Methanesulfonic acid (5R,5aR,8aR,9R)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl ester | 908355-89-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: Methanesulfonic acid (5R,5aR,8aR,9R)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl ester
• 英文别名: [(5R,5aR,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-5-yl] methanesulfonate
• CAS: 908355-89-5
• 化学式: C₂₃H₂₄O₁₀S
• 分子量: 492.504
• InChiKey: KMRXHANWGYGTOQ-MGNXDGSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (5R,5aR,8aR,9R)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl ester 在 三甲基氯硅烷 、 sodium azide 、 sodium iodide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 4.5h， 生成 (5R,5aR,8aS,9S)-9-amino-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one
  参考文献：
  名称：

  Facile and improved synthesis of 4β-aminopodophyllotoxin congeners

  摘要：

  An efficient synthesis of 4 beta-aminopodophyllotoxin from 4 beta-bromopodophyllotoxin using ammonia, and also a facile synthesis of 4 beta-amino-4'-O-demethylpodophyllotoxin from 4 beta-azidopodophyllotoxin by simultaneous azido reduction and selective demethylation at 4'-position employing chlorotrimethylsilane and sodium iodide, has been described. These are potential precursors for the various 4 beta-amino analogs of podophyllotoxin possessing DNA topoisomerase II inhibition activity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00570-8
• 作为产物：
  描述：

  甲基磺酰氯 、 鬼臼毒素 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 Methanesulfonic acid (5R,5aR,8aR,9R)-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl ester
  参考文献：
  名称：

  作为抗肿瘤剂的 4α/4β-咪唑基鬼臼毒素类似物的合成和生物学评价

  摘要：

  已经设计并合成了一系列 4α/4β-咪唑基鬼臼毒素类似物。评估了所有化合物对一组三种人类癌细胞系的抗癌活性。在测试的细胞系中，一些合成的化合物显示出有希望的抗癌活性。尤其是化合物 12 表现出显着的细胞毒性，显示出对所有肿瘤细胞系的作用，包括 K562/ADM 细胞系。

  DOI：

  10.1002/ardp.201100094

文献信息

• Stereo and chemoselective enzymatic reduction of azido functionality: Synthesis of 4-β-aminopodophyllotoxin congeners by baker's yeast
  作者：Ahmed Kamal、B. Laxminarayana、N. Lakshmi Gayatri

  DOI：10.1016/s0040-4039(97)01582-7

  日期：1997.9

  4β-Aminopodophyllotoxin congeners have been synthesized by the stereoselective biocatalytic reduction of the 4-azidopodophyllotoxins employing baker's yeast in excellent yields under mild conditions.

  通过使用贝克酵母在温和条件下以优异的产率立体选择性地生物催化还原4-叠氮基鬼臼毒素，合成了4β-氨基鬼臼毒素同源物。
• Synthesis of 4β-amido and 4β-sulphonamido analogues of podophyllotoxin as potential antitumour agents
  作者：Ahmed Kamal、B Ashwini Kumar、M Arifuddin、Sunanda G Dastidar

  DOI：10.1016/j.bmc.2003.08.019

  日期：2003.11

  The new 4beta-amido analogues of podophyllotoxin or 4'-O-demethylepipodophyllotoxin have been prepared either by the coupling of 4beta-amino podophyllotoxin or 4beta-amino-4'-O-demethyl epipodophyllotoxin with the corresponding acids in presence of DCC in dichloromethane or by treating the appropriate acid chloride or sulphonyl chloride in presence of Et3N. These 4beta-amido and 4beta-sulphonamido derivatives of podophyllotoxin have been evaluated for their cytotoxicity against six human cancer cell lines. Some of these analogues have shown promising anticancer activity. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of new chiral N-heterocyclic carbenes from naturally occurring podophyllotoxin and their application to asymmetric allylic alkylation
  作者：Shi-Jun Li、Jian-Hua Zhong、Yan-Guang Wang

  DOI：10.1016/j.tetasy.2006.06.003

  日期：2006.7

  Chiral N-heterocyclic carbenes (NHC) were synthesized from naturally occurring podophyllotoxin. Their coordination with [(eta(3)-allyl)Pd(Br)](2) afforded (NHC)Pd(allyl)Br complexes, whose structures were unambiguously established by X-ray single crystal analysis. These chiral NHC and NHC-Pd-allyl complexes were found to catalyze the substitution reaction of allylic compounds with high conversions and enantioselectivities (up to 87% ee). (c) 2006 Elsevier Ltd. All rights reserved.