(4-(methylthio)phenyl)-4H-1-benzopyran-4-one | 215999-35-2

• 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: (4-(methylthio)phenyl)-4H-1-benzopyran-4-one
• 英文别名: 2-(4-methylthiophenyl)-4H-1-benzopyran-4-one；2-(4-(methylthio)phenyl)-4H-chromen-4-one；2-(4-(methylthio)phenyl)-4H-1-benzopyran-4-one；2-(4-Methylsulfanylphenyl)chromen-4-one
• CAS: 215999-35-2
• 化学式: C₁₆H₁₂O₂S
• 分子量: 268.336
• InChiKey: JYAFOPOPHFBJLC-UHFFFAOYSA-N

物化性质

• 沸点：
  423.8±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-(methylthio)phenyl)-4H-1-benzopyran-4-one 在 Oxone 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 反应 5.0h， 生成 Trifluoro-acetic acid 4-(3-bromo-4-oxo-4H-chromen-2-yl)-phenylsulfanylmethyl ester
  参考文献：
  名称：

  2,3-Diarylbenzopyran derivatives as a novel class of selective cyclooxygenase-2 inhibitors

  摘要：

  A new series of cyclooxygenase-2(COX-2) inhibitors with naturally occurring flavone as the main skeleton has been synthesized and their biological activities were evaluated for cyclooxygenase inhibitory activity. Rational structural modifications were applied to potent COX-2 inhibitors to obtain the desired pharmacokinetic profiles for improved oral anti-inflammatory activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00952-6
• 作为产物：
  描述：

  2'-羟基苯乙酮 在 氢氧化钾 、 碘 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 生成 (4-(methylthio)phenyl)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  2,3-Diarylbenzopyran derivatives as a novel class of selective cyclooxygenase-2 inhibitors

  摘要：

  A new series of cyclooxygenase-2(COX-2) inhibitors with naturally occurring flavone as the main skeleton has been synthesized and their biological activities were evaluated for cyclooxygenase inhibitory activity. Rational structural modifications were applied to potent COX-2 inhibitors to obtain the desired pharmacokinetic profiles for improved oral anti-inflammatory activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00952-6

文献信息

• Palladium-Catalyzed Carbonylation Reaction of Aryl Bromides with 2-Hydroxyacetophenones to Form Flavones
  作者：Xiao-Feng Wu、Helfried Neumann、Matthias Beller

  DOI：10.1002/chem.201202141

  日期：2012.10.1

  Flavone of the month: A general and efficient method for the palladium‐catalyzed carbonylative synthesis of flavones has been developed (see scheme). Starting from aryl bromides and 2‐hydroxyacetophenones, the corresponding flavones have been isolated in good yields.

  本月黄酮：已开发出一种用于钯催化黄酮羰基合成的通用有效方法（请参见方案）。从芳基溴化物和2-羟基苯乙酮开始，已分离出相应的黄酮，收率很高。
• Ionic liquid mediated Cu-catalyzed cascade oxa-Michael-oxidation: efficient synthesis of flavones under mild reaction conditions
  作者：Zhiyun Du、Huifen Ng、Kun Zhang、Huaqiang Zeng、Jian Wang

  DOI：10.1039/c1ob06209c

  日期：——

  Flavonoids are a class of natural products, found in a wide range of vascular plants and dietary components. Their low toxicity and extensive biological activities, including anti-cancer and anti-bacterial, have made them attractive candidates to serve as therapeutic agents for many diseases. Herein, we disclose a highly efficient synthetic method of CuI-catalyzed cascade oxa-Michael-oxidation, using chalcones as substrates, mediated by the ionic liquid [bmim][NTf2] at a low temperature. This efficient synthetic method has demonstrated high synthetic utility and can afford flavones in good to high yields (up to 98%).

  黄酮类化合物是一类天然产物，广泛存在于维管植物和饮食成分中。它们具有低毒性和广泛的生物活性，包括抗癌和抗菌作用，使其成为治疗多种疾病的吸引人的候选治疗剂。在这里，我们揭示了一种高效的CuI催化的级联氧杂迈克尔氧化合成方法，以查尔酮为底物，在低温下通过离子液体[bmim][NTf2]介导。这种高效的合成方法展示了高度的合成实用性，可以获得高产率的黄酮类化合物（高达98%）。
• A Facile Synthetic Method of 3-Bromoflavones
  作者：Yung Hyup Joo、Jin Kwan Kim

  DOI：10.1080/00397919809458710

  日期：1998.11

  Abstract The synthesis of 3-bromoflavones by bromination-debromination using pyridinium bromide perbromide is described.

  摘要 描述了使用溴化吡啶鎓过溴化物通过溴化-脱溴合成 3-溴黄酮。
• Diarylbenzopyran derivatives as cyclooxygenase-2 inhibitors
  申请人：Pacific Corporation

  公开号：US06340694B1

  公开（公告）日：2002-01-22

  The diarylbenzopyran derivatives represented by formula I, and the pharmaceutically acceptable salts thereof, are disclosed. The composition comprising the compound of formula I, or a pharmaceutically acceptable salt thereof, shows an excellent selective inhibition of cyclooxygenase-2.

  公开了由式I表示的二芳基苯并吡喃衍生物及其药用盐。包含式I化合物或其药用盐的组合物显示出对环氧合酶-2的优异选择性抑制。
• [EN] DIARYLBENZOPYRAN DERIVATIVES AS CYCLOOXYGENASE-2 INHIBITORS<br/>[FR] DERIVES DE DIARYLBENZOPYRANE UTILISES COMME INHIBITEURS DE CYCLOOXYGENASE-2
  申请人：PACIFIC CORP

  公开号：WO2000010993A1

  公开（公告）日：2000-03-02

  The diarylbenzopyran derivatives represented by general formula (I): wherein Y is an oxygen atom or a sulfur atom; R?1 and R2¿, identical to or different from each other, are independently a hydrogen atom, a halogen atom, a C¿1?-C6 lower alkyl group, a trifluromethyl group, an alkoxy group, a hydroxy group, a nitro group, a nitrile group, or a carboxyl group; R?3¿ is a group of a formula: S(O)nR5 wherein n is an integer of 0∩2, R5 is a hydrogen atom, a C¿1?-C6 lower alkyl group, or a group of a formula: NR?6R7¿ wherein R?6 and R7¿, identical to or different from each other, are independently a hydrogen atom, or a C¿1?-C6 lower alkyl group; R?4¿ is oxazolyl, benzo[b]thienyl, furanyl, thienyl, naphthyl, thiazolyl, indolyl, pyrolyl, benzofuranyl, benzodioxoyl, or a substituted group presented by structures (a), (b), (c) or (d) wherein R8 through R12 identical to or different from one another, are independently a hydrogen atom, a halogen atom, a C¿1?-C6 lower alkyl group, a trifluromethyl group, an alkoxy group, a hydroxy group, a hydroxyalkyl group, a nitro group, a group of a formula: S(O)nR?5¿, a group of a formula NR6R7, a trifluromethoxy group, a nitrile group, a carboxyl group, an acetyl group, or a formyl group wherein n, R?5, R6 and R7¿ have the same meaning as defined X and R3 above; and R13 is a hydrogen atom, a halogen atom, a C¿1?-C6 lower alkyl group, a trifluromethyl group, an alkoxy group, a hydroxy group, a trifluromethoxy group, a carboxyl group, or an acetyl group; or their pharmaceutically acceptable salts are disclosed. And also cyclooxygenase-2 inhibitor composition, which consists of an effective amount of a diarylbenzopyran derivative and pharmaceutically acceptable salts of diarylbenzopyran derivative and shows an excellent selective inhibition, is disclosed.

  通式（I）所代表的二芳基苯并吡喃衍生物：其中Y是氧原子或硫原子；R1和R2，相同或不同，分别独立地是氢原子、卤素原子、C1-C6低烷基、三氟甲基基团、烷氧基、羟基、硝基、腈基或羧基；R3是公式S（O）nR5的基团，其中n是0-2的整数，R5是氢原子、C1-C6低烷基或公式NR6R7的基团，其中R6和R7，相同或不同，独立地是氢原子或C1-C6低烷基；R4是噁唑基、苯并[b]噻吩基、呋喃基、噻吩基、萘基、噻唑基、吲哚基、吡咯基、苯并呋喃基、苯并二氧杂环基或由结构（a）、（b）、（c）或（d）所示的取代基团，其中R8至R12相同或不同，独立地是氢原子、卤素原子、C1-C6低烷基、三氟甲基基团、烷氧基、羟基、羟基烷基基团、硝基、公式S（O）nR5的基团、公式NR6R7的基团、三氟甲氧基团、腈基、羧基、乙酰基或甲酰基，其中n、R5、R6和R7的含义与上述X和R3的定义相同；R13是氢原子、卤素原子、C1-C6低烷基、三氟甲基基团、烷氧基、羟基、三氟甲氧基团、羧基或乙酰基；或其药学上可接受的盐。还披露了环氧合酶-2抑制剂组合物，其由一种二芳基苯并吡喃衍生物的有效量和药学上可接受的二芳基苯并吡喃衍生物盐组成，并显示出优异的选择性抑制作用。