((4R,5R)-5-(4-methoxyphenyl)-2-oxooxazolidin-4-yl)methyl 4-methylbenzenesulfonate | 690230-58-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((4R,5R)-5-(4-methoxyphenyl)-2-oxooxazolidin-4-yl)methyl 4-methylbenzenesulfonate
• 英文别名: [(4R,5R)-5-(4-methoxyphenyl)-2-oxo-1,3-oxazolidin-4-yl]methyl 4-methylbenzenesulfonate
• CAS: 690230-58-1
• 化学式: C₁₈H₁₉NO₆S
• 分子量: 377.418
• InChiKey: RXARBFSOIPHURO-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  99.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ((4R,5R)-5-(4-methoxyphenyl)-2-oxooxazolidin-4-yl)methyl 4-methylbenzenesulfonate 在 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 生成 (1R,2R)-2-Amino-1-(4-methoxy-phenyl)-3-morpholin-4-yl-propan-1-ol
  参考文献：
  名称：

  New PDMP analogues inhibit process outgrowth in an insect cell line

  摘要：

  D-threo-1-Phenyl-2-aminodecanoyl-3-morpholinopropanol (D-threo-PDMP) has previously been shown to inhibit the biosynthesis of glycosphingolipids (GSLs) in mammals and mammalian cell lines by the inhibition of glucosylceramide synthase. New D-threo-PDMP analogues were synthesized from D-serine, and found to suppress neurite extension in an embryonic insect cell line from the moth Manduca sexta, and in explanted neural tissue from insect pupae. Inhibition occurred at lower concentrations than D-threo-PDMP. The observed suppression of neurite formation was found to be reversible after the removal of the compounds. Due to their small size and short life cycle, M. sexta is shown to be an ideal model organism for studies of GSL effects in cellular development, and for drug development studies. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.013
• 作为产物：
  描述：

  (+/-)-methyl (4S,5R)-5-(4-methoxyphenyl)-2-oxo-1,3-oxazolidine-4-carboxylate 在 吡啶 、 sodium tetrahydroborate 、 乙醇 作用下， 反应 4.0h， 生成 ((4R,5R)-5-(4-methoxyphenyl)-2-oxooxazolidin-4-yl)methyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  [EN] GLUCOSYLCERAMIDE SYNTHASE INHIBITORS AND THERAPEUTIC METHODS USING THE SAME
  [FR] INHIBITEURS DE LA GLUCOSYLCÉRAMIDE SYNTHASE ET MÉTHODES THÉRAPEUTIQUES LES UTILISANT

  摘要：

  公开号：

  WO2016126572A3

文献信息

• Glucosylceramide synthase inhibitors and therapeutic methods using the same
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：US10202340B2

  公开（公告）日：2019-02-12

  Glucosylceramide synthase inhibitors and compositions containing the same are disclosed. Methods of using the glucosylceramide synthase inhibitors in the treatment of diseases and conditions wherein inhibition of glucosylceramide synthase provides a benefit, like Gaucher disease and Fabry disease, also are disclosed.

  本发明公开了葡萄糖酰胺合成酶抑制剂和含有这些抑制剂的组合物。还公开了使用葡萄糖基甘油酰胺合成酶抑制剂治疗疾病和病症的方法，在这些疾病和病症中，抑制葡萄糖基甘油酰胺合成酶会带来益处，如戈谢病和法布里病。
• EP3253734B1
  申请人：——

  公开号：EP3253734B1

  公开（公告）日：2020-12-23
• GLUCOSYLCERAMIDE SYNTHASE INHIBITORS AND THERAPEUTIC METHODS USING THE SAME
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：US20180022697A1

  公开（公告）日：2018-01-25

  Glucosylceramide synthase inhibitors and compositions containing the same are disclosed. Methods of using the glucosylceramide synthase inhibitors in the treatment of diseases and conditions wherein inhibition of glucosylceramide synthase provides a benefit, like Gaucher disease and Fabry disease, also are disclosed.