Boc-D-Arg(Cbz2)-OH

• 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: Boc-D-Arg(Cbz2)-OH
• 英文别名: N^ω,N^ω-bis(benzyloxycarbonyl)-N^α-Boc-D-arginine；D-Boc-(Cbz)₂-Arg-OH；Boc-D-arg(Z)2-OH；(2R)-5-[bis(phenylmethoxycarbonylamino)methylideneamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid
• 化学式: C₂₇H₃₄N₄O₈
• 分子量: 542.589
• InChiKey: ZWRJPLNCTNRXPE-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  39
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  165
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Boc-D-Arg(Cbz2)-OH 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.5h， 生成 N^ω,N^ω-bis(benzyloxycarbonyl)-N^α-Fmoc-D-arginine
  参考文献：
  名称：

  Solid-Phase Synthesis and Configurational Reassigment of Callipeltin E. Implications for the Structures of Callipeltins A and B

  摘要：

  Two possible isomers of the natural product callipeltin E (1, 5) were synthesized by using an Fmoc-based solid-phase strategy in 7 steps, in 20% and 26% overall yields, respectively. The H-1 NMR spectrum of synthetic 5 correlated closely with that of the natural product, whereas that of 1 did not, providing confirmation of the configurational reassignment of the N-terminal residue of callipeltin E as D-allothreonine. This result strongly implies that the corresponding residue in the closely related cyclic depsipeptides callipeltins A and B should also be considered a D-allothreonine residue.

  DOI：

  10.1021/jo060351h

文献信息

• Synthesis, antiprotozoal, antimicrobial, β-hematin inhibition, cytotoxicity and methemoglobin (MetHb) formation activities of bis(8-aminoquinolines)
  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.bmc.2010.11.036

  日期：2011.1

  In continuing our search of potent antimalarials based on 8-aminoquinoline structural framework, three series of novel bis(8-aminoquinolines) using convenient one to four steps synthetic procedures were synthesized. The bisquinolines were evaluated for in vitro antimalarial (Plasmodium falciparum), antileishmanial (Leishmania donovani), antimicrobial (a panel of pathogenic bacteria and fungi), cytotoxicity

  在继续研究基于 8-氨基喹啉结构框架的有效抗疟药的过程中，使用方便的一到四步合成程序合成了三个系列的新型双（8-氨基喹啉）。对双喹啉类药物的体外抗疟（恶性 疟原虫）、抗利什曼 原虫（多诺瓦尼利什曼原虫）、抗微生物剂（一组致病细菌和真菌）、细胞毒性、β-血红素抑制和高铁血红蛋白 (MetHb) 形成活性进行了评估。与母体药物伯氨喹相比，几种化合物表现出优异的抗疟活性。选择的化合物（44，61和79时在体内血液裂殖抗疟疾活性测试）（Plasmodium berghei ) 显示出有效的血液裂殖体活动。双喹啉的 MetHb 形成可以忽略不计（0.2-1.2%），这突显了它们在治疗葡萄糖-6-磷酸脱氢酶缺乏症患者中的潜力。所述双喹啉类似物（36，73和79）也表现出体外活性antileishmanial看好，和抗菌活性（43，44和76对致病细菌和真菌的面板）。这项研究的结果提供了证据，证明双（8
• Direct and Asymmetric Aldol Reactions of <i>N</i> ‐Azidoacetyl‐1,3‐thiazolidine‐2‐thione Catalyzed by Chiral Nickel(II) Complexes. A New Approach to the Synthesis of β‐Hydroxy‐α‐Amino Acids
  作者：Saul F. Teloxa、Miguel Mellado‐Hidalgo、Stuart C. D. Kennington、Pedro Romea、Fèlix Urpí、Gabriel Aullón、Mercè Font‐Bardia

  DOI：10.1002/chem.202200671

  日期：2022.7.6

  Enantiomerically pure anti N-β-aryl-β-silyloxy-α-azidoacetyl thioimides are efficiently prepared through a direct aldol reaction from N-azidoacetyl-1,3-thiazolidine-2-thione and a wide array of aromatic aldehydes catalyzed by 2–6 mol% [Tol-BINAP]Ni(II) complexes. The straightforward removal of the heterocyclic scaffold facilitates their conversion into a variety of chiral intermediates. Indeed, treatment

  对映体纯的 抗 N -β-芳基-β-甲硅烷氧基-α-叠氮乙酰硫代酰亚胺通过N-叠氮乙酰基-1,3-噻唑烷-2-硫酮和由 2-催化的多种芳香醛的直接醛醇反应有效制备6 mol% [Tol-BINAP]Ni(II) 配合物。杂环支架的直接去除有助于它们转化为各种手性中间体。实际上，用 α-氨基酯盐酸盐处理所得硫代酰亚胺可以获得相应的二肽以及叠氮基的适当操作产生 kasumigamide 和 atrutamycin 的肽片段。
• Synthesis and Structure−Activity Relationships of an Orally Available and Long-Acting Analgesic Peptide, <i>N</i>^α-Amidino-Tyr-<scp>d</scp>-Arg-Phe-MeβAla-OH (ADAMB)
  作者：Tadashi Ogawa、Tetsuhisa Miyamae、Kimie Murayama、Kaori Okuyama、Toru Okayama、Masaki Hagiwara、Shinobu Sakurada、Tadanori Morikawa

  DOI：10.1021/jm010357t

  日期：2002.11.1

  A novel dermorphin tetrapeptide N-alpha-amidino-Tyr-D-Arg-Phe-MebetaAla-OH (ADAMB) was designed based on the structures of several dermorphin tetrapeptide analogues, including N-alpha-amidino-Tyr-D-Arg-Phe-Gly-OH (ADA-DER), H-Tyr-D-Arg-Phe-betaAla-OH (TAPA), and H-Tyr-D-Arg-Phe-Sar-OH (DAS-DER). These parent compounds were known to show a weak oral analgesic activity in animals and/or to possess a different mechanism of analgesia from othery mu-opioid peptides. Six analogues of ADAMB were also synthesized to investigate the effect on potency of N-terminal amidination and N-methyl-beta-alanine (MebetaAla) substitution at position 4. Compounds were assessed using the tail pressure test in mice after subcutaneous and oral administration. Among the peptides tested, ADAMB showed the strongest oral antinociceptive activity, with an ED50 of 5.8 vs 22.2 mg/kg for morphine, as well as a 38-fold stronger activity after subcutaneous administration. ADAMB also showed long-lasting antinociceptive activity, with 50% of the maximum effect persisting in the tail pressure test at 10 h after oral administration (10 mg/kg). In contrast, orally administered morphine (80 mg/kg) showed a rapid decrease of activity in the same. test and its antinociceptive effect disappeared within 4 h. When the antinociceptive effect of ADAMB was compared with that of analogues possessing betaAla(4) (1) or Sar(4) (2), as well as analogues with N-substitution (3-6), it was found that both the N-alpha-amidino substitution and the MebetaAla(4) were synergistically involved in creating ADAMB's exceptionally high antinociceptive activity.
• 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.
• PHARMACEUTICALLY RELEVANT AROMATIC-CATIONIC PEPTIDES
  申请人：Stealth BioTherapeutics Corp

  公开号：US20170081363A1

  公开（公告）日：2017-03-23

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