Pro-Arg(NO2)-OMe | 789451-41-8

• 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: Pro-Arg(NO2)-OMe
• 英文别名: methyl (2S)-5-[[amino(nitramido)methylidene]amino]-2-[[(2S)-pyrrolidine-2-carbonyl]amino]pentanoate
• CAS: 789451-41-8
• 化学式: C₁₂H₂₂N₆O₅
• 分子量: 330.344
• InChiKey: ATVDRWFEZNWPDD-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  164
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Pro-Arg(NO2)-OMe 在 吡啶 、 palladium 10% on activated carbon 、 水 、 氢气 、 1-丙基磷酸酐 、 三氟乙酸 、 lithium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 136.0h， 生成
  参考文献：
  名称：

  Synthesis of functionalized new conjugates of batracylin with tuftsin/retro-tuftsin derivatives and their biological evaluation

  摘要：

  New batracylin conjugates with tuftsin/retro-tuftsin derivatives were designed and synthesized using T3P as a coupling agent. The conjugates possess an amide bond formed between the carboxyl group of heterocyclic molecule and the N-termini of the tuftsin/retro-tuftsin chain. The in vitro cytotoxic activity of the new analogues and their precursors was evaluated using a series of human and murine tumor cells. BAT conjugates containing retro-tuftsin with branched side aminoacid chain, in particular with leucine or isoleucine, were about 10-fold more cytotoxic toward two human tumor cell lines (lung adenocarcinoma (A549) and myeloblastic leukemia (HL-60)). These compounds showed about 10-fold increased cytotoxicity against the two types of tumor cells compared to parent BAT. We have not observed important differences in the mechanism of action between BAT and its cytotoxic tuftsin/retro-tuftsin conjugates. We propose that high biological activity of the most active BAT conjugates is a result of their greatly increased intracellular accumulation. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.012
• 作为产物：
  描述：

  (S)-(S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic (isobutyl carbonic) anhydride 在 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 Pro-Arg(NO2)-OMe
  参考文献：
  名称：

  Synthesis of functionalized new conjugates of batracylin with tuftsin/retro-tuftsin derivatives and their biological evaluation

  摘要：

  New batracylin conjugates with tuftsin/retro-tuftsin derivatives were designed and synthesized using T3P as a coupling agent. The conjugates possess an amide bond formed between the carboxyl group of heterocyclic molecule and the N-termini of the tuftsin/retro-tuftsin chain. The in vitro cytotoxic activity of the new analogues and their precursors was evaluated using a series of human and murine tumor cells. BAT conjugates containing retro-tuftsin with branched side aminoacid chain, in particular with leucine or isoleucine, were about 10-fold more cytotoxic toward two human tumor cell lines (lung adenocarcinoma (A549) and myeloblastic leukemia (HL-60)). These compounds showed about 10-fold increased cytotoxicity against the two types of tumor cells compared to parent BAT. We have not observed important differences in the mechanism of action between BAT and its cytotoxic tuftsin/retro-tuftsin conjugates. We propose that high biological activity of the most active BAT conjugates is a result of their greatly increased intracellular accumulation. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.012

文献信息

• Synthetic studies on novel benzimidazolopeptides with antimicrobial, cytotoxic and anthelmintic potential
  作者：Rajiv Dahiya、Devender Pathak

  DOI：10.1016/j.ejmech.2006.11.015

  日期：2007.6

  presence of cupric chloride. The coupling of compounds 5-8 with different amino acid ester hydrochlorides/dipeptide/tripeptide/tetrapeptide methyl esters afforded novel benzimidazolopeptide derivatives 5a-f, 6a-h, 7a-g and 8a-g. The structures of all newly synthesized compounds were established on the basis of analytical, IR, (1)H NMR, (13)C NMR and mass spectral data. Selected peptide ester derivatives were

  在氯化铜的存在下，通过5,6-二甲基-6硝基硝基苯并咪唑与重氮化的取代/未取代的氨基苯甲酸相互作用，合成了四个取代的苯并咪唑基-苯甲酸/水杨酸5-8。将化合物5-8与不同的氨基酸酯盐酸盐/二肽/三肽/四肽甲酯偶联，得到新的苯并咪唑并肽衍生物5a-f，6a-h，7a-g和8a-g。所有新合成的化合物的结构都是基于分析，IR，（1）H NMR，（13）C NMR和质谱数据确定的。通过使用氢氧化锂（LiOH）进一步水解选定的肽酯衍生物，得到相应的酸衍生物5b（a）-d（a​​），6e（a）-g（a），7c（a）-e（a）和8e （a）-g（a）。筛选所有肽衍生物的抗微生物，驱虫和细胞毒性活性。几乎所有新合成的苯并咪唑类肽对所有三种earth均表现出中等至良好的驱虫活性，对病原性真菌白色念珠菌和黑曲霉，革兰氏阴性细菌铜绿假单胞菌和大肠杆菌具有良好的抗菌活性。化合物8g和8g（a）对道尔顿氏淋巴瘤腹
• Ferrocene tripeptide Gly-Pro-Arg conjugates: Synthesis and inhibitory effects on Alzheimer’s Aβ1–42 fibrillogenesis and Aβ-induced cytotoxicity in vitro
  作者：Binbin Zhou、Chun-Lan Li、Yuan-Qiang Hao、Muya Chabu Johnny、You-Nian Liu、Juan Li

  DOI：10.1016/j.bmc.2012.11.030

  日期：2013.1

  Alzheimer's disease (AD) is the most common cause of dementia, and currently there is no clinical treatment to cure it or to halt its progression. Aggregation and fibril formation of beta-amyloid peptides (A beta) are central events in the pathogenesis of AD. Many efforts have been spent on the development of effective inhibitors to prevent A beta fibrillogenesis and cause disaggregation of preformed A beta fibrils. In this study, the conjugates of ferrocene and Gly-Pro-Arg (GPR) tripeptide, Boc-Gly-Pro-Arg(NO2)-Fca-OMe (4, GPR-Fca) and Fc-Gly-Pro-Arg-OMe (7, Fc-GPR) (Fc: ferrocene; Fca: ferrocene amino acid) were synthesized by HOBT/HBTU protocol in solution. These ferrocene GPR conjugates were employed to inhibit A beta(1-42) fibrillogenesis and to disaggregate preformed A beta fibrils. The inhibitory properties of ferrocene GPR conjugates on A beta(1-42) fibrillogenesis were evaluated by thioflavin T (ThT) fluorescence assay, and confirmed by atomic force microscopy (AFM) analysis. The interaction between the ferrocene GPR conjugates and A beta(1-42) was monitored by electrochemical means. Our results showed that both GPR and GPR-Fca can significantly inhibit the fibril formation of A beta(1-42), and cause disaggregation of the preformed fibrils. As expected, GPR-Fca shows stronger inhibitory effect on A beta(1-42) fibrillogenesis than that of its parent peptide GPR. In contrast, Fc-GPR shows no inhibitory effect on fibrillogenesis of A beta(1-42). Furthermore, GPR-Fca demonstrates significantly protection against A beta-induced cytotoxicity and exhibits high resistance to proteolysis and good lipophilicity. (C) 2012 Elsevier Ltd. All rights reserved.
• MATSUURA, DZIRO;TAKADZAKI, NAKAO;XIRATANI, XADZIMEH;ODEHRA, YU;FUDZIXARA,+
  作者：MATSUURA, DZIRO、TAKADZAKI, NAKAO、XIRATANI, XADZIMEH、ODEHRA, YU、FUDZIXARA,+

  DOI：——

  日期：——
• Synthesis of functionalized new conjugates of batracylin with tuftsin/retro-tuftsin derivatives and their biological evaluation
  作者：Wioleta Januchta、Marcin Serocki、Krystyna Dzierzbicka、Grzegorz Cholewiński、Andrzej Skladanowski

  DOI：10.1016/j.ejmech.2015.10.012

  日期：2015.12

  New batracylin conjugates with tuftsin/retro-tuftsin derivatives were designed and synthesized using T3P as a coupling agent. The conjugates possess an amide bond formed between the carboxyl group of heterocyclic molecule and the N-termini of the tuftsin/retro-tuftsin chain. The in vitro cytotoxic activity of the new analogues and their precursors was evaluated using a series of human and murine tumor cells. BAT conjugates containing retro-tuftsin with branched side aminoacid chain, in particular with leucine or isoleucine, were about 10-fold more cytotoxic toward two human tumor cell lines (lung adenocarcinoma (A549) and myeloblastic leukemia (HL-60)). These compounds showed about 10-fold increased cytotoxicity against the two types of tumor cells compared to parent BAT. We have not observed important differences in the mechanism of action between BAT and its cytotoxic tuftsin/retro-tuftsin conjugates. We propose that high biological activity of the most active BAT conjugates is a result of their greatly increased intracellular accumulation. (C) 2015 Elsevier Masson SAS. All rights reserved.