H-Phe-Trp-OMe | 108787-56-0

• 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: H-Phe-Trp-OMe
• 英文别名: methyl (2S)-2-[[(2S)-2-amino-3-phenylpropanoyl]amino]-3-(1H-indol-3-yl)propanoate
• CAS: 108787-56-0
• 化学式: C₂₁H₂₃N₃O₃
• 分子量: 365.432
• InChiKey: WKRDIFQGZFGJAQ-HKUYNNGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  97.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  H-Phe-Trp-OMe 在 吗啉 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 环(L-苯丙氨酰-L-色氨酰)
  参考文献：
  名称：

  Synthesis and Biological Evaluations of a Series of Thaxtomin Analogues

  摘要：

  Thaxtomins are a unique family of phytotoxins with unique 4-nitroindole and diketopiperazine fragments possessing potential herbicidal activities. This work presents the total synthesis of natural product thaxtomin C and its analogues. The extensive structureactivity relationship study screens four effective compounds, including thaxtomin A and thaxtomin C. It is indicated that 4-nitro indole fragment is essential for phytotoxicity, while benzyl and m-hydroxybenzyl substituents on the diketopiperazine ring are favorable for the efficacy. The N-methylations on indole and diketopiperazine show weak influence on the herbicidal activities. The four selected compounds show effective herbicidal activities against Brassica campestris, Amaranthus retroflexus, and Abutilon theophrasti, which are comparable or better than dichlobenil, even at a dosage of 187.5 g ha(-1). Moreover, these four compounds show good crop-selective properties to different crops and exhibit moderate protoporphyrinogen oxidase (PPO) enzyme inhibition. The antifungal results indicate that thaxtomin C displays inhibition to a wide range of fungi.

  DOI：

  10.1021/jf506153t
• 作为产物：
  描述：

  Boc-Phe-Trp-OMe 在 盐酸 作用下， 以 水 、 乙酸乙酯 为溶剂， 以97 %的产率得到H-Phe-Trp-OMe
  参考文献：
  名称：

  新型碳水化合物-氨基酸杂化物的设计与合成及其抗氧化和抗β-淀粉样蛋白聚集活性

  摘要：

  在此，我们报道了通过将芳香族氨基酸和二肽与异硫氰酸基官能化的呋喃核糖环偶联制备的新型呋喃糖氨基酸和硫脲的合成。由于碳水化合物衍生的结构具有许多生物活性，合成的化合物被评估为抗淀粉样蛋白和抗氧化剂。所研究化合物的抗淀粉样蛋白活性是根据它们破坏本质上无序的 Aβ 40肽和球状鸡蛋清 (HEW) 溶菌酶的淀粉样蛋白原纤维的潜力进行评估的。化合物的破坏效率因所研究的肽而异。虽然化合物对 HEW 溶菌酶淀粉样原纤维的破坏活性可以忽略不计，但对 Aβ 40的影响淀粉样原纤维显着升高。呋喃糖α-氨基酸1及其二肽衍生物8 (Trp-Trp) 和11 (Trp-Tyr) 是最有效的抗 Aβ 原纤维化合物。合成化合物的抗氧化特性通过三种互补的体外测定（DPPH、ABTS 和 FRAP）进行评估。与 DPPH 试验相比，ABTS 试验对于评估所有测试化合物的自由基清除活性最为敏感。根据存在的氨基酸，检测到芳香族

  DOI：

  10.1016/j.bioorg.2023.106636

文献信息

• MITHRAMYCIN DERIVATIVES HAVING INCREASED SELECTIVITY AND ANTI-CANCER ACTIVITY
  申请人：University of Kentucky Research Foundation

  公开号：US20190083519A1

  公开（公告）日：2019-03-21

  Mithramycin side chain carboxylic acid (MTM-SA) derivative are provided, which include a substituted amino acid derivative, a substituted amino acid dipeptide derivative, or an unsubstituted dipeptide derivative. The MTM-SA derivatives are useful for treatment of cancer or neuro-diseases associated with an aberrant erythroblast transformation-specific transcription factor. Unique MTM-SA derivatives have increased selectively toward ETS transcription factor.

  米司麦霉素侧链羧酸（MTM-SA）衍生物包括一种取代氨基酸衍生物、一种取代氨基酸二肽衍生物或一种未取代的二肽衍生物。这些MTM-SA衍生物对于治疗与异常红细胞转化特异性转录因子相关的癌症或神经疾病很有用。独特的MTM-SA衍生物对ETS转录因子具有增强的选择性。
• Gabapentin hybrid peptides and bioconjugates
  作者：Iryna O. Lebedyeva、David A. Ostrov、John Neubert、Peter J. Steel、Kunal Patel、Sean M. Sileno、Kevin Goncalves、Mohamed A. Ibrahim、Khalid A. Alamry、Alan R. Katritzky

  DOI：10.1016/j.bmc.2013.12.017

  日期：2014.2

  Synthetic approaches to gabapentin bioconjugates that overcome the tendency of gabapentin to cyclize into its γ-lactam are studied. Gabapentin was converted by N-acylation at its N-terminus into di-, tri-, and tetrapeptides (l-Ala-Gbp, l-Val-Gbp, l-Ala-l-Phe-Gbp, Gly-l-Ala-β-Ala-Gbp). Carboxyl-activated Boc-protected gabapentin was used to N-, O-, and S-acylate small peptides and hormones to give conjugates

  研究了克服加巴喷丁环化成其γ-内酰胺的趋势的加巴喷丁生物缀合物的合成方法。加巴喷丁被转化通过在它的N-末端N-酰化成二，三，四肽和（升-Ala-英镑，升-Val-英镑，升-Ala-升-Phe-英镑，Gly-升-Ala- β-Ala-Gbp）。羧基活化的Boc保护的加巴喷丁用于N-，O-和S-酰化小肽和激素，以提供结合物，这些结合物也可提供含有受构象限制的加巴喷丁单元的前药。
• Mithramycin derivatives having increased selectivity and anti-cancer activity
  申请人：University of Kentucky Research Foundation

  公开号：US11224609B2

  公开（公告）日：2022-01-18

  Mithramycin side chain carboxylic acid (MTM-SA) derivative are provided, which include a substituted amino acid derivative, a substituted amino acid dipeptide derivative, or an unsubstituted dipeptide derivative. The MTM-SA derivatives are useful for treatment of cancer or neuro-diseases associated with an aberrant erythroblast transformation-specific transcription factor. Unique MTM-SA derivatives have increased selectively toward ETS transcription factor.

  提供了米曲霉素侧链羧酸（MTM-SA）衍生物，其中包括取代的氨基酸衍生物、取代的氨基酸二肽衍生物或未取代的二肽衍生物。MTM-SA 衍生物可用于治疗与红细胞转化特异性转录因子异常有关的癌症或神经疾病。独特的 MTM-SA 衍生物对 ETS 转录因子的选择性增加。
• Pd-Catalyzed Picolinamide-Directed C(sp2)–H Sulfonylation of Amino Acids/Peptides with Sodium Sulfinates
  作者：Raghunath Bag、Nagendra K. Sharma

  DOI：10.1021/acs.joc.4c00988

  日期：2024.7.19

  a Pd-catalyzed picolinamide-directed site-selective C(sp2)–H sulfonylation of amino acids and peptides with sodium sulfinates in moderate to good yields. Sulfonylation of levodopa and dopamine drug molecules and late-stage directed peptide sulfonylation are studied for the first time. Broad substrate scope having various functionalities, late-stage drug modifications, and various post synthetic utilities

  本报告描述了 Pd 催化的吡啶甲酰胺定向位点选择性 C（sp2）-H 氨基酸和肽与亚磺酸钠的磺酰化反应，产率中等至良好。首次研究了左旋多巴和多巴胺药物分子的磺酰化以及晚期定向肽磺酰化。潜在的优势包括具有各种功能的广泛底物范围、后期药物修饰以及各种合成后实用程序，如硫属化、溴化、烯化和芳基化。
• Development of Mithramycin Analogues with Increased Selectivity toward ETS Transcription Factor Expressing Cancers
  作者：Prithiba Mitra、Joseph M. Eckenrode、Abhisek Mandal、Amit K. Jha、Shaimaa M. Salem、Markos Leggas、Jürgen Rohr

  DOI：10.1021/acs.jmedchem.8b01107

  日期：2018.9.13

  Mithramycin A (1) was identified as the top potential inhibitor of the aberrant ETS transcription factor EWSFLI1, which causes Ewing sarcoma. Unfortunately, 1 has a narrow therapeutic window, compelling us to seek less toxic and more selective analogues. Here, we used MTMSA (2) to generate analogues via peptide coupling and fragment-based drug development strategies. Cytotoxicity assays in ETS and non-ETS dependent cell lines identified two dipeptide analogues, 60 and 61, with 19.1- and 15.6-fold selectivity, respectively, compared to 1.5-fold for 1. Importantly, the cytotoxicity of 60 and 61 is <100 nM in ETS cells. Molecular assays demonstrated the inhibitory capacity of these analogues against EWS-FLI1 mediated transcription in Ewing sarcoma. Structural analysis shows that positioning the tryptophan residue in a distal position improves selectivity, presumably via interaction with the ETS transcription factor. Thus, these analogues may present new ways to target transcription factors for clinical use.