Boc-Gln-D-Trp-Phe-OH | 126090-06-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Boc-Gln-D-Trp-Phe-OH
• 英文别名: (2S)-2-[[(2R)-2-[[(2S)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-phenylpropanoic acid
• CAS: 126090-06-0
• 化学式: C₃₀H₃₇N₅O₇
• 分子量: 579.653
• InChiKey: NZMQUVNAJVVAQX-VXNXHJTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  193
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Boc-Gln-D-Trp-Phe-OH 在 盐酸 、 二甲基硫 、 乙醇 、 1,2-乙二硫醇 、 三氟乙酸 作用下， 反应 5.0h， 生成 <*>Glu-D-Trp-Phe-OH
  参考文献：
  名称：

  Studies on neurokinin antagonists. 1. The design of novel tripeptides possessing glutaminyl-D-tryptophylphenylalanine sequence as substance P antagonists

  摘要：

  To discover a novel and low molecular weight substance P (SP) antagonist we postulated that the essential binding domain of peptide ligands was only a small portion in the whole structure. On the basis of this assumption, we selected the known octapeptide SP antagonist D-Pro-Gln-Gln-D-Trp-Phe-D-Trp-D-Trp-Phe-NH2 (1) as a lead and synthesized its fragment tripeptides which were evaluated for their activity to block H-3-SP binding on guinea pig lung membranes. The protected tripeptide N(alpha)-[N(alpha)-[N(alpha)-(tert-butyloxycarbonyl)-L-glutaminyl]-N1-formyl-D-tryptophyl]-L-phenylalanine benzyl ester [Boc-Gln-D-Trp(CHO)-Phe-OBzl (4a)], corresponding to the Gln-D-Trp-Phe part of 1, exhibited 7-fold potent inhibitory activity in comparison with 1. Studies on structure-activity relationships revealed that the D-tryptophan, L-phenylalanine, and benzyl ester were quite important to maintain the high binding affinity. It was also indicated that 4a antagonized the SP-induced contraction of isolated guinea pig trachea strips (IC50 = 4.7 x 10(-6) M).

  DOI：

  10.1021/jm00089a011
• 作为产物：
  描述：

  BOC-D-色氨酸(Nin-甲酰) 在 盐酸 、 sodium hydroxide 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 Boc-Gln-D-Trp-Phe-OH
  参考文献：
  名称：

  Studies on neurokinin antagonists. 1. The design of novel tripeptides possessing glutaminyl-D-tryptophylphenylalanine sequence as substance P antagonists

  摘要：

  To discover a novel and low molecular weight substance P (SP) antagonist we postulated that the essential binding domain of peptide ligands was only a small portion in the whole structure. On the basis of this assumption, we selected the known octapeptide SP antagonist D-Pro-Gln-Gln-D-Trp-Phe-D-Trp-D-Trp-Phe-NH2 (1) as a lead and synthesized its fragment tripeptides which were evaluated for their activity to block H-3-SP binding on guinea pig lung membranes. The protected tripeptide N(alpha)-[N(alpha)-[N(alpha)-(tert-butyloxycarbonyl)-L-glutaminyl]-N1-formyl-D-tryptophyl]-L-phenylalanine benzyl ester [Boc-Gln-D-Trp(CHO)-Phe-OBzl (4a)], corresponding to the Gln-D-Trp-Phe part of 1, exhibited 7-fold potent inhibitory activity in comparison with 1. Studies on structure-activity relationships revealed that the D-tryptophan, L-phenylalanine, and benzyl ester were quite important to maintain the high binding affinity. It was also indicated that 4a antagonized the SP-induced contraction of isolated guinea pig trachea strips (IC50 = 4.7 x 10(-6) M).

  DOI：

  10.1021/jm00089a011

文献信息

• Peptide compounds, processes for preparation thereof and pharmaceutical
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US05187156A1

  公开（公告）日：1993-02-16

  The present invention relates to DTrp-Phe containing tripeptides and pharmaceuticals, which possess tachykinin antagonism activity as well as processes of making such peptides.

  本发明涉及含有DTrp-Phe的三肽和药物，具有快速激肽拮抗作用，并涉及制备这些肽的方法。
• Studies on neurokinin antagonists. 1. The design of novel tripeptides possessing glutaminyl-D-tryptophylphenylalanine sequence as substance P antagonists
  作者：Daijiro Hagiwara、Hiroshi Miyake、Hiroshi Morimoto、Masako Murai、Takashi Fujii、Masaaki Matsuo

  DOI：10.1021/jm00089a011

  日期：1992.5

  To discover a novel and low molecular weight substance P (SP) antagonist we postulated that the essential binding domain of peptide ligands was only a small portion in the whole structure. On the basis of this assumption, we selected the known octapeptide SP antagonist D-Pro-Gln-Gln-D-Trp-Phe-D-Trp-D-Trp-Phe-NH2 (1) as a lead and synthesized its fragment tripeptides which were evaluated for their activity to block H-3-SP binding on guinea pig lung membranes. The protected tripeptide N(alpha)-[N(alpha)-[N(alpha)-(tert-butyloxycarbonyl)-L-glutaminyl]-N1-formyl-D-tryptophyl]-L-phenylalanine benzyl ester [Boc-Gln-D-Trp(CHO)-Phe-OBzl (4a)], corresponding to the Gln-D-Trp-Phe part of 1, exhibited 7-fold potent inhibitory activity in comparison with 1. Studies on structure-activity relationships revealed that the D-tryptophan, L-phenylalanine, and benzyl ester were quite important to maintain the high binding affinity. It was also indicated that 4a antagonized the SP-induced contraction of isolated guinea pig trachea strips (IC50 = 4.7 x 10(-6) M).