benzyl (4R)-5-amino-4-[(2S)-2-{[(5,5-dioxo-5,7,8,9-tetrahydro-5λ6-pyrido[1,2-b][1,2]benzisothiazol-10-yl)carbonyl]amino}propanoylamino]-5-oxopentanoate | 1332360-42-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl (4R)-5-amino-4-[(2S)-2-{[(5,5-dioxo-5,7,8,9-tetrahydro-5λ6-pyrido[1,2-b][1,2]benzisothiazol-10-yl)carbonyl]amino}propanoylamino]-5-oxopentanoate
• 英文别名: benzyl (4R)-5-amino-4-[[(2S)-2-[(5,5-dioxo-8,9-dihydro-7H-pyrido[1,2-b][1,2]benzothiazole-10-carbonyl)amino]propanoyl]amino]-5-oxopentanoate
• CAS: 1332360-42-5
• 化学式: C₂₇H₃₀N₄O₇S
• 分子量: 554.624
• InChiKey: MHQUVSRODLIWMI-LAUBAEHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  173
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl (4R)-5-amino-4-[(2S)-2-{[(5,5-dioxo-5,7,8,9-tetrahydro-5λ6-pyrido[1,2-b][1,2]benzisothiazol-10-yl)carbonyl]amino}propanoylamino]-5-oxopentanoate 、 溶剂黄146 在 palladium 10% on activated carbon 、 氢气 作用下， 以86%的产率得到(4R)-5-amino-4-[((2S)-2-{[(5,5-dioxo-5,7,8,9,10,10a-hexahydro-5λ6-pyrido[1,2-b][1,2]benzisothiazol-10-yl)carbonyl]amino}propanoyl)amino]-5-oxopentanoic acid acetate
  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：

  丁氧羰基-丙氨酸-D-谷氨酸-氨 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 benzyl (4R)-5-amino-4-[(2S)-2-{[(5,5-dioxo-5,7,8,9-tetrahydro-5λ6-pyrido[1,2-b][1,2]benzisothiazol-10-yl)carbonyl]amino}propanoylamino]-5-oxopentanoate
  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