3-bromo-N-(tert-butoxycarbonyl)-O-methyl-L-tyrosine | 1378296-80-0

• 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: 3-bromo-N-(tert-butoxycarbonyl)-O-methyl-L-tyrosine
• 英文别名: (S)-3-(3-bromo-4-methoxyphenyl)-2-((N-tert-butoxycarbonyl)-amino)propanoic acid；(2S)-3-(3-bromo-4-methoxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 1378296-80-0
• 化学式: C₁₅H₂₀BrNO₅
• 分子量: 374.232
• InChiKey: HHORDMABJWEGRW-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-bromo-N-(tert-butoxycarbonyl)-O-methyl-L-tyrosine 在 盐酸 、 1-丙基磷酸酐 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 3-bromo-O-methyl-N-[4-(2H-tetrazol-5-yl)phenyl]-L-tyrosinamide hydrochloride
  参考文献：
  名称：

  SUBSTITUTED PHENYLALANINE DERIVATIVES

  摘要：

  本发明涉及取代苯丙氨酸衍生物及其制备方法，以及将其用于生产用于治疗和/或预防疾病的药物，特别是心血管疾病和/或严重围手术期失血的药物。

  公开号：

  US20160244437A1
• 作为产物：
  描述：

  N-tert-butoxycarbonyl-3-bromo-O-methyl-(S)-tyrosine methyl ester 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 以95%的产率得到3-bromo-N-(tert-butoxycarbonyl)-O-methyl-L-tyrosine
  参考文献：
  名称：

  SUBSTITUTED PHENYLALANINE DERIVATIVES

  摘要：

  本发明涉及取代苯丙氨酸衍生物及其制备方法，以及将其用于生产用于治疗和/或预防疾病的药物，特别是心血管疾病和/或严重围手术期失血的药物。

  公开号：

  US20160244437A1

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。
• The first total synthesis and biological evaluation of marine natural products ma’edamines A and B
  作者：Sanjay Saha、Ch. Venkata Ramana Reddy、T. Chiranjeevi、Uma Addepally、T.S. Chinta Rao、Balaram Patro

  DOI：10.1016/j.bmcl.2012.12.033

  日期：2013.2

  We have developed the first total syntheses of marine natural products ma'edamines A (18) and B (20). Structurally, they contain a pyrazine-2-(1H)-one core and were screened for antiproliferative activity on several cancer cell lines. Out of the six cell lines tested, ma'edamines A and B showed significant cytotoxicity against human colon cancer line COLO 205.(IC50 7.9 and 10.3 mu M, respectively), breast cancer cell line MCF-7 (IC50: 6.9 and 10.5 mu M, respectively) and human lung adenocarcinoma cell line A549 (IC50: 12.2 and 15.4 mu M, respectively). The apoptotic effect of ma'edamines was confirmed by comet assay. Hence ma'edamines are likely to be useful as leads for development of a new class of anti-cancer agents. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and Biological Evaluation of Purpurealidin E-Derived Marine Sponge Metabolites: Aplysamine-2, Aplyzanzine A, and Suberedamines A and B
  作者：Suresh K. Kottakota、Dimitrios Evangelopoulos、Amani Alnimr、Sanjib Bhakta、Timothy D. McHugh、Mark Gray、Paul W. Groundwater、Emma C. L. Marrs、John D. Perry、Christopher D. Spilling、J. Jonathan Harburn

  DOI：10.1021/np300102z

  日期：2012.6.22

  Five purpurealidin-derived marine secondary sponge metabolies have been synthesized through the carbodiimide coupling of an appropriate bromotyrosine unit. The structure elucidations have been confirmed through direct comparison with spectroscopic data of isolated natural products. Aplyzanzine A has been shown to be the most active product against a broad bacterial and fungal screen, demonstrating MIC values 2 to 4 times lower than the other metabolites in this study. Compounds 2, 3, 4a, and 5-7 exhibit a modest inhibition against slow growing mycobacteria (MIC 25-50 mu g/mL), including Mycobacterium tuberculosis. iso-Anomoian A and suberedamine B showed antitumor activity in the NCI-DTP60 cell line screen at single-digit micromolar concentrations, with iso-anomoian A inhibiting 53 cell lines. These molecules present novel scaffolds for further optimization.
• [DE] SUBSTITUIERTE PHENYLALANIN-DERIVATE ALS FAKTOR XIA MODULATOREN<br/>[EN] SUBSTITUTED PHENYLALANINE DERIVATIVES AS MODULATORS OF FACTOR XIA<br/>[FR] DÉRIVÉS DE PHÉNYLALANINE SUBSTITUÉS SERVANT DE MODULATEURS DU FACTEUR XIA
  申请人：BAYER PHARMA AG

  公开号：WO2015044167A1

  公开（公告）日：2015-04-02

  Die Erfindung betrifft substituierte Phenylalanin-Derivate und Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Herstellung von Arzneimitteln zur Behandlung und/oder Prophylaxe von Krankheiten, insbesondere von Herz-Kreislauf-Erkrankungen und/oder perioperativem starkem Blutverlust.