7-isopropoxy-3-(4-methoxyphenyl)-4H-chromen-4-one | 354782-83-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 7-isopropoxy-3-(4-methoxyphenyl)-4H-chromen-4-one
• 英文别名: 7-isopropoxy-4'-methoxyisoflavone；3-(4-methoxyphenyl)-7-isopropoxy-4H-chromen-4-one；7-isopropyloxy-4'-methoxyisoflavone；3-(4-methoxyphenyl)-7-propan-2-yloxychromen-4-one
• CAS: 354782-83-5
• 化学式: C₁₉H₁₈O₄
• 分子量: 310.35
• InChiKey: XHKUJCCHYFEXRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-isopropoxy-3-(4-methoxyphenyl)-4H-chromen-4-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Syntheses and Crystal Structures of Two 2H-dibenzo[e, g]indazoles

  摘要：

  在这篇论文中，通过两次脱水过程，从相应的异黄酮中一锅法合成了两种2H-二苯并[e, g]吲唑，即6-甲氧基-9-异丙氧基-2H-二苯并[e, g]吲唑(1)和6-氟-9-甲氧基-2H-二苯并[e, g]吲唑(2)。通过红外光谱、核磁共振、高分辨质谱和单晶X射线衍射对其进行了表征。单晶X射线衍射分析表明，1在正交晶系P 212121中结晶，2在单斜晶系P 21中结晶。对于这两种结构，分子间氢键、π…π和C−H…π相互作用在分子堆积中起着重要作用。通过两次脱水过程，从相应的异黄酮中一锅法合成了两种2H-二苯并[e, g]吲唑，即6-甲氧基-9-异丙氧基-2H-二苯并[e, g]吲唑和6-氟-9-甲氧基-2H-二苯并[e, g]吲唑。单晶X射线衍射分析表明，氢键、π…π和C–H…π相互作用在这

  DOI：

  10.1007/s10870-020-00835-4
• 作为产物：
  描述：

  1-(2,4-二羟基苯基)-2-(4-甲氧基苯基)乙酮 在 三氟化硼乙醚 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 10.0h， 生成 7-isopropoxy-3-(4-methoxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Synthetic analogs of daidzein, having more potent osteoblast stimulating effect

  摘要：

  A series of didzein derivatives were synthesized and assessed for stimulation of osteoblast differentiation using primary cultures of rat calvarial osteoblasts. Data suggested that three synthetic analogs, 1c, 3a and 3c were several folds more potent than daidzein in stimulating differentiation and mineralization of osteoblasts. Further, these three compounds did not show any estrogen agonistic activity, however had mild estrogen antagonistic effect. Out of the three compounds, 3c was found to maximally increase the mineralization of bone marrow osteoprogenitor cells. Compound 3c also robustly increased the mRNA levels of osteogenic genes including bone morphogenetic protein-2 and osteocalcin in osteoblasts. Unlike daidzein, 3c did not inhibit osteoclastogenesis. Collectively, we demonstrate osteogenic activity of daidzein analogs at significantly lower concentrations than daidzein. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.008

文献信息

• Thallium(III)<i>p</i>-Tosylate Mediated Oxidative 2,3-Aryl Rearrangement: A New Useful Route to Ipriflavone and Its Analogs
  作者：M. Muthukrishnan、Om V. Singh

  DOI：10.1080/00397910802238734

  日期：2008.10.28

  Abstract A new route for the synthesis of ipriflavone, an antiosteoporotic agent, is described that has four steps and 60% yields starting from resacetophenone (2). The key step of the present methodology is thallium(III) p-tosylate mediated oxidative 2,3-aryl rearrangement of flavanone to generate the isoflavone ring system of ipriflavone in a highly efficient manner.

  摘要 描述了一种合成抗骨质疏松剂 ipriflavone 的新途径，它有四个步骤，从重苯乙酮 (2) 开始，产率为 60%。本方法的关键步骤是对甲苯磺酸铊 (III) 介导的黄烷酮氧化 2,3-芳基重排，以高效的方式生成 ipriflavone 的异黄酮环系统。
• One-pot synthesis of 2H-phenanthro[9,10-c]pyrazoles from isoflavones by two dehydration processes
  作者：Qiuya Wang、Zunting Zhang、Zichao Du、Huiliang Hua、Shasha Chen

  DOI：10.1039/c3gc40205c

  日期：——

  developed for one-pot synthesis of a series of 2H-phenanthro[9,10-c]pyrazoles in EtOH by two dehydration processes. Firstly, 3,4-diaryl-1H-pyrazoles were synthesized by the cyclocondensation of isoflavones and hydrazine hydrate in refluxing EtOH. Secondly, the final target products 2H-phenanthro[9,10-c]pyrazoles were given by photocyclization and dehydration of 3,4-diaryl-1H-pyrazoles in 1:1 (v/v) EtOH–H2O

  开发了一种环境友好，高效的方法，用于一锅合成一系列2 H-菲并[9,10- c ]吡唑类化合物。乙醇通过两个脱水过程。首先，通过环缩合反应合成了3,4-二芳基-1 H-吡唑类化合物。异黄酮 和 水合肼 在回流中 乙醇。其次，通过3 ：4-二芳基-1 H-吡唑以1 ：1（v / v）的光环化和脱水作用，得到最终目标产物2 H-菲并[9,10- c ]吡唑乙醇–高氧2。这种方法的优点是催化剂-合成路线短，反应条件温和且易于后处理。另外，测定了2 H-菲并[9,10- c ]吡唑的荧光性质。
• Synthesis of 7a-phenyl-1a,7a-dihydro-benzopyrano[2,3-b]azirin-7-ones via photoisomerization reaction
  作者：Qiuya Wang、Zunting Zhang、Xi Zhang、Jin Zhang、Yang Kang、Jufang Peng

  DOI：10.1039/c4ra12542h

  日期：——

  An environmentally friendly and novel protocol has been developed for the synthesis of 7a-phenyl-1a,7a-phenyl-benzopyrano[2,3-b]azirin-7-ones in moderate to high yieldsviathe photoisomerization of 4-phenyl-5-(2-hydroxyphenyl)isoxazoles.

  已经开发出一种环保且新颖的协议，用于合成7a-苯基-1a,7a-苯基苯并吡喃[2,3-b]氮杂环-7-酮，通过4-苯基-5-(2-羟基苯基)异恶唑的光异构化，以中等到高收率获得。
• ISOXAZOLE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
  申请人：Tzeng Cherng-Chyi

  公开号：US20090215768A1

  公开（公告）日：2009-08-27

  An isoxazole derivative is provided. The isoxazole derivative has following formula: wherein R 1 , R 2 , R 3 , R 4 and R 5 , independently, include hydrogen, hydroxy or C 1 -C 12 alkoxy optionally substituted with oxirane, thiirane, aziridine, amino, cycloamino, aminohydroxy or cycloaminohydroxy. The invention also provides a pharmaceutical composition for treatment of osteoporosis and cancer including an isoxazole derivative or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

  提供了一种异噁唑衍生物。该异噁唑衍生物具有以下化学式：其中R1、R2、R3、R4和R5独立地包括氢、羟基或氧化环氧烷、硫环氧烷、氮杂环丙胺、氨基、环氨基、氨基羟基或环氨基羟基的C1-C12烷氧基。该发明还提供了一种治疗骨质疏松症和癌症的药物组合物，包括一种异噁唑衍生物或其药学上可接受的盐以及一种药学上可接受的载体。
• Synthesis of Aminoalkoxy Substituted 4,5-Diphenylisoxazole Derivatives as Potential Anti-osteoporotic Agents
  作者：Yeh-Long Chen、Chih-Hua Tseng、You-Chih Lo、Ru-Wei Lin、Chain-Fu Chen、Gwo-Jaw Wang、Mei-Ling Ho、Cherng-Chyi Tzeng

  DOI：10.2174/1573406411309050015

  日期：2013.6.1

  Certain 4,5-diarylisoxazole derivatives have been found to possess broad biological effects, including antiinflammatory and anticancer activities. Recently, we have reported preparation of certain isoflavone derivatives and investigated for their anti-osteoporotic and antiproliferative activities in a detailed SAR study. The present report describes the conversion of isoflavones into novel 4,5-diphenylisoxazole

  已经发现某些4，5-二芳基异恶唑衍生物具有广泛的生物学作用，包括抗炎和抗癌活性。最近，我们报道了某些异黄酮衍生物的制备方法，并在详细的SAR研究中对其抗骨质疏松和抗增殖活性进行了研究。本报告描述了通过用NH2OH处理将异黄酮转化为新型4,5-二苯基异恶唑衍生物。烷基化，然后胺化这些4，5-二苯基异恶唑，得到所需的氨基烷氧基取代的4，5-二苯基异恶唑衍生物。在体外评估这些化合物的成骨分化和矿化定量。尽管5-异丙氧基-2- [4-（4-（4-甲氧基苯基）异恶唑-5-基]苯酚（3）表现出大约2。在促进成骨细胞活性（277％矿化），比细胞活力低（6％）和高细胞毒性（68％）方面，活性比伊普黄酮高8倍，这促使我们进一步寻求更合适的候选药物。引入了一系列氨基烷基侧链，目的是减少细胞毒性。其中，5- 4-异丙氧基-2- [4-（吡咯烷-1-基）丁氧基]苯基} -4-（4-甲氧基苯基）异唑（7a）的活性