(2R,3S,4S,4aR,10bS)-8,10-bis(heptyloxy)-3,4-dihydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c]isochromen-6(2H)-one | 1373402-11-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3S,4S,4aR,10bS)-8,10-bis(heptyloxy)-3,4-dihydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c]isochromen-6(2H)-one
• 英文别名: 8,10-bis(heptyloxy)-3,4-dihydroxy-2-(hydroxymethyl)-9-methoxy-2,3,4,4a tetrahydropyrano[3,2-c]isochromen-6(10bH)-one；(2R,3S,4S,4aR,10bS)-8,10-diheptoxy-3,4-dihydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one
• CAS: 1373402-11-9
• 化学式: C₂₈H₄₄O₉
• 分子量: 524.652
• InChiKey: JDSUWZGBYBQMAP-FOZSKDHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,4aR,10bS)-8,10-bis(heptyloxy)-3,4-dihydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c]isochromen-6(2H)-one 在 硼烷四氢呋喃络合物 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 5.0h， 生成 (2R,3S,4S,4aR,10bS)-3-(benzyloxy)-8,10-bis(heptyloxy)-4-hydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c]isochromen-6(2H)-one
  参考文献：
  名称：

  山毛榉素衍生物作为新型免疫抑制剂的合成及生物学评价

  摘要：

  Bergenin 是从Bergenia物种中分离出来的，具有多种药理特性。在寻找新型免疫抑制剂的过程中，设计合成了一系列山毛榉素衍生物，并通过CCK-8法评价了它们的免疫抑制作用。实验数据表明，化合物7和13对小鼠脾细胞增殖的抑制作用最强（IC 50分别为 3.52 和 5.39 μM）。进一步的研究表明，抑制作用可能来自对 IFN-γ 和 IL-4 细胞因子的抑制。具有正己基和正己基的山毛榉素的烷基化衍生物-庚基对两个酚羟基表现出较好的抑制活性。bergenin 衍生物的疏水性、bergenin 中 4-OH 的构型以及C -4 位上的取代基形成氢键的能力对免疫抑制活性很重要。这项工作证明了对bergenin的修饰可能代表了发现一类新的免疫抑制剂的新途径。

  DOI：

  10.1039/d1md00210d
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (2R,3S,4S,4aR,10bS)-8,10-bis(heptyloxy)-3,4-dihydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c]isochromen-6(2H)-one
  参考文献：
  名称：

  Synthesis of new bergenin derivatives as potent inhibitors of inflammatory mediators NO and TNF-α

  摘要：

  Bergenin is an isocoumarin natural product which aides in fat loss, healthy weight maintenance, enhancing the lipolytic effects of norepinephrine, inhibiting the formation of interleukin 1 alpha and cyclooxygenases-2. Here we describe the anti-inflammatory activity of new bergenin derivatives 1-15 in the respiratory burst assay. Bergenin was isolated from the crude extract of Mallotus philippenensis after repeated column chromatography and was then subjected to chemical derivatization. The structures of all compounds were elucidated by NMR and mass spectroscopic techniques. Compound 2 was also studied using single crystal X-ray diffraction. Compounds 4, (54.5 +/- 2.2%) 5 (47.5 +/- 0.5%) 5, and 15 (86.8 +/- 1.9%) showed significant (P <= 0.005) NO inhibitory activities whereas 6, 7, 11, 12 and 13 displayed moderate inhibitory activities that ranges between 16% and 31%. Furthermore compounds 4 and 15, were discovered as significant (P <= 0.005) TNF-alpha inhibitors with 98% and 96% inhibition, respectively, while compounds 3, 5, 7, 8, 11, and 12 showed low level of TNF-alpha inhibition (0.4-28%). Compounds 8, 13 and 15 exhibited moderate anti-inflammatory IC50 activities with 212, 222, and 253 mu M, respectively, compared to the standard anti-inflammatory drug indomethacin as well as the parent bergenin compound. No cytotoxic effects could be detected when the compounds were tested on 3T3 cells up to concentrations of 100 mu M. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.096

文献信息

• Synthesis of new bergenin derivatives as potent inhibitors of inflammatory mediators NO and TNF-α
  作者：Muhammad Raza Shah、Mohammad Arfan、Hazrat Amin、Zahid Hussain、Muhammad Irfan Qadir、M. Iqbal Choudhary、Donald VanDerveer、M. Ahmed Mesaik、Samreen Soomro、Almas Jabeen、Inam Ullah Khan

  DOI：10.1016/j.bmcl.2012.02.096

  日期：2012.4

  Bergenin is an isocoumarin natural product which aides in fat loss, healthy weight maintenance, enhancing the lipolytic effects of norepinephrine, inhibiting the formation of interleukin 1 alpha and cyclooxygenases-2. Here we describe the anti-inflammatory activity of new bergenin derivatives 1-15 in the respiratory burst assay. Bergenin was isolated from the crude extract of Mallotus philippenensis after repeated column chromatography and was then subjected to chemical derivatization. The structures of all compounds were elucidated by NMR and mass spectroscopic techniques. Compound 2 was also studied using single crystal X-ray diffraction. Compounds 4, (54.5 +/- 2.2%) 5 (47.5 +/- 0.5%) 5, and 15 (86.8 +/- 1.9%) showed significant (P <= 0.005) NO inhibitory activities whereas 6, 7, 11, 12 and 13 displayed moderate inhibitory activities that ranges between 16% and 31%. Furthermore compounds 4 and 15, were discovered as significant (P <= 0.005) TNF-alpha inhibitors with 98% and 96% inhibition, respectively, while compounds 3, 5, 7, 8, 11, and 12 showed low level of TNF-alpha inhibition (0.4-28%). Compounds 8, 13 and 15 exhibited moderate anti-inflammatory IC50 activities with 212, 222, and 253 mu M, respectively, compared to the standard anti-inflammatory drug indomethacin as well as the parent bergenin compound. No cytotoxic effects could be detected when the compounds were tested on 3T3 cells up to concentrations of 100 mu M. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of bergenin derivatives as new immunosuppressants
  作者：Lihua Deng、Chengcheng Song、Youhong Niu、Qin Li、Meng Wang、Yan-Fen Wu、Xin-Shan Ye

  DOI：10.1039/d1md00210d

  日期：——

  Bergenin, which is isolated from Bergenia species, exhibits various pharmacological properties. In the search for new types of immunosuppressants, a series of bergenin derivatives were designed and synthesized, and their immunosuppressive effects were evaluated by the CCK-8 assay. The experimental data demonstrated that compounds 7 and 13 showed the strongest inhibition effects on mouse splenocyte

  Bergenin 是从Bergenia物种中分离出来的，具有多种药理特性。在寻找新型免疫抑制剂的过程中，设计合成了一系列山毛榉素衍生物，并通过CCK-8法评价了它们的免疫抑制作用。实验数据表明，化合物7和13对小鼠脾细胞增殖的抑制作用最强（IC 50分别为 3.52 和 5.39 μM）。进一步的研究表明，抑制作用可能来自对 IFN-γ 和 IL-4 细胞因子的抑制。具有正己基和正己基的山毛榉素的烷基化衍生物-庚基对两个酚羟基表现出较好的抑制活性。bergenin 衍生物的疏水性、bergenin 中 4-OH 的构型以及C -4 位上的取代基形成氢键的能力对免疫抑制活性很重要。这项工作证明了对bergenin的修饰可能代表了发现一类新的免疫抑制剂的新途径。