3-iodo-2-(4-(methylsulfonyl)phenyl)-4H-1-benzopyran-4-one | 259681-69-1

• 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: 3-iodo-2-(4-(methylsulfonyl)phenyl)-4H-1-benzopyran-4-one
• 英文别名: 3-iodo-2-(4-methylsulfonylphenyl)chromen-4-one
• CAS: 259681-69-1
• 化学式: C₁₆H₁₁IO₄S
• 分子量: 426.231
• InChiKey: HUHHXIRKOZPHKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 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：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-氟苯硼酸 、 3-iodo-2-(4-(methylsulfonyl)phenyl)-4H-1-benzopyran-4-one 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 4.0h， 以59%的产率得到3-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Diarylbenzopyran derivatives as cyclooxygenase-2 inhibitors

  摘要：

  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。

  公开号：

  US06340694B1
• 作为产物：
  描述：

  2-(4-Methanesulfonyl-phenyl)-chromen-4-one 在 碘 、 [双(三氟乙酰氧基)碘]苯 作用下， 生成 3-iodo-2-(4-(methylsulfonyl)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

• [EN] PHARMACEUTICALLY ACTIVE PYRROLIDINE DERIVATIVES AS BAX INHIBITORS<br/>[FR] DERIVES DE LA PYRROLIDINE PHARMACEUTIQUEMENT ACTIFS COMME INHIBITEURS DE BAX
  申请人：APPLIED RESEARCH SYSTEMS

  公开号：WO2001074769A1

  公开（公告）日：2001-10-11

  The present invention is related to new substituted pyrrolidine derivatives of formula (I). Said compounds are preferably for use as pharmaceutically active compounds. Specifically, pyrrolidine derivatives of formula (I) are useful in the treatment and/or prevention of neurodegenerative disorders, diseases associated with polygultamine tracts, epilepsy, ischemia, infertility, cardiovascular disorders renal hypoxia, hepatitis and AIDS. Said pyrrolidine derivatives display a modulatory and most notably a down-regulating - up to an inhibitory - activity with respect to the cellular death agonist Bax and/or the activation pathways leading to Bax and allows therefore to block the release of cytochrome (c). The present invention is furthermore related to novel pharmaceutically activity substituted pyrrolidine derivatives as well as to methods of their preparation, wherein X is selected from the group consisting of O, S, CR?6R7, NOR6, NNR6R7¿; A is selected from the group consisting of -(C=O)-, -(C=O)-O-, -C(=NH)-, -(C=O)-NH-, -(C=S)-NH, -SO¿2?-, -SO2NH-; -CH2-; B is either a group -(C=O)-NR?8R9¿ or represents a heterocyclic residue having the formula (II) wherein Q is NR10, O or S; n is an integer selected of 0, 1 or 2; Y, Z and E form together with the 2 carbons to which they are attached a 5-6 membered aryl or heteroaryl ring.

  本发明涉及公式（I）的新取代吡咯烷衍生物。所述化合物优选用作药物活性化合物。具体而言，公式（I）的吡咯烷衍生物在神经退行性疾病、与多谷氨酸重复序列相关的疾病、癫痫、缺血、不孕症、心血管疾病、肾脏缺氧、肝炎和艾滋病的治疗和/或预防中有用。所述吡咯烷衍生物显示出调节性，尤其是对于细胞死亡促进剂Bax和/或导致Bax的激活途径具有下调至抑制性的活性，并因此允许阻止细胞色素（c）的释放。本发明还涉及新型药物活性取代吡咯烷衍生物以及其制备方法，其中X选自O，S，CR?6R7，NOR6，NNR6R7¿的群；A选自-(C=O)-，-(C=O)-O-，-C（=NH）-，-(C=O)-NH-，-(C=S)-NH，-SO¿2?，-SO2NH-；-CH2-；B是一个-(C=O)-NR?8R9¿基团或代表具有公式（II）的杂环残基，其中Q是NR10，O或S；n是选择的0、1或2的整数；Y、Z和E与它们所连接的2个碳一起形成一个5-6成员芳基或杂芳基环。
• [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。
• DIARYLBENZOPYRAN DERIVATIVES AS CYCLOOXYGENASE-2 INHIBITORS
  申请人：PACIFIC CORPORATION

  公开号：EP1105384A1

  公开（公告）日：2001-06-13
• PHARMACEUTICALLY ACTIVE PYRROLIDINE DERIVATIVES AS BAX INHIBITORS
  申请人：Applied Research Systems ARS Holding N.V.

  公开号：EP1268418A1

  公开（公告）日：2003-01-02
• US6340694B1
  申请人：——

  公开号：US6340694B1

  公开（公告）日：2002-01-22