Synthesis of potentially bioactive PABA-related N-(aminoalkyl)lactamic amino acids and esters via selective SNAr reactions

被引:12
作者
Goncalves, Renato S. [1 ,2 ]
Abdelnur, Patricia V. [3 ]
Santos, Vanessa G. [3 ]
Simas, Rosineide C. [3 ]
Eberlin, Marcos N. [3 ]
Magalhaes, Alvicler [4 ]
Perez Gonzalez, Eduardo R. [1 ]
机构
[1] Univ Estadual Paulista, Fac Ciencias & Tecnol, Dept Fis Quim & Biol, Lab Quim Organ Fina, BR-19060900 Presidente Prudente, SP, Brazil
[2] Univ Estadual Paulista, Programa Posgrad Ciencia & Tecnol Mat POSMAT, Sao Paulo, Brazil
[3] Univ Estadual Campinas, UNICAMP, Inst Quim, Lab ThoMSon Espectrometria Massas, Campinas, SP, Brazil
[4] Univ Estadual Campinas, UNICAMP, Inst Quim, Dept Quim Inorgan, Campinas, SP, Brazil
基金
巴西圣保罗研究基金会;
关键词
PABA derivatives; Lactams; Potential bio-activity; SNAr reaction; DERIVATIVES; INHIBITORS;
D O I
10.1007/s00726-010-0634-z
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Potentially bioactive N-(aminoalkyl)lactamic amino acids and esters were synthesized in satisfactory to good yields by SNAr reactions of aromatic acids with N-(3-aminopropyl)lactams followed by esterification with tertiary amino alcohols. The addition-elimination SNAr mechanism was confirmed by NMR and MS measurements.
引用
收藏
页码:197 / 204
页数:8
相关论文
共 27 条
  • [1] Solvent effects and mechanism for a nucleophilic aromatic substitution from QM/MM simulations
    Acevedo, O
    Jorgensen, WL
    [J]. ORGANIC LETTERS, 2004, 6 (17) : 2881 - 2884
  • [2] RAPID REACTION OF SINGLET MOLECULAR-OXYGEN (O-1(2)) WITH P-AMINOBENZOIC ACID (PABA) IN AQUEOUS-SOLUTION
    ALLEN, JM
    ENGENOLF, S
    ALLEN, SK
    [J]. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1995, 212 (03) : 1145 - 1151
  • [3] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE
    BECKE, AD
    [J]. JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) : 5648 - 5652
  • [4] BRUZE M, 1990, PHOTODERMATOL PHOTO, V7, P106
  • [5] RATIONALIZING THE REGIOSELECTIVITY IN POLYNITROARENE ANIONIC SIGMA-ADDUCT FORMATION - RELEVANCE TO NUCLEOPHILIC AROMATIC-SUBSTITUTION
    BUNCEL, E
    DUST, JM
    TERRIER, F
    [J]. CHEMICAL REVIEWS, 1995, 95 (07) : 2261 - 2280
  • [6] AROMATIC NUCLEOPHILIC SUBSTITUTION REACTIONS
    BUNNETT, JF
    ZAHLER, RE
    [J]. CHEMICAL REVIEWS, 1951, 49 (02) : 273 - 412
  • [7] p-Aminobenzoic acid derivatives as acetylcholinesterase inhibitors
    Correa-Basurto, J
    Alcántara, IV
    Espinoza-Fonseca, LM
    Trujillo-Ferrara, JG
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2005, 40 (07) : 732 - 735
  • [8] GLYCINE CONJUGATION OF PARA-AMINOBENZOIC ACID (PABA) - A QUANTITATIVE TEST OF LIVER-FUNCTION
    FURUYA, KN
    DURIE, PR
    ROBERTS, EA
    SOLDIN, SJ
    VERJEE, Z
    YUNGJATO, L
    GIESBRECHT, E
    ELLIS, L
    [J]. CLINICAL BIOCHEMISTRY, 1995, 28 (05) : 531 - 540
  • [9] SEPARATION OF WATER-SOLUBLE VITAMINS BY REVERSED-PHASE ION-INTERACTION - REAGENT HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY - APPLICATION TO MULTIVITAMIN PHARMACEUTICALS
    GENNARO, MC
    [J]. JOURNAL OF CHROMATOGRAPHIC SCIENCE, 1991, 29 (09) : 410 - 415
  • [10] Design of HIV-1 Protease Inhibitors with Pyrrolidinones and Oxazolidinones as Novel P1′-Ligands To Enhance Backbone-Binding Interactions with Protease: Synthesis, Biological Evaluation, and Protein-Ligand X-ray Studies∞
    Ghosh, Arun K.
    Leshchenko-Yashchuk, Sofiya
    Anderson, David D.
    Baldridge, Abigail
    Noetzel, Marcus
    Miller, Heather B.
    Tie, Yunfeng
    Wang, Yuan-Fang
    Koh, Yasuhiro
    Weber, Irene T.
    Mitsuya, Hiroaki
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (13) : 3902 - 3914