3-(1H-3-indolyl)-2-(tosylamino)propyl toluene-4-sulfonate | 854457-16-2

• 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: 3-(1H-3-indolyl)-2-(tosylamino)propyl toluene-4-sulfonate
• 英文别名: toluene-4-sulfonic acid 3-(1H-indol-3-yl)-2-(toluene-4-sulfonylamino)-propyl ester；[3-(1H-indol-3-yl)-2-[(4-methylphenyl)sulfonylamino]propyl] 4-methylbenzenesulfonate
• CAS: 854457-16-2
• 化学式: C₂₅H₂₆N₂O₅S₂
• 分子量: 498.624
• InChiKey: MBQQELOIHHUTKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(1H-3-indolyl)-2-(tosylamino)propyl toluene-4-sulfonate 、 氰化钾 以 甲醇 为溶剂， 反应 5.0h， 以88%的产率得到3(S)-Tosylamino-4(β-indolyl)butanonitril
  参考文献：
  名称：

  Cyanomethyl substituted N-Acyl Tryptamines

  摘要：

  本发明涉及具有以下结构的氰甲基取代的N-酰基色胺化合物，其中R1、R2、R3、R4、R5、Q、X和W的含义如描述中所定义。根据本发明的化合物是有效的FSH拮抗剂，可用于男性或女性的生育控制，或用于骨质疏松症的预防和/或治疗。

  公开号：

  EP2020404A1
• 作为产物：
  描述：

  DL-色氨酸 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 3-(1H-3-indolyl)-2-(tosylamino)propyl toluene-4-sulfonate
  参考文献：
  名称：

  Chemoenzymatic preparation of the enantiomers of β-tryptophan ethyl ester and the β-amino nitrile analogue

  摘要：

  Racemic alpha-tryptophan was chemoselectively transformed into the enantiomers of beta-tryptophan ethyl ester. The key step in achieving enantiopurity was the N-acylation of the 3-amino-4-(3-indolyl)butanenitrile intermediate with Candida antarctica lipase A (CAL-A). The enzymatic N-acylation of racemic beta-tryptophan ethyl ester was also studied. CAL-A was highly (R)-enantioselective in the present kinetic resolutions, leading to a mixture of the butanamide product with an (R)-configuration and the unreacted starting material with an (S)-configuration at 50% conversion. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.03.016

文献信息

• CYANOMETHYL SUBSTITUTED N-ACYL TRYPTAMINES
  申请人：WORTMANN Lars

  公开号：US20090069321A1

  公开（公告）日：2009-03-12

  The present invention relates to cyanomethyl substituted N-acyl tryptamines of the formula I in which R1, R2, R3, R4, R5, Q, X and W have the meaning as defined in the description. The compounds according to the invention are effective FSH antagonists and can be used for example for fertility control in men or in women, or for the prevention and/or treatment of osteoporosis.

  本发明涉及公式I中的氰甲基取代N-酰基色胺类化合物，其中R1、R2、R3、R4、R5、Q、X和W的含义如描述中所定义。本发明的化合物是有效的FSH拮抗剂，例如可以用于男性或女性的生育控制，或用于骨质疏松的预防和/或治疗。
• [EN] CYANOMETHYL SUBSTITUTED N-ACYL TRYPTAMINES<br/>[FR] N-ACYLTRYPTAMINES À SUBSTITUTION CYANOMÉTHYLE
  申请人：BAYER SCHERING PHARMA AG

  公开号：WO2009016253A2

  公开（公告）日：2009-02-05

  The present invention relates to cyanomethyl substituted N-acyl tryptamines of the formula (I) in which R1, R2, R3, R4, R5, Q, X and W have the meaning as defined in the description. The compounds according to the invention are effective FSH antagonists and can be used for example for fertility control in men or in women, or for the prevention and/or treatment of osteoporosis.
• Cyanomethyl substituted N-Acyl Tryptamines
  申请人：Bayer Schering Pharma Aktiengesellschaft

  公开号：EP2020404A1

  公开（公告）日：2009-02-04

  The present invention relates to cyanomethyl substituted N-acyl tryptamines of the formula I in which R1, R2, R3, R4, R5, Q, X and W have the meaning as defined in the description. The compounds according to the invention are effective FSH antagonists and can be used for example for fertility control in men or in women, or for the prevention and/or treatment of osteoporosis.

  本发明涉及具有以下结构的氰甲基取代的N-酰基色胺化合物，其中R1、R2、R3、R4、R5、Q、X和W的含义如描述中所定义。根据本发明的化合物是有效的FSH拮抗剂，可用于男性或女性的生育控制，或用于骨质疏松症的预防和/或治疗。
• Chemoenzymatic preparation of the enantiomers of β-tryptophan ethyl ester and the β-amino nitrile analogue
  作者：Xiang-Guo Li、Liisa T. Kanerva

  DOI：10.1016/j.tetasy.2005.03.016

  日期：2005.5

  Racemic alpha-tryptophan was chemoselectively transformed into the enantiomers of beta-tryptophan ethyl ester. The key step in achieving enantiopurity was the N-acylation of the 3-amino-4-(3-indolyl)butanenitrile intermediate with Candida antarctica lipase A (CAL-A). The enzymatic N-acylation of racemic beta-tryptophan ethyl ester was also studied. CAL-A was highly (R)-enantioselective in the present kinetic resolutions, leading to a mixture of the butanamide product with an (R)-configuration and the unreacted starting material with an (S)-configuration at 50% conversion. (C) 2005 Elsevier Ltd. All rights reserved.