[(7S,8R)-6-(1,3-dithiolan-2-yl)-8-(3,4,5-trimethoxyphenyl)-7,8-dihydrobenzo[f][1,3]benzodioxol-7-yl]methanol | 199996-64-0

• 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: [(7S,8R)-6-(1,3-dithiolan-2-yl)-8-(3,4,5-trimethoxyphenyl)-7,8-dihydrobenzo[f][1,3]benzodioxol-7-yl]methanol
• CAS: 199996-64-0
• 化学式: C₂₄H₂₆O₆S₂
• 分子量: 474.599
• InChiKey: BENLBWIQMPYIFO-VGOFRKELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(7S,8R)-6-(1,3-dithiolan-2-yl)-8-(3,4,5-trimethoxyphenyl)-7,8-dihydrobenzo[f][1,3]benzodioxol-7-yl]methanol 在 三氟化硼乙醚 、 4-甲基苯磺酸吡啶 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 水 、 苯 为溶剂， 反应 11.0h， 生成 9'-O-methyl-9-deoxy-9-oxo-α-apopicropodophyllol
  参考文献：
  名称：

  环木脂醛的合成及其抗肿瘤活性。

  摘要：

  已经制备了几种与HT-29结肠癌的选择性抗肿瘤药9-脱氧-9-氧代-α-阿朴二十碳五烯酸甲酯有关的醛，并评估了它们对四种肿瘤细胞系的细胞毒活性（P-388，A- 549，HT-29和MEL-28）。他们所有人都没有内酯环，但将细胞毒性维持在microM水平或以下。

  DOI：

  10.1016/s0223-5234(00)00176-8
• 作为产物：
  描述：

  鬼臼毒素 在 氢氧化钾 、 lithium aluminium tetrahydride 、 三甲基氯硅烷 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 [(7S,8R)-6-(1,3-dithiolan-2-yl)-8-(3,4,5-trimethoxyphenyl)-7,8-dihydrobenzo[f][1,3]benzodioxol-7-yl]methanol
  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

• Synthesis and antineoplastic activity of cyclolignan aldehydes
  作者：Marina Gordaliza、M Angeles Castro、José M Miguel del Corral、M Luisa López-Vázquez、Pablo A. García、M Dolores García-Grávalos、Arturo San Feliciano

  DOI：10.1016/s0223-5234(00)00176-8

  日期：2000.8

  Several aldehydes related to methyl 9-deoxy-9-oxo-alpha-apopicropodophyllate, a selective antitumour agent against the HT-29 colon carcinoma, have been prepared and evaluated for their cytotoxic activities on four neoplastic cell lines (P-388, A-549, HT-29 and MEL-28). All of them lacked the lactone ring but maintained their cytotoxicity at, or under, the microM level.

  已经制备了几种与HT-29结肠癌的选择性抗肿瘤药9-脱氧-9-氧代-α-阿朴二十碳五烯酸甲酯有关的醛，并评估了它们对四种肿瘤细胞系的细胞毒活性（P-388，A- 549，HT-29和MEL-28）。他们所有人都没有内酯环，但将细胞毒性维持在microM水平或以下。
• 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.