(5R,6S)-7-[1,3]Dithiolan-2-yl-5-(3,4,5-trimethoxy-phenyl)-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester | 199996-63-9

• 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: (5R,6S)-7-[1,3]Dithiolan-2-yl-5-(3,4,5-trimethoxy-phenyl)-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester
• 英文别名: methyl (7S,8R)-6-(1,3-dithiolan-2-yl)-8-(3,4,5-trimethoxyphenyl)-7,8-dihydrobenzo[f][1,3]benzodioxole-7-carboxylate
• CAS: 199996-63-9
• 化学式: C₂₅H₂₆O₇S₂
• 分子量: 502.609
• InChiKey: AQZVVVIAIMGIFP-FGZHOGPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (5R,6S)-7-[1,3]Dithiolan-2-yl-5-(3,4,5-trimethoxy-phenyl)-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以98%的产率得到[(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：

  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 、 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 22.0h， 生成 (5R,6S)-7-[1,3]Dithiolan-2-yl-5-(3,4,5-trimethoxy-phenyl)-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic 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

• Synthesis and Biological Evaluation of New Podophyllic Aldehyde Derivatives with Cytotoxic and Apoptosis-Inducing Activities
  作者：M Ángeles Castro、José M Miguel del Corral、Pablo A. García、M Victoria Rojo、Janis de la Iglesia-Vicente、Faustino Mollinedo、Carmen Cuevas、Arturo San Feliciano

  DOI：10.1021/jm901373w

  日期：2010.2.11

  Several series of nonlactonic podophyllic aldehyde analogues were prepared and evaluated against several human tumor cell lines. They had different combinations of aldehyde, imine, amine, ester, and amide functions at C-9 and C-9′ of the cyclolignan skeleton. All the compounds synthesized showed cytotoxicity levels in the μM range and below. Within the new series tested, compounds having an aldehyde

  制备了几种非内分泌的鬼臼醛类似物，并针对几种人类肿瘤细胞系进行了评估。他们在cyclolignan骨架的C-9和C-9'处具有醛，亚胺，胺，酯和酰胺官能团的不同组合。合成的所有化合物均显示在μM或以下的细胞毒性水平。在测试的新系列中，在C-9处具有醛或亚胺，在C-9'具有酯的化合物是最有效的，其GI 50值在nM范围内，其中一些对HT-29的效力高出几倍。与A-549癌相比，它可抗MB-231黑色素瘤细胞。细胞周期研究和对微管破坏能力的分析表明，对于结构密切相关的化合物，存在两种不同的细胞死亡诱导机制。
• 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.