71658-29-2Relevant academic research and scientific papers
Antiaging activity, molecular docking, and prediction of percutaneous absorption parameters of quinoline–hydrazone hybrids
Osorio, Edison,Bravo, Karent,Cardona, Wilson,Yepes, Andres,Osorio, Edison H.,Coa, Juan C.
, p. 1959 - 1973 (2019)
The application of antiaging agents can contribute to the prevention and control of skin photoaging. In the current research, nine quinoline–hydrazone hybrids were synthesized to obtain biologically active compounds as possible antiaging agents. The compounds were tested through a comprehensive in vitro evaluation of antielastase, anticollagenase, and antihyaluronidase activities along with the determination of their potential to quench reactive oxygen species (ROS) by the ORAC method. The selected hybrids were subsequently tested on human dermal fibroblasts (HDF) to reveal possible UVB photoprotective activity. The most potent antiaging protection of all the prepared compounds was shown by the trihydroxylated quinoline–hydrazones 5 and 9, which showed the best collagenase inhibition (IC50 = 39.4 and 45.6 μM, respectively). Compound 5 also showed activity against elastase and hyaluronidase (IC50 = 164.2 and 318.8 μM, respectively). The molecular docking results suggest that the difference of inhibition between 5 and 9 is principally attributed to the hydrogen bonds interactions in the residues His218 and His228, and Zn atom in collagenase, Val216 in elastase and Tyr75 in hyaluronidase. In addition, compounds 5 and 9 were able to significantly protect human skin cells from UVB radiation in vitro. These compounds significantly decreased UVB-induced MMP-1 and ROS production and inhibited the suppression of type I procollagen synthesis in cultured HDF. The in silico dermatopharmacokinetic parameters showed promising results. Therefore, our study presented promising results for antiaging drug discovery, focusing on quinoline–hydrazone hybrids as dual inhibitors of skin aging-related enzymes, antioxidants, and inhibitors of the biological effects of UVB irradiation.
Synthesis, leishmanicidal, trypanocidal and cytotoxic activity of quinoline-hydrazone hybrids
Coa, Juan Carlos,Castrillón, Wilson,Cardona, Wilson,Carda, Miguel,Ospina, Victoria,Mu?oz, July Andrea,Vélez, Iván D.,Robledo, Sara M.
, p. 746 - 753 (2015/08/06)
Abstract Cutaneous leishmaniasis and Chagas disease are vector-borne parasitic disease causing serious risks to million people living in poverty-stricken areas. Both diseases are a major health problem in Latin America, and currently drugs for the effective treatment of these diseases have important concerns related with efficacy or toxicity than need to be addressed.We report herein the synthesis and biological activities (cytotoxicity, leishmanicidal and trypanocidal activities) of ten quinolone-hydrazone hybrids. The structure of the products was elucidated by spectrometric analyses. The synthesized compounds were evaluated against amastigotes forms of L. (V) panamensis which is the most prevalent Leishmania species in Colombia and Trypanosoma cruzi that is the major pathogenic species to humans; in turn, cytotoxicity was evaluated against human U-937 macrophages.Compounds 6b, 6c and 8 showed activity against L. (V) panamensis with EC50 of 6.5 ± 0.8 μg/mL (21.2 μM), 0.8 ± 0.0 μg/mL (2.6 μM) and 3.4 ± 0.6 μg/mL (11.1 μM), respectively, while compounds 6a and 6c had activity against T. cruzi. with EC50 values of 1.4 ± 0.3 μg/mL (4.8 μM) and 6.6 ± 0.3 μg/mL (4.6 μM), respectively. Even compound 6a showed better activity against T. cruzi than the standard drug benznidazole with EC50 Combining double low line 10.5 ± 1.8 μg/mL (40.3 μM).Analysis of the results obtained against leishmaniasis indicates that antiparasite activity is related to the presence of 2-substituted quinoline (isoquinolinic core) and the hydroxyl group in positions 3 and 4 of the aromatic ring. Although the majority of these compounds were highly cytotoxic, the antiparasite activity was higher than cytotoxicity and therefore, they still have potential to be considered as hit molecules for leishmanicidal and trypanocidal drug development.
Oxovanadium(IV,V) complexes of salicylidene-2-picoloyl hydrazone Schiff base and related ligands
Sarkar, Asit R.,Mandal, Shipra,Pal, Sukdeb,Chakrabarty, Somnath,Chakrabarty, Aniruddha
, p. 185 - 190 (2007/10/03)
Oxovanadium(iv,v) complexes having O4N coordination environment have been synthesized in the solid state, formulated as M[VO2(L/ L′/L″)(H2O)], where M = K or NH4; H 2(L/L′/L″) is the Schiff base ligand, obtained by condensation of salicylaldehyde with 2-picoloyl (L), 2-quinoloyl (L′), 8-quinoloyl (L″) hydrazides. Dimeric complexes having the formulation [(VOL)2μ-O] have also been synthesized. Both the salicylidene-picoloyl hydrazone and the salicylidene-2-quinoloyl hydrazone ligands, in their dideprotonated form, coordinate to both vanadium in its +4 and +5 state, through O, N, O donor atoms, while, the ligand H2L″ will act as a NNO donor ligand. Thus, in the dioxo vanadium complexes with the ligands L and L′, the central vanadium core will have the O4N environment, which can be treated as a model to mimic the active site of vanadium haloperoxidases.
Magnesium(II), Zinc(II), Cadmium(II), Mercury(II) and Lead(II) Complexes of Salicylidene-Aroyl Hydrazides
Dutta, R. L.,Hossain, Md. Munkir
, p. 985 - 988 (2007/10/02)
Magnesium(II), zinc(II), cadmium(II), mercury(II) and lead(II) complexes of (substituted) salicylidene-benzoyl hydrazide, salicylidene-2-picoloyl hydrazide, salicylidene-2-quinoloyl hydrazide and salicylidene-8-quinoloyl hydrazide schiff bases have been s
