N-Alpha,N-ω-,N-ω’-Tri-Z-D-精氨酸 | 1947-42-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-Alpha,N-ω-,N-ω’-Tri-Z-D-精氨酸
• 中文别名: 三(苄氧羰基)-D-精氨酸
• 英文名称: Z-D-Arg(Cbz)2-OH
• 英文别名: (2R)-5-[bis(phenylmethoxycarbonylamino)methylideneamino]-2-(phenylmethoxycarbonylamino)pentanoic acid
• CAS: 1947-42-8
• 化学式: C₃₀H₃₂N₄O₈
• 分子量: 576.606
• InChiKey: HZQIQHGUQPYWSW-RUZDIDTESA-N

物化性质

• 熔点：
  137-140°C
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  42
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  165
• 氢给体数：
  4
• 氢受体数：
  9

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332

反应信息

• 作为反应物：
  描述：

  tert-butyl N5-(4-[(6-methoxyquinolin-8-yl)amino]pentyl)-L-glutaminate 、 N-Alpha,N-ω-,N-ω’-Tri-Z-D-精氨酸 在 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到tert-butyl N2-[(benzyloxy)carbonyl]-N5-(N,N'-bis[(benzyloxy)carbonyl]carbamimidoyl)-D-ornithyl-N5-(4-[(6-methoxyquinolin-8-yl)amino]pentyl)-L-glutaminate
  参考文献：
  名称：

  Amino acid, dipeptide and pseudodipeptide conjugates of ring-substituted 8-aminoquinolines: Synthesis and evaluation of anti-infective, β-haematin inhibition and cytotoxic activities

  摘要：

  Three new series of 8-aminoquinolines with modifications in the side-chain by conjugation with amino acids, dipeptides and pseudodipeptides have been synthesized. The synthesized compounds were tested for in vitro antimalarial activity against chloroquine-sensitive and chloroquine-resistant Plasmodium falciparum strains, in vitro cytotoxicity in mammalian kidney cells (Vero), in vitro antileishmanial activity against Leishmania donovani, in vitro antimicrobial activity and in vitro inhibition of beta-haematin formation. The promising compounds were also evaluated for in vivo blood-schizontocidal antimalarial activity against Plasmodium berghei infected mice. The analogues 55 and 101 produced highest antimalarial activities, in vitro. Analogues 52 and 59 exhibited promising antileishmanial and broad spectrum of antifungal activities, respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.019

文献信息

• TETRAPEPTIDE COMPOUND AND METHOD FOR PRODUCING SAME
  申请人：KANEKA CORPORATION

  公开号：US20160264623A1

  公开（公告）日：2016-09-15

  The present invention is to provide a method for the efficient production on an industrial scale of SS-31 (D-Arg-Dmt-Lys-Phe-NH 2 ), which is an SS peptide. According to the present invention, the desired SS-31 is produced by efficiently synthesizing a tetrapeptide compound as a precursor of SS-31 and improving the tetrapeptide purity by crystallization.

  本发明旨在提供一种在工业规模上高效生产SS-31（D-Arg-Dmt-Lys-Phe-NH2）的方法，该化合物是一种SS肽。根据本发明，所需的SS-31通过高效合成作为SS-31前体的四肽化合物，并通过结晶提高四肽的纯度来生产。
• Pharmaceutically relevant aromatic-cationic peptides
  申请人：STEALTH BIOTHERAPEUTICS CORP

  公开号：US10696716B2

  公开（公告）日：2020-06-30

  The present technology provides peptides, methods of generating the peptides, and pharmaceutically acceptable salts of the peptides. In some embodiments, the peptide is D-Arg-2′6′-Dmt-Lys-Phe-NH2.

  本技术提供了多肽、生成多肽的方法以及多肽的药学上可接受的盐。在某些实施方案中，多肽是D-Arg-2′6′-Dmt-Lys-Phe-NH2。
• PHARMACEUTICALLY RELEVANT AROMATIC-CATIONIC PEPTIDES
  申请人：Stealth Biotherapeutics Corp

  公开号：EP3087093B1

  公开（公告）日：2021-11-10
• [EN] PHARMACEUTICALLY RELEVANT AROMATIC-CATIONIC PEPTIDES<br/>[FR] PEPTIDES AROMATIQUES-CATIONIQUES PHARMACEUTIQUEMENT APPROPRIÉS
  申请人：STEALTH PEPTIDES INT INC

  公开号：WO2015100376A1

  公开（公告）日：2015-07-02

  The present technology provides peptides, methods of generating the peptides, and pharmaceutically acceptable salts of the peptides. In some embodiments, the peptide is D-Arg-2'6'-Dmt-Lys-Phe-NH2.
• Amino acid, dipeptide and pseudodipeptide conjugates of ring-substituted 8-aminoquinolines: Synthesis and evaluation of anti-infective, β-haematin inhibition and cytotoxic activities
  作者：Kirandeep Kaur、Meenakshi Jain、Shabana I. Khan、Melissa R. Jacob、Babu L. Tekwani、Savita Singh、Prati Pal Singh、Rahul Jain

  DOI：10.1016/j.ejmech.2012.03.019

  日期：2012.6

  Three new series of 8-aminoquinolines with modifications in the side-chain by conjugation with amino acids, dipeptides and pseudodipeptides have been synthesized. The synthesized compounds were tested for in vitro antimalarial activity against chloroquine-sensitive and chloroquine-resistant Plasmodium falciparum strains, in vitro cytotoxicity in mammalian kidney cells (Vero), in vitro antileishmanial activity against Leishmania donovani, in vitro antimicrobial activity and in vitro inhibition of beta-haematin formation. The promising compounds were also evaluated for in vivo blood-schizontocidal antimalarial activity against Plasmodium berghei infected mice. The analogues 55 and 101 produced highest antimalarial activities, in vitro. Analogues 52 and 59 exhibited promising antileishmanial and broad spectrum of antifungal activities, respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.