光核苷的光物理特征的影响，荧光核苷通常被认为是非发色和光物理良性的功能。
• Synthesis of some new thieno[3,4-<i>d</i>]pyrimidines and their<i>C</i>-nucleosides
  作者：Shirish A. Patil、Brian A. Otter、Robert S. Klein

  DOI：10.1002/jhet.5570300240

  日期：1993.3

  The synthesis of several new thieno[3,4-d]pyrimidine C-nucleosides 5-8 is described. The known 5-ribosyl-ated methyl 4-(formylamino)thiophene-3-carboxylate key intermediate 20 was obtained as a mixture of anomers in significantly improved yield by condensation of the sugar 15 with methyl 4-(formylamino)thio-phene-3-carboxylate 19 in nitromethane at 60° in the presence of stannic chloride. Attempts

  描述了几种新的噻吩并[3,4- d ]嘧啶C-核苷5-8的合成。通过将糖15与甲基4-（甲酰基氨基）噻吩-3缩合，可以以显着提高的收率获得作为已知的5-核糖基化的4-（甲酰胺基氨基）噻吩-3-羧酸甲酯关键中间体20的混合物。在氯化锡存在下，在60°C的硝基甲烷中将羧酸19羧酸酯化。尝试以制备C-7核糖基化化合物21由双环基的直接缩合β 10与15给出而不是N-1核糖基化的核苷16。描述了相应的和以前未知的噻吩并[3,4- d ]嘧啶碱12和13的合成，以及对4-甲硫基衍生物12的稳定性研究。初步的生物学研究表明，腺苷类似物7是几种哺乳动物肿瘤细胞系的有效生长抑制剂。
• Emissive RNA Alphabet
  作者：Dongwon Shin、Renatus W. Sinkeldam、Yitzhak Tor

  DOI：10.1021/ja206095a

  日期：2011.9.28

  A fluorescent ribonucleoside alphabet consisting of highly emissive purine ((th)A, (th)G) and pyrimidine (U-th, C-th) analogues, all derived from thieno[3,4-d]pyrimidine as the heterocyclic nucleus, is described. Structural and biophysical analyses demonstrated that the emissive analogues are faithful isomorphic nucleoside surrogates. Photophysical analysis established that the nucleosides offer highly desirable qualities, including visible emission, high quantum yield, and responsiveness to environmental perturbations, traits entirely lacking in their native counterparts.