FDAA | 139601-90-4

• 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: FDAA
• 英文别名: N-(5-fluoro-2,4-dinitrophenyl)-l-alanine amide；(2S)-2-amino-N-(5-fluoro-2,4-dinitrophenyl)propanamide
• CAS: 139601-90-4
• 化学式: C₉H₉FN₄O₅
• 分子量: 272.193
• InChiKey: JEBYGZRPAMNXRD-BYPYZUCNSA-N

物化性质

• 沸点：
  491.9±45.0 °C(Predicted)
• 密度：
  1.592±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  FDAA 、 D-苯丙氨酸 在 三乙胺 作用下， 以 丙酮 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Perthamides C and D, two new potent anti-inflammatory cyclopeptides from a Solomon Lithistid sponge Theonella swinhoei

  摘要：

  Two new metabolites, perthamides C and D, have been isolated from the marine sponge Theonella swinhoei. Their structures were determined by interpretation of NMR and ESIMS data. All compounds exhibited in vivo potent anti-inflammatory activity. Biological activity and structural elucidation are reported. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.026

文献信息

• [EN] SUBSTITUTED PYRAZOLO[1,5-a]PYRIMIDINE COMPOUNDS AS TRK KINASE INHIBITORS<br/>[FR] COMPOSÉS DE PYRAZOLO[1,5-A]PYRIMIDINE SUBSTITUÉS COMME INHIBITEURS DE LA TRK KINASE
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2010048314A1

  公开（公告）日：2010-04-29

  Compounds of Formula (I) in which R1, R2, R3, R4, X, Y and n have the meanings given in the specification, are inhibitors of Trk kinases and are useful in the treatment of diseases which can be treated with a Trk kinase inhibitor.

  式（I）中R1、R2、R3、R4、X、Y和n的化合物具有规范中给定的含义，是Trk激酶的抑制剂，并且在治疗可以用Trk激酶抑制剂治疗的疾病中是有用的。
• Process for the synthesis of chirally pure beta-amino-alcohols
  申请人：Wyeth

  公开号：US20030144531A1

  公开（公告）日：2003-07-31

  A process is provided for preparing chirally pure S-enantiomers of &agr;-amino acids comprising the steps of: a) preparing an organometallic reagent from an alkyl halide of the formula (R) 2 CH(CH 2 ) n CH 2 X; b) adding the organometallic reagent to carbon dioxide to afford a carboxylic acid; c) activating the carboxylic acid with an acid chloride, phosphorus trichloride, acid anhydride, or thionyl chloride in the presence of a tertiary amine base; d) reacting the product of step c) with an alkali metal salt of S-4-benzyl-2-oxazolidinone; e) treating the product of step d) with a strong non-nucleophilic base to form an enolate anion; f) trapping the enolate anion with 2,4,6-triisopropylbenzenesulfonyl azide to afford an oxazolidinone azide; g) hydrolyzing the oxazolidinone azide with an aqueous base to afford an &agr;-azido acid; h) reducing the &agr;-azido acid to the &agr;-amino acid; and i) recrystallizing the &agr;-amino acid to the chirally pure &agr;-amino acid. A process is also provided for preparing chirally pure S-enantiomers of &bgr;-amino alcohols further comprising the steps of reducing the crude &agr;-amino acid to the &bgr;-amino alcohol and recrystallizing the &bgr;-amino alcohol to the chirally pure &bgr;-amino alcohol. A process is further provided for preparing chirally pure S enantiomers of N-sulfonyl &bgr;-amino alcohols further comprising the steps of sulfonylating the &bgr;-amino alcohol with 5-chloro-thiophene-2-sulfonyl halide; and recrystallizing to afford the chirally pure N-sulfonyl &bgr;-amino alcohols.

  提供了一种制备手性纯S-对映体α-氨基酸的过程，包括以下步骤：a) 从具有化学式(R)2CH(CH2)nCH2X的烷基卤化物制备有机金属试剂；b) 将有机金属试剂加入二氧化碳以得到羧酸；c) 在三级胺碱存在下，用酸氯化物、三氯化磷、酸酐或氯化硫酰氯激活羧酸；d) 将步骤c)的产物与S-4-苄基-2-噁唑烷酮的碱金属盐反应；e) 用强非亲核碱处理步骤d)的产物以形成烯醇负离子；f) 用2,4,6-三异丙基苯磺酰氮化物捕获烯醇负离子以得到噁唑烷酮氮化物；g) 用水性碱水解噁唑烷酮氮化物以得到α-叠氮酸；h) 还原α-叠氮酸以得到α-氨基酸；i) 对α-氨基酸进行再结晶以得到手性纯α-氨基酸。还提供了一种制备手性纯S-对映体β-氨基醇的过程，进一步包括将粗α-氨基酸还原为β-氨基醇，并对β-氨基醇进行再结晶以得到手性纯β-氨基醇。还提供了一种制备手性纯S-对映体N-磺酰基β-氨基醇的过程，进一步包括用5-氯硫代苯磺酰卤化物对β-氨基醇进行磺酰化；并进行再结晶以得到手性纯N-磺酰基β-氨基醇。
• Jaspamides M–P: new tryptophan modified jaspamide derivatives from the sponge Jaspis splendans
  作者：Fulvio Gala、Maria Valeria D'Auria、Simona De Marino、Valentina Sepe、Franco Zollo、Charles D. Smith、Staci N. Keller、Angela Zampella

  DOI：10.1016/j.tet.2008.10.076

  日期：2009.1

  Four new jaspamide derivatives with antimicrofilament activity were isolated from the marine sponge Jaspis splendans. Their structures were elucidated by NMR and MS analysis. A structure–activity relationship analysis on all natural jaspamides is also reported here.

  从海洋海绵Jaspis splendans中分离到四种具有抗微丝活性的新的jaspamide衍生物。通过NMR和MS分析阐明了它们的结构。此处还报告了对所有天然jaspamides的构效关系分析。
• Fast Detection of Two Smenamide Family Members Using Molecular Networking
  作者：Alessia Caso、Germana Esposito、Gerardo Della Sala、Joseph R. Pawlik、Roberta Teta、Alfonso Mangoni、Valeria Costantino

  DOI：10.3390/md17110618

  日期：——

  Caribbean sponges of the genus Smenospongia are a prolific source of chlorinated secondary metabolites. The use of molecular networking as a powerful dereplication tool revealed in the metabolome of S. aurea two new members of the smenamide family, namely smenamide F (1) and G (2). The structure of smenamide F (1) and G (2) was determined by spectroscopic analysis (NMR, MS, ECD). The relative and the

  加勒比海海绵体（Smenospongia）属是氯化次生代谢产物的丰富来源。分子网络作为强大的去复制工具的使用在金黄色葡萄球菌的代谢组中揭示了smenamide家族的两个新成员，即smenamide F（1）和G（2）。通过光谱分析（NMR，MS，ECD）确定酰胺F（1）和G（2）的结构。根据1，3-二取代烷基链系统（即C-12 / C-18链段）的构象刚度，确定C-13，C-15和C-16处的相对和绝对构型化合物（1）的显示：Smenamide F（1）和G（2）对癌细胞系MCF-7和MDA-MB-231具有选择性的适度抗增殖活性，而对MG-63无活性。
• Recombinant <scp>l</scp> ‐Amino Acid Oxidase with Broad Substrate Spectrum for Co‐substrate Recycling in ( <i>S</i> )‐Selective Transaminase‐Catalyzed Kinetic Resolutions
  作者：Tobias Heinks、Jannik Paulus、Simon Koopmeiners、Tobias Beuel、Norbert Sewald、Matthias Höhne、Uwe T. Bornscheuer、Gabriele Fischer von Mollard

  DOI：10.1002/cbic.202200329

  日期：2022.8.17

  system consisting of a heterologous expressed and highly active l-amino acid oxidase combined with a catalase was applied for kinetic resolutions to produce enantiopure (R)-amines in ω-(S)-transaminase catalyzed reactions. Consequently, catalytic instead of stoichiometric amounts of co-substrate can be applied in preparative scale reactions.

  一种由异源表达的高活性l-氨基酸氧化酶与过氧化氢酶结合组成的高效共底物循环系统被应用于动力学分解，以在ω-(S)-转氨酶催化反应中产生对映体纯( R ) -胺。因此，催化而不是化学计量量的共底物可以应用于制备规模反应。