N-Boc-3-bromotyrosine | 113311-28-7

• 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: N-Boc-3-bromotyrosine
• 英文别名: (S)-3-(3-Bromo-4-hydroxyphenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid；(2S)-3-(3-bromo-4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 113311-28-7
• 化学式: C₁₄H₁₈BrNO₅
• 分子量: 360.205
• InChiKey: SQOXBCRLNHVHGU-JTQLQIEISA-N

物化性质

• 熔点：
  76-82 °C
• 沸点：
  502.4±50.0 °C(Predicted)
• 密度：
  1.480±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-Boc-3-bromotyrosine 在 盐酸 、 4-二甲氨基吡啶 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium periodate 、 2-羟基吡啶-N-氧化物 、 叠氮磷酸二苯酯 、 palladium on activated charcoal 、 ammonium acetate 、 氢气 、 potassium acetate 、 碳酸氢钠 、 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 220.5h， 生成 cyclo(D-alanyl-L-alanyl-N,O-dimethyl-L-tyrosyl-L-alanyl-N-methyl-L-tyrosyl-O-methyl-L-tyrosyl) cyclic 5⁴<*>6³ ether
  参考文献：
  名称：

  [EN] BOUVARDIN DERIVATIVES AND THERAPEUTIC USES THEREOF
  [FR] DÉRIVÉS DE BOUVARDINE ET LEURS UTILISATIONS THÉRAPEUTIQUES

  摘要：

  本发明涉及博瓦尔丁类似物和相关化合物，用于治疗包括癌症在内的多种疾病。本文提供了博瓦尔丁类似物和相关化合物、含有至少一种博瓦尔丁类似物或相关化合物的药物组合物和试剂盒，以及治疗包括癌症在内的疾病的方法。在某些方面，这些化合物抑制核糖体上的翻译延长。这些化合物与放射疗法或已知的化疗药物组合使用。

  公开号：

  WO2013126617A1
• 作为产物：
  描述：

  L-酪氨酸 在 溴 、 碳酸氢钠 、 溶剂黄146 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 8.0h， 生成 N-Boc-3-bromotyrosine
  参考文献：
  名称：

  无名诺卡菌（Nocardia ignorata）新型溴化二酮哌嗪的分离和结构鉴定 - 一种与地衣相关的放线菌

  摘要：

  放线菌以其在生物技术中的潜力和产生感兴趣的代谢物而闻名。地衣是新细菌菌株的有希望的来源，尤其是放线菌，它提供了广泛的化学多样性。在这种情况下，研究了从陆地地衣 Collema auriforme 中分离的无知诺卡菌放线菌的培养基。该菌株在 BioFlo 115 生物反应器中培养，并使用 XAD7HP 树脂提取培养基。五种已知的二酮哌嗪：环 (l-Pro-l-OMet) (1)、环 (l-Pro-l-Tyr) (2)、环 (d-Pro-l-Tyr) (3)、环 (l- Pro-l-Val) (4)、环 (l-Pro-l-Leu) (5) 和一种生长素衍生物：吲哚-甲醛 (8) 以及两种新的溴化二酮哌嗪：环 (d-Pro -l-Br-Tyr) (6) 和环 (l-Pro-l-Br-Tyr) (7)。

  DOI：

  10.3390/molecules22030371

文献信息

• Synthesis and SAR studies of marine natural products ma’edamines A, B and their analogues
  作者：Sanjay Saha、Ch. Venkata Ramana Reddy、Shili Xu、Saranya Sankar、Nouri Neamati、Balaram Patro

  DOI：10.1016/j.bmcl.2013.07.017

  日期：2013.9

  The synthesis of several analogues of ma’edamines A and B are reported. The synthesized compounds were tested on hormone receptor positive and HER2 positive breast cancer cell lines, by MTT assay. MED-114, 115, 117, 119, 120, 124, 128 and 131 were found to be equally active as Lapatinib on HER2 +ve cell line SKBR3.

  报告了Maededamine A和B的几种类似物的合成。通过MTT测定法在激素受体阳性和HER2阳性乳腺癌细胞系上测试了合成的化合物。发现MED-114、115、117、119、120、124、128和131在HER2 + ve细胞系SKBR3上具有与拉帕替尼同等的活性。
• Combinatorial Synthesis through Disulfide Exchange: Discovery of Potent Psammaplin A Type Antibacterial Agents Active against Methicillin-ResistantStaphylococcus aureus (MRSA)
  作者：K. C. Nicolaou、Robert Hughes、Jeffrey A. Pfefferkorn、Sofia Barluenga、A. J. Roecker

  DOI：10.1002/1521-3765(20011001)7:19<4280::aid-chem4280>3.0.co;2-3

  日期：2001.10.1

  Psammaplin A is a symmetrical bromotyrosine -derived disulfide natural product isolated from the Psammaplysilla sponge, which exhibits in vitro antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). Inspired by the structure of this marine natural product, a combinatorial scrambling strategy for the construction of heterodimeric disulfide analogues was developed and applied to the construction of a 3828-membered library starting from 88 homodimeric disulfides. These psammaplin A analogues were screened directly against various gram positive bacterial strains leading to the discovery of a series of potent antibacterial agents active against methicillin-resistant Staphylococcus aureus (MRSA), Among the most active leads derived from these studies are compounds 104. 105, 113, 115, 123, and 128. The present, catalytically-induced. disulfide exchange strategy may be extendable to other types of building blocks bearing thiol groups facilitating the construction of diverse discovery-oriented combinatorial libraries.
• <scp>l</scp>-Thyroxin and the Nonclassical Thyroid Hormone TETRAC Are Potent Activators of PPARγ
  作者：Leonie Gellrich、Pascal Heitel、Jan Heering、Whitney Kilu、Julius Pollinger、Tamara Goebel、Astrid Kahnt、Silvia Arifi、Werner Pogoda、Alexander Paulke、Dieter Steinhilber、Ewgenij Proschak、Mario Wurglics、Manfred Schubert-Zsilavecz、Apirat Chaikuad、Stefan Knapp、Iris Bischoff、Robert Fürst、Daniel Merk

  DOI：10.1021/acs.jmedchem.9b02150

  日期：2020.7.9

  Thyroid hormones (THs) operate numerous physiological processes through modulation of the nuclear thyroid hormone receptors and several other proteins. We report direct activation of the nuclear peroxisome proliferator-activated receptor gamma (PPAR gamma) and retinoid X receptor (RXR) by classical and nonclassical THs as another molecular activity of THs. The T4 metabolite TETRAC was the most active TH on PPAR gamma with nanomolar potency and binding affinity. We demonstrate that TETRAC promotes PPAR gamma/RXR signaling in cell-free, cellular, and in vivo settings. Simultaneous activation of the heterodimer partners PPAR gamma and RXR resulted in high dimer activation efficacy. Compared to fatty acids as known natural ligands of PPAR gamma and RXR, TETRAC differs markedly in its molecular structure and the PPAR gamma-TETRAC complex revealed a distinctive binding mode of the TH. Our observations suggest a potential connection of TH and PPAR signaling through overlapping ligand recognition and may hold implications for TH and PPAR pharmacology.
• Racemization in Suzuki Couplings: A Quantitative Study Using 4-Hydroxyphenylglycine and Tyrosine Derivatives as Probe Molecules
  作者：Mònica Prieto、Silvia Mayor、Katy Rodríguez、Paul Lloyd-Williams、Ernest Giralt

  DOI：10.1021/jo0621266

  日期：2007.2.1

  Reaction conditions considered to be typical in Suzuki couplings can cause significant (up to 34% of the unwanted enantiomer) loss of optical purity in sensitive substrates such as hydroxyphenylglycine 1. This may be remedied using sodium succinate instead of sodium carbonate as base, but chemical yields are somewhat lower. Optically pure biaryl amino acids related to those found in the chloropeptins and vancomycin were synthesized by Suzuki coupling of 1 with indolylboronic acids 6-8 and with cyclic boronic acid 9.
• Improved Synthesis of L,L-Cycloisodityrosine Subunit of Antitumor Agents Deoxybouvardin and RA-VII
  作者：Samir Ghosh、A. Sanjeev Kumar、G. N. Mehta、R. Soundararajan

  DOI：10.1080/00397910903245166

  日期：2010.7.27

  A facile synthesis of the core cycloisodityrosine 14-membered ring system is detailed from commercially available L-tyrosine through a novel synthetic approach to aryl boronic acid 12 via intramolecular cyclization.