(3,5-dibromo-4-hydroxyphenyl)(1,2-dimethyl-1H-indol-3-yl)methanone | 1352799-87-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (3,5-dibromo-4-hydroxyphenyl)(1,2-dimethyl-1H-indol-3-yl)methanone
• 英文别名: (3,5-Dibromo-4-hydroxyphenyl)-(1,2-dimethylindol-3-yl)methanone
• CAS: 1352799-87-1
• 化学式: C₁₇H₁₃Br₂NO₂
• 分子量: 423.104
• InChiKey: XCYOTGZJAXHMJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,2-二甲基吲哚 在 二硫化碳 、 N-溴代丁二酰亚胺(NBS) 、 乙硫醇钠 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.5h， 生成 (3,5-dibromo-4-hydroxyphenyl)(1,2-dimethyl-1H-indol-3-yl)methanone
  参考文献：
  名称：

  [EN] DEVELOPING POTENT URATE TRANSPORTER INHIBITORS: COMPOUNDS DESIGNED FOR THEIR URICOSURIC ACTION
  [FR] DÉVELOPPEMENT DE PUISSANTS INHIBITEURS DES TRANSPORTEURS D'URATE : COMPOSÉS CONÇUS POUR LEUR ACTION URICOSURIQUE

  摘要：

  公开号：

  WO2012048058A3

文献信息

• DEVELOPING POTENT URATE TRANSPORTER INHIBITORS: COMPOUNDS DESIGNED FOR THEIR URICOSURIC ACTION
  申请人：Wempe Michael F.

  公开号：US20130225673A1

  公开（公告）日：2013-08-29

  A compound represented by the general Formula I: a pharmaceutically acceptable salt or ester thereof, a solvate thereof, a chelate thereof, a non-covalent complex thereof, a pro-drug thereof, a deuterated radio-labeled analog thereof, and mixtures of any of the foregoing, wherein: A-K are individually selected from carbon or nitrogen; X═—O, —NR 1 , or —S; R 1-11 are individually selected from the group consisting of —H, C 1 -C 6 alkyl, C 6 -C 14 aryl, substituted C 6 -C 14 aryl, C 1 -C 14 -alkoxy, halogen, hydroxyl, carboxy, cyano, C 1 -C 6 -alkanoyloxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfonyl, trifluoromethyl, hydroxy, C 2 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkanoylamino, —O—R 12 , S—R 12 , —SO 2 —R 12 , —NHSO 2 R 12 and —NHCO 2 R 12 , wherein R 12 is phenyl, naphthyl, or phenyl or naphthly substituted with one to three groups selected from C 1 -C 6 -alkyl, C 6 -C 10 aryl, C 1 -C 6 -alkoxy and halogen, and C 4 -C 20 hydroxyheteroaryl wherein the heteroatoms are selected from the group consisting of sulfur, nitrogen, and oxygen.

  一种由通式I表示的化合物：其中，该化合物为药学上可接受的盐或酯、溶剂化物、螯合物、非共价复合物、前药、氘标记的放射性类似物或任何上述物质的混合物，其中：A-K分别选择自碳或氮；X═—O、—NR1或—S；R1-11分别选择自—H、C1-C6烷基、C6-C14芳基、取代的C6-C14芳基、C1-C14烷氧基、卤素、羟基、羧基、氰基、C1-C6-烷酰氧基、C1-C6-烷基硫基、C1-C6-烷基磺酰基、三氟甲基、羟基、C2-C6-烷氧羰基、C2-C6-烷酰胺基、—O—R12、S—R12、—SO2—R12、—NHSO2R12和—NHCO2R12，其中R12为苯基、萘基或苯基或萘基，且其上选择了一到三个来自C1-C6烷基、C6-C10芳基、C1-C6烷氧基和卤素的基团以及C4-C20羟基杂芳基，其中杂原子选择自硫、氮和氧。
• Developing potent urate transporter inhibitors: compounds designed for their uricosuric action
  申请人：Wempe Michael F.

  公开号：US10005750B2

  公开（公告）日：2018-06-26

  A compound represented by the general Formula I: a pharmaceutically acceptable salt or ester thereof, a solvate thereof, a chelate thereof, a non-covalent complex thereof, a pro-drug thereof, a deuterated radio-labeled analog thereof, and mixtures of any of the foregoing, wherein: A-K are individually selected from carbon or nitrogen; X═—O, —NR1, or —S; R1-11 are individually selected from the group consisting of —H, C1-C6 alkyl, C6-C14 aryl, substituted C6-C14 aryl, C1-C14-alkoxy, halogen, hydroxyl, carboxy, cyano, C1-C6-alkanoyloxy, C1-C6-alkylthio, C1-C6-alkylsulfonyl, trifluoromethyl, hydroxy, C2-C6-alkoxycarbonyl, C2-C6-alkanoylamino, —O—R12, S—R12, —SO2—R12, —NHSO2R12 and —NHCO2R12, wherein R12 is phenyl, naphthyl, or phenyl or naphthly substituted with one to three groups selected from C1-C6-alkyl, C6-C10 aryl, C1-C6-alkoxy and halogen, and C4-C20 hydroxyheteroaryl wherein the heteroatoms are selected from the group consisting of sulfur, nitrogen, and oxygen.

  通式 I 所代表的化合物： 其药学上可接受的盐或酯、其溶液、其螯合物、其非共价络合物、其原药、其氚化放射性标记类似物，以及上述任何物质的混合物，其中：A-K分别选自碳或氮； X═-O、-NR1 或 -S；R1-11各自选自由-H、C1-C6-烷基、C6-C14-芳基、取代的C6-C14-芳基、C1-C14-烷氧基、卤素、羟基、羧基、氰基、C1-C6-烷酰氧基、C1-C6-烷硫基、C1-C6-烷磺酰基、三氟甲基、羟基、C2-C6-烷氧羰基、C2-C6-烷酰氨基、-O-R12、S-R12、-SO2-R12、-NHSO2R12 和 -NHCO2R12，其中 R12 是苯基、萘基或被一至三个选自 C1-C6-烷基、C6-C10 芳基、C1-C6-烷氧基和卤素的基团取代的苯基或萘基，以及 C4-C20 羟基杂芳基，其中杂原子选自由硫、氮和氧组成的组。
• [EN] DEVELOPING POTENT URATE TRANSPORTER INHIBITORS: COMPOUNDS DESIGNED FOR THEIR URICOSURIC ACTION<br/>[FR] DÉVELOPPEMENT DE PUISSANTS INHIBITEURS DES TRANSPORTEURS D'URATE : COMPOSÉS CONÇUS POUR LEUR ACTION URICOSURIQUE
  申请人：PHARMA CO LTD J

  公开号：WO2012048058A3

  公开（公告）日：2012-05-31
• Human Uric Acid Transporter 1 (hURAT1): An Inhibitor Structure–Activity Relationship (SAR) Study
  作者：M. F. Wempe、B. Quade、P. Jutabha、T. Iwen、M. Frick、P. J. Rice、S. Wakui、H. Endou

  DOI：10.1080/15257770.2011.594031

  日期：2011.12

  The current study describes the chemical synthesis of a series of (2-ethylbenzofuran-3-yl)(substituted-phenyl) methanone compounds and their subsequent in vitro testing via oocytes expressing hURAT1. The experimental data support the notion that a potent hURAT1 inhibitor requires an anion (i.e., a formal negative charge) to interact with the positively charged hURAT1 binding pocket. An anion appears to be a primary requirement in order to be a hURAT1 substrate (i.e., urate) or inhibitor. We discuss the inhibitor structure-activity relationship and how electronically donating or withdrawing groups attached to the B-ring can decrease or increase inhibitory potency, respectively.