(3aS,4R,6aR)-4-((4R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxolane | 596103-04-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,4R,6aR)-4-((4R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxolane
• 英文别名: (3aS,4R,6aR)-4-((4R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrothieno[3,4-d][1,3]dioxole；1,4-anhydro-2,3,5,6-di-O-isopropylidene-4-thio-D-allitol；(3aS,4R,6aR)-4-((4R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxole；(3aS,4R,6aR)-4-((4R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxole；(3aS,4R,6aR)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrothieno[3,4-d][1,3]dioxole
• CAS: 596103-04-7
• 化学式: C₁₂H₂₀O₄S
• 分子量: 260.354
• InChiKey: QDMSJAPLEVJBRD-XFWSIPNHSA-N

物化性质

• 沸点：
  337.7±42.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aS,4R,6aR)-4-((4R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxolane 在 吡啶 、 lead(IV) acetate 、 sodium tetrahydroborate 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 17.42h， 生成 benzoic acid (3aS,4R,6aR)-6-acetoxy-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-ylmethyl ester
  参考文献：
  名称：

  N⁶-Substituted D-4‘-Thioadenosine-5‘-methyluronamides:  Potent and Selective Agonists at the Human A₃ Adenosine Receptor

  摘要：

  4'-Thio analogues 3-5 of Cl-IB-MECA (2) (K-i = 1.0 +/- 0.2 nM at the human A(3) adenosine receptor) were synthesized from D-gulono-gamma-lactone via 4-thioribosyl acetate 14 as the key intermediate. All synthesized 4-thionucleosides exhibited higher binding affinity to the human A(3) adenosine receptor than Cl-IB-MECA, among which 4 showed the most potent binding affinity (K-i = 0.28 +/- 0.09 nM). 4 was also selective for A(3) vs human A(1) and human A(2A) receptors by 4800- and 36000-fold, respectively.

  DOI：

  10.1021/jm034098e
• 作为产物：
  描述：

  2,3:5,6-di-O-isopropylidene-D-gulitol 在 吡啶 、 sodium sulfide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 (3aS,4R,6aR)-4-((4R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxolane
  参考文献：
  名称：

  与天然葡萄糖苷酶抑制剂salacinol相关的硒和锍离子的设计和合成

  摘要：

  合成了天然存在的葡萄糖苷酶抑制剂 salacinol 的四个系列类似物，用于使用不同的糖苷酶进行结构-活性研究。目标两性离子复合...

  DOI：

  10.1139/v06-100

文献信息

• Purine nucleosides
  申请人：Jeong Shin Lak

  公开号：US20050256143A1

  公开（公告）日：2005-11-17

  Disclosed are purine nucleoside compounds that are selective to A 3 adenosine receptors and are useful for the treatment of cancer and inflammatory diseases. The compounds are shown by the following general formula (I), including isomers thereof: wherein X is sulfur or oxygen; R 1 is hydrogen, alkyl, benzyl, halobenzyl, or phenylalkyl; R 2 is hydrogen, halogen, alkoxy, alkenyl, alkynyl, alkylthio, or thio; R 3 and R 3′ are hydrogen, hydroxyalkyl, alkoxycarbonyl, or alkylaminocabonyl, whereas R 3 and R 3 ′ do not have identical substituents simultaneously; and R 4 is hydrogen or alkyl. Also disclosed are a pharmaceutical composition comprising a compound of formula (I), an isomer, or its pharmacologically acceptable salt as an active ingredient and a method for preventing or treating various diseases, state, or condition, including asthma, inflammation, cerebral ischemia, heart diseases, and cancer.

  揭示了对A3腺苷受体具有选择性的嘌呤核苷化合物，可用于治疗癌症和炎症性疾病。所述化合物由以下一般式（I）表示，包括其异构体：其中X为硫或氧；R1为氢、烷基、苄基、卤代苄基或苯基烷基；R2为氢、卤素、烷氧基、烯基、炔基、烷基硫基或硫基；R3和R3'为氢、羟基烷基、烷氧羰基或烷基氨羰基，其中R3和R3'不同时具有相同的取代基；R4为氢或烷基。还揭示了一种包含一种式（I）的化合物、其异构体或其药理学上可接受的盐作为活性成分的药物组合物，以及一种用于预防或治疗各种疾病、状态或症状的方法，包括哮喘、炎症、脑缺血、心脏疾病和癌症。
• N⁶-Substituted D-4‘-Thioadenosine-5‘-methyluronamides:  Potent and Selective Agonists at the Human A₃ Adenosine Receptor
  作者：Lak Shin Jeong、Dong Zhe Jin、Hea Ok Kim、Dae Hong Shin、Hyung Ryong Moon、Prashantha Gunaga、Moon Woo Chun、Yong-Chul Kim、Neli Melman、Zhan-Guo Gao、Kenneth A. Jacobson

  DOI：10.1021/jm034098e

  日期：2003.8.1

  4'-Thio analogues 3-5 of Cl-IB-MECA (2) (K-i = 1.0 +/- 0.2 nM at the human A(3) adenosine receptor) were synthesized from D-gulono-gamma-lactone via 4-thioribosyl acetate 14 as the key intermediate. All synthesized 4-thionucleosides exhibited higher binding affinity to the human A(3) adenosine receptor than Cl-IB-MECA, among which 4 showed the most potent binding affinity (K-i = 0.28 +/- 0.09 nM). 4 was also selective for A(3) vs human A(1) and human A(2A) receptors by 4800- and 36000-fold, respectively.
• PURINE NUCLEOSIDES
  申请人：THE GOVERNMENT OF THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：EP1578758A2

  公开（公告）日：2005-09-28
• US7199127B2
  申请人：——

  公开号：US7199127B2

  公开（公告）日：2007-04-03
• US8389565B2
  申请人：——

  公开号：US8389565B2

  公开（公告）日：2013-03-05