(S)-5-((1-hydroxypropan-2-ylamino)methyl)-3-methoxy-9H-xanthen-9-one | 1423876-74-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (S)-5-((1-hydroxypropan-2-ylamino)methyl)-3-methoxy-9H-xanthen-9-one
• 英文别名: (S)-4-((1-hydroxypropan-2-ylamino)methyl)-6-methoxy-9H-xanthen-9-one；5-[[[(2S)-1-hydroxypropan-2-yl]amino]methyl]-3-methoxyxanthen-9-one
• CAS: 1423876-74-7
• 化学式: C₁₈H₁₉NO₄
• 分子量: 313.353
• InChiKey: ZGIVCOVEGQBZSM-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-methoxy-5-methyl-9H-xanthen-9-one 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 作用下， 以 四氯化碳 、 甲苯 为溶剂， 生成 (S)-5-((1-hydroxypropan-2-ylamino)methyl)-3-methoxy-9H-xanthen-9-one
  参考文献：
  名称：

  Anticonvulsant evaluation of aminoalkanol derivatives of 2- and 4-methylxanthone

  摘要：

  A series of 17 new aminoalkanol derivatives of 6-methoxy- or 7-chloro-2-methylxanthone as well as 6-methoxy-4-methylxanthone was synthesized and evaluated for anticonvulsant activity. All compounds were verified in mice after intraperitoneal (ip) administration in maximal electroshock (MES) and subcutaneous pentetrazole (scMet) induced seizures as well as neurotoxicity assessment. Eleven of the tested substances showed protection against electrically evoked seizures in the majority of the tested mice at the dose of 100 mg/kg. Additionally, one was effective at the dose of 30 mg/kg. Five substances were active at the dose of 300 mg/kg or at the dose of 100 mg/kg in the minority of the tested mice. The most promising compound revealed ED50 value of 47.57 mg/kg in MES (mice, ip, 1 h after administration) and at the same time its TD50 was evaluated as above 400 mg/kg. Those values gave PI (calculated as TD50/ED50) of more than 8.41. Three other synthesized xanthone derivatives also proved to act as anticonvulsants and showed ED50 values in MES test (mice, ip) ranged 80-110 mg/kg. Results were quite encouraging and suggested that in the group of xanthone derivatives new potential anticonvulsants might be found. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.051

文献信息

• Anticonvulsant evaluation of aminoalkanol derivatives of 2- and 4-methylxanthone
  作者：Natalia Szkaradek、Agnieszka Gunia、Anna M. Waszkielewicz、Lucyna Antkiewicz-Michaluk、Marek Cegła、Edward Szneler、Henryk Marona

  DOI：10.1016/j.bmc.2012.12.051

  日期：2013.3

  A series of 17 new aminoalkanol derivatives of 6-methoxy- or 7-chloro-2-methylxanthone as well as 6-methoxy-4-methylxanthone was synthesized and evaluated for anticonvulsant activity. All compounds were verified in mice after intraperitoneal (ip) administration in maximal electroshock (MES) and subcutaneous pentetrazole (scMet) induced seizures as well as neurotoxicity assessment. Eleven of the tested substances showed protection against electrically evoked seizures in the majority of the tested mice at the dose of 100 mg/kg. Additionally, one was effective at the dose of 30 mg/kg. Five substances were active at the dose of 300 mg/kg or at the dose of 100 mg/kg in the minority of the tested mice. The most promising compound revealed ED50 value of 47.57 mg/kg in MES (mice, ip, 1 h after administration) and at the same time its TD50 was evaluated as above 400 mg/kg. Those values gave PI (calculated as TD50/ED50) of more than 8.41. Three other synthesized xanthone derivatives also proved to act as anticonvulsants and showed ED50 values in MES test (mice, ip) ranged 80-110 mg/kg. Results were quite encouraging and suggested that in the group of xanthone derivatives new potential anticonvulsants might be found. (C) 2013 Elsevier Ltd. All rights reserved.