N-cyclohexyl-4-((((2S,3S)-3-hydroxy-2,6-dimethylheptyl)oxy)methyl)-N-methylbenzene sulfonamide | 1574549-93-1

• 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: N-cyclohexyl-4-((((2S,3S)-3-hydroxy-2,6-dimethylheptyl)oxy)methyl)-N-methylbenzene sulfonamide
• 英文别名: N-cyclohexyl-4-[[(2S,3S)-3-hydroxy-2,6-dimethylheptoxy]methyl]-N-methylbenzenesulfonamide
• CAS: 1574549-93-1
• 化学式: C₂₃H₃₉NO₄S
• 分子量: 425.633
• InChiKey: RWYFUHIZWIGIIR-CVDCTZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-甲基-1-戊醇 在 锂硼氢 、 三氟甲磺酸二丁硼 、 sodium hydride 、 N,N-二异丙基乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.33h， 生成 N-cyclohexyl-4-((((2S,3S)-3-hydroxy-2,6-dimethylheptyl)oxy)methyl)-N-methylbenzene sulfonamide
  参考文献：
  名称：

  Development of new LXR modulators that regulate LXR target genes and reduce lipogenesis in human cell models

  摘要：

  Four new mimics of 22-S-hydroxycholesterol (22SHC) were synthesized and evaluated using molecular modeling and tested in human muscle cells (primary myotubes) and hepatocytes (HepG2 cells). The new compounds (9, 12, 15a and 15b) showed good interrelationship between docking scores, to both LXR alpha and LXR beta, and in vitro results. The LXR agonist T0901317 increased the expressions of genes involved in lipogenesis (SCD1, FAS) and cholesterol efflux (ABCA1), but only 22SHC counteracted the up-regulation of SCD1 and FAS by T0901317. Compound 9 and 12 decreased the expression of SCD1, while 9 also decreased the expression of FAS. Compounds 15a showed a significant antagonistic effect on ABCA1 expression, but neither 15a nor 15b were able to counteract the effect of T0901317 on all genes examined. Lipogenesis was increased after T0901317 treatment and only 22SHC significantly counteracted this effect. Treatment with 22SHC and compound 12 reduced lipogenesis compared to control. An increased glucose uptake was observed for all compounds, except for 15b. In summary, the new synthetic 22SHC mimics showed antagonistic effects similar to that of 22SHC, but the new substances were less potent. The sulfonamide 12 showed similar effects to 22SHC and the best effect on gene expression of the new mimics, however, it was not able to reduce the effect of T0901317 as observed for 22SHC. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.003

文献信息

• Development of new LXR modulators that regulate LXR target genes and reduce lipogenesis in human cell models
  作者：Ove Alexander Høgmoen Åstrand、Ingvei Gikling、Ingebrigt Sylte、Arild Christian Rustan、G. Hege Thoresen、Pål Rongved、Eili Tranheim Kase

  DOI：10.1016/j.ejmech.2014.01.003

  日期：2014.3

  Four new mimics of 22-S-hydroxycholesterol (22SHC) were synthesized and evaluated using molecular modeling and tested in human muscle cells (primary myotubes) and hepatocytes (HepG2 cells). The new compounds (9, 12, 15a and 15b) showed good interrelationship between docking scores, to both LXR alpha and LXR beta, and in vitro results. The LXR agonist T0901317 increased the expressions of genes involved in lipogenesis (SCD1, FAS) and cholesterol efflux (ABCA1), but only 22SHC counteracted the up-regulation of SCD1 and FAS by T0901317. Compound 9 and 12 decreased the expression of SCD1, while 9 also decreased the expression of FAS. Compounds 15a showed a significant antagonistic effect on ABCA1 expression, but neither 15a nor 15b were able to counteract the effect of T0901317 on all genes examined. Lipogenesis was increased after T0901317 treatment and only 22SHC significantly counteracted this effect. Treatment with 22SHC and compound 12 reduced lipogenesis compared to control. An increased glucose uptake was observed for all compounds, except for 15b. In summary, the new synthetic 22SHC mimics showed antagonistic effects similar to that of 22SHC, but the new substances were less potent. The sulfonamide 12 showed similar effects to 22SHC and the best effect on gene expression of the new mimics, however, it was not able to reduce the effect of T0901317 as observed for 22SHC. (C) 2014 Elsevier Masson SAS. All rights reserved.