Carbonic anhydrase inhibitors: Synthesis, molecular docking, cytotoxic and inhibition of the human carbonic anhydrase isoforms I, II, IX, XII with novel benzenesulfonamides incorporating pyrrole, pyrrolopyrimidine and fused pyrrolopyrimidine moieties

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 14, 2014, Pages 3684-3695

  Ghorab, Mostafa M ^a,b   Alsaid, Mansour S ^a   Ceruso, Mariangela ^c   Nissan, Yassin M ^d   Supuran, Claudiu T ^c  

^a KING SAUD UNIVERSITY   (Saudi Arabia)

^b HOT LABORATORIES CENTER   (Egypt)

^c UNIVERSITY OF FLORENCE   (Italy)

^d CAIRO UNIVERSITY   (Egypt)

Author keywords

Carbonic anhydrase inhibitors; Cytotoxic activity; Molecular docking; Pyrrolopyrimidines; Sulfonamide

Indexed keywords

4 [13 AMINO 3 (4 BROMOPHENYL) 12 CYANO 5,7,9,10,14 PENTAZATRICYCLO [7.5.0.02,6] TETRADECA 1(14),2(6),3,7,10,12 HEXAEN 5 YL]BENZENESULFONAMIDE; 4 [13 AMINO 3 (4 BROMOPHENYL) 12 ETHOXYCARBONYL 5,7,9,10,14 PENTAZATRICYCLO [7.5.0.02,6] TETRADECA 1(14),2(6),3,7,10,12 HEXAEN 5 YL]BENZENESULFONAMIDE; 4 [2 ACETYLMETHYL 9 (4 BROMOPHENYL) 7H PYRROLO[3,2 E][1,2,4]TRIAZOLO[1,5 C]PYRIMIDIN 2 YL]ACETATE; 4 [2 AMINO 4 (4 BROMOPHENYL) 3 CYANO 1H PYRROL 1 YL]BENZENESULFONAMIDE; 4 [2 CARBOETHOXY 9 (4 BROMOPHENYL) 7H PYRROLO[3,2 E][1,2,4]TRIAZOLO[1,5 C]PYRIMIDIN 2 YL]ACETATE; 4 [2 OXO 10 (4 BROMOPHENYL) 3,4 DIHYDROPYRROLO[2,3 D] PYRIMIDO [3,4 E][1,2,4] TRIAZIN 8 YL]BENZENESULFONAMIDE; 4 [2,3 DIOXO 10 (4 BROMOPHENYL) 3,4 DIHYDROPYRROLO[2,3 D]PYRIMIDO[3,4 E][1,2,4]TRIAZIN 8 YL]BENZENESULFONAMIDE; 4 [3 (1 ACETYL 2 OXOINDOLIN 3 YLIDENEAMINO) 5 (4 BROMOPHENYL) 4 IMINO 3,4 DIHYDROPYRROLO[2,3 D]PYRIMIDIN-7 YL]BENZENESULFONAMIDE; 4 [3 (4 BROMOPHENYL) 11 METHYL 13 PHENYL 5,7,9,10,14 PENTAZATRICYCLO [7.5.0.02,6] TETRADECA 1(14),2(6),3,7,10,12 HEXAEN 5 YL]BENZENESULFONAMIDE; 4 [3 (4 BROMOPHENYL) 11,13 DIMETHYL 5.7.9.10.14 PENTAZATRICYCLO[7.5.0.02,6]TETRA DECA 1(14),2(6),3,7,10 PENTAEN 5YL]BENZENESULFONAMIDE; 4 [3 AMINO 5 (4 BROMOPHENYL) 4 IMINO 3,4 DIHYDROPYRROLO[2,3 D]PYRIMIDIN 7 YL]BENZENESULFONAMIDE; 4 [5 (4 BROMOPHENYL) 2,7,9,11,12,20 HEXAZAPENTACYCLO [11.7.0.03,11.04,8.014,19] ICOSA 1(20), 2,4(8),5,9,12,14(19),15,17 NONAEN 7 YL]BENZENESULFONAMIDE; 4 [5 (4 BROMOPHENYL) 4 IMINO 3 (4 OXO 4 PHENYLBUTAN 2 YLIDENEAMINO) 3,4 DIHYDROPYRROLO[2,3 D]PYRIMIDIN 7 YL]BENZENESULFONAMIDE; 4 [8 AMINO 9 CYANO 1 (4 BROMOPHENYL) 3H PYRAZOLO[1,5 C]PYRROLO[3,2 E]PYRIMIDIN 3 YL]BENZENESULFONAMIDE; ACETAZOLAMIDE; BENZENESULFONAMIDE DERIVATIVE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE IX; CARBONATE DEHYDRATASE XII; DOXORUBICIN; ETHYL 2 [9 (4 BROMOPHENYL) 7 (4 SULFAMOYLPHENYL) 7H PYRROLO[3,2 E][1,2,4]TRIAZOLO[1,5 C]PYRIMIDIN 2 YL]ACETATE; ETHYL 9 (4 BROMOPHENYL) 7 (4 SULFAMOYLPHENYL) 7H PYRROLO[3,2 E][1,2,4]TRIAZOLO[1,5 C]PYRIMIDINE 2 CARBOXYLATE; PYRROLE DERIVATIVE; PYRROLOPYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; BENZENESULFONAMIDE; CARBONATE DEHYDRATASE; ISOENZYME; PYRIMIDINE DERIVATIVE; PYRROLOPYRIMIDINE; SULFONAMIDE;

ARTICLE; BREAST CANCER; CANCER CELL; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; MCF 7 CELL LINE; MOLECULAR DOCKING; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG SCREENING; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASES; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; ISOENZYMES; MOLECULAR STRUCTURE; PYRIMIDINES; PYRROLES; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 84902543916     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.05.009     Document Type: Article

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