neosalaprinol | 1301687-74-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: neosalaprinol
• 英文别名: 1,4-dideoxy-1,4-{(R)-[(2S)-2,3-dihydroxypropyl]episulfoniumylidene}-D-arabinitol chloride
• CAS: 1301687-74-0
• 化学式: C₈H₁₇O₅S*Cl
• 分子量: 260.739
• InChiKey: PWHLBCGJJAIRKH-YYPRZBTOSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -5.94
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  101.15
• 氢给体数：
  5.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  salaprinol 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 neosalaprinol
  参考文献：
  名称：

  Isolation, structure identification and SAR studies on thiosugar sulfonium salts, neosalaprinol and neoponkoranol, as potent α-glucosidase inhibitors

  摘要：

  Two hitherto missing members of sulfonium salts family in Salacia genus plants as a new class of a-glucosidase inhibitors, neoponkoranol (7) and neosalaprinol (8), were isolated from the water extracts, and their structures were unambiguously identified. For further SAR studies on this series of sulfonium salts, several epimers of 7 and 8 were synthesized, and their inhibitory activities against rat small intestinal alpha-glucosidases were evaluated. Among them, 3'-epimer of 7 was found most potent in this class of molecules, and revealed as potent as currently used antidiabetics, voglibose and acarbose. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.052

文献信息

• Practical Route to Neokotalanol and Its Natural Analogues: Sulfonium Sugars with Antidiabetic Activities
  作者：Yuhao Huang、Yunlong Gao、Weigang He、Zihao Wang、Wei Li、Aijun Lin、Jinyi Xu、Genzoh Tanabe、Osamu Muraoka、Xiaoming Wu、Weijia Xie

  DOI：10.1002/anie.201900761

  日期：2019.5.6

  time. The key strategy features a coupling reaction between thiol derivatives and a diiodide counterpart. The newly designed thiol coupling partner presents high chemical stability, while the diiodide partner could be easily obtained with increased overall yields compared with conventional routes. The intermolecular nucleophilic substitution reaction followed by a diastereoselective intramolecular cyclization

  首次报道了一种高效，多样化的方法，用于合成最初从S藜属植物中分离的所有四种脱-O-磺化α型α-葡萄糖苷酶抑制剂。关键策略是硫醇衍生物与二碘化物对应物之间的偶联反应。新设计的硫醇偶合剂具有较高的化学稳定性，而与常规方法相比，二碘化物偶合剂可以轻松获得，总收率更高。分子间亲核取代反应，随后进行非对映选择性分子内环化，提供了目标五元sulf盐结构，该结构以α-方向连接至多羟基化的侧链部分。
• Isolation, structure identification and SAR studies on thiosugar sulfonium salts, neosalaprinol and neoponkoranol, as potent α-glucosidase inhibitors
  作者：Weijia Xie、Genzoh Tanabe、Junji Akaki、Toshio Morikawa、Kiyofumi Ninomiya、Toshie Minematsu、Masayuki Yoshikawa、Xiaoming Wu、Osamu Muraoka

  DOI：10.1016/j.bmc.2011.01.052

  日期：2011.3

  Two hitherto missing members of sulfonium salts family in Salacia genus plants as a new class of a-glucosidase inhibitors, neoponkoranol (7) and neosalaprinol (8), were isolated from the water extracts, and their structures were unambiguously identified. For further SAR studies on this series of sulfonium salts, several epimers of 7 and 8 were synthesized, and their inhibitory activities against rat small intestinal alpha-glucosidases were evaluated. Among them, 3'-epimer of 7 was found most potent in this class of molecules, and revealed as potent as currently used antidiabetics, voglibose and acarbose. (C) 2011 Elsevier Ltd. All rights reserved.