Isosteres of chiral clofibric acid analogs: Synthesis, resolution, absolute configuration and HPLC detection of the optical purity

被引:0
|
作者
Ferorelli, S
Loiodice, F
Tortorella, V
Amoroso, R
Bettoni, G
ConteCamerino, D
DeLuca, A
机构
[1] DIPARTIMENTO FARMACOCHIM, I-70126 BARI, ITALY
[2] UNIV G DANNUNZIO, IST SCI FARM, I-66100 CHIETI, ITALY
[3] DIPARTIMENTO FARMACOBIOL, I-70126 BARI, ITALY
来源
FARMACO | 1997年 / 52卷 / 6-7期
关键词
D O I
暂无
中图分类号
R9 [药学];
学科分类号
1007 ;
摘要
Both racemic and enantiomeric forms of some isosteres of chiral clofibric acid analogs have been synthesized. Also, the absolute configuration has been established by chemical cell-elation and the optical purity determined by a simple HPLC procedure. Moreover, these studies show that the isosteric substitution of the ether oxygen atom of alpha-aryloxy-alkanoic acids with sulfur, amino and methylene groups lead to compounds in which both biological activity and stereoselectivity regarding chloride channel are highly reduced.
引用
收藏
页码:367 / 374
页数:8
相关论文
共 50 条
  • [21] Synthesis, Chiral Resolution and Enantiomers Absolute Configuration of 4-Nitropropranolol and 7-Nitropropranolol
    Sparaco, Rosa
    Scognamiglio, Antonia
    Corvino, Angela
    Caliendo, Giuseppe
    Fiorino, Ferdinando
    Magli, Elisa
    Perissutti, Elisa
    Santagada, Vincenzo
    Severino, Beatrice
    Luciano, Paolo
    Casertano, Marcello
    Aiello, Anna
    De Nucci, Gilberto
    Frecentese, Francesco
    MOLECULES, 2023, 28 (01):
  • [22] Synthesis, Chiral Resolution, and Absolute Configuration of Functionalized Troger's Base Derivatives: Part II
    Benkhaeuser-Schunk, Christian
    Wezisla, Boris
    Urbahn, Kirstin
    Kiehne, Ulf
    Daniels, Joerg
    Schnakenburg, Gregor
    Neese, Frank
    Luetzen, Arne
    CHEMPLUSCHEM, 2012, 77 (05): : 396 - 403
  • [23] Synthesis, Chiral Resolution, and Absolute Configuration of Functionalized Troger's Base Derivatives: Part III
    Jarzebski, Andreas
    Bannwarth, Christoph
    Tenten, Christina
    Benkhaeuser, Christian
    Schnakenburg, Gregor
    Grimme, Stefan
    Luetzen, Arne
    SYNTHESIS-STUTTGART, 2015, 47 (20): : 3118 - 3132
  • [24] Synthesis, Chiral Resolution, and Absolute Configuration of Dissymmetric 4,15-Difunctionalized [2.2]Paracyclophanes
    Meyer-Eppler, Georg
    Sure, Rebecca
    Schneider, Andreas
    Schnakenburg, Gregor
    Grimme, Stefan
    Luetzen, Arne
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (14): : 6679 - 6687
  • [25] Synthesis, Chiral Resolution, and Absolute Configuration of Dissymmetric 4,12-Difunctionalized [2.2]Paracyclophanes
    Meyer-Eppler, Georg
    Vogelsang, Elisabeth
    Benkhaeuser, Christian
    Schneider, Andreas
    Schnakenburg, Gregor
    Luetzen, Arne
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (21) : 4523 - 4532
  • [26] HPLC OPTICAL RESOLUTION OF TRICARBONYL(2,3-DIHYDROTROPONE)IRON AND ITS ABSOLUTE-CONFIGURATION
    SOTOKAWA, H
    TAJIRI, A
    MORITA, N
    KABUTO, C
    HATANO, M
    ASAO, T
    TETRAHEDRON LETTERS, 1987, 28 (47) : 5873 - 5876
  • [27] A SIMPLE AND EFFICIENT SYNTHESIS OF CHIRAL ACETIC-ACID OF HIGH OPTICAL PURITY
    KOBAYASHI, K
    JADHAV, PK
    ZYDOWSKY, TM
    FLOSS, HG
    JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (20): : 3510 - 3512
  • [28] ABSOLUTE CONFIGURATION OF ALPHA-ISOPROPYLPHENYLACETIC ACID AND DETERMINING ITS OPTICAL PURITY BY NUCLEAR MAGNETIC RESONANCE
    HOREAU, A
    GUETTE, JP
    COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L ACADEMIE DES SCIENCES SERIE C, 1968, 267 (03): : 257 - &
  • [29] CHIRAL ALPHA-SUBSTITUTED ALPHA-ARYLOXY ACETIC-ACIDS - SYNTHESIS, ABSOLUTE-CONFIGURATION, CHEMICAL RESOLUTION, AND DIRECT SEPARATION BY HPLC
    BETTONI, G
    FERORELLI, S
    LOIODICE, F
    TANGARI, N
    TORTORELLA, V
    GASPARRINI, F
    MISITI, D
    VILLANI, C
    CHIRALITY, 1992, 4 (03) : 193 - 203
  • [30] RESOLUTION OF (+/-)-2-TETRADECYLOXIRANECARBOXYLIC ACID - ABSOLUTE-CONFIGURATION AND CHIRAL SYNTHESIS OF THE HYPOGLYCEMIC R ENANTIOMER AND BIOLOGICAL-ACTIVITY OF ENANTIOMERS
    HO, W
    TARHAN, O
    KIORPES, TC
    TUTWILER, GF
    MOHRBACHER, RJ
    JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (06) : 1094 - 1097