3,4,5-trimethoxybenzyl 5-(4-methyl-2-nitrophenyl)-2-furoate | 1365714-44-8

• 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: 3,4,5-trimethoxybenzyl 5-(4-methyl-2-nitrophenyl)-2-furoate
• 英文别名: (3,4,5-Trimethoxyphenyl)methyl 5-(4-methyl-2-nitrophenyl)furan-2-carboxylate
• CAS: 1365714-44-8
• 化学式: C₂₂H₂₁NO₈
• 分子量: 427.411
• InChiKey: LGHSVFJKCJKPMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苄醇 、 5-(4-甲基-2-硝基苯基)-2-糠酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以10%的产率得到3,4,5-trimethoxybenzyl 5-(4-methyl-2-nitrophenyl)-2-furoate
  参考文献：
  名称：

  Effect of Phosphodiesterase 7 (PDE7) Inhibitors in Experimental Autoimmune Encephalomyelitis Mice. Discovery of a New Chemically Diverse Family of Compounds

  摘要：

  Phosphodiesterase (PDE) 7 is involved in proinflammatory processes, being widely expressed both on lymphocytes and on certain brain regions. Specific inhibitors of PDE7 have been recently reported as potential new drugs for the treatment of neurological disorders because of their ability to increase intracellular levels of cAMP and thus to modulate the inflammatory process, as a neuroprotective well-established strategy. Multiple sclerosis is an unmet disease in which pathologies on the immune system, T-cells, and specific neural cells are involved simultaneously. Therefore, PDE7 inhibitors able to interfere with all these targets may represent an innovative therapy for this pathology. Here, we report a new chemically diverse family of heterocyclic PDE7 inhibitors, discovered and optimized by using molecular modeling studies, able to increase cAMP levels in cells, decrease inflammatory activation on primary neural cultures, and also attenuate the clinical symptoms in the experimental autoimmune encephalomyelitis (EAE) mouse model. These results led us to propose the use of PDE7 inhibitors as innovative therapeutic agents for the treatment of multiple sclerosis.

  DOI：

  10.1021/jm201720d

文献信息

• Effect of Phosphodiesterase 7 (PDE7) Inhibitors in Experimental Autoimmune Encephalomyelitis Mice. Discovery of a New Chemically Diverse Family of Compounds
  作者：Miriam Redondo、José Brea、Daniel I. Perez、Ignacio Soteras、Cristina Val、Concepción Perez、Jose A. Morales-García、Sandra Alonso-Gil、Nuria Paul-Fernandez、Rocío Martin-Alvarez、María Isabel Cadavid、María Isabel Loza、Ana Perez-Castillo、Guadalupe Mengod、Nuria E. Campillo、Ana Martinez、Carmen Gil

  DOI：10.1021/jm201720d

  日期：2012.4.12

  Phosphodiesterase (PDE) 7 is involved in proinflammatory processes, being widely expressed both on lymphocytes and on certain brain regions. Specific inhibitors of PDE7 have been recently reported as potential new drugs for the treatment of neurological disorders because of their ability to increase intracellular levels of cAMP and thus to modulate the inflammatory process, as a neuroprotective well-established strategy. Multiple sclerosis is an unmet disease in which pathologies on the immune system, T-cells, and specific neural cells are involved simultaneously. Therefore, PDE7 inhibitors able to interfere with all these targets may represent an innovative therapy for this pathology. Here, we report a new chemically diverse family of heterocyclic PDE7 inhibitors, discovered and optimized by using molecular modeling studies, able to increase cAMP levels in cells, decrease inflammatory activation on primary neural cultures, and also attenuate the clinical symptoms in the experimental autoimmune encephalomyelitis (EAE) mouse model. These results led us to propose the use of PDE7 inhibitors as innovative therapeutic agents for the treatment of multiple sclerosis.