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1.
Eur J Med Chem ; 41(10): 1180-9, 2006 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-16777268

RESUMO

Three series of novel 2-benzylthio-4-chloro-5-R1-benzenesulfonamides bearing the N-(benzoxazol-2-yl) (10-19), N-(benzothiazol-2-yl) (20-21) or N-(1,3-dihydro-2H-benzimidazol-2-ylidene) (22-25) moiety were synthesized by reacting N-(2-benzylthio-4-chloro-5-R1-benzenesulfonyl)cyanamide potassium salts (5-9) with 2-aminophenols, 2-aminothiophenol and o-phenylenediamines, respectively. Compounds with carbamoyl substituent at position 5 (14-16, 21 and 25, R1=CONH2) were further dehydrated to the corresponding nitriles (26-30, R1=CN). The in vitro antitumor activity of the compounds obtained was determined at the National Cancer Institute (NCI), and the structure-activity relationships were discussed. N-(2-benzoxazolyl)-2-benzylthio-4-chloro-5-(4-fluorophenylcarbamoyl)benzenesulfonamide (18) is the prominent of the compounds due to its remarkable activity and selectivity toward non-small cell lung cancer (NCI-H522) and melanoma (SK-MEL-2) cell lines (GI50=0.1 microM, TGI=0.5-0.6 microM).


Assuntos
Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Compostos de Benzil/síntese química , Compostos de Benzil/farmacologia , Sulfonamidas/síntese química , Sulfonamidas/farmacologia , Antineoplásicos/química , Compostos de Benzil/química , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Estrutura Molecular , Estereoisomerismo , Relação Estrutura-Atividade , Sulfonamidas/química
2.
Eur J Med Chem ; 37(9): 709-20, 2002 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-12350288

RESUMO

The syntheses and antitumor activities of novel 2-amino-4-(3,5,5-trimethyl-2-pyrazolino)-1,3,5-triazine derivatives 4-38 are described. All the compounds prepared were screened at the National Cancer Institute (NCI) for their activities against a panel of 60 tumor cell lines and relationships between structure and antitumor activity in vitro are discussed. The triazines 11, 16, 20, 23, 23 and 34-38 exhibited modest or fairly high activity against one or more human tumor cell lines. Prominent compound with remarkable activity (log GI50, < - 8.00- - 5.00) to all investigated cell lines and highly potent (log GI50 < - 8.00- - 7.64) against some cell lines of Leukemia (CCRF-CEM, K-562, RPMI-8226, SR), CNS Cancer (SF-539) and Breast Cancer (T-47D) was 2-[2-amino-4-(3,5,5-trimethyl-2-pyrazolino)-1,3,5-triazin-6-yl]-3-(5-nitro-2-thienyl)acrylonitrile (25).


Assuntos
Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Triazinas/síntese química , Triazinas/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Indicadores e Reagentes , Espectroscopia de Ressonância Magnética , Espectrofotometria Infravermelho , Relação Estrutura-Atividade , Células Tumorais Cultivadas
3.
Diabetologia ; 45(7): 1034-7, 2002 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-12136403

RESUMO

AIMS/HYPOTHESIS: Vascular complications observed in diabetes are often related to altered platelet functions. The most widely used hypoglycaemic drugs for treating Type II (non-insulin-dependent) diabetes mellitus are sulphonylurea derivatives. The purposes of this study were to evaluate the inhibitory effects of hypoglycaemic agents on platelet aggregation, to measure their lipophilicity and identify their structural parameters which assess their antiaggregatory activity. METHODS: An antiaggregatory test in vitro was carried out for 13 sulphonylurea derivatives. Aggregation of platelets, incubated with the agents at concentrations varying from 7.5 to 480 micromol/l, was induced by 10 micromol/l ADP. Drug lipophilicity parameter, log k(w), was measured by gradient HPLC and the agents were subjected to molecular modelling. RESULTS: The most pronounced inhibition of platelet aggregation was by glimepiride, gliclazide, gliquidone, glibenclamide and compound 2A. The IC(25) values were 15.9, 18.6, 20.4, 28.5 and 34.7 micromol/l, respectively. Quantitative structure-activity relationships indicate that antiaggregatory activity is mainly affected by electronic and not by lipophilic properties of the agents. CONCLUSION/INTERPRETATION: Glimepiride appeared to be a more potent ADP-induced platelet aggregation inhibitor in vitro than gliclazide. Antiaggregatory activity was shown for gliquidone and confirmed for glibenclamide. The QSAR analysis supports the hypothesis of a free radical mechanism of action of sulphonylurea derivatives previously suggested for gliclazide.


Assuntos
Plaquetas/fisiologia , Hipoglicemiantes/farmacologia , Inibidores da Agregação Plaquetária/farmacologia , Agregação Plaquetária/efeitos dos fármacos , Compostos de Sulfonilureia/farmacologia , Adulto , Plaquetas/efeitos dos fármacos , Humanos , Técnicas In Vitro , Pessoa de Meia-Idade , Relação Quantitativa Estrutura-Atividade , Valores de Referência , Fumar
4.
Eur J Med Chem ; 37(4): 285-93, 2002 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-11960663

RESUMO

A series of 3-allylamino-6-chloro-7-R-1,1-dioxo-1,4,2-benzodithiazines (2a-e) was obtained by the reaction of 6-chloro-3-methylthio-1,4,2-benzodithiazine-1,1-dioxides (1a-e) with allylamine. Selective hydrazinolysis of the allylaminobenzodithiazines (2a-e) gave the appropriate 1-allyl-3-amino-2-(4-chloro-2-mercaptobenzenesulphonyl)guanidines (3a-e) in good yields. The reaction of 3a with dimethylsulphate under alkaline conditions provided the methylthio derivative 4. The structures of these compounds were confirmed on the basis of elemental analysis, spectral data (IR, 1H- and 13C-NMR) and X-ray analysis. Screening data indicated that the compounds 3a and 3d exhibited significant in vitro activities against numerous human tumour cell lines, whereas compounds 3b and 3c showed a moderate activity.


Assuntos
Antineoplásicos/síntese química , Guanidinas/síntese química , Sulfonas/síntese química , Antineoplásicos/química , Antineoplásicos/farmacologia , Cristalografia por Raios X , Ensaios de Seleção de Medicamentos Antitumorais , Guanidinas/química , Guanidinas/farmacologia , Humanos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Relação Estrutura-Atividade , Sulfonas/química , Sulfonas/farmacologia , Células Tumorais Cultivadas
5.
Biotechnol Prog ; 16(3): 408-15, 2000.
Artigo em Inglês | MEDLINE | ID: mdl-10835243

RESUMO

A new type of polymer, starch-modified by acrylamide, has been developed for application in aqueous two-phase systems (ATPS) for protein separation. Partial hydrolysis and acrylamide modification of starch to different degrees make it suitable for forming ATPS with poly(ethylene glycol) in a moderate concentration range. The potential of the polymer to form ATPS with the thermoprecipitating copolymer of 1-vinylimidazole with N-vinylcaprolactam (poly-VI/VCL) has been evaluated. The thermoprecipitation properties of poly-VI/VCL and Cu(II)-loaded poly-VI/VCL have been studied for application in metal affinity partitioning. The formation of ATPS with Cu(II)-loaded thermoprecipitating copolymer was critically achieved for poly-VI/VCL (10/90) copolymer in under-loaded metal concentrations. With the Cu(II)-loaded copolymer, poly-VI/VCL in the top phase and modified starch in the bottom phase, the ATPS formed was used for the purification of alpha-amylase inhibitor from wheat meal. The protein partitioned in the top phase and phase-separated polymer-protein complex could be precipitated by salt. The protein inhibitor was recovered with a yield of 75%.


Assuntos
Caprolactama/análogos & derivados , Imidazóis/química , Polímeros/química , Acrilamida/química , Caprolactama/química , Cobre/química , Polivinil , Água/química
6.
Eur J Med Chem ; 35(12): 1053-64, 2000 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-11248404

RESUMO

The syntheses, structural elucidation based on NMR spectroscopy and X-ray analysis of 8 as well as antitumor activities of novel 2,4-diamino-1,3,5-triazine derivatives 5 and 7-22 are described. Screenings performed at NCI showed that most derivatives possessed a moderate to strong growth inhibition activity on various tumor panel cell lines between 0.148 and 56.2 microM concentrations. 2-Amino-6-bromomethyl-4-(3,5,5-trimethyl-2-pyrazoline)-1,3,5-triazine 11 showed the most potent antitumor activity with the mean midpoint values of log(10) GI50, log(10) TGI50 and log(10) LC50 of all tests equal to -5.26, -4.81 and -4.37, respectively and therefore, it can be considered as a lead structure for further development of anticancer agents.


Assuntos
Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Triazinas/síntese química , Triazinas/farmacologia , Antineoplásicos/química , Cristalografia por Raios X , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Espectroscopia de Ressonância Magnética , Conformação Molecular , Triazinas/química , Células Tumorais Cultivadas
7.
Acta Pol Pharm ; 56(2): 135-42, 1999.
Artigo em Inglês | MEDLINE | ID: mdl-10635357

RESUMO

Several 2-(hydroxy or alkoxy)-1-[(4-chloro-5-R1-2-mercaptophenyl)sulfonyl]limidazoles [II-VI, IX-XI] and bis ¿5-chloro-4-methyl-2-[(2-aryloxyimidazol-1-yl)sulfonyl]phenyl disulfides [XII-XV] were obtained by either the selective hydrolysis or alcoholysis of the appropriate 7-R1-8-chloroimidazo[1,2-b] [1,4,2]benzodithiazine 5,5-dioxides [Ia-d]. The structures of the products and their S-substituted derivatives [VII, VIII] were established on the basis of elemental analysis and spectral data (IR, 1H and 13C NMR). Preliminary screening data indicated that the investigated compounds [III, X, XII and XIII] exhibited weak [III, X], moderate [XII] or fairly high [XIII] activity against some human tumor cell lines (Table 1).


Assuntos
Anticarcinógenos/síntese química , Imidazóis/síntese química , Anticarcinógenos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Hidrólise , Imidazóis/farmacologia , Células Tumorais Cultivadas/efeitos dos fármacos
8.
Acta Pol Pharm ; 55(3): 233-8, 1998.
Artigo em Inglês | MEDLINE | ID: mdl-9735704

RESUMO

A series of 4-[(4-chloro-5-methyl-2-methylthiophenyl) sulphonyl]-1-(aryl)semicarbazides [IV-XI] and N-[(4-chloro-5-methylthiophenyl)sulphonyl]-N'-(4-chlorophenyl)urea [XII] were prepared and evaluated in vitro for anticancer activity [IV-VII, IX-XII]. All compounds exhibited weak [V-VII, IX] or moderate [IV, X-XII] activity against some human tumor cell lines, whereas the compound [XII] showed a relatively high activity (Table 3).


Assuntos
Antineoplásicos/síntese química , Semicarbazidas/síntese química , Ureia/análogos & derivados , Antineoplásicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Semicarbazidas/farmacologia , Células Tumorais Cultivadas , Ureia/síntese química , Ureia/farmacologia
9.
Acta Pol Pharm ; 55(5): 375-9, 1998.
Artigo em Inglês | MEDLINE | ID: mdl-9921115

RESUMO

A series of 4-chloro-2-mercapto-5-methyl-N- (1,2,4-triazolo[4,3-a]pyrid-3-yl) benzenesulfonamides [IIIa-IIId] was obtained by the reaction of 6-chloro-7-methyl-3-methylthio- 1,4,2-benzodithiazine 1,1-dioxide with some 2-hydrazinopyridines. Preliminary screening data indicated that compounds [IIIa-IIId] exibited moderate or fairly high anti-HIV activity and moderate anticancer activity.


Assuntos
Fármacos Anti-HIV/síntese química , Antineoplásicos/síntese química , Benzenossulfonatos/síntese química , Fármacos Anti-HIV/farmacologia , Antineoplásicos/farmacologia , Benzenossulfonatos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Humanos
10.
Acta Pol Pharm ; 55(6): 473-80, 1998.
Artigo em Inglês | MEDLINE | ID: mdl-10073134

RESUMO

A series of 2-mercapto-N-(1,2,4-triazol-3-yl)benzenesulfonamide derivatives containing the triazole moiety fused with a variety of heteroaromatic rings [XVI-XXVIII] was obtained by the reactions of 3-methylthio-1,4-2-benzodithiazine 1,1-dioxide derivatives [Ia-d] with 2-hydrazines [IIa-f]. Some of the intermediate 1,1-dioxide-1,4,2-benzodithiazin-3-ylhydrazines [III-XV] initially formed were also isolated. Preliminary screening data indicated that compounds [XVI-XIX and XXVII] were anti-HIV inactive, whereas other compounds showed a high [XXI and XXIII], fairly high [XXIII and XXVI] or moderate [XX, XXIV, XXV and XXVIII] activity. The compound [XXI] exhibited also high activity against ten selected HIV mutants.


Assuntos
Fármacos Anti-HIV/síntese química , Sulfonamidas/síntese química , Triazóis/síntese química , Fármacos Anti-HIV/farmacologia , Fenômenos Químicos , Físico-Química , Resistência Microbiana a Medicamentos , HIV-1/efeitos dos fármacos , HIV-1/genética , HIV-2/efeitos dos fármacos , Humanos , Espectroscopia de Ressonância Magnética , Mutação , Espectrofotometria Infravermelho , Sulfonamidas/farmacologia , Triazóis/farmacologia , Zidovudina/farmacologia
11.
Acta Pol Pharm ; 54(4): 293-8, 1997.
Artigo em Inglês | MEDLINE | ID: mdl-9511457

RESUMO

A series of N-(6-chloro-7-R-1,1-dioxo-1,4,2-benzodithiazin-3- yl)aminoacetaldehyde dimethyl acetals [IIa-IIh] was obtained by the reaction of 6-chloro-7-R-3-methylthio-1,4,2-benzodithiazine 1,1-dioxides [Ia-Ih] with aminoacetaldehyde dimethyl acetal. Cyclization of benzodithiazinylaminoacetaldehyde dimethyl acetals [IIa-IIh] with 98% sulfuric acid gave the appropriate 7-substituted 8-chloroimidazo[1,2-b][1,4,2]benzodithiazine 5,5-dioxides [IIIa-IIIh] in good to high yields. The structures of these compounds were established on the basis of elemental analysis and spectral data (IR, 1H and 13C NMR). Preliminary screening data indicated that compound [IIIa] exhibit moderate anti-HIV activity, and compounds [IIId-IIIg] anticancer activity.


Assuntos
Acetais/síntese química , Antineoplásicos/síntese química , Tiazinas/síntese química , Acetais/química , Acetais/farmacologia , Antineoplásicos/química , Antineoplásicos/farmacologia , Espectroscopia de Ressonância Magnética , Tiazinas/química , Tiazinas/farmacologia , Células Tumorais Cultivadas/efeitos dos fármacos
12.
Acta Pol Pharm ; 54(3): 215-21, 1997.
Artigo em Inglês | MEDLINE | ID: mdl-9511447

RESUMO

Syntheses of 4-chloro-2-mercapto-5-methyl-N-(5-R1-6-R2-benzimidazol-2-yl) benzenesulphonamides [II-V], their disulfides [IIa-IVa] and S,N-substituted derivatives [VI-IX] were described. The probable mechanism for the reactions was suggested. The moderate anticancer activity was observed in vitro for compounds [II-IV].


Assuntos
Fármacos Anti-HIV/síntese química , Antineoplásicos/síntese química , Benzimidazóis/síntese química , Sulfonamidas/síntese química , Fármacos Anti-HIV/farmacologia , Antineoplásicos/farmacologia , Benzimidazóis/farmacologia , Sulfonamidas/farmacologia , Células Tumorais Cultivadas/efeitos dos fármacos
13.
Acta Pol Pharm ; 53(4): 269-76, 1996.
Artigo em Inglês | MEDLINE | ID: mdl-9415195

RESUMO

A series of 2-mercapto-4-R1-5-R2-N-[1-R4-5-(R3-amino)-1,2,4- triazol-3-yl] benzenesulphonamides [IIa-IIg, IIIa-IIId] was obtained by the reaction of N-(1,1-dioxo-6-R1-7-R2- 1,2,4-benzodithiazin-3-yl)-N'-R3-guanidines [Ia-Ig] with some hydrazines in methanol or pyridine medium. The mechanism for the reaction has been suggested. Preliminary screening data indicated that compounds [IIIa-IIIb] exhibit moderate anti HIV activity, and compounds [IIIa-IIId] anticancer activity. Some structure-activity relationships are also discussed.


Assuntos
Fármacos Anti-HIV/síntese química , Antineoplásicos/síntese química , Derivados de Benzeno/síntese química , Compostos de Sulfidrila/síntese química , Sulfonamidas/síntese química , Fármacos Anti-HIV/farmacologia , Antineoplásicos/farmacologia , Derivados de Benzeno/farmacologia , Espectroscopia de Ressonância Magnética , Relação Estrutura-Atividade , Compostos de Sulfidrila/farmacologia , Sulfonamidas/farmacologia
14.
Acta Pol Pharm ; 52(4): 287-92, 1995.
Artigo em Inglês | MEDLINE | ID: mdl-8960258

RESUMO

The 4-chloro-2-mercapto-5-methyl-N-[5-R1-amino-S-triazol-3-yl] benzenesulphonamides (I-III; R1 = H, Ph or 3-MeOPh) were converted into S-substituted derivatives IV-XIV as potential anti-HIV-1 and/or anticancer agents. Preliminary screening data of compounds [IV-V, VII-XI] and [XIV] indicate that some of them exhibit weak anticancer activity [IV and XI] and moderate anti-HIV-1 activity [IV]. Some structure-activity relationships are also discussed.


Assuntos
Fármacos Anti-HIV/síntese química , Antineoplásicos/síntese química , Sulfonamidas/síntese química , Fármacos Anti-HIV/farmacologia , Antineoplásicos/farmacologia , Divisão Celular/efeitos dos fármacos , Humanos , Dose Letal Mediana , Oxirredução , Relação Estrutura-Atividade , Sulfonamidas/farmacologia , Células Tumorais Cultivadas
15.
Acta Pol Pharm ; 52(3): 223-30, 1995.
Artigo em Inglês | MEDLINE | ID: mdl-8960253

RESUMO

The syntheses of salts [III, IV] and amides [V, V.HCl] of 2-[5-chloro-4-methyl-2-[(5-amino-s-triazol-3-yl)aminosulphonyl+ ++] phenylthio] alkanoic acids, as well as 5-amino-2-[2-(2,4-dimethylpiperidino) ethyl]-3-[4-chloro-2-[2-(2,6-dimethylpiperidino) ethylthio]-5-methylbenzenesulphonylimino]-1-methyl-delta 4-1,2,4-triazoline dihydrochloride [X] and 5-(amino-, 4-chloroanilino- or 3,4,5-trimethoxyanilino)-1,2-di[2-(2,6-dimethylpiperidino) ethyl]-3-(4-chloro-2-[2-(2,6-dimethylpiperidino) ethylthio]-5-methylbenzenesulphonylimino)-delta 4-1,2,4-triazoline trihydrochlorides [XI-XIII] are described. The results of preliminary pharmacological examinations such as acute toxicity and influence on circulatory system of compounds III, IV, V.HCl and X-XIII are presented. The antiarrhythmic effect of the most active [XI] was stronger or comparable to the reference drugs quinidine and procainamide.


Assuntos
4-Cloromercuriobenzenossulfonato/síntese química , 4-Cloromercuriobenzenossulfonato/farmacologia , Antiarrítmicos/farmacologia , Arritmias Cardíacas/tratamento farmacológico , Coração/efeitos dos fármacos , Triazóis/síntese química , Triazóis/farmacologia , 4-Cloromercuriobenzenossulfonato/toxicidade , Aconitina , Animais , Arritmias Cardíacas/induzido quimicamente , Compostos de Bário , Cloretos , Dose Letal Mediana , Camundongos , Ratos , Triazóis/toxicidade
16.
Acta Pol Pharm ; 52(2): 91-101, 1995.
Artigo em Inglês | MEDLINE | ID: mdl-8960241

RESUMO

N-(1,1-Dioxo-1,4,2-benzodithiazin-3-yl)-N'-R3-guanidines [IIa-IIo] were prepared from the corresponding 3-methylthio-1,4,2-benzodithiazine 1,1-dioxide derivatives [Ia-Id]. Depending on electronic effects of R3 substituents, hydrazinolysis of the benzodithiazinylguanidines [II] afforded the following derivatives in good yields: either 2-mercapto-N-(5-amino-1,2,4-triazol-3-yl)benzenesulphonamides [IIIa-IIIc] (82-90% yields for R3 = H, Bu and Bzl) or 2-mercapto-N-[5-(R3-amino)-1,2,4-triazol-3-yl]benzenesulphonamides [IIIa-IIIm] (42-80% yields for R3 = Ph or substituted phenyl). The mechanism of the reaction has been suggested. Preliminary screening data indicated that compounds [IIId, IIIf-IIIi, IIIk] exhibit moderate anti-HIV-1 activity, and compounds [IIIe, IIIj, III l] anticancer activity.


Assuntos
Fármacos Anti-HIV/síntese química , Antineoplásicos/síntese química , Sulfonamidas/síntese química , Fármacos Anti-HIV/farmacologia , Antineoplásicos/farmacologia , Humanos , Sulfonamidas/farmacologia , Células Tumorais Cultivadas
18.
Acta Pol Pharm ; 50(4-5): 345-52, 1993.
Artigo em Inglês | MEDLINE | ID: mdl-8036920

RESUMO

Tree methods of synthesis of 2-(2-[2-(3,4,5-trimethoxybenzamido)ethylthio] benzenesulphonyl)guanidines (IVa-b, Va-XIVa, VIII-XII) are described. The results of preliminary pharmacological examinations such as acute toxicity and influence on circulatory system of compound [IVb, VIa, XIa-XIVa] and substrates [IIIc-f] are presented. Some structure-activity relationship is discussed.


Assuntos
Antiarrítmicos/farmacologia , Pressão Sanguínea/efeitos dos fármacos , Guanidinas/síntese química , Guanidinas/farmacologia , Frequência Cardíaca/efeitos dos fármacos , Sulfonamidas/síntese química , Sulfonamidas/farmacologia , Animais , Antiarrítmicos/síntese química , Arritmias Cardíacas/induzido quimicamente , Arritmias Cardíacas/tratamento farmacológico , Guanidinas/química , Guanidinas/toxicidade , Injeções Intravenosas , Camundongos , Ratos , Espectrofotometria Infravermelho , Relação Estrutura-Atividade , Sulfonamidas/química , Sulfonamidas/toxicidade
19.
Acta Pol Pharm ; 50(4-5): 353-8, 1993.
Artigo em Inglês | MEDLINE | ID: mdl-8036921

RESUMO

Synthesis of 2-[2 (alkylaminoalkylthio)-4-R1-5-R2-benzenesulphonamide]-5-R3-im idazoline [IV-IX], their hydrochlorides [IVa-IXa], as well needful substrates [IIc, III] are described. The results of preliminary pharmacological examinations such as acute toxicity and influence on circulatory system of compound IVa-IXa are presented. Some structure-activity relationship is also discussed.


Assuntos
Antiarrítmicos/síntese química , Pressão Sanguínea/efeitos dos fármacos , Frequência Cardíaca/efeitos dos fármacos , Imidazóis/síntese química , Imidazóis/farmacologia , Sulfonamidas/síntese química , Sulfonamidas/farmacologia , Animais , Antiarrítmicos/farmacologia , Antiarrítmicos/toxicidade , Arritmias Cardíacas/induzido quimicamente , Arritmias Cardíacas/tratamento farmacológico , Imidazóis/toxicidade , Camundongos , Peso Molecular , Ratos , Relação Estrutura-Atividade , Sulfonamidas/toxicidade
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