ethyl 3-[3-((1S)-1-{[(5,5-dioxo-5,7,8,9-tetrahydro-5λ6-pyrido[1,2-b][1,2]benzisothiazol-10-yl)carbonyl]amino}ethyl)-1,2,4-oxadiazol-5-yl]propanoate | 1332360-89-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: ethyl 3-[3-((1S)-1-{[(5,5-dioxo-5,7,8,9-tetrahydro-5λ6-pyrido[1,2-b][1,2]benzisothiazol-10-yl)carbonyl]amino}ethyl)-1,2,4-oxadiazol-5-yl]propanoate
• CAS: 1332360-89-0
• 化学式: C₂₁H₂₄N₄O₆S
• 分子量: 460.511
• InChiKey: URZUKDOUWHOLGB-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  131.7
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-[3-((1S)-1-{[(5,5-dioxo-5,7,8,9-tetrahydro-5λ6-pyrido[1,2-b][1,2]benzisothiazol-10-yl)carbonyl]amino}ethyl)-1,2,4-oxadiazol-5-yl]propanoate 在 lithium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以63%的产率得到3-[3-((1S)-1-{[(5,5-dioxo-5,7,8,9-tetrahydro-5λ6-pyrido[1,2-b][1,2]benzisothiazol-10-yl)carbonyl]amino}ethyl)-1,2,4-oxadiazol-5-yl]propanoic acid
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel desmuramyldipeptide analogs

  摘要：

  A series of novel desmuramyldipeptides have been designed and synthesized as part of our search for therapeutically useful muramyldipeptide (MOP) analogs. Their immunomodulatory properties were initially assessed in vitro, evaluating their effect on lipopolysaccharide (LPS)-induced cytokine release in THP-1 cells. Following the initial screening, selected compounds were further investigated for immunomodulatory properties using LPS and phorbol 12-myristate 13-acetate (PMA)/ionomycin-stimulated human peripheral blood mononuclear cells. The results confirmed the immunomodulatory properties of some of the synthesized desmuramyldipeptide analogs. Taken together, presented data confirmed the immunostimulatory effect of compound 44, MDP derivative incorporating a pyrido-fused [1,2]-benzisothiazole moiety, while for compounds 32 and 39, indole scaffold-based derivatives of MOP, an immunosuppressive effect was observed. Further studies will be necessary to address their potential therapeutic use as immunomodulatory drugs, both as immunostimulants or anti-inflammatory agents. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.042
• 作为产物：
  描述：

  在 氯化亚砜 、 乙醇 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 5.5h， 生成 ethyl 3-[3-((1S)-1-{[(5,5-dioxo-5,7,8,9-tetrahydro-5λ6-pyrido[1,2-b][1,2]benzisothiazol-10-yl)carbonyl]amino}ethyl)-1,2,4-oxadiazol-5-yl]propanoate
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel desmuramyldipeptide analogs

  摘要：

  A series of novel desmuramyldipeptides have been designed and synthesized as part of our search for therapeutically useful muramyldipeptide (MOP) analogs. Their immunomodulatory properties were initially assessed in vitro, evaluating their effect on lipopolysaccharide (LPS)-induced cytokine release in THP-1 cells. Following the initial screening, selected compounds were further investigated for immunomodulatory properties using LPS and phorbol 12-myristate 13-acetate (PMA)/ionomycin-stimulated human peripheral blood mononuclear cells. The results confirmed the immunomodulatory properties of some of the synthesized desmuramyldipeptide analogs. Taken together, presented data confirmed the immunostimulatory effect of compound 44, MDP derivative incorporating a pyrido-fused [1,2]-benzisothiazole moiety, while for compounds 32 and 39, indole scaffold-based derivatives of MOP, an immunosuppressive effect was observed. Further studies will be necessary to address their potential therapeutic use as immunomodulatory drugs, both as immunostimulants or anti-inflammatory agents. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.042