Novel Thiosemicarbazone Derivatives from Furan-2-Carbaldehyde: Synthesis, Characterization, Crystal Structures, and Antibacterial, Antifungal, Antioxidant, and Antitumor Activities

Ten new thiosemicarbazone derivatives, furan-2-carbaldehyde thiosemicarbazone (1), 3-methyl-furan-2-carbaldehyde thiosemicarbazone (2), 5-hydroxymethyl-furan-2-carbaldehyde thiosemicarbazone (3), 5-trifluoromethyl-furan-2-carbaldehyde thiosemicarbazone (4), 5-nitro-furan-2-carbaldehyde thiosemicarbazone (5), 5-phenyl-furan-2-carbaldehyde thiosemicarbazone (6), 5-(2-fluorophenyl)-furan-2-carbaldehyde thiosemicarbazone (7), 5-(4-methoxyphenyl)-furan-2-carbaldehyde thiosemicarbazone (8), 5-(1-naphthyl)-furan-2-carbaldehyde thiosemicarbazone (9), and 5-(1H-Pyrazol-5-yl)-furan-2-carbaldehyde thiosemicarbazone (10) were synthesized by condensing thiosemicarbazide with the respective furan-2-carbaldehyde in methanol. The prepared compounds were characterized by spectroscopic studies (FT-IR and NMR) and electrospray mass spectrometry. The molecular structures of 2, 6, 7, and 8 have also been determined by X-ray crystallography. Compounds 2, 6, and 7 crystallize in the E conformation about the N1-C6, N1-C11, and N1-C11 bonds, respectively, while 8 adopts the Z conformation about the N1-C12 bond with the presence of an intramolecular N2-H.O2 hydrogen bond. All prepared thiosemicarbazone derivatives were evaluated for their in vitro antibacterial, antifungal, and antitumor activities against Staphylococcus aureus strains, Candida albicans/Candida tropicalis fungi, and seven human tumor cell lines (HuTu80, H460, DU145, M-14, HT-29, MCF-7, and LNCaP), respectively. The antioxidant activity was also studied by the DPPH assay. Compound 5 exhibited significant antibacterial activity against Staphylococcus aureus ATCC700699 (MIC = 1 µg/mL) compared to the nitrofurantoin and gentamicin reference drugs (MIC = 1-25 and 10->100 µg/mL, respectively). Compound 4 was ten times less active than amphotericin B (MIC = 5 µg/mL) against Candida albicans (ATCC90028 and ATCC10231), while 1 exhibited a moderate effect of scavenging of DPPH radical (IC50 = 40.9 µg/mL) in comparison to ascorbic acid reference compound (IC50 = 22.0 µg/mL). Among all the studied thiosemicarbazones, 5 showed a higher cytotoxic activity (IC50 = 13.36-27.73 µ¿) in relation to the other tested compounds (IC50 = 34.84 - >372.34 µ¿) against all tested cell lines, except the LNCaP cell line, exhibiting its highest antiproliferative activity (IC50 = 13.36 µ¿) on the HuTu80 cell line. Besides, 8 and 9 exhibited high antitumor activity (IC50 = 13.31 and 7.69 µ¿, respectively) against the LNCaP cells.Revisión por pare

Synthesis and Characterization of New Palladium(II) Complexes with Ligands Derived from Furan-2-carbaldehyde and Benzaldehyde Thiosemicarbazone and their in vitro Cytotoxic Activities against Various Human Tumor Cell Lines

With the ligands 4-phenyl-1-(furan-2-carbaldehyde)thiosemicarbazone, HTSC1, (1), 4-phenyl-1- (5 -phenyl-furan-2-carbaldehyde)thiosemicarbazone, HTSC2 (2), o-methoxy-benzaldehydethiosemicarbazone, HTSC3 (3), and o-cyano-benzaldehydethiosemicarbazone, HTSC4 (4), the corresponding palladium(II) complexes, Pd(TSC1)2 (5), Pd(TSC2)2 (6), Pd(TSC3)2 (7), and Pd(TSC4)2 (8) were synthesized and characterized by elemental analysis and spectroscopic techniques. The crystal structure of Pd(TSC3)2 (7) was determined by single-crystal X-ray diffraction. Complex 7 shows a squareplanar geometry, where two deprotonated ligands are coordinated to the PdII center through the nitrogen and sulfur atoms in a trans arrangement. In vitro antitumor studies against different human tumor cell lines have revealed that the palladium(II) complexes 5– 8 are more cytotoxic (IC50 values in the range of 0.21 – 3.79 µM) than their corresponding ligands (1 – 4) (> 60 µM). These results indicate that the antiproliferative activity is enhanced when thiosemicarbazone ligands are coordinated to the metal. Among the studied palladium(II) complexes, 8 exhibits high antitumor activity on K562 chronic myelogenous leukemia cells with a low value of the inhibitory concentration (IC50 = 0.21 µM)

Synthesis and Characterization of New Palladium(II) Thiosemicarbazone Complexes and Their Cytotoxic Activity against Various Human Tumor Cell Lines

The palladium(II) bis-chelate complexes of the type [Pd(TSC1-5)2] (6–10), with their corresponding ligands 4-phenyl-1-(acetone)-thiosemicarbazone, HTSC1 (1), 4-phenyl-1-(2'-chloro-benzaldehyde)-thiosemicarbazone, HTSC2 (2), 4-phenyl-1-(3'-hydroxy-benzaldehyde)-thiosemicarbazone, HTSC3 (3), 4-phenyl-1-(2'-naphthaldehyde)-thiosemicarbazone, HTSC4 (4), and 4-phenyl-1-(1'-nitro-2'-naphthaldehyde)-thiosemicarbazone, HTSC5 (5), were synthesized and characterized by elemental analysis and spectroscopic techniques (IR and 1H- and 13C-NMR). The molecular structure of HTSC3, HTSC4, and [Pd(TSC1)2] (6) have been determined by single crystal X-ray crystallography. Complex 6 shows a square planar geometry with two deprotonated ligands coordinated to through the azomethine nitrogen and thione sulfur atoms in a cis arrangement. The in vitro cytotoxic activity measurements indicate that the palladium(II) complexes (–9.87¿M) exhibited higher antiproliferative activity than their free ligands (–70.86 and >250¿M) against different types of human tumor cell lines. Among all the studied palladium(II) complexes, the [Pd(TSC3)2] (8) complex exhibited high antitumor activity on the DU145 prostate carcinoma and K562 chronic myelogenous leukemia cells, with low values of the inhibitory concentration (0.01 and 0.02¿M, resp.)

Synthesis, Spectroscopic Characterization, Structural Studies, and in Vitro Antitumor Activities of Pyridine-3-carbaldehyde Thiosemicarbazone Derivatives

Eight new thiosemicarbazone derivatives, 6-(1-trifluoroethoxy)pyridine-3-carbaldehyde thiosemicarbazone (1), 6-(4'-fluorophenyl)pyridine-3-carbaldehyde thiosemicarbazone (2), 5-chloro-pyridine-3-carbaldehyde thiosemicarbazone (3), 2-chloro-5-bromo-pyridine-3-carbaldehyde thiosemicarbazone (4), 6-(3',4'-dimethoxyphenyl)pyridine-3-carbaldehyde thiosemicarbazone (5), 2-chloro-5-fluor-pyridine-3-carbaldehyde thiosemicarbazone, (6), 5-iodo-pyridine-3-carbaldehyde thiosemicarbazone (7), and 6-(3',5'-dichlorophenyl)pyridine-3-carbaldehyde thiosemicarbazone (8) were synthesized, from the reaction of the corresponding pyridine-3-carbaldehyde with thiosemicarbazide. The synthesized compounds were characterized by ESI-Mass, UV-Vis, IR, and NMR (1H, 13C, 19F) spectroscopic techniques. Molar mass values and spectroscopic data are consistent with the proposed structural formulas. The molecular structure of 7 has been also confirmed by single crystal X-ray diffraction. In the solid state 7 exists in the E conformation about the N2-N3 bond; 7 also presents the E conformation in solution, as evidenced by 1H NMR spectroscopy. The in vitro antitumor activity of the synthesized compounds was studied on six human tumor cell lines: H460 (lung large cell carcinoma), HuTu80 (duodenum adenocarcinoma), DU145 (prostate carcinoma), MCF-7 (breast adenocarcinoma), M-14 (amelanotic melanoma), and HT-29 (colon adenocarcinoma). Furthermore, toxicity studies in 3T3 normal cells were carried out for the prepared compounds. The results were expressed as IC50 and the selectivity index (SI) was calculated. Biological studies revealed that 1 (IC50 = 3.36 to 21.35 µM) displayed the highest antiproliferative activity, as compared to the other tested thiosemicarbazones (IC50 = 40.00 to >582.26 µM) against different types of human tumor cell lines. 1 was found to be about twice as cytotoxic (SI = 1.82) than 5-fluorouracile (5-FU) against the M14 cell line, indicating its efficiency in inhibiting the cell growth even at low concentrations. A slightly less efficient activity was shown by 1 towards the HuTu80 and MCF7 tumor cell lines, as compared to that of 5-FU. Therefore, 1 can be considered as a promising candidate to be used as a pharmacological agent, since it presents significant activity and was found to be more innocuous than the 5-FU anticancer drug against the 3T3 mouse embryo fibroblast cells

Nuevos materiales bioorgánicos de actividad antitumoral

El presente trabajo describe la síntesis, caracterización y evaluación de la actividad antitumoral in vitro de nuevos compuestos orgánicos derivados del 4-R-fenil-1-(X-tiazol-2/5-carbaldehído) tiosemicarbazona (R=H, fenilo; X=fenilo, o-/m-/p-OCH3-fenilo, p-Cl/F-fenilo, morfolinilo, Cl, N(CH3)2, metilo) y Xtriazol- 5-carbaldehído tiosemicarbazona (X=H, fenilo, p-Cl-fenilo). La preparación de estos compuestos se realizó mediante la reacción de condensación entre la tiosemicarbazida o 4-feniltiosemicarbazida y los derivados tiazol-2/5-carbaldehído o triazol-5-carbaldehído, para lo cual se empleó como solvente el metanol. La caracterización química se realizó mediante análisis elemental, espectrometría de masas, técnicas espectroscópicas de infrarrojo (FT-IR) y resonancia magnética nuclear (1H, 13C), y difracción de rayos X.El presente trabajo describe la síntesis, caracterización y evaluación de la actividad antitumoral in vitro de nuevos compuestos orgánicos derivados del 4-R-fenil-1-(X-tiazol-2/5-carbaldehído) tiosemicarbazona (R=H, fenilo; X=fenilo, o-/m-/p-OCH3-fenilo, p-Cl/F-fenilo, morfolinilo, Cl, N(CH3)2, metilo) y Xtriazol- 5-carbaldehído tiosemicarbazona (X=H, fenilo, p-Cl-fenilo). La preparación de estos compuestos se realizó mediante la reacción de condensación entre la tiosemicarbazida o 4-feniltiosemicarbazida y los derivados tiazol-2/5-carbaldehído o triazol-5-carbaldehído, para lo cual se empleó como solvente el metanol. La caracterización química se realizó mediante análisis elemental, espectrometría de masas, técnicas espectroscópicas de infrarrojo (FT-IR) y resonancia magnética nuclear (1H, 13C), y difracción de rayos X

5to. Congreso Internacional de Ciencia, Tecnología e Innovación para la Sociedad. Memoria académica

El V Congreso Internacional de Ciencia, Tecnología e Innovación para la Sociedad, CITIS 2019, realizado del 6 al 8 de febrero de 2019 y organizado por la Universidad Politécnica Salesiana, ofreció a la comunidad académica nacional e internacional una plataforma de comunicación unificada, dirigida a cubrir los problemas teóricos y prácticos de mayor impacto en la sociedad moderna desde la ingeniería. En esta edición, dedicada a los 25 años de vida de la UPS, los ejes temáticos estuvieron relacionados con la aplicación de la ciencia, el desarrollo tecnológico y la innovación en cinco pilares fundamentales de nuestra sociedad: la industria, la movilidad, la sostenibilidad ambiental, la información y las telecomunicaciones. El comité científico estuvo conformado formado por 48 investigadores procedentes de diez países: España, Reino Unido, Italia, Bélgica, México, Venezuela, Colombia, Brasil, Estados Unidos y Ecuador. Fueron recibidas un centenar de contribuciones, de las cuales 39 fueron aprobadas en forma de ponencias y 15 en formato poster. Estas contribuciones fueron presentadas de forma oral ante toda la comunidad académica que se dio cita en el Congreso, quienes desde el aula magna, el auditorio y la sala de usos múltiples de la Universidad Politécnica Salesiana, cumplieron respetuosamente la responsabilidad de representar a toda la sociedad en la revisión, aceptación y validación del conocimiento nuevo que fue presentado en cada exposición por los investigadores. Paralelo a las sesiones técnicas, el Congreso contó con espacios de presentación de posters científicos y cinco workshops en temáticas de vanguardia que cautivaron la atención de nuestros docentes y estudiantes. También en el marco del evento se impartieron un total de ocho conferencias magistrales en temas tan actuales como la gestión del conocimiento en la universidad-ecosistema, los retos y oportunidades de la industria 4.0, los avances de la investigación básica y aplicada en mecatrónica para el estudio de robots de nueva generación, la optimización en ingeniería con técnicas multi-objetivo, el desarrollo de las redes avanzadas en Latinoamérica y los mundos, la contaminación del aire debido al tránsito vehicular, el radón y los riesgos que representa este gas radiactivo para la salud humana, entre otros

Síntesis y caracterización estructural de los ligandos Tiomicarbazona, (X)-Ph-CH=N-NH-C(=S)-NR1R2 y sus respectivos complejos de platino (II) y paladio (II)

The present work reports on the synthesis and structural characterization of organic ligands derived from thiosemicarbazone (X)-Ph-CH=N-NH-C(=S)-NR!R2,; (X=H, 0-C=N, o-OCH3, = m-OH; R1H, R2=Ph) and their respective palladium(II) and platinum (ll) complexes. The two-dimensional Spectroscopy confirm that ligand LU1, present trans isomeric with respect to the imine group (ON) The molecular structure of palladium (ll) complex with o-methoxybenzaldehyde íhiosemicarbazone, carried out by X-ray diffraction, reveals a square-planar geometry with two bidentads desprotonated ligands (N, S) coordinated to the palladium in a trans- configuration.TesisEl presente trabajo informa acerca de la síntesis y caracterización estructural de los ligandos orgánicos derivados de la tiosemicarbazona, (X)-Ph-CH=N-NH-C(:=S)-NR!R2 (X=o-C=N, 0-OCHs, = m-OH; R1==H, R2=Ph) y sus respectivos complejos de platino(II) y paladio(II). Los Espectros bidimensionales confirman que el ligando LU1 (o-cianobenzaldehído tiosemicarbazona) presenta una isomería trans con respecto al enlace imino (ON). La estructura molecular del complejo de paladio(II) con el ligando o-etoxibenzaldehído tiosemicarbazona, realizada mediante difracción de rayos X, revela una geometría cuadrada plana ligeramente distorsionada donde dos ligandos bidentados (N, S) desprotonados se encuentran coordinados al ion paladio(II) en una configuración trans.

Complejos de cobre(II) y cobalto (II) con derivados de la piridina2/3-carbaldehído tiosemicarbazona como agentes antitumorales

Con la finalidad de usar menores concentraciones de fármacos en el rango micromolar y de disminuir los efectos secundarios en tratamientos anticancerígenos, este estudio describirá la preparación y evaluará la actividad antitumoral in vitro de los complejos de cobre(II) y cobalto(II) con ligandos derivados de la piridina-2/3-carbaldehído tiosemicarbazona. El efecto antiproliferante que se espera alcanzar de los compuestos se evidenciará por los bajos valores CI50 (concentración micromolar requerida para inhibir el 50 % de crecimiento celular) frente a las diferentes líneas de células tumorales de humano y los elevados valores CI50 ante una línea de células normales.Con la finalidad de usar menores concentraciones de fármacos en el rango micromolar y de disminuir los efectos secundarios en tratamientos anticancerígenos, este estudio describirá la preparación y evaluará la actividad antitumoral in vitro de los complejos de cobre(II) y cobalto(II) con ligandos derivados de la piridina-2/3-carbaldehído tiosemicarbazona. El efecto antiproliferante que se espera alcanzar de los compuestos se evidenciará por los bajos valores CI50 (concentración micromolar requerida para inhibir el 50 % de crecimiento celular) frente a las diferentes líneas de células tumorales de humano y los elevados valores CI50 ante una línea de células normales

Novel Thiosemicarbazone Derivatives from Furan-2-Carbaldehyde: Synthesis, Characterization, Crystal Structures, and Antibacterial, Antifungal, Antioxidant, and Antitumor Activities

Ten new thiosemicarbazone derivatives, furan-2-carbaldehyde thiosemicarbazone (1), 3-methyl-furan-2-carbaldehyde thiosemicarbazone (2), 5-hydroxymethyl-furan-2-carbaldehyde thiosemicarbazone (3), 5-trifluoromethyl-furan-2-carbaldehyde thiosemicarbazone (4), 5-nitro-furan-2-carbaldehyde thiosemicarbazone (5), 5-phenyl-furan-2-carbaldehyde thiosemicarbazone (6), 5-(2-fluorophenyl)-furan-2-carbaldehyde thiosemicarbazone (7), 5-(4-methoxyphenyl)-furan-2-carbaldehyde thiosemicarbazone (8), 5-(1-naphthyl)-furan-2-carbaldehyde thiosemicarbazone (9), and 5-(1H-Pyrazol-5-yl)-furan-2-carbaldehyde thiosemicarbazone (10) were synthesized by condensing thiosemicarbazide with the respective furan-2-carbaldehyde in methanol. The prepared compounds were characterized by spectroscopic studies (FT-IR and NMR) and electrospray mass spectrometry. The molecular structures of 2, 6, 7, and 8 have also been determined by X-ray crystallography. Compounds 2, 6, and 7 crystallize in the E conformation about the N1-C6, N1-C11, and N1-C11 bonds, respectively, while 8 adopts the Z conformation about the N1-C12 bond with the presence of an intramolecular N2-H.O2 hydrogen bond. All prepared thiosemicarbazone derivatives were evaluated for their in vitro antibacterial, antifungal, and antitumor activities against Staphylococcus aureus strains, Candida albicans/Candida tropicalis fungi, and seven human tumor cell lines (HuTu80, H460, DU145, M-14, HT-29, MCF-7, and LNCaP), respectively. The antioxidant activity was also studied by the DPPH assay. Compound 5 exhibited significant antibacterial activity against Staphylococcus aureus ATCC700699 (MIC = 1 µg/mL) compared to the nitrofurantoin and gentamicin reference drugs (MIC = 1-25 and 10->100 µg/mL, respectively). Compound 4 was ten times less active than amphotericin B (MIC = 5 µg/mL) against Candida albicans (ATCC90028 and ATCC10231), while 1 exhibited a moderate effect of scavenging of DPPH radical (IC50 = 40.9 µg/mL) in comparison to ascorbic acid reference compound (IC50 = 22.0 µg/mL). Among all the studied thiosemicarbazones, 5 showed a higher cytotoxic activity (IC50 = 13.36-27.73 µ¿) in relation to the other tested compounds (IC50 = 34.84 - >372.34 µ¿) against all tested cell lines, except the LNCaP cell line, exhibiting its highest antiproliferative activity (IC50 = 13.36 µ¿) on the HuTu80 cell line. Besides, 8 and 9 exhibited high antitumor activity (IC50 = 13.31 and 7.69 µ¿, respectively) against the LNCaP cells