6,7,8,9-tetrahydrobenzoindole | 67720-26-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 6,7,8,9-tetrahydrobenzoindole
• 英文别名: 6,7,8,9-tetrahydro-1H-benzo[g]indole；6,7,8,9-Tetrahydro-1H-benzo[g]indole；6,7,8,9-tetrahydro-1H-benz[g]indole；6,7,8,9-Tetrahydro<6,7>benzindol；8,9,10,11-Tetrahydro-6,7-benzindol；Tetrahydro-6,7-benzindol
• CAS: 67720-26-7
• 化学式: C₁₂H₁₃N
• 分子量: 171.242
• InChiKey: VOGFQCWPTBIAFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  6,7,8,9-tetrahydrobenzoindole 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 sodium hydroxide 、 锂硼氢 、 氯化亚砜 、 氢气 、 硝酸 、 sodium 、 碳酸氢钠 、 N,N'-二环己基碳二亚胺 、 硫酸二甲酯 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 、 水 、 溶剂黄146 、 乙酸乙酯 、 乙腈 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 184.59h， 生成 (4S,7S)-4-(hydroxymethyl)-7-isopropyl-8-methyl-1,3,4,5,7,8,10,11,12,13-decahydro-6H-benzo[g][1,4]diazonino[7,6,5-cd]indol-6-one
  参考文献：
  名称：

  Synthesis and stereochemistry of indolactam-v, an active fragment of teleocidins. Structural requirements for tumor-promoting activity

  摘要：

  DOI：

  10.1016/s0040-4020(01)96073-9
• 作为产物：
  描述：

  6,7,8,9-tetrahydrobenzoindole-2-carboxylic acid ethyl ester 在 盐酸 、 氢氧化钾 、 铜 作用下， 以 喹啉 、 乙醇 、 水 为溶剂， 反应 3.0h， 生成 6,7,8,9-tetrahydrobenzoindole
  参考文献：
  名称：

  Synthesis and stereochemistry of indolactam-v, an active fragment of teleocidins. Structural requirements for tumor-promoting activity

  摘要：

  DOI：

  10.1016/s0040-4020(01)96073-9

文献信息

• Condensed indoline derivatives and their use as 5HT, in particular 5HT2c, receptor ligands
  申请人：Roffey Richard Anthony Jonathan

  公开号：US20050187282A1

  公开（公告）日：2005-08-25

  A chemical compound of formula (I) wherein R 1 and R 2 are independently selected from hydrogen and alkyl; R 3 is alkyl; R 4 and R 5 are selected from hydrogen and alkyl; R 6 and R 7 are independently selected from hydrogen, halogen, hydroxyl, alkyl, aryl, amino, alkylamino, dialkylamino, alkoxy, aryloxy, alkylthio, alkylsulfoxyl, nitro, carbonitrile, carbo-alkoxy, carbo-aryloxy and carboxyl; and A is a 5- or 6-membered ring optionally containing one or more heteroatoms wherein the atoms of the ring A, other than the unsaturated carbon atoms of the phenyl ring to which the ring A is fused, are saturated or unsaturated, and pharmaceutically acceptable salts, addition compounds and prodrugs thereof; and the use thereof in therapy, particularly as an agonist or antagonist of a 5HT receptor, particularly a 5HT 2C receptor, for instance in the treatment of disorders of the central nervous system; damage to the central nervous system; cardiovascular disorders; gastrointestinal disorders; diabetes insipidus, and sleep apnea, and particularly for the treatment of obesity.

  化学式（I）的化合物，其中R1和R2分别选自氢和烷基；R3是烷基；R4和R5选自氢和烷基；R6和R7分别选自氢、卤素、羟基、烷基、芳基、氨基、烷基氨基、二烷基氨基、烷氧基、芳氧基、烷基硫基、烷基亚砜基、硝基、氰基、羧酸酯基、羧酸芳酯基和羧基；A是一个含有一个或多个杂原子的5-或6元环，其中环A的原子除了与环A融合的苯环的不饱和碳原子外，可以是饱和的或不饱和的，以及其药学上可接受的盐、加合物和前药；以及其在治疗中的用途，特别是作为5HT受体的激动剂或拮抗剂，特别是5HT2C受体，例如在治疗中枢神经系统疾病；中枢神经系统损伤；心血管疾病；胃肠道疾病；尿崩症和睡眠呼吸暂停症，特别是用于肥胖症的治疗。
• Condensed indoline derivatives and their use as 5HT, in particular 5HT2C, receptor ligands
  申请人：Roffey Richard Anthony Jonathan

  公开号：US20050192334A1

  公开（公告）日：2005-09-01

  A chemical compound of formula (I) wherein R 1 and R 2 are independently selected from hydrogen and alkyl; R 3 is alkyl; R 4 and R 5 are selected from hydrogen and alkyl; R 6 and R 7 are independently selected from hydrogen, halogen, hydroxyl, alkyl, aryl, amino, alkylamino, dialkylamino, alkoxy, aryloxy, alkylthio, alkylsulfoxyl, nitro, carbonitrile, carbo-alkoxy, carbo-aryloxy and carboxyl; and A is a 5- or 6-membered ring optionally containing one or more heteroatoms wherein the atoms of the ring A, other than the unsaturated carbon atoms of the phenyl ring to which the ring A is fused, are saturated or unsaturated, and pharmaceutically acceptable salts, addition compounds and prodrugs thereof; and the use thereof in therapy, particularly as an agonist or antagonist of a 5HT receptor, particularly a 5HT 2C receptor, for instance in the treatment of disorders of the central nervous system; damage to the central nervous system; cardiovascular disorders; gastrointestinal disorders; diabetes insipidus, and sleep apnea, and particularly for the treatment of obesity.

  化学式为（I）的化合物，其中R1和R2独立地选自氢和烷基；R3为烷基；R4和R5选自氢和烷基；R6和R7独立地选自氢、卤素、羟基、烷基、芳基、氨基、烷基氨基、二烷基氨基、烷氧基、芳氧基、烷硫基、烷基亚砜基、硝基、氰基、羧基酯基、芳羧基酯基和羧基；A是一个5-或6-成员环，可选地含有一个或多个杂原子，其中环A的原子除与环A融合的苯环的不饱和碳原子外，均为饱和或不饱和的，以及其药学上可接受的盐、加合物和前药；以及其在治疗中的使用，特别是作为5HT受体的激动剂或拮抗剂，特别是5HT2C受体，例如在中枢神经系统疾病、中枢神经系统损伤、心血管疾病、胃肠道疾病、尿崩症和睡眠呼吸暂停症的治疗中，特别是用于肥胖症的治疗。
• Condensed indoline derivatives and their use as 5HT , in particular 5hHT2c, receptor ligands
  申请人：Roffey Anthony Jonathan Richard

  公开号：US20070105889A1

  公开（公告）日：2007-05-10

  A chemical compound of formula (I) wherein R 1 and R 2 are independently selected from hydrogen and alkyl; R 3 is alkyl; R 4 and R 5 are selected from hydrogen and alkyl; R 6 and R 7 are independently selected from hydrogen, halogen, hydroxyl, alkyl, aryl, amino, alkylamino, dialkylamino, alkoxy, aryloxy, alkylthio, alkylsulfoxyl, nitro, carbonitrile, carbo-alkoxy, carbo-aryloxy and carboxyl; and A is a 5- or 6-membered ring optionally containing one or more heteroatoms wherein the atoms of the ring A, other than the unsaturated carbon atoms of the phenyl ring to which the ring A is fused, are saturated or unsaturated, and pharmaceutically acceptable salts, addition compounds and prodrugs thereof; and the use thereof in therapy, particularly as an agonist or antagonist of a 5HT receptor, particularly a 5HT 2C receptor, for instance in the treatment of disorders of the central nervous system; damage to the central nervous system; cardiovascular disorders; gastrointestinal disorders; diabetes insipidus, and sleep apnea, and particularly for the treatment of obesity.

  化学式为（I）的化合物，其中R1和R2分别选自氢和烷基；R3为烷基；R4和R5选自氢和烷基；R6和R7分别选自氢、卤素、羟基、烷基、芳基、氨基、烷基氨基、二烷基氨基、烷氧基、芳氧基、烷硫基、烷基亚砜基、硝基、氰基、羧甲氧基、羧芳氧基和羧基；A是一个5或6元环，可以包含一个或多个杂原子，环A的原子，除了与环A融合的苯环的不饱和碳原子外，都是饱和或不饱和的，并且其药物可接受的盐、加成物和前药；以及其在治疗中的应用，特别是作为5HT受体的激动剂或拮抗剂，特别是5HT2C受体，例如在中枢神经系统疾病的治疗中；中枢神经系统损伤；心血管疾病；胃肠道疾病；尿崩症和睡眠呼吸暂停症，特别是用于肥胖症的治疗。
• Condensed indoline derivatives and their use as 5HT, in particular 5HT2C, Receptor ligands
  申请人：Roffey Jonathan Richard Anthony

  公开号：US20080125455A1

  公开（公告）日：2008-05-29

  A chemical compound of formula (I) wherein R 1 and R 2 are independently selected from hydrogen and alkyl; R 3 is alkyl; R 4 and R 5 are selected from hydrogen and alkyl; R 6 and R 7 are independently selected from hydrogen, halogen, hydroxyl, alkyl, aryl, amino, alkylamino, dialkylamino, alkoxy, aryloxy, alkylthio, alkylsulfoxyl, nitro, carbonitrile, carbo-alkoxy, carbo-aryloxy and carboxyl; and A is a 5- or 6-membered ring optionally containing one or more heteroatoms wherein the atoms of the ring A, other than the unsaturated carbon atoms of the phenyl ring to which the ring A is fused, are saturated or unsaturated, and pharmaceutically acceptable salts, addition compounds and prodrugs thereof; and the use thereof in therapy, particularly as an agonist or antagonist of a 5HT receptor, particularly a 5HT 2C receptor, for instance in the treatment of disorders of the central nervous system; damage to the central nervous system, cardiovascular disorders; gastrointestinal disorders; diabetes insipidus, and sleep apnea, and particularly for the treatment of obesity.

  化学式为（I）的化合物，其中R1和R2独立地选自氢和烷基；R3是烷基；R4和R5选自氢和烷基；R6和R7独立地选自氢、卤素、羟基、烷基、芳基、氨基、烷基氨基、二烷基氨基、烷氧基、芳氧基、烷硫基、烷基亚砜基、硝基、氰基、羧甲氧基、羧芳氧基和羧基；A是一个5或6成员环，可选地含有一个或多个杂原子，其中环A的原子，除了与环A融合的苯环的不饱和碳原子外，均为饱和或不饱和的，并且其药学上可接受的盐、加合物和前药；以及在治疗中的使用，特别是作为5HT受体的激动剂或拮抗剂，特别是5HT2C受体，例如用于治疗中枢神经系统疾病；中枢神经系统损伤、心血管疾病；胃肠道疾病；尿崩症和睡眠呼吸暂停症，特别是用于治疗肥胖症。
• Condensed indoline derivatives and their use as 5-HT, in particular 5-HT2C, receptor ligands
  申请人：Vernalis Research Limited

  公开号：US07323473B2

  公开（公告）日：2008-01-29

  A chemical compound of formula (I) wherein R1 and R2 are independently selected from hydrogen and alkyl; R3 is alkyl; R4 and R5 are selected from hydrogen and alkyl; R6 and R7 are independently selected from hydrogen, halogen, hydroxyl, alkyl, aryl, amino, alkylamino, dialkylamino, alkoxy, aryloxy, alkylthio, alkylsulfonyl, nitro, carbonitrile, carbo-alkoxy, carbo-aryloxy and carboxyl; and A is a 5- or 6-membered ring optionally containing one or more heteroatoms wherein the atoms of the ring A, other than the unsaturated carbon atoms of the phenyl ring to which the ring A is fused, are saturated or unsaturated, and pharmaceutically acceptable salts, addition compounds and prodrugs thereof; and the use thereof in therapy, particularly as an agonist or antagonist of a 5HT receptor, particularly a 5HT2C receptor, for instance in the treatment of disorders of the central nervous system; damage to the central nervous system; cardiovascular disorders; gastrointestinal disorders; diabetes insipidus, and sleep apnea, and particularly for the treatment of obesity.

  化学式为（I）的化合物，其中R1和R2独立选择氢和烷基；R3是烷基；R4和R5选择自氢和烷基；R6和R7独立选择自氢、卤素、羟基、烷基、芳基、氨基、烷基氨基、二烷基氨基、烷氧基、芳氧基、烷硫基、烷基磺酰基、硝基、碳氰基、羧甲氧基、羧芳氧基和羧基；A是一个5-或6-成员环，可选含有一个或多个杂原子，其中环A的原子，除了与环A融合的苯环的不饱和碳原子外，都是饱和或不饱和的，并且其药物可接受的盐、加合物和前药；以及在治疗中的使用，特别是作为5-HT受体的激动剂或拮抗剂，特别是5-HT2C受体，例如在中枢神经系统紊乱的治疗中；中枢神经系统的损伤；心血管疾病；胃肠疾病；尿崩症和睡眠呼吸暂停症，特别是用于肥胖症的治疗。