deoxypicropodophyllinic acid methyl ester | 140147-76-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: deoxypicropodophyllinic acid methyl ester
• 英文别名: Desoxypicropodophyllinsaeure-methylester；methyl (5R,6S,7R)-7-(hydroxymethyl)-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6-carboxylate
• CAS: 140147-76-8
• 化学式: C₂₃H₂₆O₈
• 分子量: 430.455
• InChiKey: MXGHOMGUPJFHLU-LVXYXVKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  deoxypicropodophyllinic acid methyl ester 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 methyl (5R,6S,7R)-7-formyl-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6-carboxylate
  参考文献：
  名称：

  Preparation and cytotoxicity of podophyllotoxin derivatives lacking the lactone ring

  摘要：

  Several cyclolignans lacking of the lactone moiety can easily be prepared from naturally occurring lignans such as podophyllotoxin and deoxypodophyllotoxin by simple chemical transformations. Their cytotoxicity has been studied in four tumoral cell lines. Most of the compounds show similar effects in all the neoplastic systems tested, except the aldehyde 9 (methyl 9-deoxy-9-oxo-alpha-apopicropodophyllate) and the hydrazones 16 and 17 which show a highly selective cytotoxicity towards HT-29 human colon carcinoma. Additionally, several molecular modeling studies have been done with aldehyde 9 and the corresponding saturated aldehyde 13 in comparison with podophyllotoxin. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10042-4
• 作为产物：
  描述：

  去氧鬼臼毒素 在 氢氧化钾 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 0.5h， 生成 deoxypicropodophyllinic acid methyl ester
  参考文献：
  名称：

  Preparation and cytotoxicity of podophyllotoxin derivatives lacking the lactone ring

  摘要：

  Several cyclolignans lacking of the lactone moiety can easily be prepared from naturally occurring lignans such as podophyllotoxin and deoxypodophyllotoxin by simple chemical transformations. Their cytotoxicity has been studied in four tumoral cell lines. Most of the compounds show similar effects in all the neoplastic systems tested, except the aldehyde 9 (methyl 9-deoxy-9-oxo-alpha-apopicropodophyllate) and the hydrazones 16 and 17 which show a highly selective cytotoxicity towards HT-29 human colon carcinoma. Additionally, several molecular modeling studies have been done with aldehyde 9 and the corresponding saturated aldehyde 13 in comparison with podophyllotoxin. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10042-4

文献信息

• Lignans from polar extracts ofJuniperus thurifera
  作者：Arturo San Feliciano、Jose M. Miguel Del Corral、Jose L. Lopez、Beatriz De Pascual-Teresa

  DOI：10.1016/0031-9422(91)83051-l

  日期：1992.1

  Abstract Three new natural lignans, methyl deoxypodophyllotoxinate, podophyllotoxinic acid and 7β-hydroxydihydrosesamin, 11 known lignans and two cinnamyl alcohols were isolated and identified from a chloroform extract of Juniperus thurifera leaves. Assignment of the 13 C NMR spectrum of β-methyl peltatin B was also performed through direct and long-range heteronuclear 2D NMR analysis, amending previous

  摘要 从杜松叶氯仿提取物中分离鉴定出3种新的天然木脂素，即脱氧鬼臼毒素甲酯、鬼臼毒素酸和7β-羟基二氢芝麻素，11种已知木脂素和2种肉桂醇。β-甲基peltatin B 的 13 C NMR 光谱的分配也通过直接和远程异核 2D 核磁共振分析进行，修改了以前的分配。
• Hata, Nippon Kagaku Kaishi/Journal of the Chemical Society of Japan, 1942, vol. 63, p. 1540,1543
  作者：Hata

  DOI：——

  日期：——
• Notes - Methyl Desoxypodophyllate and Its Methyl Ether
  作者：Anthony Schrecker、Mary Trail

  DOI：10.1021/jo01099a619

  日期：1958.5
• JONES, DAVID W.;THOMPSON, ADRIAN M., J. CHEM. SOC. CHEM. COMMUN.,(1988) N 16, C. 1095-1096
  作者：JONES, DAVID W.、THOMPSON, ADRIAN M.

  DOI：——

  日期：——
• Preparation and cytotoxicity of podophyllotoxin derivatives lacking the lactone ring
  作者：Marina Gordaliza、MaAngeles Castro、JoséMa Miguel del Corral、MaLuisa López-Vázquez、Pablo A. García、Arturo San Feliciano、MaDolores García-Grávalos、Howard Broughton

  DOI：10.1016/s0040-4020(97)10042-4

  日期：1997.11

  Several cyclolignans lacking of the lactone moiety can easily be prepared from naturally occurring lignans such as podophyllotoxin and deoxypodophyllotoxin by simple chemical transformations. Their cytotoxicity has been studied in four tumoral cell lines. Most of the compounds show similar effects in all the neoplastic systems tested, except the aldehyde 9 (methyl 9-deoxy-9-oxo-alpha-apopicropodophyllate) and the hydrazones 16 and 17 which show a highly selective cytotoxicity towards HT-29 human colon carcinoma. Additionally, several molecular modeling studies have been done with aldehyde 9 and the corresponding saturated aldehyde 13 in comparison with podophyllotoxin. (C) 1997 Elsevier Science Ltd.