13-chloro-3,15-dioxogibberellic acid methyl ester | 1064193-59-4

• 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: 13-chloro-3,15-dioxogibberellic acid methyl ester
• 英文别名: 13-chloro-3,15-dioxomethyl gibberellate；GA-13315；methyl (1R,2R,5S,8R,9S,10R,11S)-5-chloro-11-methyl-6-methylidene-7,12,16-trioxo-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadec-13-ene-9-carboxylate
• CAS: 1064193-59-4
• 化学式: C₂₀H₁₉ClO₆
• 分子量: 390.82
• InChiKey: QYIJUHQXYQFFOO-FJXLXCJVSA-N

物化性质

• 沸点：
  611.6±55.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  13-chloro-3,15-dioxogibberellic acid methyl ester 在 potassium fluoride 作用下， 以 乙腈 为溶剂， 以22%的产率得到methyl (1S,4aR,4bR,7S,9aR,10S,10aR)-7-fluoro-1-methyl-8-methylene-2,9,13-trioxo-1,2,4b,5,6,7,8,9,10,10a-decahydro-4a,1-(epoxymethano)-7,9a-methanobenzo[a]azulene-10-carboxylate
  参考文献：
  名称：

  Synthesis of gibberellin derivatives with anti-tumor bioactivities

  摘要：

  A series of gibberellin based molecules were designed and synthesized. Gibberellin derivatives bearing two alpha,beta-unsaturated ketone units showed strong anticancer activities in MTT assay towards a number of human cancer cell lines including HT29, A549, HepG2 and MKN28. The most potent gibberellin derivative (compound 10, IC50 = 2.9 mu M against HT29) inhibited completely the topoisomerase I activity at 8 mu g/ml. level. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.090
• 作为产物：
  描述：

  在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到13-chloro-3,15-dioxogibberellic acid methyl ester
  参考文献：
  名称：

  Synthesis of gibberellin derivatives with anti-tumor bioactivities

  摘要：

  A series of gibberellin based molecules were designed and synthesized. Gibberellin derivatives bearing two alpha,beta-unsaturated ketone units showed strong anticancer activities in MTT assay towards a number of human cancer cell lines including HT29, A549, HepG2 and MKN28. The most potent gibberellin derivative (compound 10, IC50 = 2.9 mu M against HT29) inhibited completely the topoisomerase I activity at 8 mu g/ml. level. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.090

文献信息

• 多硫代赤霉酸酯类化合物及其制备方法与抗肿瘤用途
  申请人：云南大学

  公开号：CN108276369B

  公开（公告）日：2022-04-01

  本发明公开一种如通式(Ⅰ)所示的多硫代赤霉酸酯类化合物、以其为活性成分的药物组合物、其制备方法及其在制备抗肿瘤药物中的应用。本发明的多硫代赤霉酸酯类化合物具有赤霉酸基本骨架结构，1‑位、13‑位和17‑位连接两个或三个相同的烷硫基基团。该类化合物显示了对多种人肿瘤细胞珠良好的抑制活性。此类多硫代赤霉酸酯类化合物的制备是以含双α,β‑不饱和酮结构的赤霉酸衍生物与含巯基化合物在不同条件下反应制备的。
• Inclusion complex of GA-13315 with cyclodextrins: Preparation, characterization, inclusion mode and properties
  作者：Rui Yang、Jing-Bo Chen、Xiao-Yang Dai、Rong Huang、Chuan-Fan Xiao、Zhan-Yong Gao、Bo Yang、Li-Juan Yang、Sheng-Jiao Yan、Hong-Bin Zhang、Chen Qing、Jun Lin

  DOI：10.1016/j.carbpol.2012.02.054

  日期：2012.6

  preliminary in vitro cytotoxicity assay showed that the complexes still maintain antitumor activities, compared with GA-13315 or adriamycin (ADM, positive control) as the positive control. The results showed that the water solubility and stability of GA-13315 were obviously improved in the inclusion complex with cyclodextrins, suggesting the inclusion complexes as promising future therapeutic agents.

  GA-13315（13-氯-3,15-二氧-赤霉酸甲酯）是由GA3（赤霉素）半合成的潜在抗癌药。为了追求其有希望的应用，环糊精被用于形成复合物以克服其缺点，例如差的水溶性和稳定性。因此，用天然的β-环糊精及其衍生物（羟丙基-β-环糊精（HPβCD））制备了GA-13315 / CD复合物，并通过液相色谱法研究了它们在溶液和固体中的包合络合行为，表征和结合能力。 UV，XRD，DSC，SEM，（1）H和2D NMR光谱 此外，初步的体外细胞毒性试验表明，与GA-13315或阿霉素（ADM，阳性对照）作为阳性对照相比，该复合物仍保持抗肿瘤活性。
• Synthesis of gibberellin derivatives with anti-tumor bioactivities
  作者：Jingbo Chen、Zhuxian Sun、Yanli Zhang、Xianghui Zeng、Chen Qing、Jianping Liu、Liang Li、Hongbin Zhang

  DOI：10.1016/j.bmcl.2009.07.090

  日期：2009.9

  A series of gibberellin based molecules were designed and synthesized. Gibberellin derivatives bearing two alpha,beta-unsaturated ketone units showed strong anticancer activities in MTT assay towards a number of human cancer cell lines including HT29, A549, HepG2 and MKN28. The most potent gibberellin derivative (compound 10, IC50 = 2.9 mu M against HT29) inhibited completely the topoisomerase I activity at 8 mu g/ml. level. (C) 2009 Elsevier Ltd. All rights reserved.