2,3,5,6-di-O-isopropylidene-1,4-anhydro-1-seleno-D-talitol | 902138-30-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5,6-di-O-isopropylidene-1,4-anhydro-1-seleno-D-talitol
• 英文别名: 2,3,5,6-di-O-isopropyIidene-1,4-anhydro-D-talitol；(3aR,4S,6aS)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydroselenopheno[3,4-d][1,3]dioxole
• CAS: 902138-30-1
• 化学式: C₁₂H₂₀O₄Se
• 分子量: 307.248
• InChiKey: XJAKIOKRFNICOX-KYXWUPHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 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：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3,5,6-di-O-isopropylidene-1,4-anhydro-1-seleno-D-talitol 在 乙酰氯 作用下， 以 甲醇 为溶剂， 反应 3.17h， 生成 1,4-anhydro-4-seleno-D-talitol
  参考文献：
  名称：

  [EN] SELENO-COMPOUNDS AND THERAPEUTIC USES THEREOF
  [FR] COMPOSÉS SÉLÉNO ET LEURS UTILISATIONS THÉRAPEUTIQUES

  摘要：

  本发明涉及作为抗氧化剂有用的化合物和组合物，特别是公式(I)中含硒的化合物，其中n为1、2或3；m为2、3、4或5；每个R]独立地为-(可选择地取代的C1-C3烷基) p-OH，其中p为0或1，或其盐。该发明还涉及在治疗由髓过氧化物酶(MPO)产生的氧化剂水平增加引起的疾病或症状中使用这些硒化合物，例如动脉粥样硬化。

  公开号：

  WO2012054988A1
• 作为产物：
  描述：

  2,3,5,6-di-isopropyIidene-1,4-dihydroxy-D-mannitol 在 吡啶 、 selenium 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 18.5h， 生成 2,3,5,6-di-O-isopropylidene-1,4-anhydro-1-seleno-D-talitol
  参考文献：
  名称：

  从作为潜在糖苷酶抑制剂的 D-甘露糖合成两性离子硒和硫酸锍

  摘要：

  合成了四种天然糖苷酶抑制剂salacinol 的链延长类似物，用于不同糖苷酶的结构活性研究。合成涉及异丙叉保护的 1,4-硫代-和 1,4-硒-D-塔糖醇与衍生自 D-甘露糖的 1,5-硫代-和 1,5-硒-L-gulitols 与亚苄基和异亚丙基保护的 1,3- 环硫酸盐，也衍生自 D-甘露糖。产物的脱保护提供了由杂环五元和六元环核心结构组成的新型硒和锍硫酸盐，具有多羟基化的六碳原子无环链。 关键词：糖苷酶抑制剂，两性离子硒和锍硫酸盐，环硫酸盐

  DOI：

  10.1139/v06-027

文献信息

• Preventing Protein Oxidation with Sugars: Scavenging of Hypohalous Acids by 5-Selenopyranose and 4-Selenofuranose Derivatives
  作者：Corin Storkey、David I. Pattison、Jonathan M. White、Carl H. Schiesser、Michael J. Davies

  DOI：10.1021/tx3003593

  日期：2012.11.19

  Heme peroxidases including myeloperoxidase (MPO) are released at sites of inflammation by activated leukocytes. MPO generates hypohalous acids (HOX, X = Cl, Br, SCN) from H2O2; these oxidants are bactericidal and are key components of the inflammatory response. However, excessive, misplaced or mistimed production can result in host tissue damage, with this implicated in multiple inflammatory diseases. We report here methods for the conversion of simple monosaccharide sugars into selenium- and sulfur-containing species that may act as potent water-soluble scavengers of HOX. Competition kinetic studies show that the seleno species react with HOC with rate constants in the range 0.8-1.0 X 10(8) M-1 s(-1), only marginally slower than those for the most susceptible biological targets including the endogenous antioxidant, glutathione. The rate constants for the corresponding sulfur sugars are considerably slower (1.4-1.9 X 10(6) M-1 s(-1)). Rate constants for reaction of the seleno-sugars with HOBr are, similar to 8 times lower than those for HOCl (1.0-1.5 X 10(7) M-1 s(-1)). These values show little variation with differing sugar structures. Reaction with HOSCN is slower (similar to 10(2) M-1 s(-1)) The seleno-sugars decreased the extent of HOCI-mediated oxidation of Met, His, Tip, Lys, and Tyr residues, and 3-chlorotyrosine formation, on both isolated bovine serum albumin and human plasma proteins, at concentrations as low as 50 mu M. These studies demonstrate that novel selenium (and to a lesser extent, sulfur) derivatives of monosaccharides could be potent modulators of peroxidase-mediated damage at sites of acute and chronic inflammation, and in multiple human pathologies.
• [EN] SELENO-COMPOUNDS AND THERAPEUTIC USES THEREOF<br/>[FR] COMPOSÉS SÉLÉNO ET LEURS UTILISATIONS THÉRAPEUTIQUES
  申请人：UNIV MELBOURNE

  公开号：WO2012054988A1

  公开（公告）日：2012-05-03

  The present invention relates to compounds and compositions useful as antioxidants and in particular to selenium containing compounds of formula (I): wherein n is 1, 2, or 3; m is 2, 3, 4, or 5; and each R] is independently -(optionally substituted C 1 -C3 alkylene) p-OH, where p is 0 or 1, or a salt thereof. The invention also relates to the use of these seleno-compounds in the treatment of diseases or conditions associated with increased levels of oxidants produced by myeloperoxidase (MPO), such as for instance, atherosclerosis.

  本发明涉及作为抗氧化剂有用的化合物和组合物，特别是公式(I)中含硒的化合物，其中n为1、2或3；m为2、3、4或5；每个R]独立地为-(可选择地取代的C1-C3烷基) p-OH，其中p为0或1，或其盐。该发明还涉及在治疗由髓过氧化物酶(MPO)产生的氧化剂水平增加引起的疾病或症状中使用这些硒化合物，例如动脉粥样硬化。
• Synthesis of zwitterionic selenonium and sulfonium sulfates from <scp>D</scp>-mannose as potential glycosidase inhibitors
  作者：Hui Liu、B Mario Pinto

  DOI：10.1139/v06-027

  日期：2006.4.1

  studies with different glycosidase enzymes. The syntheses involved the reaction of isopropylidene-protected 1,4-thio- and 1,4-seleno-D-talitols and 1,5-thio- and 1,5-seleno-L-gulitols, derived from D-mannose, with a benzylidene- and isopropylidene-protected 1,3-cyclic sulfate, also derived from D-mannose. Deprotection of the products afforded the novel selenonium and sulfonium sulfates composed of heterocyclic

  合成了四种天然糖苷酶抑制剂salacinol 的链延长类似物，用于不同糖苷酶的结构活性研究。合成涉及异丙叉保护的 1,4-硫代-和 1,4-硒-D-塔糖醇与衍生自 D-甘露糖的 1,5-硫代-和 1,5-硒-L-gulitols 与亚苄基和异亚丙基保护的 1,3- 环硫酸盐，也衍生自 D-甘露糖。产物的脱保护提供了由杂环五元和六元环核心结构组成的新型硒和锍硫酸盐，具有多羟基化的六碳原子无环链。 关键词：糖苷酶抑制剂，两性离子硒和锍硫酸盐，环硫酸盐