para-bromo-N-methyl-L-phenylalanine

• 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: para-bromo-N-methyl-L-phenylalanine
• 英文别名: (2S)-3-(4-bromophenyl)-2-(methylamino)propanoic acid
• 化学式: C₁₀H₁₂BrNO₂
• 分子量: 258.115
• InChiKey: BLLAWTXMWGOAEH-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 copper(ll) bromide 、 盐酸 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 70.0~145.0 ℃ 、1.38 MPa 条件下， 反应 0.42h， 生成 meta-bromo-N-methyl-L-phenylalanine 、 para-bromo-N-methyl-L-phenylalanine
  参考文献：
  名称：

  Generation of Broad-Spectrum Antifungal Drug Candidates from the Natural Product Compound Aureobasidin A

  摘要：

  The natural product aureobasidin A (AbA) is a potent, well-tolerated antifungal agent with robust efficacy in animals. Although native AbA is active against a number of fungi, it has little activity against Aspergillus fumigatus, an important human pathogen, and attempts to improve the activity against this organism by structural modifications have to date involved chemistries too complex for continued development. This report describes novel chemistry for the modification of AbA. The key step involves functionalization of the phenylalanine residues in the compound by iridium-catalyzed borylation. This is followed by displacement of the pinacol boron moiety to form the corresponding bromide or iodide and substitution by Suzuki biaryl coupling. The approach allows for synthesis of a truly wide range of derivatives and has produced compounds with A. fumigatus minimal inhibitory concentrations (MIC) of <0.5 mu g/mL. The approach is readily adaptable to large-scale synthesis and industrial production.

  DOI：

  10.1021/acsmedchemlett.5b00029

文献信息

• Thienopyrimidine Inhibitors of Atypical Protein Kinase C
  申请人：Cancer Research Technology Limited

  公开号：US20140323435A1

  公开（公告）日：2014-10-30

  The present application provides a compound of formula (I) or a salt thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , A, G, M, Q and X are as defined herein. A compound of formula (I) and its salts have aPKC inhibitory activity, and may be used to treat proliferative disorders.

  本申请提供了公式（I）的化合物或其盐，其中R1、R2、R3、R4、R5、R6、A、G、M、Q和X的定义如本文所述。公式（I）的化合物及其盐具有aPKC抑制活性，可用于治疗增殖性疾病。
• SUBSTITUIERTE PHENYLALANIN-DERIVATE
  申请人：Bayer Pharma Aktiengesellschaft

  公开号：EP3049390A1

  公开（公告）日：2016-08-03
• SUBSTITUIERTE PHENYLALANIN-DERIVATE UND IHRE VERWENDUNG ZUR BEHANDLUNG VON THROMBOTISCHEN / THROMBOEMBOLISCHEN ERKRANKUNGEN
  申请人：Bayer Pharma Aktiengesellschaft

  公开号：EP3049406A1

  公开（公告）日：2016-08-03
• SUBSTITUIERTE PHENYLALANIN-DERIVATE ALS FAKTOR XIA MODULATOREN
  申请人：Bayer Pharma Aktiengesellschaft

  公开号：EP3049410A1

  公开（公告）日：2016-08-03
• THIENOPYRIMIDINE INHIBITORS OF ATYPICAL PROTEIN KINASE C
  申请人：Cancer Research Technology Limited

  公开号：US20170158706A1

  公开（公告）日：2017-06-08

  The present application provides a compound of formula (I) or a salt thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , A, G, M, Q and X are as defined herein. A compound of formula (I) and its salts have aPKC inhibitory activity, and may be used to treat proliferative disorders.