4-bromo-α-mangostin | 1146966-46-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-bromo-α-mangostin
• 英文别名: 4-Bromo-1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methylbut-2-enyl)xanthen-9-one
• CAS: 1146966-46-2
• 化学式: C₂₄H₂₅BrO₆
• 分子量: 489.363
• InChiKey: JONRVSFLVDRTNN-UHFFFAOYSA-N

物化性质

• 沸点：
  659.1±55.0 °C(predicted)
• 密度：
  1.436±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-bromo-α-mangostin 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以67%的产率得到4-Bromo-1-hydroxy-3,6,7-trimethoxy-2,8-bis(3-methylbut-2-enyl)xanthen-9-one
  参考文献：
  名称：

  Synthetic Studies of Mangostin Derivatives with an Inhibitory Activity on PDGF-Induced Human Aortic Smooth Cells Proliferation

  摘要：

  The mangostin derivatives 3-10, were synthesized by halogenation, electrochemical oxidation, and mCPBA oxidation of alpha- and gamma-mangostins (1, 2). Among them, the hydroxyl 9 and the benzopyran 10 derivatives produced by mCPBA, showed remarkable antiproliferative activities against human aortic smooth muscle cells (HASMC) induced by platelet-derived growth factor (PDGF).

  DOI：

  10.3987/com-08-s(f)65
• 作为产物：
  描述：

  α-倒捻子素 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 以51%的产率得到4-bromo-α-mangostin
  参考文献：
  名称：

  Synthetic Studies of Mangostin Derivatives with an Inhibitory Activity on PDGF-Induced Human Aortic Smooth Cells Proliferation

  摘要：

  The mangostin derivatives 3-10, were synthesized by halogenation, electrochemical oxidation, and mCPBA oxidation of alpha- and gamma-mangostins (1, 2). Among them, the hydroxyl 9 and the benzopyran 10 derivatives produced by mCPBA, showed remarkable antiproliferative activities against human aortic smooth muscle cells (HASMC) induced by platelet-derived growth factor (PDGF).

  DOI：

  10.3987/com-08-s(f)65

文献信息

• Design, synthesis and structure–activity relationships of mangostin analogs as cytotoxic agents
  作者：Xiao-Qian Chi、Cheng-Ting Zi、Hong-Mei Li、Liu Yang、Yong-Feng Lv、Jin-Yu Li、Bo Hou、Fu-Cai Ren、Jiang-Miao Hu、Jun Zhou

  DOI：10.1039/c8ra08409b

  日期：——

  their cytotoxicity against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7 and SW480) using MTT assays. Most of them showed cytotoxicity and most of all, compounds 1a and 2h showed the highest cytotoxic potency by HL-60 cancer cell lines with IC50 values of 5.96 μM and 6.90 μM respectively; compound 3e showed the highest cytotoxic potency against SMMC-7221 cancer cell line with

  为了更好地了解山竹素的构效关系，设计合成了一系列基于α-山竹素的呫吨酮衍生物。使用 MTT 分析评估了所有化合物对一组五种人类癌细胞系（HL-60、SMMC-7721、A-549、MCF-7 和 SW480）的细胞毒性。它们中的大多数显示出细胞毒性，最重要的是，化合物1a和2h对HL-60癌细胞系显示出最高的细胞毒性效力，IC 50值分别为5.96 μM和6.90 μM；化合物3e对SMMC-7221癌细胞系表现出最高的细胞毒效力，IC 50值为3.98 μM；化合物2e和2m分别对 HL-60 和 SMMC-7221 癌细胞系表现出比 α-mangostin 更低的细胞毒性但更高的选择性。构效关系分析表明，异戊烯基团在 C-8 上的维持对细胞毒活性至关重要。
• Design, synthesis and cholinesterase inhibitory activity of <i>α</i>-mangostin derivatives
  作者：Xiao-Qian Chi、Bo Hou、Liu Yang、Cheng-Ting Zi、Yong-Feng Lv、Jin-Yu Li、Fu-Cai Ren、Ming-Yan Yuan、Jiang-Miao Hu、Jun Zhou

  DOI：10.1080/14786419.2018.1510925

  日期：2020.5.18

  xanthone derivative, was mainly isolated from pericarps of the mangosteen fruit (Garcinia mangostana L.). In present investigation, a series of derivatives were designed, synthesised and evaluated in vitro for their inhibitory activity of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). Among the synthesised xanthones, compounds 1, 9, 13 and 16 showed AChE selective inhibitory activity, 15

  α-mangostin是一种多酚黄酮衍生物，主要从山竹果（Garcinia mangostana L.）的果皮中分离得到。在目前的研究中，在体外设计，合成和评估了一系列衍生物对乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BuChE）的抑制活性。在合成的氧杂蒽之中，化合物1、9、13和16显示出AChE选择性抑制活性，化合物15是一种BuChE选择性抑制剂，而化合物2、3、5、6、7、12和14是双重抑制剂。AChE的最强抑制剂为16，而BuChE的最强抑制剂为5，IC50值分别为5.26μM和7.55μM。
• Synthetic Studies of Mangostin Derivatives with an Inhibitory Activity on PDGF-Induced Human Aortic Smooth Cells Proliferation
  作者：Shigeru Nishiyama、Yuko Nishihama、Takahisa Ogamino、Wen Lei Shi、Byung-Yoon Cha、Takayuki Yonezawa、Toshiaki Teruya、Kazuo Nagai、Kiyotake Suenaga、Je-Tae Woo

  DOI：10.3987/com-08-s(f)65

  日期：——

  The mangostin derivatives 3-10, were synthesized by halogenation, electrochemical oxidation, and mCPBA oxidation of alpha- and gamma-mangostins (1, 2). Among them, the hydroxyl 9 and the benzopyran 10 derivatives produced by mCPBA, showed remarkable antiproliferative activities against human aortic smooth muscle cells (HASMC) induced by platelet-derived growth factor (PDGF).