6,6'-bis(2-hydroxybenzoyl)-α,α-D-trehalose | 1148111-80-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,6'-bis(2-hydroxybenzoyl)-α,α-D-trehalose
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(2-hydroxybenzoyl)oxymethyl]oxan-2-yl]oxyoxan-2-yl]methyl 2-hydroxybenzoate
• CAS: 1148111-80-1
• 化学式: C₂₆H₃₀O₁₅
• 分子量: 582.515
• InChiKey: OAYKKBZTIFGCKQ-LSISOBETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  242
• 氢给体数：
  8
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  2,2',3,3',4,4'-hexabenzyl-6,6'-bis(2-hydroxybenzoyl)-α,α-D-trehalose 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 以65%的产率得到6,6'-bis(2-hydroxybenzoyl)-α,α-D-trehalose
  参考文献：
  名称：

  Synthesis and structure–activity relationships studies of brartemicin analogs as anti-invasive agents

  摘要：

  Brartemicin是一种由Nonomuraea属放线菌产生的基于海藻糖的肿瘤细胞侵袭抑制剂。为了寻找更有效的抗侵袭剂并研究结构—活性关系，研究人员通过两条合成路线从α,α-D-海藻糖合成了一系列19种brartemicin类药物，并评估了它们的抗侵袭活性。化合物4f，6,6′-二(2,3-二甲氧基苯甲酰基)-α,α-D-海藻糖，比天然的brartemicin更为有效。它对小鼠结肠26-L5、结肠癌SW620、黑素瘤B16-BL6和乳腺MDA-MB-231细胞的侵袭抑制作用的IC50值分别为0.15、2.35、4.12和2.61μM。类药物4p，6,6′-二(3,4-二甲氧基肉桂酰基)-α,α-D-海藻糖，在体外对小鼠结肠26-L5癌细胞的侵袭抑制作用与brartemicin相当。这些新型基于海藻糖的化合物的结构—活性关系进行了总结。

  DOI：

  10.1038/ja.2013.37

文献信息

• Brartemicin, an Inhibitor of Tumor Cell Invasion from the Actinomycete <i>Nonomuraea</i> sp.
  作者：Yasuhiro Igarashi、Tsukasa Mogi、Saeko Yanase、Satoshi Miyanaga、Tsuyoshi Fujita、Hiroaki Sakurai、Ikuo Saiki、Ayumi Ohsaki

  DOI：10.1021/np9000575

  日期：2009.5.22

  Brartemicin (1), a new trehalose-derived metabolite, was isolated from the culture broth of the actinomycete of the genus Nonomuraea. Its structure and absolute configuration were determined by spectroscopic analyses. The new compound inhibited the invasion of murine colon carcinoma 26-L5 cells with an IC50 value of 0.39 mu M in a concentration-dependent manner without showing cytotoxic effects.
• Synthesis and structure–activity relationships studies of brartemicin analogs as anti-invasive agents
  作者：Yong-Li Jiang、Satoshi Miyanaga、Xiu-Zhen Han、Long-Qiang Tang、Yasuhiro Igarashi、Ikuo Saiki、Zhao-Peng Liu

  DOI：10.1038/ja.2013.37

  日期：2013.9

  Brartemicin is a trehalose-based inhibitor of tumor cell invasion produced by the actinomycete of the genus Nonomuraea. In order to find more potent anti-invasive agents and study the structure–activity relationships, a series of 19 brartemicin analogs were prepared via two synthetic routes from α,α-D-trehalose and evaluated for their anti-invasive activities. Compound 4f, 6,6′-bis(2,3-dimethoxybenzoyl)-α,α-D-trehalose, was more potent than the natural brartemicin. It inhibited the invasion of murine colon 26-L5, colon carcinoma SW620, melanoma B16-BL6 and breast MDA-MB-231 cells with IC50 values of 0.15, 2.35, 4.12 and 2.61 μM, respectively. Analog 4p, 6,6′-bis(3,4-dimethoxycinnamoyl)-α,α-D-trehalose, was as potent as brartemicin against invasion of murine colon 26-L5 carcinoma cells in vitro. The structure–activity relationships of these novel trehalose-based compounds were summarized.

  Brartemicin是一种由Nonomuraea属放线菌产生的基于海藻糖的肿瘤细胞侵袭抑制剂。为了寻找更有效的抗侵袭剂并研究结构—活性关系，研究人员通过两条合成路线从α,α-D-海藻糖合成了一系列19种brartemicin类药物，并评估了它们的抗侵袭活性。化合物4f，6,6′-二(2,3-二甲氧基苯甲酰基)-α,α-D-海藻糖，比天然的brartemicin更为有效。它对小鼠结肠26-L5、结肠癌SW620、黑素瘤B16-BL6和乳腺MDA-MB-231细胞的侵袭抑制作用的IC50值分别为0.15、2.35、4.12和2.61μM。类药物4p，6,6′-二(3,4-二甲氧基肉桂酰基)-α,α-D-海藻糖，在体外对小鼠结肠26-L5癌细胞的侵袭抑制作用与brartemicin相当。这些新型基于海藻糖的化合物的结构—活性关系进行了总结。