benzoic acid (2R,4R)-2-(dodecanoylamino)-4-methoxy-4-phenylbutyl ester | 596807-11-3

• 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: benzoic acid (2R,4R)-2-(dodecanoylamino)-4-methoxy-4-phenylbutyl ester
• 英文别名: [(2R,4R)-2-(dodecanoylamino)-4-methoxy-4-phenylbutyl] benzoate
• CAS: 596807-11-3
• 化学式: C₃₀H₄₃NO₄
• 分子量: 481.676
• InChiKey: KYZSRWRMWHKLFV-VSGBNLITSA-N

物化性质

• 沸点：
  631.2±55.0 °C(Predicted)
• 密度：
  1.034±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  35
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzoic acid (2R,4R)-2-(dodecanoylamino)-4-methoxy-4-phenylbutyl ester 在 乙醇 、 sodium ethanolate 作用下， 反应 10.0h， 以96%的产率得到N-[(2R,4R)-1-hydroxy-4-methoxy-4-phenylbutan-2-yl]dodecanamide
  参考文献：
  名称：

  Stereoselective Synthesis and Structure−Activity Relationship of Novel Ceramide Trafficking Inhibitors. (1R,3R)-N-(3-Hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide and Its Analogues

  摘要：

  New ceramide trafficking inhibitors, (1R,3R)-N-(3-hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide (HPA-12) and a series of its analogues, were synthesized in diastereomerically and enantiomerically pure forms, and the structure-activity relationship was investigated. These analogues were stereoselectively synthesized via catalytic enantioselective Mannich-type reactions using a Cu(II)-chiral diamine 4 complex. Analysis of HPA-12 analogues having various lengths of the amide side chain showed that the optimal chain length for the inhibition of sphingomyelin biosynthesis is 13 with an IC50 of similar to50 nM. Masking of the hydroxy group at the 2'- or 3-position of HPA-12 was carried out by methylation, and it was revealed that these hydroxy groups were essential for the activity. Installation of another hydroxy group onto HPA-12 at the same position as that in the natural ceramide was also conducted, but no enhancement of the activity was observed.

  DOI：

  10.1021/jm0300779
• 作为产物：
  描述：

  (2R)-2-dodecanoylamino-4-oxo-4-phenylbutyric acid ethyl ester hydrochloride 在 potassium tri-sec-butyl-borohydride 、 三乙胺 、 silver(l) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 63.25h， 生成 benzoic acid (2R,4R)-2-(dodecanoylamino)-4-methoxy-4-phenylbutyl ester
  参考文献：
  名称：

  Stereoselective Synthesis and Structure−Activity Relationship of Novel Ceramide Trafficking Inhibitors. (1R,3R)-N-(3-Hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide and Its Analogues

  摘要：

  New ceramide trafficking inhibitors, (1R,3R)-N-(3-hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide (HPA-12) and a series of its analogues, were synthesized in diastereomerically and enantiomerically pure forms, and the structure-activity relationship was investigated. These analogues were stereoselectively synthesized via catalytic enantioselective Mannich-type reactions using a Cu(II)-chiral diamine 4 complex. Analysis of HPA-12 analogues having various lengths of the amide side chain showed that the optimal chain length for the inhibition of sphingomyelin biosynthesis is 13 with an IC50 of similar to50 nM. Masking of the hydroxy group at the 2'- or 3-position of HPA-12 was carried out by methylation, and it was revealed that these hydroxy groups were essential for the activity. Installation of another hydroxy group onto HPA-12 at the same position as that in the natural ceramide was also conducted, but no enhancement of the activity was observed.

  DOI：

  10.1021/jm0300779