(2E,6Z,10E)-6-(hydroxymethyl)-2,9,9-trimethylcycloundeca-2,6,10-trien-1-one | 142299-69-2

• 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: (2E,6Z,10E)-6-(hydroxymethyl)-2,9,9-trimethylcycloundeca-2,6,10-trien-1-one
• 英文别名: (2E,6Z,10E)-6-hydroxymethyl-2,9,9-trimethylcycloundeca-2,6,10-trienone；15-hydroxyhumula-1(10)E,4Z,7E-trien-9-one
• CAS: 142299-69-2；142338-93-0；143305-37-7；142299-70-5
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: IZKAIJSKFKIFNZ-QIDRTHSXSA-N

物化性质

• 沸点：
  378.0±42.0 °C(Predicted)
• 密度：
  0.958±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,6Z,10E)-6-(hydroxymethyl)-2,9,9-trimethylcycloundeca-2,6,10-trien-1-one 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 作用下， 以 水 、 乙腈 、 叔丁醇 为溶剂， 反应 22.0h， 生成 (1Z,5E,8E)-4,4,8-trimethyl-7-oxocycloundeca-1,5,8-triene-1-carboxylic acid
  参考文献：
  名称：

  Target profiling of zerumbone using a novel cell-permeable clickable probe and quantitative chemical proteomics

  摘要：

  通过定量竞争化学蛋白质组学和细胞可渗透探针，确定了活体癌细胞中zerumbone的第一个靶标。

  DOI：

  10.1039/c4cc09527h
• 作为产物：
  描述：

  花薑酮 在 N-溴代丁二酰亚胺(NBS) 、 水 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 22.02h， 生成 (2E,6Z,10E)-6-(hydroxymethyl)-2,9,9-trimethylcycloundeca-2,6,10-trien-1-one
  参考文献：
  名称：

  Target profiling of zerumbone using a novel cell-permeable clickable probe and quantitative chemical proteomics

  摘要：

  通过定量竞争化学蛋白质组学和细胞可渗透探针，确定了活体癌细胞中zerumbone的第一个靶标。

  DOI：

  10.1039/c4cc09527h

文献信息

• Anticancer Activity of the Bioreductive and Non-Bioreductive Zerumbone Derivatives
  作者：Siripit Pitchuanchom、Uraiwan Songsiang、Natthida Weerapreeyakul、Chavi Yenjai

  DOI：10.2174/157018011795906811

  日期：2011.7.1

  Zerumbonoquinone 10 and zerumbonaminone 11 have been designed to release toxic moieties selectively and preferentially under reductive conditions. These compounds were synthesized by coupling the quinone delivery system with zerumbone alcohol 8 and amine 9. All compounds were evaluated for cytotoxicity against KB (non reductase overexpressing cells), NCI-H187 and MCF-7 (reductase overexpressing cells) and normal cells (Vero cells). Bioreductive compounds 10 and 11 were found to act as bioreductive anticancer agents exhibiting less cytotoxicity than the parents 8 and 9 in KB cells with good stability, and were partially bioreductively active against MCF-7 and NCI-H187 cells.

  零姆伯诺醌10和零姆伯胺醌11已被设计在还原条件下选择性和优先释放有毒基团。这些化合物是通过将醌传递系统与零姆酮醇8和胺9结合合成的。所有化合物都针对KB（非还原酶过表达细胞）、NCI-H187和MCF-7（还原酶过表达细胞）以及正常细胞（Vero细胞）进行了细胞毒性评估。生化还原化合物10和11被发现是生化还原抗癌剂，与它们的母体化合物8和9相比，在KB细胞中表现出较少的细胞毒性，并且稳定性良好，对MCF-7和NCI-H187细胞有一定的生化还原活性。
• Novel synthesis of zerumbone-pendant derivatives and their biological activity
  作者：Takashi Kitayama、Maki Nakahira、Kae Yamasaki、Hiromi Inoue、Chika Imada、Yuji Yonekura、Masataka Awata、Hikaru Takaya、Yasushi Kawai、Kohta Ohnishi、Akira Murakami

  DOI：10.1016/j.tet.2013.09.026

  日期：2013.11

  Zerumbone 1, having powerful latent reactivity and containing two conjugated double bonds and a double conjugated carbonyl group is the major component of the essential oil of wild ginger, Zingiber zerumbet Smith. The conjugation system plays an important role in the expression of biological activity. N-Bromosuccinimide (NBS) reaction of 1 gave high reactive intermediate 2 with an exo-methylene group, which was obtained from 1 quantitatively. Treatment of 2 with nucleophiles gave various zerumbonependant derivatives, including C-H, C-O, C-N, and C-C bond formation, maintaining the conjugation system through S(N)2'-type reaction. Almost all zerumbone-pendant derivatives showed a good value of IC50 against the suppressive effect of NO generation. Among them, amine derivative 5, binding with 2 mol of zerumbone, showed the strongest activity (IC50: 0.24 mu M). (C) 2013 Elsevier Ltd. All rights reserved.