2'-羟基黄烷酮 | 35244-11-2

• 物质功能分类: 有机原料 - 酮类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 2'-羟基黄烷酮
• 中文别名: 2-羟基黄酮；2'-羟基黄烷酮,98；2"-羟基黄烷酮
• 英文名称: 2'-hydroxyflavone
• 英文别名: 2'-Hydroxyflavon；2′-hydroxyflavone；2-(2-hydroxyphenyl)-4H-chromen-4-one；2’-hydroxyflavone；2-(2-hydroxyphenyl)chromen-4-one
• CAS: 35244-11-2
• 化学式: C₁₅H₁₀O₃
• 分子量: 238.243
• InChiKey: ZZLQHXCRRMUGQJ-UHFFFAOYSA-N

物化性质

• 熔点：
  238.5 °C
• 沸点：
  410.0±45.0 °C(Predicted)
• 密度：
  1.340±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（轻微）、甲醇（非常轻微）
• 稳定性/保质期：
  常规情况下不会分解，没有危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• 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

ADMET

代谢

2p-羟基黄酮已知的人体代谢物包括黄酮2p-O-葡萄糖苷酸。

2p-Hydroxyflavone has known human metabolites that include Flavone 2p-O-glucuronide.

来源:NORMAN Suspect List Exchange

安全信息

• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2914501900

反应信息

• 作为反应物：
  描述：

  2'-羟基黄烷酮 在 sodium hydroxide 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 7.0h， 生成 2'-[3-(N,N-dimethylamino)-2-hydroxypropoxy]flavone
  参考文献：
  名称：

  Synthesis, antiplatelet and vasorelaxing effects of monooxygenated flavones and flavonoxypropanolamines

  摘要：

  摘要 合成了一系列黄酮类化合物和黄酮氧丙胺类化合物，并在体外测试它们对洗净的兔血小板和人类富含血小板的聚集抑制能力，以及对大鼠胸主动脉的血管收缩作用。在黄酮B环中羟基团的不同取代位置以及在黄酮C-2′位置取代的各种氧丙胺侧链改变了抗血小板效果。在人类富含血小板中测试的所有化合物均显示出对肾上腺素（肾上腺素）诱导的次级聚集有显著抑制作用，这表明这些化合物的抗血小板作用主要是通过抑制血栓素形成产生的。化合物11和12还在大鼠胸主动脉中表现出强效的血管舒张作用。选择的化合物11抑制了苯肾上腺素和高钾引起的大鼠主动脉中45Ca2+的内流。这一结果表明，11对大鼠胸主动脉中高钾介质和去甲肾上腺素（去甲肾上腺素）引起的收缩反应的抑制作用主要是通过抑制通过电压依赖和受体操作的Ca2+通道的Ca2+内流。

  DOI：

  10.1211/0022357011778205
• 作为产物：
  描述：

  色酮 在 potassium nitrite 、 iron(III) trifluoromethanesulfonate 、 palladium diacetate 、 三溴化硼 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三甲基乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 2'-羟基黄烷酮
  参考文献：
  名称：

  通过钯催化的C ？高效合成Frutinone A及其衍生物 H活化/羰基化

  摘要：

  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。

  DOI：

  10.1002/asia.201402876

文献信息

• Accurate Prediction of Glucuronidation of Structurally Diverse Phenolics by Human UGT1A9 Using Combined Experimental and In Silico Approaches
  作者：Baojian Wu、Xiaoqiang Wang、Shuxing Zhang、Ming Hu

  DOI：10.1007/s11095-012-0666-z

  日期：2012.6

  Catalytic selectivity of human UGT1A9, an important membrane-bound enzyme catalyzing glucuronidation of xenobiotics, was determined experimentally using 145 phenolics and analyzed by 3D-QSAR methods. Catalytic efficiency of UGT1A9 was determined by kinetic profiling. Quantitative structure activity relationships were analyzed using CoMFA and CoMSIA techniques. Molecular alignment of substrate structures was made by superimposing the glucuronidation site and its adjacent aromatic ring to achieve maximal steric overlap. For a substrate with multiple active glucuronidation sites, each site was considered a separate substrate. 3D-QSAR analyses produced statistically reliable models with good predictive power (CoMFA: q2 = 0.548, r2 = 0.949, r pred 2  = 0.775; CoMSIA: q2 = 0.579, r2 = 0.876, r pred 2  = 0.700). Contour coefficient maps were applied to elucidate structural features among substrates that are responsible for selectivity differences. Contour coefficient maps were overlaid in the catalytic pocket of a homology model of UGT1A9, enabling identification of the UGT1A9 catalytic pocket with a high degree of confidence. CoMFA/CoMSIA models can predict substrate selectivity and in vitro clearance of UGT1A9. Our findings also provide a possible molecular basis for understanding UGT1A9 functions and substrate selectivity.

  通过实验使用145种酚类化合物，并通过3D-QSAR方法分析，确定了人UGT1A9的催化选择性。UGT1A9是一种重要的膜结合酶，催化外源性物质的葡糖醛酸化反应。通过动力学分析确定了UGT1A9的催化效率。使用CoMFA和CoMSIA技术分析了定量结构活性关系。通过将葡糖醛酸化位点及其相邻的芳香环重叠，实现了底物结构的最大立体重叠。对于具有多个活性葡糖醛酸化位点的底物，每个位点被视为单独的底物。3D-QSAR分析产生了统计上可靠的模型，具有良好的预测能力（CoMFA：q2=0.548，r2=0.949，r pred 2=0.775；CoMSIA：q2=0.579，r2=0.876，r pred 2=0.700）。通过轮廓系数图阐明了底物中负责选择性差异的结构特征。将轮廓系数图叠加在UGT1A9的同源模型的催化口袋中，能够高度自信地识别UGT1A9的催化口袋。CoMFA/CoMSIA模型可以预测底物的选择性和UGT1A9的体外清除率。我们的发现还提供了理解UGT1A9功能和底物选择性的可能分子基础。
• A practical synthesis of flavones from methyl salicylate
  作者：Dhanapalan Nagarathnam、Mark Cushman

  DOI：10.1016/s0040-4020(01)87119-2

  日期：1991.1

  A facile synthetic method has been developed for the conversion of methyl salicylate (5) into flavones 1a-i in high yields. Compound 5 on treatment with t-butyldimethylsilyl chloride (6) gave the O-silyl protected ester 7. Condensation of this ester 7 with the lithium anion generated from acetophenones 3a-i yielded the 1.3-diarylpropane-1,3-diones 8a-i, which on treatment with glacial acetic acid containing

  已经开发了一种简便的合成方法，用于将水杨酸甲酯（5）以高收率转化为黄酮1a-i。用叔丁基二甲基甲硅烷基氯（6）处理化合物5，得到O-甲硅烷基保护的酯7。将该酯7与由苯乙酮3a -i生成的锂阴离子进行缩合，得到1.3-二芳基丙烷-1,3-二酮8a-i，将其用含0.5％H 2 SO 4的冰醋酸在95- ℃处理3小时。 100°C以83–94％的收率提供了所需的黄酮1a-i。
• Preference for<i>O</i>-demethylation reactions in the oxidation of 2′-, 3′-, and 4′-methoxyflavones by human cytochrome P450 enzymes
  作者：Haruna Nagayoshi、Norie Murayama、Masaki Tsujino、Shigeo Takenaka、Jun Katahira、Vitchan Kim、Donghak Kim、Masayuki Komori、Hiroshi Yamazaki、F. Peter Guengerich、Tsutomu Shimada

  DOI：10.1080/00498254.2020.1759157

  日期：2020.10.2

  2'-, 3'-, and 4'-Methoxyflavones (MeFs) were incubated with nine forms of recombinant human cytochrome P450 (P450 or CYP) enzymes in the presence of an NADPH-generating system and the products formed were analyzed with LC-MS/MS methods.CYP1B1.1 and 1B1.3 were highly active in demethylating 4'MeF to form 4'-hydroxyflavone (rate of 5.0 nmol/min/nmol P450) and further to 3',4'-dihydroxyflavone (rates

  在产生NADPH的系统中，将2'-，3'-和4'-甲氧基黄酮（MeFs）与9种形式的重组人细胞色素P450（P450或CYP）酶一起孵育，并用LC- MS / MS方法.CYP1B1.1和1B1.3在4'MeF脱甲基形成4'-羟基黄酮（5.0 nmol / min / nmol P450的速率）和进一步生成3'，4'-二羟基黄酮（速率为5％的活性）方面具有很高的活性。分别为2.1和0.66 nmol / min / nmol P450）。发现3'MeF被P450氧化为m / z 239（M-14）产物（大概为3'-羟基黄酮），然后氧化为3'，4'-二羟基黄酮。P450还将2'MeF催化氧化为m / z 239（M-14）和m / z 255（M-14，M-14 + 16）产品，可能分别是单羟基和二羟基产品。将这些MeF与P450一起孵育时，至少形成了两种类型的具有m / z 269片段的环
• The Novel UDP Glycosyltransferase 3A2: Cloning, Catalytic Properties, and Tissue Distribution
  作者：Peter I. MacKenzie、Anne Rogers、David J. Elliot、Nuy Chau、Julie-Ann Hulin、John O. Miners、Robyn Meech

  DOI：10.1124/mol.110.069336

  日期：2011.3

  The human UDP glycosyltransferase (UGT) 3A family is one of three families involved in the metabolism of small lipophilic compounds. Members of these families catalyze the addition of sugar residues to chemicals, which enhances their excretion from the body. The UGT1 and UGT2 family members primarily use UDP glucuronic acid to glucuronidate numerous compounds, such as steroids, bile acids, and therapeutic drugs. We showed recently that UGT3A1, the first member of the UGT3 family to be characterized, is unusual in using UDP N -acetylglucosamine as sugar donor, rather than UDP glucuronic acid or other UDP sugar nucleotides ( J Biol Chem 283: 36205–36210, 2008). Here, we report the cloning, expression, and characterization of UGT3A2, the second member of the UGT3 family. Like UGT3A1, UGT3A2 is inactive with UDP glucuronic acid as sugar donor. However, in contrast to UGT3A1, UGT3A2 uses both UDP glucose and UDP xylose but not UDP N -acetylglucosamine to glycosidate a broad range of substrates including 4-methylumbelliferone, 1-hydroxypyrene, bioflavones, and estrogens. It has low activity toward bile acids and androgens. UGT3A2 transcripts are found in the thymus, testis, and kidney but are barely detectable in the liver and gastrointestinal tract. The low expression of UGT3A2 in the latter, which are the main organs of drug metabolism, suggests that UGT3A2 has a more selective role in protecting the organs in which it is expressed against toxic insult rather than a more generalized role in drug metabolism. The broad substrate and novel UDP sugar specificity of UGT3A2 would be advantageous for such a function.

  人UDP-葡萄糖基转移酶(UGT)3A家族是涉及小脂溶性化合物代谢的三个家族之一。这些家族的成员催化糖残基添加到化学物质上,从而增强它们的排泄。UGT1和UGT2家族成员主要使用UDP-葡萄糖醛酸来糖苷化许多化合物,如类固醇、胆汁酸和治疗药物。我们最近表明,UGT3A1是第一个被表征的UGT3家族成员,它使用UDP N-乙酰葡萄糖胺作为糖供体,而不是UDP-葡萄糖醛酸或其他UDP糖核苷酸(J Biol Chem 283: 36205-36210, 2008)。在这里,我们报告了UGT3A2的克隆、表达和表征,UGT3A2是UGT3家族的第二个成员。与UGT3A1一样,UGT3A2在使用UDP-葡萄糖醛酸作为糖供体时无活性。然而,与UGT3A1不同,UGT3A2使用UDP葡萄糖和UDP木糖,但不使用UDP N-乙酰葡萄糖胺来糖苷化包括4-甲基伞形酮、1-羟基芘、生物类黄酮和雌激素在内的广泛底物。它对胆汁酸和雄激素的活性较低。UGT3A2的转录本存在于胸腺、睾丸和肾脏中,但在肝脏和胃肠道中几乎检测不到。UGT3A2在后者的主要器官中低表达,表明UGT3A2在这些器官中发挥选择性保护作用,抵御毒性损害,而不是在药物代谢中发挥更普遍的作用。UGT3A2广泛的底物和新颖的UDP糖特异性将有利于这种功能。
• Method of producing an alkoxyflavone derivative
  申请人：Tokiwa Phytochemical Co., Ltd.

  公开号：US10889557B1

  公开（公告）日：2021-01-12

  A method of producing an alkoxyflavone derivative involves a step of reacting hydroxyflavone derivative which is shown in the below chemical formula and dialkyl sulfate in the presence of dimethyl sulfoxide and an alkali hydroxide. Further, in the chemical formula below, R11-R14, R21-R25 and R3 are independently one of hydrogen, hydroxyl group, ester group, alkoxy group, alkylenedioxy group, sulfonyl group and alkyl group, respectively. However, at least two of R21-R25 and R3 are hydroxyl groups.

  生产烷氧基黄酮衍生物的方法涉及在二甲基亚砜和碱性氢氧化物存在下，通过下面的化学式所示的羟基黄酮衍生物与二烷基硫酸酯反应的步骤。此外，在下面的化学式中，R11-R14、R21-R25和R3分别独立地是氢、羟基、酯基、烷氧基、烷二氧基基团、磺酰基和烷基中的一种。然而，至少两个R21-R25和R3是羟基。