(2-Oxido-4-phenyl-1,2,5-oxadiazol-2-ium-3-yl)methyl 2-(1,3-dioxoisoindol-2-yl)benzoate | 1394345-29-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (2-Oxido-4-phenyl-1,2,5-oxadiazol-2-ium-3-yl)methyl 2-(1,3-dioxoisoindol-2-yl)benzoate
• 英文别名: (2-oxido-4-phenyl-1,2,5-oxadiazol-2-ium-3-yl)methyl 2-(1,3-dioxoisoindol-2-yl)benzoate
• CAS: 1394345-29-9
• 化学式: C₂₄H₁₅N₃O₆
• 分子量: 441.4
• InChiKey: DYGDFRSMSRRCRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  cinnamic alcohol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 sodium nitrite 作用下， 以 二氯甲烷 为溶剂， 反应 29.0h， 生成 (2-Oxido-4-phenyl-1,2,5-oxadiazol-2-ium-3-yl)methyl 2-(1,3-dioxoisoindol-2-yl)benzoate
  参考文献：
  名称：

  Design, Synthesis, and Pharmacological Evaluation of Novel Hybrid Compounds to Treat Sickle Cell Disease Symptoms. Part II: Furoxan Derivatives

  摘要：

  Phthalimide derivatives containing furoxanyl subunits as nitric oxide (NO)-donors (3a-g) were designed, synthesized, and evaluated in vitro and in vivo for their potential uses in the oral treatment of sickle cell disease symptoms. All compounds (3a-g) demonstrated NO-donor properties at different levels. Moreover, compounds 3b and 3c demonstrated analgesic activity. Compound 3b was determined to be a promising drug candidate for the aforementioned uses, and it was further evaluated in K562 culture cells to determine its ability to increase levels of gamma-globin expression. After 96 h at 5 mu M, compound 3b was able to induce gamma-globin expression by nearly three times. Mutagenic studies using micronucleus tests in peripheral blood cells of mice demonstrated that compound 3b reduces the mutagenic profile as compared with hydroxyurea. Compound 3b has emerged as a new leading drug candidate with multiple beneficial effects for the treatment of sickle cell disease symptoms and provides an alternative to hydroxyurea treatment.

  DOI：

  10.1021/jm300602n

文献信息

• Design, Synthesis, and Pharmacological Evaluation of Novel Hybrid Compounds to Treat Sickle Cell Disease Symptoms. Part II: Furoxan Derivatives
  作者：Jean Leandro Dos Santos、Carolina Lanaro、Rafael Consolin Chelucci、Sheley Gambero、Priscila Longhin Bosquesi、Juliana Santana Reis、Lídia Moreira Lima、Hugo Cerecetto、Mercedes González、Fernando Ferreira Costa、Man Chin Chung

  DOI：10.1021/jm300602n

  日期：2012.9.13

  Phthalimide derivatives containing furoxanyl subunits as nitric oxide (NO)-donors (3a-g) were designed, synthesized, and evaluated in vitro and in vivo for their potential uses in the oral treatment of sickle cell disease symptoms. All compounds (3a-g) demonstrated NO-donor properties at different levels. Moreover, compounds 3b and 3c demonstrated analgesic activity. Compound 3b was determined to be a promising drug candidate for the aforementioned uses, and it was further evaluated in K562 culture cells to determine its ability to increase levels of gamma-globin expression. After 96 h at 5 mu M, compound 3b was able to induce gamma-globin expression by nearly three times. Mutagenic studies using micronucleus tests in peripheral blood cells of mice demonstrated that compound 3b reduces the mutagenic profile as compared with hydroxyurea. Compound 3b has emerged as a new leading drug candidate with multiple beneficial effects for the treatment of sickle cell disease symptoms and provides an alternative to hydroxyurea treatment.