2,3,4-呋喃三醇,四氢-,三乙酸酯,(3R,4R)- | 186495-36-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2,3,4-呋喃三醇,四氢-,三乙酸酯,(3R,4R)-
• 英文名称: 1,2,3-tri-O-acetyl-D-erythrofuranose
• 英文别名: 1,2,3-tri-O-acetyl-D-erythrose；D-erythrose 1,2,3-triacetate；[(3R,4R)-4,5-diacetyloxyoxolan-3-yl] acetate
• CAS: 186495-36-3
• 化学式: C₁₀H₁₄O₇
• 分子量: 246.217
• InChiKey: XUFJVJSLEQLSTG-MGRQHWMJSA-N

物化性质

• 沸点：
  306.8±42.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3,4-呋喃三醇,四氢-,三乙酸酯,(3R,4R)- 在 四丁基氟化铵 、 四氯化锡 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 75.25h， 生成 N⁴-benzoyl-1-[2-O-(2,3-di-O-acetyl-β-D-erythrofuranosyl)-β-D-ribofuranosyl]cytosine
  参考文献：
  名称：

  Oligonucleotides Containing Disaccharide Nucleosides

  摘要：

  Disaccharide nucleosides with 2'-O-(D-arabinofuranosyl), 2'-O-(L-arabinofuranosyl), 2'-O-(D-ribopyranosyl), 2'-O-(D-erythrofuranosyl), and 2'-O-(5-azido-5-deoxy-D-ribofuranosyl) substituents were synthesized. These modified nucleosides were incorporated into oligonucleotides (see Table). Single substitution resulted in a DeltaT(m) of +0.5 to -1.4 degrees for DNA/RNA and a DeltaT(m) of - 0.8 to -4.7 degrees for DNA/DNA duplexes. These disaccharide nucleosides can be well accommodated in RNA/DNA duplexes, and the presence of a NH2- C(5") group has a beneficial effect on duplex stability.

  DOI：

  10.1002/1522-2675(20010815)84:8<2387::aid-hlca2387>3.0.co;2-f
• 作为产物：
  描述：

  D-erythronolactone acetonide 在 硫酸 、 二异丁基氢化铝 作用下， 以 水 、 甲苯 为溶剂， 反应 22.83h， 生成 2,3,4-呋喃三醇,四氢-,三乙酸酯,(3R,4R)-
  参考文献：
  名称：

  A2A 및 A3 아데노신 수용체에 길항작용을 하는 아데노신 유도체 및 이의 제조방법

  摘要：

  本发明涉及在胺的碳2、碳8和碳6和/或碳9上引入取代基、可作为A和A腺苷受体拮抗剂的腺苷衍生物、包含其的药物组合物及其制备方法，其中所述腺苷衍生物可调节A或A腺苷受体的活性，从而有效预防或治疗所述受体参与的脑部疾病、心血管疾病、睡眠障碍、炎症和免疫系统疾病等。

  公开号：

  KR20220134465A

文献信息

• SYNTHESIS, STRUCTURE, AND CONFORMATION OF ANTI-TUMOR AGENTS IN THE SOLID AND SOLUTION STATES: HYDROXYL DERIVATIVES OF FTORAFUR
  作者：David M. Stokes、Brajeswar Paul、James L. Alderfer、Robert M. Wollman、Thamarapu Srikrishnan

  DOI：10.1081/ncn-120016611

  日期：2002.12.31

  distance and vice versa. The sugar rings show a wide variation of conformations ranging from C2'-endo through C3'-endo to C4'-exo. The crystal structures are stabilized by hydrogen bonds involving the base nitrogen atom N3 and the hydroxyl oxygen atoms of the sugar rings as donors and the keto oxygens O2 and O4 of the base and the hydroxyl oxygen atoms O2' and O3' as acceptors. The NMR studies were carried

  嘧啶抗代谢药Ftorafur [FT; 5-氟-1-（四氢-2-呋喃基）尿嘧啶]在几种腺癌中显示出显着的抗肿瘤活性，其活性谱与5-氟尿嘧啶（5-FU）相似，但毒性较小。它被认为是前药，可以作为5-FU的长效制剂，因此这两种药物表现出相似的化学治疗活性。当将羟基引入四氢呋喃部分时，呋喃糠在动物和人类中代谢。这些代谢物也被认为与氟呋喃一样有活性，但毒性不如5-FU。羟基衍生物：2'-羟基呋喃糠（III），3'-羟基呋喃糠（IV）和2'，3' 合成了-dihydroxyftorafur（II），并在我们的实验室中对这些羟基衍生物进行了X射线和NMR研究，以研究Ftorafur及其代谢物在固体和溶液状态下的结构和构象特征。用在CAD-4衍射仪上收集的数据进行X射线晶体学研究。在PDP 11/34和Microvax计算机上使用Enraf-Nonius的SDP晶体学软件包对结构进行了解析和改进。所有研
• 5-Aza-7-deazapurine derivatives for treating Flaviviridae
  申请人：Gosselin Gilles

  公开号：US20060040944A1

  公开（公告）日：2006-02-23

  This invention is directed to a method for treating a host, especially a human, infected with hepatitis C, flavivirus and/or pestivirus, comprising administering to that host an effective amount of an anti-flavivirus or anti-pestivirus, biologically active compound has a 5-aza-7-deazapurine moiety. The 5-aza-7-deazapurine moiety may be substituted or unsubstituted, and may comprise a nucleoside analogue, or a salt or prodrug thereof. The compound of the present invention may be administered alone or in combination with another anti-hepatitis C, anti-flavivirus and/or anti-pestivirus agent.

  本发明涉及一种治疗宿主，特别是感染丙型肝炎、黄热病毒和/或瘟疫病毒的人类的方法，包括向该宿主施用有效量的具有5-aza-7-deazapurine基团的抗黄热病毒或抗瘟疫病毒生物活性化合物。5-aza-7-deazapurine基团可以是取代或未取代的，并且可以包括核苷类似物或其盐或前药。本发明的化合物可以单独或与另一种抗丙型肝炎、抗黄热病毒和/或抗瘟疫病毒药物组合使用。
• ADENOSINE DERIVATIVE HAVING ANTAGONISTIC ACTION ON A2A AND A3 ADENOSINE RECEPTORS AND METHOD FOR PREPARING SAME
  申请人：Future Medicine Co., Ltd.

  公开号：EP4296273A1

  公开（公告）日：2023-12-27

  The present invention relates to: an adenosine derivative capable of acting as an antagonist on A2A and A3 adenosine receptors through the introduction of substituents into the 2nd and 8th carbons and 6th and/or 9th amine(s); a pharmaceutical composition including the same; and a method for preparing the same. The adenosine derivative regulates the activity of an A2A or A3 adenosine receptor, and thus can effectively prevent or treat brain diseases, cardiovascular diseases, sleep disorders, inflammation, immune system diseases and the like in which the receptors are involved.

  本发明涉及以下内容：一种腺苷衍生物，其通过在2号和8号碳以及6号和/或9号氨基引入取代基，能够作为A2A和A3腺苷受体的拮抗剂；包含该衍生物的药物组合物；以及制备该衍生物的方法。所述腺苷衍生物调节A2A或A3腺苷受体的活性，因此能够有效预防或治疗涉及这些受体的脑疾病、心血管疾病、睡眠障碍、炎症、免疫系统疾病等。
• Structure-Activity Relationships of 9-Alkyladenine and Ribose-Modified Adenosine Derivatives at Rat A3 Adenosine Receptors
  作者：Kenneth A. Jacobson、Suhaib M. Siddiqi、Mark E. Olah、Xiao-duo Ji、Neli Melman、Kamala Bellamkonda、Yacov Meshulam、Gary L. Stiles、Hea O. Kim

  DOI：10.1021/jm00010a017

  日期：1995.5

  9-Alkyladenine derivatives and ribose-modified N-6-benzyladenosine derivatives were synthesized in an effort to identify selective ligands for the rat A(3) adenosine receptor and leads for the development of antagonists. The derivatives contained structural features previously determined to be important for A(3) selectivity in adenosine derivatives, such as an N-6-(3-iodobenzyl) moiety, and were further substituted at the 2-position with halo, amino, or thio groups. Affinity was determined in radioligand binding assays at rat brain A(3) receptors stably expressed in Chinese hamster ovary (CHO) cells, using [I-125]]AB-MECA (N-6-(4-amino-3-iodobenzyl)adenosine-5'-(N-methyluronamid)), and at rat brain A(1) and A(2a) receptors using [H-3]-N-6-PIA ((R)-N-6-phenylisopropyladenosine) and [H-3]CGS 21680 (2-[[[4-(2-carboxyethyl)-phenyl]ethyl]amino]-5'-(N-ethylcarbamoyl)adenosine), respectively. A series of N-6-(3-iodobenzyl) 2-amino derivatives indicated that a small 2-alkylamino group, e.g., methylamino, was favored at A(3) receptors. N-6-(3-Iodobenzyl)-9-methyl-2-(methylthio)adenine was 61-fold more potent than the corresponding 2-methoxy ether at A(3) receptors and of comparable affinity at A(1) and A(2a) receptors, resulting in a 3-6-fold selectivity for A(3) receptors. A pair of chiral N-6-(3-iodobenzyl) 9-(2,3-dihydroxypropyl) derivatives showed stereoselectivity, with the R-enantiomer favored at A(3) receptors by 5.7-fold. 2-Chloro-9-(beta-D-erythrofuranosyl)-N-6-(3-iodobenzyl)adenine had a K-i value at A(3) receptors of 0.28 mu M. 2-Chloro-9-[2-amino-2,3-dideoxy-beta-D-5-(methylcarbamoyl)-arabinofuranosyl]-N-6-(3-iodobenzyl)adenine was moderately selective for A(1) and A(3) VS A(2a) receptors. A 3'-deoxy analogue of a highly A(3)-selective adenosine derivative retained selectivity in binding and was a full agonist in the inhibition of adenylyl cyclase mediated via cloned rat A(3) receptors expressed in CHO cells. The 3'-OH and 4'-CH2OH groups of adenosine are not required for activation at A(3) receptors. A number of 2',3'-dideoxyadenosines and 9-acyclic-substituted adenines appear to inhibit adenylyl cyclase at the allosteric ''P'' site.
• (13C)-Substituted erythronucleosides: synthesis and conformational analysis by proton and carbon-13 NMR spectroscopy
  作者：Paul C. Kline、Anthony S. Serianni

  DOI：10.1021/jo00032a032

  日期：1992.3

  The erythronucleosides, 9-beta-D-erythrofuranosyladenine (1b), 1-beta-D-erythrofuranosylcytosine (2b), 9-beta-D-erythrofuranosylguanine (3b), and 1-beta-D-erythrofuranosyluracil (4b), were synthesized with and without C-13-substitution at C1' of the furanose ring. 75-MHz C-13 and 620-MHz H-1 NMR spectra of 1-4b were interpreted, in the latter case with the assistance of spectral simulation, and H-1-H-1, C-13-H-1, and C-13-C-13 spin couplings were used to assess furanose conformation. 3J(HH) data in (H2O)-H-2 were treated by computer to determine the preferred north and south conformers, their puckering amplitudes, and their mole fractions in solution, and J(CH) data were used to complement this analysis. A similar treatment of spin coupling data for the corresponding ribonucleosides 1-4a was also conducted to permit a comparison of furanose conformations in both series of compounds. Results show that the removal of the exocyclic hydroxymethyl group from 1-4a, giving 1-4b, significantly enhances the proportion of south conformers in aqueous ((H2O)-H-2) solution.