丹参二醇 B | 97465-70-8

• 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
• 中文名称: 丹参二醇 B
• 中文别名: 丹参二醇B
• 英文名称: (−)-(3S,4R)-tanshindiol B
• 英文别名: (-)-(3S,4R)-tanshindiol B；tanshindiol B；(6R,7S)-6,7-dihydroxy-1,6-dimethyl-8,9-dihydro-7H-naphtho[1,2-g][1]benzofuran-10,11-dione
• CAS: 97465-70-8
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: RTKDBIDPGKCZJS-KPZWWZAWSA-N

物化性质

• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 储存条件：
  存储条件：密封、干燥、避光，温度范围：2-8°C

制备方法与用途

丹参二醇B是一种萘醌二萜，可通过诱导NQO1依赖性坏死（noptosis）来抑制胶质母细胞瘤的生长。

反应信息

• 作为反应物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 、 丹参二醇 B 在 glucosyltransferase from Andrographis paniculata 作用下， 以 aq. buffer 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Glucosyltransferase Capable of Catalyzing the Last Step in Neoandrographolide Biosynthesis

  摘要：

  ApUGT, a diterpene glycosyltransferase from Andrographis paniculata, could transfer a glucose to the C-19 hydroxyl moiety of andrograpanin to form neoandrographolide. This glycosyltransferase has a broad substrate scope, and it can glycosylate 26 natural and unnatural compounds of different structural types. This study provides a basis for exploring the glycosylation mechanism of ent-labdane-type diterpenes and plays an important role in diversifying the structures used in drug discovery.

  DOI：

  10.1021/acs.orglett.8b02146
• 作为产物：
  描述：

  (5S,9R)-7,7,9,17-tetramethyl-6,8,15-trioxapentacyclo[11.7.0.02,10.05,9.014,18]icosa-1(13),2(10),11,14(18),16-pentaene-19,20-dione 生成 丹参二醇 B
  参考文献：
  名称：

  LEE, JUNNING;SNYDER, JOHN K., J. ORG. CHEM., 55,(1990) N7, C. 4995-5008

  摘要：

  DOI：

文献信息

• DITERPENE DERIVATIVES FOR THE TREATMENT OF CARDIOVASCULAR, CANCER AND INFLAMMATORY DISEASES
  申请人：Dev Inderjit Kumar

  公开号：US20070207989A1

  公开（公告）日：2007-09-06

  The present invention relates to useful diterpenes and pharmaceutical compositions containing them of the formula: for use in the treatment of cardiovascular and inflammatory diseases and for cancers susceptible to an NF-κB inhibitor and an endothelin receptor inhibitor. The present invention also relates to compounds and methods useful to inhibit cell proliferation and for the induction of apoptosis.

  本发明涉及有用的二萜化合物及包含它们的药物组合物，用于治疗心血管和炎症性疾病，以及对NF-κB抑制剂和内皮素受体抑制剂敏感的癌症。本发明还涉及用于抑制细胞增殖和诱导凋亡的化合物和方法。
• Total synthesis of (±)-tanshinol B, tanshinone I, and (±)-tanshindiol B and C
  作者：Fan Wang、Hong Yang、Shujuan Yu、Yu Xue、Zhoulong Fan、Gaolin Liang、Meiyu Geng、Ao Zhang、Chunyong Ding

  DOI：10.1039/c8ob00567b

  日期：——

  A concise and efficient approach was established for the divergent total synthesis of (±)-tanshindiol B and C and tanshinone I from a ubiquitous ene intermediate in 1–2 steps. This critical intermediate was derived from (±)-tanshinol B, which was synthesized in 50% overall yield over 3 steps using an ultrasound-promoted cycloaddition as a key step. Compared to a previously reported strategy, our approach

  建立了一种简捷有效的方法，以1至2个步骤从无处不在的烯中间体分步进行总合成（±）-丹参二醇B和C和丹参酮I。该关键中间体衍生自（±）-丹参酚B，使用超声波促进的环加成反应为关键步骤，可在3个步骤中以50％的总收率合成。与以前报告的策略相比，我们的方法更具阶梯性，从而大大提高了合成效率。生物活性评估表明，丹参二醇的二醇立体化学对EZH2抑制活性有影响。
• Glucosyltransferase Capable of Catalyzing the Last Step in Neoandrographolide Biosynthesis
  作者：Yuan Li、Hui-Xin Lin、Jian Wang、Jian Yang、Chang-Jiang-Sheng Lai、Xing Wang、Bao-Wei Ma、Jin-Fu Tang、Yong Li、Xin-Lin Li、Juan Guo、Wei Gao、Lu-Qi Huang

  DOI：10.1021/acs.orglett.8b02146

  日期：2018.10.5

  ApUGT, a diterpene glycosyltransferase from Andrographis paniculata, could transfer a glucose to the C-19 hydroxyl moiety of andrograpanin to form neoandrographolide. This glycosyltransferase has a broad substrate scope, and it can glycosylate 26 natural and unnatural compounds of different structural types. This study provides a basis for exploring the glycosylation mechanism of ent-labdane-type diterpenes and plays an important role in diversifying the structures used in drug discovery.
• LEE, JUNNING;SNYDER, JOHN K., J. ORG. CHEM., 55,(1990) N7, C. 4995-5008
  作者：LEE, JUNNING、SNYDER, JOHN K.

  DOI：——

  日期：——