(R)-2-[5-(2,5-dimethylpyrrol-1-yl)-1H-indol-3-ylmethyl]pyrrolidine-1-carboxylic acid benzyl ester | 160906-87-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-[5-(2,5-dimethylpyrrol-1-yl)-1H-indol-3-ylmethyl]pyrrolidine-1-carboxylic acid benzyl ester
• 英文别名: benzyl (2R)-2-[[5-(2,5-dimethylpyrrol-1-yl)-1H-indol-3-yl]methyl]pyrrolidine-1-carboxylate
• CAS: 160906-87-6
• 化学式: C₂₇H₂₉N₃O₂
• 分子量: 427.546
• InChiKey: HWUSRZZLIQDEQO-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  50.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-[5-(2,5-dimethylpyrrol-1-yl)-1H-indol-3-ylmethyl]pyrrolidine-1-carboxylic acid benzyl ester 在 palladium dihydroxide 、 盐酸羟胺 、 氢气 、 三乙胺 作用下， 以 乙酸乙酯 、 异丙醇 为溶剂， 反应 54.0h， 生成 1-吡咯烷羧酸,2-[(5-氨基-1H-吲哚-3-基)甲基]-,1,1-二甲基乙基酯,(R)-
  参考文献：
  名称：

  Discovery of 5-Arylsulfonamido-3- (pyrrolidin-2-ylmethyl)-1H-indole Derivatives as Potent, Selective 5-HT₆ Receptor Agonists and Antagonists

  摘要：

  5-Arylsulfonylamido-3-(pyrrolidin-2-ylmethyl)-1H-indoles have been identified as high-affinity 5-HT6 receptor ligands. Within this class, several of the (R)-enantiomers were potent agonists having EC50 values of 1 nM or less and functioning as full agonists while the (S)-enantiomers displayed moderate antagonist activity.

  DOI：

  10.1021/jm049243i
• 作为产物：
  描述：

  2-[5-(2,5-dimethylpyrrol-1-yl)-1H-indole-3-carbonyl]pyrrolidine-1-carboxylic acid benzyl ester 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以85%的产率得到(R)-2-[5-(2,5-dimethylpyrrol-1-yl)-1H-indol-3-ylmethyl]pyrrolidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Discovery of 5-Arylsulfonamido-3- (pyrrolidin-2-ylmethyl)-1H-indole Derivatives as Potent, Selective 5-HT₆ Receptor Agonists and Antagonists

  摘要：

  5-Arylsulfonylamido-3-(pyrrolidin-2-ylmethyl)-1H-indoles have been identified as high-affinity 5-HT6 receptor ligands. Within this class, several of the (R)-enantiomers were potent agonists having EC50 values of 1 nM or less and functioning as full agonists while the (S)-enantiomers displayed moderate antagonist activity.

  DOI：

  10.1021/jm049243i

文献信息

• 5-arylindolederivatives and their use as serotonin(5-ht1)agonists
  申请人：PFIZER INC.

  公开号：EP1094064A1

  公开（公告）日：2001-04-25

  A compound of the formula wherein R1 is n is 0, 1, or 2; A, B, C, and D are each independently nitrogen or carbon; R2, R3, R4, and R5 are each independently hydrogen, C1 to C6 alkyl, aryl, C1 to C3 alkyl-aryl, halogen, cyano, nitro, -(CH2)mNR14R15, -(CH2)mOR9, -SR9, -SO2NR14R15, -(CH2)mNR14SO2R15, -(CH2)mNR14CO2R9, -(CH2)mNR14COR9, -(CH2)mNR14CONHR9, -CONR14R15, or -CO2R9; R2 and R3, R3 and R4, or R4 and R5 may be taken together to form a five- to seven-membered alkyl ring, a six-membered aryl ring, a five- to seven-membered heteroalkyl ring having 1 heteroatom of N, O, or S, or a five- to six-membered heteroaryl ring having 1 or 2 heteroatoms of N, O, or S; R6 is hydrogen, -OR10, or -NHCOR10; R7, R8, R14, and R15 are each independently hydrogen, C1 to C6 alkyl, -(CH2)xOR11, C1 to C3 alkyl-aryl, aryl; R7 and R8 or R14 and R15 may be taken together to form a three- to six-membered ring; R9 is hydrogen, C1 to C6 alkyl, C1 to C3 alkyl-aryl, or aryl; R10 is hydrogen, C1 to C6 alkyl, or C1 to C3 alkyl-aryl; R11 is hydrogen, C1 to C6 alkyl, or C1 to C3 alkyl-aryl; m is 0, 1, 2, or 3; x is 2 or 3; a broken line represents an optional double bond; and the above aryl groups and the aryl moieties of the above alkyl-aryl groups are independently phenyl or substituted phenyl, wherein said substituted phenyl may be substituted with one to three of C1 to C4 alkyl, halogen, hydroxy, cyano, carboxamido, nitro, or C1 to C4 alkoxy; or a pharmaceutically acceptable satt thereof.

  式中的化合物 其中 R1 是 n为0、1或2；A、B、C和D各自独立地为氮或碳；-(CH2)mOR9、-SR9、-SO2NR14R15、-(CH2)mNR14SO2R15、-(CH2)mNR14CO2R9、-(CH2)mNR14COR9、-(CH2)mNR14CONHR9、-CONR14R15 或 -CO2R9；R2 和 R3、R3 和 R4 或 R4 和 R5 可组合成五至七元烷基环、六元芳基环、具有 1 个 N、O 或 S 杂原子的五至七元杂烷基环或具有 1 或 2 个 N、O 或 S 杂原子的五至六元杂芳基环；R6是氢、-OR10或-NHCOR10； R7、R8、R14和R15各自独立地是氢、C1至C6烷基、-(CH2)xOR11、C1至C3烷基芳基、芳基；R7 和 R8 或 R14 和 R15 可结合在一起形成三至六元环；R9 是氢、C1 至 C6 烷基、C1 至 C3 烷基芳基或芳基；R10 是氢、C1 至 C6 烷基或 C1 至 C3 烷基芳基；R11 是氢、C1 至 C6 烷基或 C1 至 C3 烷基芳基；m 是 0、1、2 或 3；x 是 2 或 3；断线代表任选双键；上述芳基和上述烷基芳基的芳基独立地为苯基或取代苯基，其中所述取代苯基可被 C1 至 C4 烷基、卤素、羟基、氰基、羧酰胺基、硝基或 C1 至 C4 烷氧基中的一至三个取代；或其药学上可接受的酯。
• 5-ARYLINDOLE DERIVATIVES AND THEIR USE AS SEROTONIN (5-HT 1) AGONISTS
  申请人：PFIZER INC.

  公开号：EP0666858B1

  公开（公告）日：2001-06-13
• US5886008A
  申请人：——

  公开号：US5886008A

  公开（公告）日：1999-03-23
• Discovery of 5-Arylsulfonamido-3- (pyrrolidin-2-ylmethyl)-1<i>H</i>-indole Derivatives as Potent, Selective 5-HT₆ Receptor Agonists and Antagonists
  作者：Derek C. Cole、William J. Lennox、Sabrina Lombardi、John W. Ellingboe、Ronald C. Bernotas、Gregory J. Tawa、Hossein Mazandarani、Deborah L. Smith、Guoming Zhang、Joseph Coupet、Lee E. Schechter

  DOI：10.1021/jm049243i

  日期：2005.1.1

  5-Arylsulfonylamido-3-(pyrrolidin-2-ylmethyl)-1H-indoles have been identified as high-affinity 5-HT6 receptor ligands. Within this class, several of the (R)-enantiomers were potent agonists having EC50 values of 1 nM or less and functioning as full agonists while the (S)-enantiomers displayed moderate antagonist activity.