((3R,4R,5R)7αR)-3<(3,4,5-trimethoxyphenyl)hydroxymethyl>-4-<<2-methoxy-3,4-(methylenedioxy)phenyl>(1,3-propylenedithio)methyl>-5-(1-methyloxy)dihydro-2(3H)-furanone | 163779-33-7

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: ((3R,4R,5R)7αR)-3<(3,4,5-trimethoxyphenyl)hydroxymethyl>-4-<<2-methoxy-3,4-(methylenedioxy)phenyl>(1,3-propylenedithio)methyl>-5-(1-methyloxy)dihydro-2(3H)-furanone
• 英文别名: (3S,4R,5R)-3-[(S)-hydroxy-(3,4,5-trimethoxyphenyl)methyl]-4-[2-(4-methoxy-1,3-benzodioxol-5-yl)-1,3-dithian-2-yl]-5-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxyoxolan-2-one
• CAS: 163779-33-7
• 化学式: C₃₆H₄₈O₁₀S₂
• 分子量: 704.903
• InChiKey: FWJXKTKZAMNQQO-AGOJHZHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  48
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  ((3R,4R,5R)7αR)-3<(3,4,5-trimethoxyphenyl)hydroxymethyl>-4-<<2-methoxy-3,4-(methylenedioxy)phenyl>(1,3-propylenedithio)methyl>-5-(1-methyloxy)dihydro-2(3H)-furanone 在 calcium carbonate 、 mercury dichloride 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 反应 0.5h， 以67%的产率得到((3R,4R,5R)7αR)-3-<(3,4,5-trimethoxyphenyl)hydroxymethyl>-4-<<2-methoxy-3,4-(methylenedioxy)phenyl>oxomethyl>-5-(1-menthyloxy)dihydro-2(3H)-furanone
  参考文献：
  名称：

  Synthesis and Cytotoxicity of Novel Lignans

  摘要：

  In this study the syntheses of 11 novel lignans are described. Their cytotoxicities are studied in GLC(4), a human small cell lung carcinoma cell line, using the microculture tetrazolium (MTT) assay. Ten of these compounds were substituted with a menthyloxy group on the 5-position of the lactone. These compounds can easily be prepared in (novel) 'one-pot', three- or four-step syntheses. In addition, methods for controlling the stereogenic centers are described. Furthermore, five naturally occurring podophyllotoxin-related compounds were tested. The cytotoxicities of all lignan compounds, and of three non-lignan intermediates originating from the syntheses, were compared with the clinically applied anticancer agents etoposide, teniposide, and cisplatin. Most compounds showed moderate to high activities against GLC(4), and two of the compounds containing a menthyloxy group showed activities comparable to the reference cytotoxic agents.

  DOI：

  10.1021/jm00012a010
• 作为产物：
  描述：

  (5R)-(L-menthyloxy)-2(5H)-furanone 、 3,4,5-三甲氧基苯甲醛 、 1,2-(methylenedioxy)-3-methoxy-4-<(1,3-propylenedithio)methyl>benzene 在 正丁基锂 、 Chloro-tris(diethylamino)titan 作用下， 生成 ((3R,4R,5R)7αR)-3<(3,4,5-trimethoxyphenyl)hydroxymethyl>-4-<<2-methoxy-3,4-(methylenedioxy)phenyl>(1,3-propylenedithio)methyl>-5-(1-methyloxy)dihydro-2(3H)-furanone
  参考文献：
  名称：

  Synthesis and Cytotoxicity of Novel Lignans

  摘要：

  In this study the syntheses of 11 novel lignans are described. Their cytotoxicities are studied in GLC(4), a human small cell lung carcinoma cell line, using the microculture tetrazolium (MTT) assay. Ten of these compounds were substituted with a menthyloxy group on the 5-position of the lactone. These compounds can easily be prepared in (novel) 'one-pot', three- or four-step syntheses. In addition, methods for controlling the stereogenic centers are described. Furthermore, five naturally occurring podophyllotoxin-related compounds were tested. The cytotoxicities of all lignan compounds, and of three non-lignan intermediates originating from the syntheses, were compared with the clinically applied anticancer agents etoposide, teniposide, and cisplatin. Most compounds showed moderate to high activities against GLC(4), and two of the compounds containing a menthyloxy group showed activities comparable to the reference cytotoxic agents.

  DOI：

  10.1021/jm00012a010

文献信息

• Synthesis and Cytotoxicity of Novel Lignans
  作者：Oskar Middel、Herman J. Woerdenbag、Wim van Uden、Arjan van Oeveren、Johan F. G. A. Jansen、Ben L. Feringa、Antonius W. T. Konings、Niesko Pras、Richard M. Kellogg

  DOI：10.1021/jm00012a010

  日期：1995.6

  In this study the syntheses of 11 novel lignans are described. Their cytotoxicities are studied in GLC(4), a human small cell lung carcinoma cell line, using the microculture tetrazolium (MTT) assay. Ten of these compounds were substituted with a menthyloxy group on the 5-position of the lactone. These compounds can easily be prepared in (novel) 'one-pot', three- or four-step syntheses. In addition, methods for controlling the stereogenic centers are described. Furthermore, five naturally occurring podophyllotoxin-related compounds were tested. The cytotoxicities of all lignan compounds, and of three non-lignan intermediates originating from the syntheses, were compared with the clinically applied anticancer agents etoposide, teniposide, and cisplatin. Most compounds showed moderate to high activities against GLC(4), and two of the compounds containing a menthyloxy group showed activities comparable to the reference cytotoxic agents.