5-[4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-cyclopentyl-phenoxysulfonyl]-4-methoxy-thiophene-3-carboxylic acid methyl ester | 250609-50-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-[4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-cyclopentyl-phenoxysulfonyl]-4-methoxy-thiophene-3-carboxylic acid methyl ester
• 英文别名: methyl 5-[4-(9-bromo-2,3-dimethylbenzo[f][1]benzothiol-4-yl)-2-cyclopentylphenoxy]sulfonyl-4-methoxythiophene-3-carboxylate
• CAS: 250609-50-8
• 化学式: C₃₂H₂₉BrO₆S₃
• 分子量: 685.681
• InChiKey: QWBPNFVPDYFSMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  42
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-[4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-cyclopentyl-phenoxysulfonyl]-4-methoxy-thiophene-3-carboxylic acid methyl ester 、 磷酸 在 盐酸 、 氢氧化钾 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以0.596 g (85%)的产率得到5-[4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-cyclopentyl-phenoxysulfonyl]-4-methoxy-thiophene-3-carboxylic acid
  参考文献：
  名称：

  Naphtho[2,3-B]heteroar-4-yl derivatives

  摘要：

  这项发明提供了具有结构的化合物，其中R.sup.1、R.sup.2、R.sup.3、R.sup.4、R.sup.5、W、R.sup.9、X、R.sup.6、p、Y、Z、R.sup.7和R.sub.8如规范中定义，或其药用盐，可用于治疗与胰岛素抵抗或高血糖相关的代谢紊乱。

  公开号：

  US06121271A1
• 作为产物：
  描述：

  2-cyclopentyl-4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-phenol 、 5-氯磺酰-4-甲氧基噻酚-3-羧酸甲酯 在 盐酸 作用下， 以 N,N-DMF 、 NaH 、 mineral oil 为溶剂， 以0.593 g, (64%)的产率得到5-[4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-cyclopentyl-phenoxysulfonyl]-4-methoxy-thiophene-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Naphtho[2,3-B]heteroar-4-yl derivatives

  摘要：

  这项发明提供了具有结构的化合物，其中R.sup.1、R.sup.2、R.sup.3、R.sup.4、R.sup.5、W、R.sup.9、X、R.sup.6、p、Y、Z、R.sup.7和R.sub.8如规范中定义，或其药用盐，可用于治疗与胰岛素抵抗或高血糖相关的代谢紊乱。

  公开号：

  US06121271A1

文献信息

• NAPHTHO[2,3-B]HETEROAR-4-YL DERIVATIVES
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP1077968A1

  公开（公告）日：2001-02-28
• US6121271A
  申请人：——

  公开号：US6121271A

  公开（公告）日：2000-09-19
• [EN] NAPHTHO[2,3-B]HETEROAR-4-YL DERIVATIVES<br/>[FR] DERIVES DE NAPHTO[2,3-B]HETEROAR-4-YLE
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：WO1999058522A1

  公开（公告）日：1999-11-18

  (EN) This invention provides compounds of structural Formula (I), wherein R1 and R2 are each, independently, hydrogen, nitrile, nitro, amino, alkylamino of 1-6 carbon atoms, dialkylamino of 1-6 carbon atoms per alkyl group, cycloalkylamino of 3-8 carbon atoms, alkyl of 1-6 carbon atoms, perfluoroalkyl of 1-6 carbon atoms, halogen, cycloalkyl of 3-8 carbon atoms, thienyl, furyl, phenyl or phenyl mono-, di-, or tri-substituted with halogen, hydroxy, alkyl of 1-6 carbon atoms, perfluoroalkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms, or perfluoroalkoxy of 1-6 carbon atoms; R3 and R4 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, perfluoroalkyl of 1-6 carbon atoms, hydroxyalkyl of 1-6 carbon atoms, aminoalkyl of 1-6 carbon atoms, acyl of 2-7 carbon atoms; R5 is hydrogen, halogen, alkyl of 1-6 carbon atoms, perfluoroalkyl of 1-6 carbon atoms, nitrile, alkoxy of 1-6 carbon atoms, aryloxy, arylalcoxy of 2-12 carbon atoms, arylsulfanyl; W is S, O, or NR9; R9 is hydrogen or alkyl of 1-6 carbon atoms; X is O, -NR6-, or -(CH2)pNR6-; R6 is hydrogen, or alkyl of 1-6 carbon atoms; p is 1 to 4; Y is methylene, carbonyl, -SO2-, or -SO-; Z is phenyl, heteroaryl, or naphthyl; R7 and R8 are each, independently, hydrogen, carboxyl, acyl of 2-7 carbon atoms, hydroxyl, hydroxyalkyl of 1-6 carbon atoms, hydroxyalkanoyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms, perfluoroalkoxy of 1-6 carbon atoms, alkoxycarbonyl of 2-7 carbon atoms, perfluoroalkoxycarbonyl of 2-7 carbon atoms, alkyl of 1-6 carbon atoms, perfluoroalkyl of 1-6 carbon atoms, aryl, aryloxy, aryloxycarbonyl, heteroaryloxycarbonyl, arylalkoxy of 6-12 carbon atoms, heteroaryl, alkanoyloxy of 1-6 carbon atoms, perfluoroalkanoyloxy of 1-6 carbon atoms, heteroaroyloxy, aroyloxy, tetrazolyl, mercapto, nitrile, amino, carbamoy, aminoalkyl of 1-6 carbon atoms, -NHSO2CF3, carboxyaldehyde, halogen, nitro, acylamino, or pyrimidyl optionally substituted with mercapto, 3-hydroxy-cyclobut-3-ene-4-yl-1,2-dione, or tetronic acid; or a pharmaceutically acceptable salt thereof, which are useful in treating metabolic disorders related to insulin resistance or hyperglycemia.(FR) L'invention concerne des composés de la formule structurelle (I) dans laquelle R1 et R2 représentent chacun indépendamment, hydrogène, nitrile, nitro, amino, alkylamino C1-6, dialkylamino comprenant 1 à 6 atomes de carbone par groupe alkyle, cycloalkyl-amino C3-8, alkyle C1-6, perfluoroalkyle C1-6, halogène, cycloalkyle C3-8, thiényle, furyle, phényle ou phényle mono-, di- ou tri-substitué par halogène, hydroxy, alkyle C1-6, perfluoroalkyle C1-6, alcoxy C1-6, ou perfluoroalcoxy C1-6; R3 et R4 représentent chacun indépendamment hydrogène, alkyle C1-6, perfluoroalkyle C1-6, hydroxyalkyle C1-6, aminoalkyle C1-6, acyle C2-7; R5 représente hydrogène, halogène, alkyle C1-6, perfluoroalkyle C1-6, nitrile, alcoxy C1-6, aryloxy, arylalcoxy C2-12, arylsulfanyle; W représente S, O ou NR9; R9 représente hydrogène ou alkyle C1-6, X représente O, -NR6-, ou (CH2)pNR6-; R6 représente hydrogène, ou alkyle C1-6; p vaut 1 à 4; Y représente méthylène, carbonyle, -SO2-, ou SO-; Z représente phényle, hétéroaryle ou naphtyle; R7 et R8 représentent chacun indépendamment hydrogène, carboxyle, acyle C2-7, hydroxyle, hydroxyalkyle C1-6, hydroxyalcanoyle C1-6, alcoxy C1-6, perfluoroalcoxy C1-6, alcoxycarbonyle C2-7, perfluoroalcoxycarbonyle C2-7, alkyle C1-6, perfluoroalkyle C1-6, aryle, aryloxy, aryloxycarbonyle, hétéroaryloxycarbonyle, arylalcoxy C6-12, héréroaryle, alcanoyloxy C1-6, perfluoroalcanoyloxy C1-6, hétéroaroyloxy, aroyloxy, tétrazolyle, mercapto, nitrile, amino, carbamoyle, aminoalkyle C1-6, -NHSO2CF3, carboxyaldéhyde, halogène, nitro, acylamino, ou pyrimidyle éventuellement substitué par mercapto, 3-hydroxy-cyclobut-3-ène-4-yl-1,2-dione, ou acide tétronique. L'invention concerne également des sels de ces composés, acceptables sur le plan pharmacologique. Ces sels et composés sont utiles dans le traitement de troubles métaboliques associés à l'insulinorésistance ou à l'hyperglycémie.