(3S)-3-amino-4-phenylbutanamide | 200949-84-4

• 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: (3S)-3-amino-4-phenylbutanamide
• CAS: 200949-84-4
• 化学式: C₁₀H₁₄N₂O
• 分子量: 178.234
• InChiKey: NDWZRNAVFZPUIR-VIFPVBQESA-N

物化性质

• 沸点：
  392.8±35.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  69.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S)-3-amino-4-phenylbutanamide 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 反应 0.5h， 生成
  参考文献：
  名称：

  Synthesis of gastrin antagonists, analogs of the C-terminal tetrapeptide of gastrin, by introduction of a .beta.-homo residue

  摘要：

  A series of analogues of Boc-Trp-Leu-Asp-Phe-NH2, a potent gastrin agonist, were synthesized by introducing a beta-homo residue in the sequence. These compounds were tested in vivo on acid secretion, in the anesthetized rat, and for their ability to inhibit binding of labeled gastrin to its receptors on gastric mucosal cells. These analogues behaved as gastrin antagonists. The most potent compounds in this series were Boc-Trp-Leu-beta-homo-Asp-NHCH2C6H5 (10) (IC50 = 1 microM, ED50 = 0.2 mg/kg), Boc-Trp-Leu-beta-homo-Asp-NHCH2CH2C6H5 (11) (IC50 = 0.75 microM, ED50 = 0.5 mg/kg), Boc-Trp-Leu-beta-homo-Asp-Phe-NH2 (12) (IC50 = 1.5 microM, ED50 = 0.1 mg/kg), and Boc-Trp-Leu-beta-homo-Asp-D-Phe-NH2 (13) (IC50 = 2 microM, ED50 = 0.1 mg/kg). We could demonstrate the importance of the region of the peptide bond between leucine and aspartic acid and of the structure of the C-terminal dipeptide Asp-Phe-NH2, for exhibiting biological activity on acid secretion.

  DOI：

  10.1021/jm00123a003
• 作为产物：
  描述：

  Z-β-homo-Phe-NH2 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 5.0h， 生成 (3S)-3-amino-4-phenylbutanamide
  参考文献：
  名称：

  Synthesis of gastrin antagonists, analogs of the C-terminal tetrapeptide of gastrin, by introduction of a .beta.-homo residue

  摘要：

  A series of analogues of Boc-Trp-Leu-Asp-Phe-NH2, a potent gastrin agonist, were synthesized by introducing a beta-homo residue in the sequence. These compounds were tested in vivo on acid secretion, in the anesthetized rat, and for their ability to inhibit binding of labeled gastrin to its receptors on gastric mucosal cells. These analogues behaved as gastrin antagonists. The most potent compounds in this series were Boc-Trp-Leu-beta-homo-Asp-NHCH2C6H5 (10) (IC50 = 1 microM, ED50 = 0.2 mg/kg), Boc-Trp-Leu-beta-homo-Asp-NHCH2CH2C6H5 (11) (IC50 = 0.75 microM, ED50 = 0.5 mg/kg), Boc-Trp-Leu-beta-homo-Asp-Phe-NH2 (12) (IC50 = 1.5 microM, ED50 = 0.1 mg/kg), and Boc-Trp-Leu-beta-homo-Asp-D-Phe-NH2 (13) (IC50 = 2 microM, ED50 = 0.1 mg/kg). We could demonstrate the importance of the region of the peptide bond between leucine and aspartic acid and of the structure of the C-terminal dipeptide Asp-Phe-NH2, for exhibiting biological activity on acid secretion.

  DOI：

  10.1021/jm00123a003

文献信息

• [EN] BENZOTHIAZO AND RELATED HETEROCYCLIC GROUP-CONTAINING CYSTEINE AND SERINE PROTEASE INHIBITORS<br/>[FR] INHIBITEURS BENZOTHIAZO, OU CONTENANT DES GROUPES HETEROCYCLIQUES APPARENTES, DE LA CYSTEINE OU DES PROTEASES SERINES
  申请人：CEPHALON, INC.

  公开号：WO1998021186A1

  公开（公告）日：1998-05-22

  (EN) The present invention is directed to novel benzothiazo and related heterocyclic group-containing inhibitors of cysteine or serine proteases. Methods for using the same are also described.(FR) L'invention porte sur de nouveaux inhibiteurs benzothiazo, ou contenant des groupes hétérocycliques apparentés, de la cystéine ou des protéases sérines, et sur leurs procédés d'utilisation.

  （中文翻译）本发明涉及一种新型的含有苯并噻唑和相关杂环基团的半胱氨酸或丝氨酸蛋白酶抑制剂。同时还描述了使用这些抑制剂的方法。
• CYTOTOXIN AND CONJUGATE, USES OF SAME, AND PREPARATION METHOD THEREFOR
  申请人：Sichuan Kelun-Biotech Biopharmaceutical Co., Ltd.

  公开号：EP3617221A1

  公开（公告）日：2020-03-04

  The present invention belongs to the technical field of medicine, and relates to a cytotoxin, a linker and a conjugate, a method for preparing the cytotoxin or the conjugate, and uses of the cytotoxin and of the conjugate in preventing and/or treating tumor diseases.

  本发明属于医学技术领域，涉及一种细胞毒素、连接体和共轭物，一种制备细胞毒素或共轭物的方法，以及细胞毒素和共轭物在预防和/或治疗肿瘤疾病中的用途。
• Syntheses and biological activities of bombesin analogs modified in the C-terminal dipeptide part
  作者：M Llinares、C Devin、J Azay、G Bergé、JA Fehrentz、J Martinez

  DOI：10.1016/s0223-5234(99)80063-4

  日期：1997.10

  Bombesin receptor antagonists are possible therapeutic agents due to their ability to act as inhibitors of cellular proliferation. On the basis of our hypothesis on the mechanism of action of gastrin associating an activating enzyme system to the receptor and on the results reported in the litterature, we have synthesized bombesin analogues which have been modified in the C-terminal Leu(13)-Leu(14) amide part. We have shown that modification in the C-terminal part of the bombesin strongly affected the biological activity in rat pancreatic acini. The most potent compound which is described here, H-D-Phe- Gln-Trp-Ala-Val-Gly-His-Leu-psi(CH2)Leu-NH2, was able to recognize the bombesin receptor on rat pancreatic acini (Ki 4.3 nM) and antagonized the bombesin stimulated amylase secretion (Ki 7.7 nM).
• EP0938477A4
  申请人：——

  公开号：EP0938477A4

  公开（公告）日：1999-12-29
• BENZOTHIAZO AND RELATED HETEROCYCLIC GROUP-CONTAINING CYSTEINE AND SERINE PROTEASE INHIBITORS
  申请人：CEPHALON, INC.

  公开号：EP0938477A1

  公开（公告）日：1999-09-01