ABSTRACT
Due to the rapidly growing bacterial resistance to antibiotics and the scarcity of novel agents under development, bacterial infections are still a pressing global problem, making new types of antibacterial agents, which are effective both alone and in combination with traditional antibiotics, urgently needed. In this paper, seven series of N-arylsulfonylindole analogs 5-11 bearing rhodanine moieties were synthesized, characterized, and evaluated for antibacterial activity. According to the in vitro antimicrobial results, half of the synthesized compounds showed potent inhibition against four Gram-positive bacteria, with MIC values in the range of 0.5-8 µg/mL. For multidrug-resistant strains, compounds 6a and 6c were the most potent, with MIC values of 0.5 µg/mL, having comparable activity to gatifloxacin, moxiflocaxin and norfloxacin and being 128-fold more potent than oxacillin (MIC = 64 µg/mL) and 64-fold more active than penicillin (MIC = 32 µg/mL) against Staphylococcus aureusATCC 43300.
Subject(s)
Anti-Bacterial Agents/chemistry , Arylsulfonic Acids/chemistry , Escherichia coli/drug effects , Indoles/chemistry , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/pharmacology , Arylsulfonic Acids/chemical synthesis , Arylsulfonic Acids/pharmacology , Humans , Indoles/chemical synthesis , Indoles/pharmacology , Microbial Sensitivity Tests , Rhodanine/chemical synthesis , Rhodanine/chemistry , Rhodanine/pharmacology , Structure-Activity RelationshipABSTRACT
A series of novel carboxamide compounds 19a-19j, 20a-20j and 22a-22d containing piperazine and arylsulfonyl moieties have been synthesized. The bioassay results showed that some compounds exhibited favorable herbicidal activities against dicotyledonous plants and many of them possessed excellent antifungal activities. Among 24 novel compounds, some showed superiority over the commercial fungicides Chlorothalonil, Dimethomorph, Thiophanate-methyl, Iprodione, and Zhongshengmycin at 500 mg/L concentration. Some compounds also exhibited high KARI inhibitory activity at 100 µg/mL concentration and could be used as new KARI lead inhibitors for further studies. Moreover, SAR of these new compounds were comprehensively investigated using different computational methods in which 3D-QSAR model obtained provided useful information for further structural optimization for the discovery of new fungicides. The results of this research will contribute to explore comprehensive biological activities of piperazine-containing compounds in different areas of chemistry.
Subject(s)
Amides/chemical synthesis , Antifungal Agents/chemical synthesis , Herbicides/chemical synthesis , Quantitative Structure-Activity Relationship , Amides/pharmacology , Antifungal Agents/pharmacology , Arylsulfonic Acids/chemistry , Herbicides/pharmacology , Piperazine , Piperazines/chemistryABSTRACT
The distribution of the two main anionic surfactants manufactured and used in the world, alkyl ethoxysulfates (AES) and linear alkylbenzene sulfonates (LAS), has been studied in sediments from a salt marsh and an estuary of the Bay of Cadiz (southwest of Spain). The identification and quantification of AES and LAS was carried out after automated Soxhlet extraction with methanol, followed by solid-phase extraction and liquid chromatography coupled to electrospray mass spectrometry. The latter procedure permitted the unequivocal identification of every LAS homologue as well as the AES homologues of up to 16 carbon atoms in their alkyl chain and of up to 12 ethylene oxide groups. Recoveries were in the range of 51% to 84% and limits of detection from 1 to 5 microg/kg. We have focused our attention particularly on AES because, in spite of their great use, these compounds have received less attention than LAS and their occurrence has not been described in marine environmental samples. Alkyl ethoxysulfates concentration values range between 100 and 400 microg/kg in the topmost layer of sediments at the sampling areas. The relative distribution of AES homologues shows higher percentages for the longer alkyl chain homologues in sediments as well as for the shorter ethoxymers. A decrease in LAS concentrations has been found relative to past studies in one of the sampling areas as a consequence of the reduction of urban wastewater discharges.
Subject(s)
Alkanesulfonic Acids/chemistry , Environmental Monitoring/methods , Geologic Sediments , Sulfates/chemistry , Anions , Arylsulfonic Acids/chemistry , Chromatography, Liquid , Ecosystem , Environmental Pollution , Ethylene Oxide/chemistry , Mass Spectrometry , Models, Chemical , Seawater , Soil Pollutants , Spain , Surface-Active Agents/chemistry , Time Factors , Water , Water Pollutants , Water Pollutants, ChemicalABSTRACT
8-(Sulfostyryl)xanthine derivatives were synthesized as water-soluble A2A-selective adenosine receptor (AR) antagonists. meta- and para-sulfostyryl-DMPX (3,7-dimethyl-1-propargylxanthine) derivatives 11a and 11b exhibited high affinity to rat A2A-AR in submicromolar concentrations, and were 20- to 30-fold selective versus rat A1-AR. Styryl-DMPX derivatives were inactive at human A2B- and A3-AR. 1,3-Dipropyl-8-p-sulfostyrylxanthine (13) or only a 7-methyl derivative (14) showed similar (13) or higher (14) A2A affinity than 11a and 11b but showed no (13) or only a low degree (14) of selectivity versus A1-, A2B-, and A3-AR. The A2A-selective sulfostyryl-DMPX derivatives exhibit high water-solubility and may be useful research tools for in vivo studies.
