2-cyclohexyl-4H-benzo[h]chromen-4-one | 1251738-89-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 2-cyclohexyl-4H-benzo[h]chromen-4-one
• 英文别名: 2-Cyclohexylbenzo[h]chromen-4-one
• CAS: 1251738-89-2
• 化学式: C₁₉H₁₈O₂
• 分子量: 278.351
• InChiKey: RQNBFPHWLIDOBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-乙酰基-1-萘酚 在 氯化亚砜 、 硫酸 、 potassium tert-butylate 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 2.67h， 生成 2-cyclohexyl-4H-benzo[h]chromen-4-one
  参考文献：
  名称：

  Design and synthesis of selective CYP1B1 inhibitor via dearomatization of α-naphthoflavone

  摘要：

  Selective cytochrome P450 (CYP) 1B1 inhibition has potential as an anticancer strategy that is unrepresented in the current clinical arena. For development of a selective inhibitor, we focused on the complexity caused by sp(3)-hybridized carbons and synthesized a series of benzo[h] chromone derivatives linked to a non-aromatic B-ring using alpha-naphthoflavone (ANF) as the lead compound. Ring structure comparison suggested compound 37 as a suitable cyclohexyl-core with improved solubility. Structural evolution of 37 produced the azide-containing cis-49a, which had good properties in three important respects: (1) selectivity for CYP1B1 over CYP1A1 and CYP1A2 (120-times and 150-times, respectively), (2) greater inhibitory potency of > 2 times that of ANF, and (3) improved solubility. The corresponding aromatic B-ring compound 59a showed low selectivity and poor solubility. To elucidate the binding mode, we performed X-ray crystal structure analysis, which revealed the interaction mode and explained the subtype selectivity of cis-49a.

  DOI：

  10.1016/j.bmc.2018.11.045

文献信息

• Hypervalent Iodine-Mediated Selective Oxidative Functionalization of (Thio)chromones with Alkanes
  作者：Rishikesh Narayan、Andrey P. Antonchick

  DOI：10.1002/chem.201400186

  日期：2014.4.14

  functionalization of aliphatic CH bonds of alkanes with chromones and (thio)chromones. A wide range of alkanes, both cyclic and acyclic, has been found to react selectively and predictably in good yields. The developed methodology is also the first report of a direct oxidative functionalization of the C‐2 position of (thio)chromones with alkanes to access bioactive compounds.

  Ç  C键的形成是为在有机分子链增长最根本的办法。通过串联氧化两个不同的CH键获得的成就代表了有机合成的最新技术。普遍存在的脂族CH键的选择性官能化为这种氧化交叉偶联方法提供了一个有吸引力的选择。在温和和“无金属”的条件下开发这样的方法仍然具有挑战性。在这里，我们报告脂肪族的C高价碘介导的选择性氧化功能化烷烃与色酮和（硫代）色酮的氢键。已经发现，广泛的环状和非环状烷烃都能选择性地和可预测地以良好的收率反应。发达的方法学也是关于用烷烃直接氧化（硫代）色酮的C-2位以获取生物活性化合物的第一份报告。
• New synthetic flavone derivatives induce apoptosis of hepatocarcinoma cells
  作者：Huachen Liu、Aijun Dong、Chunmei Gao、Chunyan Tan、Zhenhua Xie、Xuyu Zu、Long Qu、Yuyang Jiang

  DOI：10.1016/j.bmc.2010.07.019

  日期：2010.9

  Natural flavonoids have broad biological activity, including anticancer. In this study, a series of novel flavone derivatives were synthesized with the substitutions of chlorine, isopropyl, methoxy, and nitro groups on the benzene ring of flavone skeleton to develop effective anticancer agents. Antiproliferative assays showed that the synthesized chemicals possess notable activity against hepatocarcinoma cells (HepG-2); in particular, the compound 6f with chlorine and dimethoxy modifications at the two benzene rings showed an IC(50) at 1.1 mu M to HepG-2. The 6f also displayed marked anticancer activity towards a panel of cancer cells, including nasopharyngeal carcinoma cells (CNE-2 and CNE-1), breast adenocarcinoma cell (MCF-7), and epithelial carcinoma cells (Hela). Exposing HepG-2 cells to compound 6f at 10 mu M induced chromatin condensation, nuclear disassembly, and DNA fragmentation. In 6f-treated HepG-2 cells, the sub-G(o) population was remarkably increased; and in these cells, both caspase-8 and caspase-9 activity was significantly increased, which in turn activated caspase-3. In addition, proapoptotic Bax was upregulated by compound 6f while the antiapoptotic Bcl-2 was downregulated. Taken together, our data suggest that the new flavonoid derivative 6f triggers apoptosis through both death-receptor and mitochondria-dependent intrinsic pathways, being a potent therapeutic agent against hepatocarcinoma. (C) 2010 Elsevier Ltd. All rights reserved.
• Design and synthesis of selective CYP1B1 inhibitor via dearomatization of α-naphthoflavone
  作者：Makoto Kubo、Keiko Yamamoto、Toshimasa Itoh

  DOI：10.1016/j.bmc.2018.11.045

  日期：2019.1

  Selective cytochrome P450 (CYP) 1B1 inhibition has potential as an anticancer strategy that is unrepresented in the current clinical arena. For development of a selective inhibitor, we focused on the complexity caused by sp(3)-hybridized carbons and synthesized a series of benzo[h] chromone derivatives linked to a non-aromatic B-ring using alpha-naphthoflavone (ANF) as the lead compound. Ring structure comparison suggested compound 37 as a suitable cyclohexyl-core with improved solubility. Structural evolution of 37 produced the azide-containing cis-49a, which had good properties in three important respects: (1) selectivity for CYP1B1 over CYP1A1 and CYP1A2 (120-times and 150-times, respectively), (2) greater inhibitory potency of > 2 times that of ANF, and (3) improved solubility. The corresponding aromatic B-ring compound 59a showed low selectivity and poor solubility. To elucidate the binding mode, we performed X-ray crystal structure analysis, which revealed the interaction mode and explained the subtype selectivity of cis-49a.