Carbonic anhydrase inhibitors. Synthesis, and molecular structure of novel series N-substituted N′-(2-arylmethylthio-4-chloro-5- methylbenzenesulfonyl)guanidines and their inhibition of human cytosolic isozymes i and II and the transmembrane tumor-associated isozymes IX and XII

European Journal of Medicinal Chemistry

Volumn 71, Issue , 2014, Pages 135-147

  Zołnowska, Beata ^a   Sławiński, Jarosław ^a   Pogorzelska, Aneta ^a   Chojnacki, Jarosław ^b   Vullo, Daniela ^c   Supuran, Claudiu T ^c  

^a MEDICAL UNIVERSITY OF GDANSK   (Poland)

^b GDANSK UNIVERSITY OF TECHNOLOGY   (Poland)

^c UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Anticancer activity; Carbonic anhydrase isozymes I, II, IX and XII inhibitors; Sulfonamide; Sulfonylguanidine; Synthesis

Indexed keywords

1 (2 BENZYLTHIO 4 CHLORO 5 METHYLBENZENESULFONYL) 3 (2 SULFAMOYL 1,3,4 THIADIAZOL 5 YL)GUANIDINE; 1 (2 BENZYLTHIO 4 CHLORO 5 METHYLBENZENESULFONYL) 3 (2 SULFAMOYLPHENYL)GUANIDINE; 1 (2 BENZYLTHIO 4 CHLORO 5 METHYLBENZENESULFONYL) 3 (3 SULFAMOYLPHENYL)GUANIDINE; 1 (2 BENZYLTHIO 4 CHLORO 5 METHYLBENZENESULFONYL) 3 (4 SULFAMOYBENZYL)GUANIDINE; 1 (2 BENZYLTHIO 4 CHLORO 5 METHYLBENZENESULFONYL) 3 (4 SULFAMOYLPHENYL)GUANIDINE; 1 (2 BENZYLTHIO 4 CHLORO 5 METHYLBENZENESULFONYL) 3 (4 SULFAMOYLPHENYLAMINO)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (2 OXO 1,2 DIHYDROQUINOLIN 4 YLMETHYLTHIO)BENZENESULFONYL] 3 (2 SULFAMOYLPHENYL)GAUNIDINE; 1 [4 CHLORO 5 METHYL 2 (2 OXO 1,2 DIHYDROQUINOLIN 4 YLMETHYLTHIO)BENZENESULFONYL] 3 (3 SULFAMOYLPHENYL)GAUNIDINE; 1 [4 CHLORO 5 METHYL 2 (2 OXO 1,2 DIHYDROQUINOLIN 4 YLMETHYLTHIO)BENZENESULFONYL] 3 (4 SULFAMOYLPHENYL)GAUNIDINE; 1 [4 CHLORO 5 METHYL 2 (3 TRIFLUOROMETHYLBENZYLTHIO)BENZENESULFONYL] 3 (2 SULFAMOYLPHENYL)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (3 TRIFLUOROMETHYLBENZYLTHIO)BENZENESULFONYL] 3 (3 SULFAMOYLPHENYL)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (3 TRIFLUOROMETHYLBENZYLTHIO)BENZENESULFONYL] 3 (4 SULFAMOYLPHENYL)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (4 TRIFLUOROMETHYLBENZYLTHIO)BENZENESULFONYL] 3 (2 SULFAMOYL1,3,4 THIADIAZOL 5 YL)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (4 TRIFLUOROMETHYLBENZYLTHIO)BENZENESULFONYL] 3 (2 SULFAMOYPHYNYL)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (4 TRIFLUOROMETHYLBENZYLTHIO)BENZENESULFONYL] 3 (3 SULFAMOYPHYNYL)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (4 TRIFLUOROMETHYLBENZYLTHIO)BENZENESULFONYL] 3 (4 SULFAMOYLBENZYL)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (4 TRIFLUOROMETHYLBENZYLTHIO)BENZENESULFONYL] 3 (4 SULFAMOYLPHENYLAMINO)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (4 TRIFLUOROMETHYLBENZYLTHIO)BENZENESULFONYL] 3 (4 SULFAMOYPHYNYL)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (NAPHTHALEN 1 YLMETHYLTHIO)BENZENESULFONYL] 3 (2 SULFAMOYPHENYL)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (NAPHTHALEN 1 YLMETHYLTHIO)BENZENESULFONYL] 3 (3 SULFAMOYPHENYL)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (NAPHTHALEN 1 YLMETHYLTHIO)BENZENESULFONYL] 3 (4 SULFAMOYL 1,3,4 THIADIAZOL 5 YL)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (NAPHTHALEN 1 YLMETHYLTHIO)BENZENESULFONYL] 3 (4 SULFAMOYLBENZYLAMINO)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (NAPHTHALEN 1 YLMETHYLTHIO)BENZENESULFONYL] 3 (4 SULFAMOYPHENYL)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (NAPHTHALEN 1 YLMETHYLTHIO)BENZENESULFONYL] 3 (4 SULFAMOYPHENYLAMINO)GUANIDINE; ANTINEOPLASTIC AGENT; CARBONATE DEHYDRATASE INHIBITOR; GUANIDINE DERIVATIVE; ISOENZYME; N [4 CHLORO 2 (6 CHLOROBENZO[D][1,3]DIOXOL 5 YLMETHYLTHIO) 5 METHYLBENZENESULFONYL]CYANAMIDE POTASSIUM SALT; UNCLASSIFIED DRUG; UNINDEXED DRUG; 1 [4 CHLORO 5 METHYL 2 (2 OXO 1,2 DIHYDROQUINOLIN 4YLMETHYLTHIO)BENZENESULFONYL] 3 (3 SULFAMOYLPHENYL)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (2 OXO 1,2 DIHYDROQUINOLIN 4YLMETHYLTHIO)BENZENESULFONYL] 3 (4 SULFAMOYLPHENYL)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (3 TRIFLUOROMETHYLBENZYLTHIO)BENZENESULFONYL] 3 (2 SULFAMOYL 1,3,4 THIADIAZOL 5 YL)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (3 TRIFLUOROMETHYLBENZYLTHIO)BENZENESULFONYL] 3 (4 SULFAMOYLPHENYLAMINO)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (4 TRIFLUOROMETHYLBENZYLTHIO)BENZENESULFONYL] 3 (2 SULFAMOYL 1,3,4 THIADIAZOL 5 YL)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (4 TRIFLUOROMETHYLBENZYLTHIO)BENZENESULFONYL] 3 (2 SULFAMOYLPHENYL)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (4 TRIFLUOROMETHYLBENZYLTHIO)BENZENESULFONYL] 3 (3 SULFAMOYLPHENYL)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (4 TRIFLUOROMETHYLBENZYLTHIO)BENZENESULFONYL] 3 (4 SULFAMOYLPHENYL)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (NAPHTHALEN 1 YLMETHYLTHIO)BENZENESULFONYL] 3 (2 SULFAMOYL 1,3,4 THIADIAZOL 5 YL)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (NAPHTHALEN 1 YLMETHYLTHIO)BENZENESULFONYL] 3 (2 SULFAMOYLPHENYL)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (NAPHTHALEN 1 YLMETHYLTHIO)BENZENESULFONYL] 3 (3 SULFAMOYLPHENYL)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (NAPHTHALEN 1 YLMETHYLTHIO)BENZENESULFONYL] 3 (4 SULFAMOYLPHENYL)GUANIDINE; 1 [4 CHLORO 5 METHYL 2 (NAPTHALEN 1 YLMETHYLTHIO)BENZENESULFONYL] 3 (4 SULFAMOYLPHENYLAMINO)GUANIDINE; 2 (2 BENZYLTHIO 4 CHLORO 5 METHYLBENZENESULFONYL) 3 (4 SULFAMOYLBENZYL)GUANIDINE; 2 [4 CHLORO 5 METHYL 2 (3 TRIFLUOROMETHYLBENZYLTHIO)BENZENESULFONYL] 3 (4 SULFAMOYLBENZYL)GUANIDINE; 2 [4 CHLORO 5 METHYL 2 (NAPHTHALEN 1 YLMETHYLTHIO)BENZENESULFONYL] 3 (4 SULFAMOYLBENZYL)GUANIDINE; N' (2 ARYLMETHYLTHIO 4 CHLORO 5 METHYLBENZENESULFONYL)GUANIDINE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CHEMICAL STRUCTURE; COLON CANCER; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; GEOMETRY; HUMAN; HUMAN CELL; HYDROGEN BOND; IN VITRO STUDY; KIDNEY CANCER; LEUKEMIA; LUNG NON SMALL CELL CANCER; MALE; MELANOMA; NATIONAL HEALTH ORGANIZATION; OVARY CANCER; PROSTATE CANCER; SUBSTITUTION REACTION; TUMOR CELL LINE; CARBON NUCLEAR MAGNETIC RESONANCE; ENZYME INHIBITION; PROTON NUCLEAR MAGNETIC RESONANCE;

ANTICANCER ACTIVITY; CARBONIC ANHYDRASE ISOZYMES I, II, IX AND XII INHIBITORS; SULFONAMIDE; SULFONYLGUANIDINE; SYNTHESIS;

ANTIGENS, NEOPLASM; ANTINEOPLASTIC AGENTS; CARBONIC ANHYDRASE I; CARBONIC ANHYDRASE II; CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASES; CELL LINE, TUMOR; CYTOSOL; GUANIDINES; HUMANS; ISOENZYMES; MODELS, MOLECULAR; NEOPLASMS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84888266626     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.10.081     Document Type: Article

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