28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosylbetulinic acid | 22333-84-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosylbetulinic acid
• 英文别名: [(2S,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl] (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate
• CAS: 22333-84-2
• 化学式: C₆₄H₇₄O₁₂
• 分子量: 1035.28
• InChiKey: WRJFCPMBDUIFLG-JFTLSOKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.8
• 重原子数：
  76
• 可旋转键数：
  17
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosylbetulinic acid 、 2,3,4-tri-O-benzoyl-β-L-arabinopyranosyl trichloroacetimidate-⁴C₁ 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以63%的产率得到28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosylbetulinic acid 3β-O-2,3,4-tri-O-benzoyl-α-L-arabinopyranoside
  参考文献：
  名称：

  Synthesis and Cytotoxicity of Bidesmosidic Betulin and Betulinic Acid Saponins

  摘要：

  The naturally occurring cytotoxic saponin 28-O-beta-D-glucopyranosylbetulinic acid 3 beta-O-alpha-L-arabinopyranoside (3) was easily synthesized along with seven bidesmosidic saponins starting from the lupane-type triterpenoids betulin (1) and betulinic acid (2). As highlighted by the preliminary cytotoxicity evaluation against A549, DLD-1, MCF7, and PC-3 human cancer cell lines, the bidesmosidic betulin saponin 22a, bearing alpha-L-rhamnopyranoside moieties at both C-3 and C-28 positions, was determined to be a potent cytotoxic agent (IC50 1.8-1.9 mu M).

  DOI：

  10.1021/np800579x
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoylglucosyl bromide 、 白桦脂酸 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 6.0h， 以90%的产率得到28-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosylbetulinic acid
  参考文献：
  名称：

  [EN] BIDESMOSIDIC BETULIN AND BETULINIC ACID DERIVATIVES AND USES THEREOF AS ANTITUMOR AGENTS
  [FR] DÉRIVÉS DE BÉTULINE BIDESMOSIDIQUE ET D'ACIDE BÉTULINIQUE, ET LEURS UTILISATIONS EN TANT QU'AGENTS ANTICANCÉREUX

  摘要：

  该即时申请涉及到公式(I)的双萜基萜苷类的白桦酸和白桦酸皂苷衍生物，以及其作为抗肿瘤剂的用途。具体来说，所述化合物在治疗肺癌、结肠腺癌、乳腺腺癌和前列腺腺癌方面具有有效性。还公开了通过选择性糖基化C-28和C-3位置合成所述化合物的方法，以及用于识别适合通过所述化合物治疗的肿瘤的诊断方法。

  公开号：

  WO2010028487A1

文献信息

• Efficient Synthesis of Lupane-Type Saponins via Gold(I)-Catalyzed Glycosylation with Glycosyl <i>ortho</i>-Alkynylbenzoates as Donors
  作者：Yan Li、Jiansong Sun、Biao Yu

  DOI：10.1021/ol202232v

  日期：2011.10.21

  Glycosylation of the acid labile betulin and betulinic acid derivatives was achieved with glycosyl ortho-hexynyibenzoates as donors under the catalysis of PPh3AuNTf2; this enabled the efficient synthesis of lupane-type saponins, as exemplified by the total synthesis of the proposed betulinic acid trisaccharide from Bersama engleriana.
• BETULINIC ACID AND DERIVATIVES THEREOF USEFUL FOR THE TREATMENT OF NEUROECTODERMAL TUMORS
  申请人：Deutsches KrebsforschungszentrumStiftung des öffentlichen Rechts

  公开号：EP1124842A1

  公开（公告）日：2001-08-22
• US6369109B1
  申请人：——

  公开号：US6369109B1

  公开（公告）日：2002-04-09
• [EN] BETULINIC ACID AND DERIVATIVES THEREOF USEFUL FOR THE TREATMENT OF NEUROECTODERMAL TUMORS<br/>[FR] ACIDE BETULINIQUE ET DERIVES DE CET ACIDE POUR LE TRAITEMENT DE TUMEURS NEUROECTODERMIQUES
  申请人：DEUTSCHES KREBSFORSCH

  公开号：WO2000024762A1

  公开（公告）日：2000-05-04

  The present invention is, generally, directed to the use of betulinic acid and derivatives thereof for the treatment of neuroectodermal tumors. The present invention is based on the discovery that betulinic acid and its deriatives are potent anti-neuroectodermal agents. As disclosed herein, betulinic acid and its derivatives are useful for the treatment of neurodectodermal tumors, including, due to its distinct mechanism of action, neuroectodermal tumors that are resistant to conventional chemotherapeutical agents. In addition to the new use of known compounds, the invention discloses novel compounds and pharmaceutical compositions for the treatment of neuroectodermal tumors.