methanesulfonic acid (S)-((4R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-((4S,5S)-5-methanesulfonyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester | 117859-45-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methanesulfonic acid (S)-((4R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-((4S,5S)-5-methanesulfonyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester
• 英文别名: methanesulfonic acid (S)-((4R)-2,2-dimethyl-[1,3]dioxolan-4-yl)((4S,5S)-5-methanesulfonyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)methyl ester；1,4-bis(methanesulphonyl)-2,3:5,6-di-O-isopropylidene-D-gulitol；2,3,5,6-di-O-isopropylidene-1,4-di-O-methansulfonyl-D-gulitol；methanesulfonic acid {(4R)-(2,2-dimethyl[1,3]dioxolan-4-yl)}-{(4S,5S)-(5-methanesulfonyloxymethyl-2,2-dimethyl[1,3]dioxolan-4-yl)}-(S)methyl ester；[(4S,5S)-5-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-methylsulfonyloxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl methanesulfonate
• CAS: 117859-45-7
• 化学式: C₁₄H₂₆O₁₀S₂
• 分子量: 418.486
• InChiKey: GSDSCWGTQKUWGC-RHYQMDGZSA-N

物化性质

• 沸点：
  568.6±35.0 °C(Predicted)
• 密度：
  1.312±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：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methanesulfonic acid (S)-((4R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-((4S,5S)-5-methanesulfonyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester 在 sodium tetrahydroborate 、 sodium periodate 、 20 % Pd(OH)2/C 、 水 、 氢气 、 sodium hydride 、 溶剂黄146 、 三氟乙酸 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 75.0h， 生成 (2R,3R,4S)-2-([(9Z)-octadec-9-en-1-yloxy]methyl)pyrrolidine-3,4-diol
  参考文献：
  名称：

  Anti-cancer activity of 5-O-alkyl 1,4-imino-1,4-dideoxyribitols

  摘要：

  New derivatives of 1,4-dideoxy-1,4-imino-D-ribitol have been prepared and evaluated for their cytotoxicity on solid and haematological malignancies. 1,4-Dideoxy-5-O-[(9Z)-octadec-9-en-1-yl]-1,4-imino-Dribitol (13, IC50 similar to 2 mu M) and its C-18-analogues (IC50 < 10 mu M) are cytotoxic toward SKBR3 (breast cancer) cells. 13 also inhibits (IC50 similar to 8 mu M) growth of JURKAT cells. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2011.07.053
• 作为产物：
  描述：

  D-(-)-古洛糖酸-gamma-内酯 在 吡啶 、 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 6.5h， 生成 methanesulfonic acid (S)-((4R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-((4S,5S)-5-methanesulfonyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester
  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。
• Glycosidase inhibitors and methods of synthesizing same
  申请人：Pinto Mario Brian

  公开号：US20060247222A1

  公开（公告）日：2006-11-02

  Methods for synthesizing Salacinol, its stereoisomers, and analogues, homologues and other derivatives thereof potentially useful as glycosidase inhibitors are described. In some embodiments the compounds of the invention may have the general formula (I) or (II): The synthetic schemes may comprise reacting a cyclic sulfate with a 5-membered ring sugar containing a heteroatom (X). The heteroatom preferably comprises sulfur, selenium, or nitrogen. The cyclic sulfate and ring sugar reagents may be readily prepared from carbohydrate precursors, such as D-glucose, L-glucose, D-xylose and L-xylose. The target compounds are prepared by opening of the cyclic sulfates by nucleophilic attack of the heteroatoms on the 5-membered ring sugars. The resulting heterocyclic compounds have a stable, inner salt structure comprising a heteroatom cation and a sulfate anion. The synthetic schemes yield various stereoisomers of the target compounds in moderate to good yields with limited side-reactions. Chain-extended analogues of Salacinol are also described.

  本文描述了合成Salacinol及其立体异构体、类似物、同系物和其他衍生物的方法，这些化合物可能用作糖苷酶抑制剂。在某些实施例中，本发明的化合物可能具有通式(I)或(II)。合成方案可以包括将环状硫酸酯与含有杂原子（X）的五元环糖反应。所述杂原子优选包括硫、硒或氮。环状硫酸酯和环状糖试剂可以从碳水化合物前体，如D-葡萄糖、L-葡萄糖、D-木糖和L-木糖中轻松制备。目标化合物通过杂原子对五元环糖的亲核攻击打开环状硫酸酯而制备得到。所得到的杂环化合物具有稳定的内盐结构，包括一个杂原子阳离子和一个硫酸盐阴离子。合成方案以中等到良好的产率产生目标化合物的各种立体异构体，并且副反应有限。还描述了Salacinol的链延长类似物。
• Structure−Activity Relationships of 2-Chloro-<i>N</i>⁶-substituted-4‘-thioadenosine-5‘-uronamides as Highly Potent and Selective Agonists at the Human A₃ Adenosine Receptor
  作者：Lak Shin Jeong、Hyuk Woo Lee、Kenneth A. Jacobson、Hea Ok Kim、Dae Hong Shin、Jeong A Lee、Zhan-Guo Gao、Changrui Lu、Heng T. Duong、Prashantha Gunaga、Sang Kook Lee、Dong Zhe Jin、Moon Woo Chun、Hyung Ryong Moon

  DOI：10.1021/jm050595e

  日期：2006.1.1

  We have established structure-activity relationships of novel 4'-thionucleoside analogues as the A(3) adenosine receptor (AR) agonists. Binding affinity, selectivity toward other AR subtypes.. and efficacy in inhibition of adenylate cyclase were studied. From this study, 2-chloro-N-6-methyl-4'-thioadenosine-5'-methyluronamide (36a) emerged as the most potent and selective agonist at the human A(3) AR. We have also revealed that. similar to 4'-oxoadenosine analogues, at least one hydrogen on the 5'-uronamide moiety was necessary for high-affinity binding at the human A(3) AR, presumably to allow this group to donate a H bond within the binding site. Furthermore, bulky substituents on the 5'-uronarnide reduced binding affinity, but in some cases large 5'-uronamide substituents, such as substituted benzyl and 2-phenylethyl groups. maintained moderate affinity with reduced efficacy, leading to A(3) AR partial agonists or antagonists. In several cases for which the corresponding 4'-oxonucleosides have been studied, the 4'-thionucleosides showed higher binding affinity to the A(3) AR.
• 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.
• Polyhydroxylated pyrrolidines from sugar lactomes: Synthesis of 1,4-dideoxy-1,4-imino-d-glucitol from d-galactonolactone and syntheses of 1,4-dideoxy-1,4-imino-d-allitol, 1,4-dideoxy-1,4-imino-d-ribitol, and (2s,3r,4s)-3,4-dihydroxyproline from d-gulonolactone
  作者：George W.J. Fleet、Jong Chan Son

  DOI：10.1016/s0040-4020(01)81716-6

  日期：1988.1