(S)-3-(9-fluorenylmethoxycarbonylamino)-2-(5-methoxy-1H-indol-3-yl)propionic acid | 1313710-70-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-3-(9-fluorenylmethoxycarbonylamino)-2-(5-methoxy-1H-indol-3-yl)propionic acid
• 英文别名: (2S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-2-(5-methoxy-1H-indol-3-yl)propanoic acid
• CAS: 1313710-70-1
• 化学式: C₂₇H₂₄N₂O₅
• 分子量: 456.498
• InChiKey: BFLRJOTXMSWOMP-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-3-(9-fluorenylmethoxycarbonylamino)-2-(5-methoxy-1H-indol-3-yl)propionic acid 、 Fmoc-O-叔丁基-L-酪氨酸 、 N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 、 Fmoc-Pbf-L-精氨酸 在 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 哌啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and changes in affinity for NOP and opioid receptors of novel hexapeptides containing β2-tryptophan analogues

  摘要：

  We report the synthesis and the biological activity of new analogues of Ac-RFMWMK-NH2 and Ac-RYYRWK-NH2, modified in position 4 and 5, respectively, with incorporation of newly synthesized beta(2)-tryptophan analogues. Trp was substituted by the (S)-2-(1-methyl-1H-indol-3-yl)propionic residue or by (S)-2-(5-methoxy-1H-indol-3-yl)propionic residue. The biological activity (pEC(50) and E-max) of these compounds was tested on electrically stimulated preparations of rat vas deferens. The 5-methoxy beta-tryptophan group reverses the affinity of the compounds. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.064
• 作为产物：
  描述：

  [N-(4-benzyloxycarbonylphenyl)-4,4-dimethyl-2-oxopyrrolidin-3-yl] (3'R,2S)-2-(5-methoxy-1H-indol-3-yl)-3-nitropropionate 在 palladium 10% on activated carbon 、 氢气 、 碳酸氢钠 、 三甲基氢氧化锡 作用下， 以 水 、 1,2-二氯乙烷 、 丙酮 为溶剂， 20.0~85.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 生成 (S)-3-(9-fluorenylmethoxycarbonylamino)-2-(5-methoxy-1H-indol-3-yl)propionic acid
  参考文献：
  名称：

  β的不对称合成2通过吲哚的弗里德尔-克拉夫茨烷基化与手性Nitroacrylate -色氨酸类似物

  摘要：

  在硝基还原并除去手性助剂后，各种吲哚与手性硝基丙烯酸酯的不对称Friedel-Crafts烷基化反应提供了旋光性的β-色氨酸类似物。该反应通常以高收率和高非对映选择性（高达90:10）进行。

  DOI：

  10.1021/jo200733t

文献信息

• Synthesis and analgesic effects of novel β2-tryptophan hexapeptide analogs
  作者：Adriana Bocheva、Hristina Nocheva、Nikola Pavlov、Petar Todorov、Monique Calmès、Jean Martinez、Emilia Naydenova

  DOI：10.1007/s00726-013-1555-4

  日期：2013.10

  Aiming to develop more potent analgesic substances a new series of hexapeptides containing beta(2)-tryptophan analogues was synthesized. The Trp in position 4 and 5, respectively in Ac-Arg-Phe-Met-Trp-Met-Lys-NH2 (opioid receptor antagonist) and Ac-Arg-Tyr-Tyr-Arg-Trp-Lys-NH2 (highly potent and selective NOP-receptor agonist) was substituted by the (S)-2-(1-methyl-1H-indol-3-yl)propionic residue or the (S)-2-(5-methoxy-1H-indol-3-yl)propionic residue. The analgesic effect of the four newly synthesized compounds has been evaluated in male Wistar rats by PP- and HP tests and compared to the native templates. Further estimation of the mechanisms of action of each compound was achieved using specific antagonists-naloxone for opioid and JTC801 for the NOP receptor. Replacement of Trp with beta(2)-tryptophan analogues in 4th position (Ac-Arg-Phe-Met-Trp-Met-Lys-NH2) led to increased and longer lasting analgesic effect. The results obtained permit us to assume that both opioid and NOP receptors take part in the newly synthesized compounds analgesic effects.
• Synthesis and changes in affinity for NOP and opioid receptors of novel hexapeptides containing β2-tryptophan analogues
  作者：Rositsa Zamfirova、Nikola Pavlov、Petar Todorov、Polina Mateeva、Jean Martinez、Monique Calmès、Emilia Naydenova

  DOI：10.1016/j.bmcl.2013.05.064

  日期：2013.7

  We report the synthesis and the biological activity of new analogues of Ac-RFMWMK-NH2 and Ac-RYYRWK-NH2, modified in position 4 and 5, respectively, with incorporation of newly synthesized beta(2)-tryptophan analogues. Trp was substituted by the (S)-2-(1-methyl-1H-indol-3-yl)propionic residue or by (S)-2-(5-methoxy-1H-indol-3-yl)propionic residue. The biological activity (pEC(50) and E-max) of these compounds was tested on electrically stimulated preparations of rat vas deferens. The 5-methoxy beta-tryptophan group reverses the affinity of the compounds. (C) 2013 Elsevier Ltd. All rights reserved.
• Asymmetric Synthesis of β²-Tryptophan Analogues via Friedel–Crafts Alkylation of Indoles with a Chiral Nitroacrylate
  作者：Nikola Pavlov、Pierre Gilles、Claude Didierjean、Emmanuel Wenger、Emilia Naydenova、Jean Martinez、Monique Calmès

  DOI：10.1021/jo200733t

  日期：2011.8.5

  The asymmetric Friedel–Crafts alkylation of various indoles with a chiral nitroacrylate provides optically active β-tryptophan analogues after reduction of the nitro group and removal of the chiral auxiliary. This reaction generally occurs in good yield and high diastereoselectivity (up to 90:10).

  在硝基还原并除去手性助剂后，各种吲哚与手性硝基丙烯酸酯的不对称Friedel-Crafts烷基化反应提供了旋光性的β-色氨酸类似物。该反应通常以高收率和高非对映选择性（高达90:10）进行。