2'-hydroxy-α-naphthoflavone | 125574-17-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2'-hydroxy-α-naphthoflavone
• 英文别名: 2'-Hydroxy-alpha-naphthoflavone；2-hydroxy-a-naphthoflavone；2-(2-hydroxy-phenyl)-benzo[h]chromen-4-one；2-(2-Hydroxy-phenyl)-benzo[h]chromen-4-on；2-(2-Hydroxyphenyl)benzo[h]chromen-4-one
• CAS: 125574-17-6
• 化学式: C₁₉H₁₂O₃
• 分子量: 288.302
• InChiKey: ZKMLQDNHMSFULN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2'-hydroxy-α-naphthoflavone 在 copper diacetate 、 zinc trifluoromethanesulfonate 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 以85%的产率得到7H-benzo[h]benzofuro[3,2-b]chromen-7-one
  参考文献：
  名称：

  通过黄酮和香豆素的CH官能化合成杂环稠合的苯并呋喃。

  摘要：

  通过色酮和香豆素的CH官能化开发了一种有效的CO环化方法，提供了杂环稠合的苯并呋喃。

  DOI：

  10.1039/c3cc44456b
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢氧化钾 作用下， 生成 2'-hydroxy-α-naphthoflavone
  参考文献：
  名称：

  Haenni, Jahrbuch der Philosophischen Fakultaet 2 [Zweite] der Universitaet Bern, 1921, vol. 1, p. 111

  摘要：

  DOI：

文献信息

• Synthesis of heterocyclic-fused benzopyrans via the Pd(<scp>ii</scp>)-catalyzed C–H alkenylation/C–O cyclization of flavones and coumarins
  作者：Yechan Kim、Youngtaek Moon、Dahye Kang、Sungwoo Hong

  DOI：10.1039/c4ob00180j

  日期：——

  derivatives. The synthetic utility of the one-pot sequence was demonstrated by obtaining convenient access to coumarin-annelated benzopyrans. The reaction scope for the transformation was found to be fairly broad, affording good yields of a wide range of flavone- or coumarin-fused benzopyran motifs, which are privileged structures in many biologically active compounds.

  通过黄酮衍生物的C–H功能化，已经实现了实现串联C–H烯基化/ C–O环化的有效方法。通过方便地获得香豆素退火的苯并吡喃，证明了一锅法序列的合成效用。发现该转化的反应范围相当宽，提供了广泛的黄酮-或香豆素-融合的苯并吡喃基序的良好产率，其是许多生物活性化合物中的优先结构。
• Naphthoflavone propargyl ether inhibitors of cytochrome P450
  作者：Naijue Zhu、Danielle Lightsey、Maryam Foroozesh、William Alworth、Amit Chaudhary、Kristine L. Willett、Cheryl L. Klein Stevens

  DOI：10.1007/s10870-005-9061-5

  日期：2006.5

  Cytochrome P450 enzymes protect the body from foreign substances through a mechanism that involves oxidation of those substances into more readily excretable polar compounds. It has been shown that some naphthoflavones function as substrates of certain P450 enzymes (CYP1A1 and CYP1B1) and with appropriate structural changes may become inhibitors. Moreover, propargyl ether derivatives of adamantane have been shown to function as selective inactivators of some P450 enzymes (CYP2B1 and CYP2B5). In an attempt to improve the potency and selectivity of inhibition, we have designed and synthesized a series of naphthoflavone propargyl ethers. We report here the synthesis, X-ray crystal structures, and inhibition data (IC50 of EROD inhibition in CYP1A1 and CYP1B1 enzymes) of α-naphthoflavone 2′-propargyl ether, β-naphthoflavone 2′-propargyl ether, α-naphthoflavone 4′-propargyl ether, and β-naphthoflavone 4′-propargyl ether. Crystallographic data: α-naphthoflavone 2′-propargyl ether, $$P\bar 1$$ , a=7.775(1) Å, b=8.062(1) Å, c=13.110(1) Å, α=84.32(1)°, β=75.42(1)°, γ=86.56(1)°, V=790.8(2) Å3; β-naphthoflavone 2′-propargyl ether, $$P\bar 1$$ , a=7.605(2) Å, b=7.793(1) Å, c=14.167(2) Å, α=77.06(1)°, β=75.41(1)°, γ=89.54(1)°, V=790.9(2) Å3; α-naphthoflavone 4′-propargyl ether, P21/n, a=14.595(2) Å, b=4.708(1) Å, c=24.745(6) Å, β=106.31(2)°, V=1631.8(7) Å3; β-naphthoflavone 4′-propargyl ether, P1, a=4.8871(5) Å, b= 7.9597(7) Å, c=21.788(3) Å, α=81.771(9)°, β=89.918(10)°, γ=72.223(8)°, V= 797.9(2) Å3.

  细胞色素P450酶通过将外来物质氧化成更易于排泄的极性化合物，从而保护身体免受这些物质的伤害。已有研究表明，某些萘黄酮可以作为特定P450酶（CYP1A1和CYP1B1）的底物，并且在适当结构改变后可能成为抑制剂。此外，金刚烷的炔丙基醚衍生物已被证明可以作为某些P450酶（CYP2B1和CYP2B5）的选择性灭活剂。为了提高抑制作用的效力和选择性，我们设计和合成了一系列萘黄酮炔丙基醚。在此，我们报告了α-萘黄酮2′-炔丙基醚、β-萘黄酮2′-炔丙基醚、α-萘黄酮4′-炔丙基醚和β-萘黄酮4′-炔丙基醚的合成、X射线晶体结构和抑制数据（CYP1A1和CYP1B1酶中EROD抑制的IC50值）。结晶学数据：α-萘黄酮2′-炔丙基醚，$$P\bar 1$$，a=7.775(1) Å，b=8.062(1) Å，c=13.110(1) Å，α=84.32(1)°，β=75.42(1)°，γ=86.56(1)°，V=790.8(2) Å3；β-萘黄酮2′-炔丙基醚，$$P\bar 1$$，a=7.605(2) Å，b=7.793(1) Å，c=14.167(2) Å，α=77.06(1)°，β=75.41(1)°，γ=89.54(1)°，V=790.9(2) Å3；α-萘黄酮4′-炔丙基醚，P21/n，a=14.595(2) Å，b=4.708(1) Å，c=24.745(6) Å，β=106.31(2)°，V=1631.8(7) Å3；β-萘黄酮4′-炔丙基醚，P1，a=4.8871(5) Å，b=7.9597(7) Å，c=21.788(3) Å，α=81.771(9)°，β=89.918(10)°，γ=72.223(8)°，V=797.9(2) Å3。
• Efficient Synthesis of Frutinone A and Its Derivatives through Palladium-Catalyzed CH Activation/Carbonylation
  作者：Yongje Shin、Changho Yoo、Youngtaek Moon、Yunho Lee、Sungwoo Hong

  DOI：10.1002/asia.201402876

  日期：2015.4

  Frutinone A, a biologically active ingredient of an antimicrobial herbal extract, demonstrates potent inhibitory activity towards the CYP1A2 enzyme. A three‐step total synthesis of frutinone A with an overall yield of 44 % is presented. The construction of the chromone‐annelated coumarin core was achieved through palladium‐catalyzed CH carbonylation of 2‐phenolchromones. The straightforward synthetic

  Frutinone A是一种抗微生物草药提取物的生物活性成分，对CYP1A2酶表现出有效的抑制活性。提出了三步完全合成果胶酮A的方法，总产率为44％。色酮-稠合的香豆素芯的构造通过实现钯催化Ç  H的2-phenolchromones羰基化。简单的合成路线可在果胶酮A核心周围轻松替换，因此可以快速探索衍生物的结构-活性关系（SAR）谱。测定了合成的果胶酮A衍生物对CYP1A2的抑制活性，并且十种化合物对CYP1A2酶表现出一到两位数的纳摩尔抑制活性。
• Synthesis of heterocyclic-fused benzofurans via C–H functionalization of flavones and coumarins
  作者：Youngtaek Moon、Yechan Kim、Hyerim Hong、Sungwoo Hong

  DOI：10.1039/c3cc44456b

  日期：——

  An efficient method to effect C-O cyclization was developed via the C-H functionalization of chromones and coumarins, affording heterocyclic-fused benzofurans.

  通过色酮和香豆素的CH官能化开发了一种有效的CO环化方法，提供了杂环稠合的苯并呋喃。
• Haenni, Jahrbuch der Philosophischen Fakultaet 2 [Zweite] der Universitaet Bern, <hi>1921</hi>, vol. 1, p. 111
  作者：Haenni

  DOI：——

  日期：——