Synthesis, antimalarial activity, structure–activity relationship analysis of thieno-[3,2-b]benzothiazine S,S-dioxide analogs

An improved procedure for the synthesis of 3-amino-9-arylsubstituted-thieno[3,2-b]benzothiazine S,S-dioxide 2-decarboxylated is reported. Thieno-[3,2-b]benzothiazine S,S-dioxide derivatives were investigated for their abilities to inhibit β-hematin formation, hemoglobin hydrolysis and in vivo for their efficacy in rodent Plasmodium berghei. Compounds 5j-o were the most promising as inhibitors of hemoglobin hydrolysis, however, the compounds are not as efficient as chloroquine. A structure-activity relationship (SAR) study was carried out in this series. Our results allow us to determine the minimal structural requirements to produce the biological response.Fil: Barazarte, Arthur. Universidad Central de Venezuela; VenezuelaFil: Camacho, José. Universidad Central de Venezuela; VenezuelaFil: Domínguez, José. Universidad Central de Venezuela; VenezuelaFil: Lobo, Gricela. Universidad Central de Venezuela; VenezuelaFil: Gamboa, Neira. Universidad Central de Venezuela; VenezuelaFil: Rodrigues, Juan. Universidad Central de Venezuela; VenezuelaFil: Capparelli, Mario V.. Universidad Central de Venezuela; VenezuelaFil: Álvarez Larena, Ángel. Universitat Autònoma de Barcelona; EspañaFil: Andujar, Sebastian Antonio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; ArgentinaFil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; ArgentinaFil: Charris, Jaime. Universidad Central de Venezuela; Venezuel

Synthesis of 6-carbomethoxy-3-Phenyl-5-(4-dimethylaminophenyl)-cyclohexenone

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4,6-Diamino-5-[4-(dimethylamino)benzylidene]pyrimidin-2(5H)- one

A new compound, 4,6-diamino-5-[4-(dimethylamino)benzylidene]pyrimidin-2(5H)-one, was synthesized and its IR, 1H NMR and 13C NMR and MS spectroscopic data are presented

Síntesis y actividad antimicrobiana de derivados de 4,6-diaminopirimidinas análogos de citosina

A new synthesis of novel 4,6-diaminopyrimidines 2a-j, cytosine analogous, is described. This involves the base-assisted cyclization reaction of benzylidenemalononitriles 1a-j (BMNs) with urea. Compounds 1a-j were prepared by a Knoevenagel condensation reaction from benzaldehyde and malononitrile using EtOH as solvent at room temperature conditions. The antimicrobial activity against Gram-positive microorganisms: Staphylococcus aureus (ATCC 25923) and Bacillus cereus (ATCC 14579) and Gram-negative: Escherichia coli (ATCC 35218) and Pseudomonas aeruginosa (ATCC 27853) and th yeast Candida tropicalis (MLDM 372) is also reported. The compounds 2c, 2e, 2f, 2g, 2i and 2j are considered wide spectrum. Antimicrobial activity, Benzylidenemalononitriles (BMNs), Cytosine, Diaminopyrimidine, Urea

4,6-Diamino-5-(3,4-dichlorobenzylidene)pyrimidin-2(5H)-one

A new compound, 4,6-diamino-5-(3,4-dichlorobenzylidene)pyrimidin-2(5H)-one, was synthesized and its IR, 1H NMR,13C NMR, MS spectroscopic data and elemental analysis are presented

Synthesis of [(7-Chloroquinolin-4-yl)amino]chalcones: Potential Antimalarial and Anticancer Agents

[(7-Chloroquinolin-4-yl)amino]chalcone derivatives derived from the corresponding 3- or 4-[(7-chloroquinolin-4-yl)amino]acetophenone were synthesized and evaluated for in vitro antimalarial and anticancer activity. The most active compounds 12, 13, 15, 17 and 19 from the 3-substituted series displayed inhibitory values against heme cristallization in the range of 93.14 ± 1.74 – 94.93 ± 1.50 % as an antimalarial mechanism and cytotoxic effect with IC50 values of 7.93 ± 2.05, 7.11 ± 2.06 and 6.95 ± 1.62 μg/mL for 13, 17 and 19 respectively against humane prostate LNCaP tumor cells

Synthesis, Characterization, Crystal Structure and Antimalarial Activity of (2E)-2-(1-{4-[(7-chloroquinolin-4-yl)amino]phenyl} ethylidene)hydrazine Carbothioamide

A simple synthesis and study by UV-vis, IR, NMR, ESI-CID-MS2 and X-ray diffraction of ((2E)-2-(1-{4-[(7-chloroquinolin-4-yl)amino]phenyl}ethylidene)hydrazinecarbothioamide is reported. It was tested in vitro against chloroquine-resistant strain (W2) of Plasmodium falciparum, hemozoin (β-hematin) formation and cysteine protease falcipain-2. In general, it was found to possess a proved activity in its inhibitory power on the parasite but less active on the formation of hemozoin (β-hematin) and falcipain-2. Also, the X-ray analysis presented an unexpected electronic density that can be assigned like S(2). This electronic density can be attributed to autocondensation of thiosemicarbazide, generating H2S as a subproduct. DOI: http://dx.doi.org/10.17807/orbital.v9i4.1001<br /

4,6-Diamino-5-(4-methylbenzylidene)pyrimidin-2(5H)-one

A new compound, 4,6-diamino-5-(methylbenzylidene)pyrimidin-2(5H)-one, was synthesized and its IR, 1H NMR,13C NMR and MS spectroscopic data are presented