3-deoxy-1,2-isopropylidene-α-D-ribofuronic acid | 163042-94-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-deoxy-1,2-isopropylidene-α-D-ribofuronic acid
• 英文别名: (3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carboxylic acid；(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carboxylic acid
• CAS: 163042-94-2
• 化学式: C₈H₁₂O₅
• 分子量: 188.18
• InChiKey: YCBCOSFVWUHSQS-HBPOCXIASA-N

物化性质

• 沸点：
  306.8±42.0 °C(predicted)
• 密度：
  1.282±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-deoxy-1,2-isopropylidene-α-D-ribofuronic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 methyl 3-deoxy-1,2-isopropylidene-α-D-ribofuronamide
  参考文献：
  名称：

  Structure-Activity Relationships of 9-Alkyladenine and Ribose-Modified Adenosine Derivatives at Rat A3 Adenosine Receptors

  摘要：

  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.

  DOI：

  10.1021/jm00010a017
• 作为产物：
  描述：

  3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 在 ruthenium(IV) oxide 、 sodium tetrahydroborate 、 sodium periodate 、 乙醇 、 溶剂黄146 作用下， 以 甲醇 、 氯仿 、 水 、 乙腈 为溶剂， 反应 34.0h， 生成 3-deoxy-1,2-isopropylidene-α-D-ribofuronic acid
  参考文献：
  名称：

  TLR7 AGONISTS

  摘要：

  本发明涉及根据式I的TLR7激动剂及其在治疗癌症和传染病等疾病中的应用。

  公开号：

  US20210155652A1

文献信息

• Stereoselective synthesis of the viridiofungin analogue NA808 from a chiral tetrahydrofuran-carboxylic acid
  作者：Masatoshi Murakata、Takuma Ikeda

  DOI：10.1039/c7ob01608e

  日期：——

  The viridiofungin analogue NA808 was synthesized by the stereoselective Ireland–Claisen rearrangement of dienylmethyl ester, regioselective bromolactonization of β-divinylpropanoic acid and retro-bromolactonization.

  viridiofunginung类似物NA808是通过二烯基甲酯的选择性爱尔兰-克莱森重排，β-二乙烯基丙酸的区域选择性溴内酯化和反溴内酯化合成的。
• US9441008B2
  申请人：——

  公开号：US9441008B2

  公开（公告）日：2016-09-13
• [EN] TLR7 AGONISTS<br/>[FR] AGONISTES DE TLR7
  申请人：PRIMMUNE THERAPEUTICS INC

  公开号：WO2021108649A1

  公开（公告）日：2021-06-03

  The present invention relates to TLR7 agonists according to Formula (I) and their use in the treatment of diseases such as cancer and infectious disease.
• 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.
• TLR7 AGONISTS
  申请人：Primmune Therapeutics, Inc.

  公开号：US20210155652A1

  公开（公告）日：2021-05-27

  The present invention relates to TLR7 agonists according to Formula I and their use in the treatment of diseases such as cancer and infectious disease.

  本发明涉及根据式I的TLR7激动剂及其在治疗癌症和传染病等疾病中的应用。