Natural and synthetic sulfur-bearing organic compounds have many applications in medicinal chemistry. This article reports the preparation of amphiphilic β-hydroxy sulfides, sulfoxides, and sulfones derived from cardanol and glycerol. Thiolysis of cardanol epoxide 3 with various thiols (4a-4j) in ethanol or water yielded the corresponding β-hydroxy sulfides 5a-5j (61-95%). Treatment with 30% H2O2 in acetic acid at ambient temperature completely converted these products into β-hydroxy sulfoxides 6a-6j and sulfones 7a, 7c-7f, 7h-7j. The synthesized compounds were characterized by 1H nuclear magnetic resonance (NMR), 13C NMR, high-resolution mass spectroscopy (HRMS) and performed the in vitro evaluation antimicrobial activities against standard strains of Staphylococcus aureus and Escherichia coli. Compounds 5a, 5d-5f, and 5h-5j proved moderately active against S. aureus. None of the compounds were active against E. coli. β-Hydroxy-sulfides 5a-5j were also evaluated for antioxidant properties but failed to exhibit significant activity.

The synthesis of novel amino alcohol derivatives based on cardanol and glycerol were achieved in good yields and characterized by 1H and 13C NMR (nuclear magnetic resonance) and MS (mass spectrometry). In addition, we evaluated the in vitro antimicrobial activity against Gram-positive (Staphylococcus aureus, standard and clinical strains), Gram-negative (Escherichia coli) and M. tuberculosis bacterial strains. The bioassay results indicated that four compounds showed activity against S. aureus, including the clinical resistant strain, with MIC (minimum inhibitory concentration) ranging from 3.90 to 15.60 µg mL-1 and M. tuberculosis, with MIC90 (minimum inhibitory concentration required to inhibit the growth of 90% of organisms) ranging from 3.18 to 7.36 µg mL-1.

ABSTRACT Cardanol is a constituent of Cashew Nut Shell Liquid that presents larvicidal activity against Aedes aegypti. The isolation of cardanol is somewhat troublesome, however, in this work we describe an efficient and inexpensive method to obtain it as a pure material. The compound was used as starting material to make chemical transformation leading to saturated cardanol, epoxides and, halohydrins. These derivatives were tested for toxicity against Aedes aegypti larvae. The results showed that iodohydrins are very promising compounds for making commercial products to combat the vector mosquito larvae presenting a LC50 of 0.0023 ppm after 72 h of exposure.

Octocrylene (2-ethylhexyl 2-cyano-3,3-diphenyl-2-propenoate) is present in several sunscreens and is known to work synergistically with UV filters. We prepared eight octocrylene-related compounds to test their photoprotective activities by measuring diffuse transmittance. The compounds had varied photoprotection profiles, with Sun Protection Factors (SPF) ranging from 1 to 5 and UVA Protection Factors (UVAPF) ranging from 1 to 8. Compounds 4, 5, and 7 showed the best protection against UVB sunrays, while compounds 5, 6, and 7 presented the best results for protection from UVA, so compound 7 had the most balanced protection overall. Results for compounds 4, 8, and 9 are reported for the first time in the literature.

We extended our previous exploration of sulfur bridges as bioisosteric replacements for atoms forming the bridge between the aromatic rings of combretastatin A-4. Employing coupling reactions between 5-iodo-1,2,3-trimethoxybenzene and substituted thiols, followed by oxidation to sulfones with m-CPBA, different locations for attaching the sulfur atom to ring A through the synthesis of nine compounds were examined. Antitubulin activity was performed with electrophoretically homogenous bovine brain tubulin, and activity occurred with the 1,2,3-trimethoxy-4-[(4-methoxyphenyl)thio]benzene (12), while the other compounds were inactive. The compounds were also tested for leishmanicidal activity using promastigote forms of Leishmania braziliensis (MHOM/BR175/M2904), and the greatest activity was observed with 1,2,3-trimethoxy-4-(phenylthio)benzene (10) and 1,2,3-trimethoxy-4-[(4-methoxyphenyl) sulfinyl]benzene (15).

Cytotoxic activity of eight plant extracts, native from the Mid-West of Brazil comprising Cerrado, Pantanal and semideciduous forest, was evaluated for MDA-MB-435, SF-295, and HCT-8 cancer cell strains. A single 100 µg.mL-1 dose of each extract was employed with 72 h of incubation for all tests. Doxorubicin (1 µg.mL-1) was used as the positive control and the MTT method was used to detect the activity. Cytotoxicity of distinct polarities was observed in thirty extracts (46%), from different parts of the following species: Tabebuia heptaphylla (Vell.) Toledo, Bignoniaceae, Tapirira guianensis Aubl., Anacardiaceae, Myracrodruon urundeuva Allemão, Anacardiaceae, Schinus terebinthifolius Raddi, Anacardiaceae, Gomphrena elegans Mart., Amaranthaceae, Attalea phalerata Mart. ex Spreng., Arecaceae, Eugenia uniflora L., Myrtaceae, and Annona dioica A. St.-Hil., Annonaceae. Extracts of at least two tested cell strains were considered to be highly active since their inhibition rate was over 75%.

No presente trabalho foi avaliada a atividade inseticida de extratos de limbos foliares de Tapirira guianensis Aubl. (Anacardiaceae), Attalea phalerata (Mart. ex Spreng.) Burret (Arecaceae), Eugenia uniflora L. (Myrtaceae) e Gomphrena elegans Mart. (Amaranthaceae) e de caules de Myracrodruon urundeuva Allemão (Anacardiaceae). Foram testados quatro extratos e 18 frações, com diferentes polaridades. Dez gramas de grãos de trigo foram pulverizados com 1 mL de cada extrato a 10% (p/v). Após a evaporação do solvente a 38 ºC, os grãos foram acondicionados em recipientes juntamente com 20 indivíduos adultos de Sitophilus zeamais não sexados, com 10 a 20 dias de idade. As avaliações foram feitas no quinto e no décimo dia, contando-se o número de insetos mortos e descartando-os. Os extratos foliares de G. elegans ocasionaram mortalidade de 27% a 60% até o quinto dia, enquanto os demais extratos testados, quando ativos, não ultrapassaram a faixa de 20% de mortalidade no mesmo período. No décimo dia, os extratos mais ativos foram o proveniente de A. phalerata (hexânico, 36,5%) e todos os de G. elegans (52% a 80,5%), enquanto os demais extratos causaram até 30% de mortalidade.

This paper reports on an evaluation of the insecticidal activity of extracts prepared from leaves of Tapirira guianensis Aubl. (Anacardiaceae), Attalea phalerata (Mart. ex Spreng.) Burret (Arecaceae), Eugenia uniflora L. (Myrtaceae), and Gomphrena elegans Mart. (Amaranthaceae) and from stems of Myracrodruon urundeuva Allemão (Anacardiaceae). Four extracts and 18 fractions with a range of polarities were tested. Ten-gram batches of wheat grains were each nebulized with 1 mL of a separate extract at 10% w/v. After solvent evaporation at 38 ºC, the grains were placed into flasks along with 20 unsexed 10- to 20-day old adult individuals of Sitophilus zeamais. The assessment was carried out on the fifth and tenth day by counting and discarding the dead insects. Leaf extracts of G. elegans showed an insecticidal effect ranging from 27% to 60% by the fifth day, whereas the effect of the remaining extracts tested (if active at all) did not exceed 20% in the same period. By the tenth day, the most active extracts were those of A. phalerata (hexanic, 36.5%) and all those of G. elegans (5280.5%), whereas the effect of the other extracts did not exceed 30%.