deangeloylgomisin B

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: deangeloylgomisin B
• 英文别名: Schisantherol A；(8S,9S,10S)-3,4,5,19-tetramethoxy-9,10-dimethyl-15,17-dioxatetracyclo[10.7.0.02,7.014,18]nonadeca-1(19),2,4,6,12,14(18)-hexaene-8,9-diol
• 化学式: C₂₃H₂₈O₈
• 分子量: 432.471
• InChiKey: BFELOFVXWJZJNF-JHWMDXGOSA-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：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  95.8
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  deangeloylgomisin B 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以55.3%的产率得到6,7-Secoschisantherol A
  参考文献：
  名称：

  Lignans from Schisandra sphenathera Rehd. et Wils. and semisynthetic schisantherin A analogues: Absolute configuration, and their estrogenic and anti-proliferative activity

  摘要：

  A new dibenzocyclooctene-type lignan, named schisandrin A1 (1), together with nine known lignans (2-10), was isolated from the stems of Schisandra sphenathera. The structure of schisandrin A1, which contains a spirocyclic epoxy unit, was established by means of spectroscopic methods. The absolute configurations of schisandrin A1 (1) and schisantherin A (2) were determined by electronic circular dichroism (CD) and TDDFT calculations, with 2 further confirmed by X-ray crystallographic data. Ten new schisantherin A derivatives (11-20) and 6,7-secoschisantherol A (2b) were synthesized. In addition, natural lignans and semisynthetic schisantherin A derivatives showed the antiproliferative activity on four human cancer cell lines and Id1 (an inhibitor of DNA binding protein) and estrogenic potency. Compounds 5, 7, and 8 exhibited very potent estrogenic activity. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.003
• 作为产物：
  描述：

  gomisin C 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 以94%的产率得到deangeloylgomisin B
  参考文献：
  名称：

  新颖的设计，合成和抗增殖活性7'- ö取代五味子酯A衍生物†往最‡

  摘要：

  利用山口酯在甲壳素A核的C-7'位置上的酯化反应（2,4,6-三氯苯甲酰氯，Et 3 N，THF，DMAP，甲苯）有效地合成了一系列壳聚糖素A（1）衍生物。使用磺基罗丹明B测定法评价合成的衍生物对SIHA，PANC 1，MDA-MB-231，IMR-32，DU-145和A549癌细胞的抗癌活性。在测试的新系列中，化合物29对人宫颈癌细胞系（SIHA）表现出最有希望的细胞毒性作用，GI 50值＜0.01μM，与标准药物阿霉素相当。行动机制研究验证了29起到微管抑制剂的作用。另外，几种其他类似物对被测细胞系表现出有效的活性。根据获得的结果，建立了结构-活性关系（SAR），并观察和讨论了活性之间的相关性。

  DOI：

  10.1039/c6md00097e

文献信息

• Synthesis of the first unnatural schisantherins and their effects in multidrug-resistant cancer cells
  作者：Rainer Schobert、Werner Kern、Wolfgang Milius、Tamara Ackermann、Miroslava Zoldakova

  DOI：10.1016/j.tetlet.2008.03.134

  日期：2008.5

  Schisandrol A, a dibenzocyclooctadiene lignan, was obtained by a simplified procedure from Schisandra chinensis fruits. Its reaction with carboxylic acids to give new esters (schisantherins) required special conditions such as microwave irradiation. An X-ray single crystal structure analysis of schisandrol A revealed a sterical shielding of the secondary OH group as the likely reason. The cinnamoate inhibited the P-gp drug transporters of multidrug-resistant human Kb-V1 cervix carcinoma cells better than the natural benzoate and comparable to the clinical sensitizer verapamil. (C) 2008 Elsevier Ltd. All rights reserved.
• Design, synthesis and anti-proliferative activities of novel 7′-<i>O</i>-substituted schisantherin A derivatives
  作者：A. Venkanna、Ch. Pavan Kumar、B. Poornima、Bandi Siva、Nishant Jain、K. Suresh Babu

  DOI：10.1039/c6md00097e

  日期：——

  Yamaguchi esterification (2,4,6-trichlorobenzoyl chloride, Et3N, THF, DMAP, toluene) at the C-7′ position of the schisantherin A core. The synthesized derivatives were evaluated for their anti-cancer activities against SIHA, PANC 1, MDA-MB-231, IMR-32, DU-145 and A549 cancer cell lines using sulforhodamine B assay. Within the new series tested, compound 29 displayed the most promising cytotoxic effect against

  利用山口酯在甲壳素A核的C-7'位置上的酯化反应（2,4,6-三氯苯甲酰氯，Et 3 N，THF，DMAP，甲苯）有效地合成了一系列壳聚糖素A（1）衍生物。使用磺基罗丹明B测定法评价合成的衍生物对SIHA，PANC 1，MDA-MB-231，IMR-32，DU-145和A549癌细胞的抗癌活性。在测试的新系列中，化合物29对人宫颈癌细胞系（SIHA）表现出最有希望的细胞毒性作用，GI 50值＜0.01μM，与标准药物阿霉素相当。行动机制研究验证了29起到微管抑制剂的作用。另外，几种其他类似物对被测细胞系表现出有效的活性。根据获得的结果，建立了结构-活性关系（SAR），并观察和讨论了活性之间的相关性。
• Lignans from Schisandra sphenathera Rehd. et Wils. and semisynthetic schisantherin A analogues: Absolute configuration, and their estrogenic and anti-proliferative activity
  作者：Han-Wei Liu、Xiu-Zhu Yu、Daniele Padula、Gennaro Pescitelli、Zhi-Wei Lin、Fei Wang、Kai Ding、Ming Lei、Jin-Ming Gao

  DOI：10.1016/j.ejmech.2012.11.003

  日期：2013.1

  A new dibenzocyclooctene-type lignan, named schisandrin A1 (1), together with nine known lignans (2-10), was isolated from the stems of Schisandra sphenathera. The structure of schisandrin A1, which contains a spirocyclic epoxy unit, was established by means of spectroscopic methods. The absolute configurations of schisandrin A1 (1) and schisantherin A (2) were determined by electronic circular dichroism (CD) and TDDFT calculations, with 2 further confirmed by X-ray crystallographic data. Ten new schisantherin A derivatives (11-20) and 6,7-secoschisantherol A (2b) were synthesized. In addition, natural lignans and semisynthetic schisantherin A derivatives showed the antiproliferative activity on four human cancer cell lines and Id1 (an inhibitor of DNA binding protein) and estrogenic potency. Compounds 5, 7, and 8 exhibited very potent estrogenic activity. (C) 2012 Elsevier Masson SAS. All rights reserved.