Decreasing acidity in a series of aldose reductase inhibitors: 2-Fluoro-4-(1H-pyrrol-1-yl)phenol as a scaffold for improved membrane permeation

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 7, 2014, Pages 2194-2207

  Chatzopoulou, Maria ^a   Patsilinakos, Alexandros ^b   Vallianatou, Theodosia ^c   Prnova, Marta Soltesova ^d   Žakelj, Simon ^e   Ragno, Rino ^b   Stefek, Milan ^d   Kristl, Albin ^e   Tsantili Kakoulidou, Anna ^c   Demopoulos, Vassilis J ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

^c UNIVERSITY OF ATHENS   (Greece)

^d INSTITUTE OF EXPERIMENTAL PHARMACOLOGY AND TOXICOLOGY   (Slovakia)

^e UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

Cross docking; Fluoroacetylation; Inhibition of sorbitol accumulation; Non anionic aldose reductase inhibitors; Physicochemical profiling

Indexed keywords

1 (3,4 DIFLUOROPHENYL) 1H PYRROLE; 2 FLUORO 4 (1H PYRROL 1YL)PHENOL; 3 (3 BENZOYL 1H PYRROL 1 YL) 2 HYDROXYBENZALDEHYDE; 4 (3 BENZOYL 1H PYRROL 1 YL) 2 HYDROXYBENZALDEHYDE; ALDEHYDE REDUCTASE; ALDOSE REDUCTASE INHIBITOR; CARBOXYLIC ACID; EPALRESTAT; FIDARESTAT; MINALRESTAT; PLACEBO; RANIRESTAT; SORBINIL; SORBITOL; TOLRESTAT; UNCLASSIFIED DRUG; UNINDEXED DRUG; ZENARESTAT; ZOPOLRESTAT; [1 (2 HYDROXYPHENYL) 1H PYRROL 3 YL]PHENYLMETHANONE; [1 (3 FLUORO 4 HYDROXYPHENYL) 1H PYRROL 2 YL](4 METHOXYPHENYL)METHANONE; [1 (3 FLUORO 4 HYDROXYPHENYL) 1H PYRROL 2 YL]PHENYLMETHANONE; [1 (3 FLUORO 4 HYDROXYPHENYL) 1H PYRROL 3 YL](3 METHOXYPHENYL)METHANONE; [1 (3 FLUORO 4 HYDROXYPHENYL) 1H PYRROL 3 YL](4 METHOXYPHENYL)METHANONE; [1 (3 FLUORO 4 HYDROXYPHENYL) 1H PYRROL 3 YL]PHENYLMETHANONE; [1 (3 FLUORO 4 HYDROXYPHENYL) 1H PYRROL 3 YL][4 (TRIFLUOROMETHOXY)PHENYL]METHANONE; [1 (3 HYDROXYPHENYL) 1H PYRROL 3 YL]PHENYLMETHANONE; [1 (3,4 DIFLUOROPHENYL) 1H PYRROL 3 YL]PHENYLMETHANONE; [1 (4 HYDROXYPHENYL) 1H PYRROL 3 YL]PHENYLMETHANONE; [1,1' BIPHENYL] 4 YL[1 (3, FLUORO 4 HYDROXYPHENYL) 1H PYRROL 3 YL]METHANONE; [1,1' BIPHENYL] 4 YL[1 (3, FLUORO 4 HYDROXYPHENYL) 1H PYRROL 3 YL]PHENYLMETHANONE; 1-(4-BENZOYL-1-(3-FLUORO-4-HYDROXYPHENYL)-1H-PYRROL-2-YL)-2,2-DIFLUOROETHANONE; ENZYME INHIBITOR; PHENOL DERIVATIVE; PYRROLE DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; DIABETIC NEUROPATHY; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; HYDROGEN BOND; IC 50; IN VITRO STUDY; JEJUNUM; MALE; MEMBRANE TRANSPORT; MOLECULAR DOCKING; NONHUMAN; PH; PHYSICAL CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; STRUCTURE ACTIVITY RELATION; ANIMAL; ANTAGONISTS AND INHIBITORS; CELL MEMBRANE PERMEABILITY; CHEMICAL STRUCTURE; CHEMISTRY; CYTOLOGY; DOSE RESPONSE; DRUG EFFECTS; METABOLISM; OPTICAL INSTRUMENTATION; SYNTHESIS; WISTAR RAT;

RATTUS;

ALDEHYDE REDUCTASE; ANIMALS; CELL MEMBRANE PERMEABILITY; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; JEJUNUM; LENSES; MALE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHENOLS; PYRROLES; RATS; RATS, WISTAR; SORBITOL; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84897423822     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.02.016     Document Type: Article

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