| 1401003-85-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• CAS: 1401003-85-7
• 化学式: C₂₁H₂₉N₃O₄
• 分子量: 387.479
• InChiKey: ODWUTXYTPHJKOW-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  104.31
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  在 盐酸 、 endo-N-Hydroxy-5-norbornene-2,3-dicarboximide 、 水 、 N,N-二异丙基乙胺 、 N,N'-二异丙基碳二亚胺 作用下， 反应 0.5h， 生成 Trp-His(4-t-butylphenyl)-NHBzl
  参考文献：
  名称：

  Synthesis and antimicrobial activities of His(2-aryl)-Arg and Trp-His(2-aryl) classes of dipeptidomimetics

  摘要：

  在这份通讯中，我们报告了超短肽类模拟物的设计、合成和体外抗菌活性。

  DOI：

  10.1039/c4md00041b
• 作为产物：
  描述：

  N-α-trifluoroacetyl-2-(4-tert-butylphenyl)-L-histidine methyl ester 在 盐酸 、 水 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Synthesis and antimicrobial activities of His(2-aryl)-Arg and Trp-His(2-aryl) classes of dipeptidomimetics

  摘要：

  在这份通讯中，我们报告了超短肽类模拟物的设计、合成和体外抗菌活性。

  DOI：

  10.1039/c4md00041b

文献信息

• Discovery of a Membrane-Active, Ring-Modified Histidine Containing Ultrashort Amphiphilic Peptide That Exhibits Potent Inhibition of <i>Cryptococcus neoformans</i>
  作者：Krishna K. Sharma、Indresh Kumar Maurya、Shabana I. Khan、Melissa R. Jacob、Vinod Kumar、Kulbhushan Tikoo、Rahul Jain

  DOI：10.1021/acs.jmedchem.7b00481

  日期：2017.8.10

  The new structural classes of ultrashort peptides that exhibit potent microbicidal action have potential as future drugs. Herein, we report that C-2 arylated histidines containing tripeptides His(2-Ar)-Trp-His(2-Ar) exhibit potent antifungal activity against Cryptococcus neoformans with high selectivity. The most potent peptide 12f [His(2-biphenyl)-Trp-His(2-biphenyl)] displayed high in vitro activity against C. neoformans (IC50 = 0.35 mu g/mL, MIC = MFC = 0.63 mu g/mL) with a selectivity index of >28 and 2 times higher potency compared to amphotericin B. Peptide 12f exhibited proteolytic stability, with no apparent hemolytic activity. The mechanism of action study of 12f by confocal laser scanning microscopy and electron microscopy indicates nuclear fragmentation and membrane disruption of C. neoformans cells. Combinations of 12f with fluconazole and amphotericin B at subinhibitory concentration were synergistic against C. neoformans. This study suggests that 12f is a new structural class of amphiphilic peptide with rapid fungicidal activity caused by C. neoformans.
• Discovery of Short Peptides Exhibiting High Potency against <i>Cryptococcus neoformans</i>
  作者：Amit Mahindra、Nitin Bagra、Nishima Wangoo、Shabana I. Khan、Melissa R. Jacob、Rahul Jain

  DOI：10.1021/ml500011v

  日期：2014.4.10

  Rapid increase in the emergence of resistance against existing antifungal drugs created a need to discover new structural classes of antifungal agents. In this study we describe the synthesis of a new structural class of short antifungal peptidomimetcis, their activity, and plausible mechanism of action. The results of the study show that peptides lie and Ware more potent than the control drug amphotericin B, with no cytotoxicity to human cancer cells and noncancerous mammalian kidney cells. The selectivity of peptides to fungus is depicted by transmission electron microscopy studies, and it revealed that lie possibly disrupts the model membrane of the fungal pathogen.
• Regiospecific Direct C-H Arylation at the 2-Position of l-Histidine Using Arylboronic Acids
  作者：Rahul Jain、Amit Mahindra

  DOI：10.1055/s-0031-1290381

  日期：2012.7

  The first regiospecific direct C-2 arylation procedure for histidine using arylboronic acids has been developed. The reaction allows a one-step synthesis of a large variety of 2-aryl-L-histidines using ammonium persulfate and catalytic silver nitrate in TFA and CH2Cl2/H2O (1:1) at ambient temperature.