2-acetamido-2-[2-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]ethyl]propane-1,3-diol diacetate | 845550-78-9

• 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: 2-acetamido-2-[2-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]ethyl]propane-1,3-diol diacetate
• 英文别名: 2-acetamide-1,3-bisacetoxy-2-{2-[4-(4,4,5,5-tetramethyl [1,3,2]dioxaborolan-2-yl)phenyl]ethyl}propane；N-{1,1-bis(acetoxymethyl)-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propyl}acetamide；[2-Acetamido-2-(acetyloxymethyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]butyl] acetate
• CAS: 845550-78-9
• 化学式: C₂₃H₃₄BNO₇
• 分子量: 447.336
• InChiKey: VZALCNLDUWUBGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-acetamido-2-[2-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]ethyl]propane-1,3-diol diacetate 、 trifluoromethanesulfonic acid 5-benzyloxynaphthalen-1-yl ester 在 2-双环己基膦-2',6'-二甲氧基联苯 、 palladium diacetate potassium phosphate 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 生成 N-{1,1-bis(acetoxymethyl)-3-[4-(5-benzyloxynaphthalen-1-yl)phenyl]propyl}acetamide
  参考文献：
  名称：

  2-AMINOBUTANOL COMPOUND AND USE THEREOF FOR MEDICAL PURPOSES

  摘要：

  公开号：

  EP2017257B1
• 作为产物：
  描述：

  2-acetamido-2-[2-(4-bromophenyl)ethyl]propane-1,3-diol diacetate 、 联硼酸频那醇酯 在 双(三环己基膦)二氯化钯 potassium acetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 9.0h， 生成 2-acetamido-2-[2-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]ethyl]propane-1,3-diol diacetate
  参考文献：
  名称：

  [EN] BI-ARYL COMPOUND HAVING IMMUNOSUPPRESSIVE ACTIVITY
  [FR] COMPOSE BI-ARYLE PRESENTANT UNE ACTIVITE IMMUNOSUPPRESSIVE

  摘要：

  公开号：

  WO2005014525A3

文献信息

• Removal of Sphingosine 1-Phosphate Receptor-3 (S1P₃) Agonism is Essential, But Inadequate to Obtain Immunomodulating 2-Aminopropane-1,3-diol S1P₁ Agonists with Reduced Effect on Heart Rate
  作者：Maiko Hamada、Mitsuharu Nakamura、Masatoshi Kiuchi、Kaoru Marukawa、Ayumi Tomatsu、Kyoko Shimano、Noriko Sato、Kunio Sugahara、Mahoko Asayama、Kan Takagi、Kunitomo Adachi

  DOI：10.1021/jm901776q

  日期：2010.4.22

  A series of 2-substituted 2-aminopropane-1,3-diols having a biphenyl moiety and their phosphate esters were synthesized to obtain sphingosine 1-phosphate receptor-1 (S1P(1)) receptor agonists with potent immunomodulatory activity accompanied by little or no effect on heart rate. Many of the synthesized compounds sufficiently decreased the number of peripheral blood lymphocytes. Some of the phosphates had potent agonism at S1P(1) but no agonism at S1P(3), which had been reported to be a receptor responsible for heart rate reduction. Although high S1P(1)/S1P(3) selectivity was considered to be favorable to reduce the effect on heart rate, almost all the phosphates showed a remarkable heart rate lowering effect in vivo. The results suggest that other factors in addition to S1P(3) agonism should be responsible for the heart rate reduction caused by S1P(1) agonists. Only 2-amino-2-[2-[2'-fluoro-4'-(4-methylphenylthio)biphenyl-4-yl]ethyl]propane-1,3-diol (6d) was identified as a desired S1P(1) receptor agonist having both the immunomodulatory activity and an attenuated effect on heart rate by a unique screening flow using in vivo evaluating systems primarily.