244219-99-6Relevant articles and documents
Synthesis, characterization, and biologic activity of new acyl hydrazides and 1,3,4-oxadiazole derivatives
Bleotu, Coralia,Diaconu, Carmen Cristina,Hanganu, Anamaria,Ionita, Petre,Limban, Carmen,Matei, Lilia,Nemes, Roxana Maria,Nicolau, Ioana,Nuta, Diana Camelia,P?un, Anca,Radulescu, Cristiana,Tatibou?t, Arnaud,Zarafu, Irina
, (2020/08/28)
Starting from isoniazid and carboxylic acids as precursors, thirteen new hydrazides and 1,3,4-oxadiazoles of 2-(4-substituted-phenoxymethyl)-benzoic acids were synthesized and characterized by appropriate means. Their biological properties were evaluated in terms of apoptosis, cell cycle blocking, and drug metabolism gene expression on HCT-8 and HT-29 cell lines. In vitro antimicrobial tests were performed by the microplate Alamar Blue assay for the anti-mycobacterial activities and an adapted agar disk diffusion technique for other non-tubercular bacterial strains. The best antibacterial activity (anti-Mycobacterium tuberculosis effects) was proved by 9. Compounds 7, 8, and 9 determined blocking of G1 phase. Compound 7 proved to be toxic, inducing apoptosis in 54percent of cells after 72 h, an effect that can be predicted by the increased expression of mRNA caspases 3 and 7 after 24 h. The influence of compounds on gene expression of enzymes implicated in drug metabolism indicates that synthesized compounds could be metabolized via other pathways than NAT2, spanning adverse effects of isoniazid. Compound 9 had the best antibacterial activity, being used as a disinfectant agent. Compounds 7, 8, and 9, seemed to have antitumor potential. Further studies on the action mechanism of these compounds on the cell cycle may bring new information regarding their biological activity.
New substituted benzoylthiourea derivatives: From design to antimicrobial applications
Bleotu, Coralia,Caproiu, Miron Teodor,Chifiriuc, Mariana Carmen,Dumitrascu, Florea,Ferbinteanu, Marilena,Limban, Carmen,Marutescu, Luminita Gabriela,Nuta, Diana Camelia,Pintilie, Lucia,Stefaniu, Amalia,Vlad, Ilinca Margareta
, (2020/04/10)
The increasing threat of antimicrobial resistance to all currently available therapeutic agents has urged the development of novel antimicrobials. In this context, a series of new benzoylthiourea derivatives substituted with one or more fluorine atoms and
Bioevaluation of novel anti-biofilm coatings based on PVP/Fe 3O4 nanostructures and 2-((4-Ethylphenoxy)methyl)-N- (arylcarbamothioyl)benzamides
Limban, Carmen,Missir, Alexandru Vasile,Grumezescu, Alexandru Mihai,Oprea, Alexandra Elena,Grumezescu, Valentina,Vasile, Bogdan Stefan,Socol, Gabriel,Trusca, Roxana,Caproiu, Miron Teodor,Chifiriuc, Mariana Carmen,Galateanu, Bianca,Costache, Marieta,Morusciag, Laurentiu,Pircalabioru, Gratiela,Nuta, Diana Camelia
, p. 12011 - 12030 (2014/12/10)
Novel derivatives were prepared by reaction of aromatic amines with 2-(4-ethylphenoxymethyl)benzoyl isothiocyanate, affording the N-[2-(4-ethylphenoxymethyl) benzoyl]-N′-(substituted phenyl)thiourea. Structural elucidation of these compounds was performed by IR, NMR spectroscopy and elemental analysis. The new compounds were used in combination with Fe 3O4 and polyvinylpyrrolidone (PVP) for the coating of medical surfaces. In our experiments, catheter pieces were coated by Matrix Assisted Pulsed Laser Evaporation (MAPLE) technique. The microbial adherence ability was investigated in 6 multi-well plates by using culture based methods. The obtained surfaces were also assessed for their cytotoxicity with respect to osteoblast cells, by using fluorescence microscopy and MTT assay. The prepared surfaces by advanced laser processing inhibited the adherence and biofilm development ability of Staphylococcus aureus and Pseudomonas aeruginosa tested strains while cytotoxic effects on the 3T3-E1 preosteoblasts embedded in layer shaped alginate hydrogels were not observed. These results suggest that the obtained medical surfaces, based on the novel thiourea derivatives and magnetic nanoparticles with a polymeric shell could represent a promising alternative for the development of new and effective anti-infective strategies.
Synthesis and antimicrobial properties of new 2-((4-ethylphenoxy)methyl) benzoylthioureas
Limban, Carmen,Missir, Alexandru V.,Chirita, Ileana C.,Nitulescu, George M.,Caproiu, Miron T.,Chifiriuc, Mariana C.,Israil, Anca M.
scheme or table, p. 60 - 69 (2012/01/14)
New acylthiourea derivatives, 2-((4-ethylphenoxy)methyl)-N- (phenylcarbamothioyl)benzamides, were tested by qualitative and quantitative methods on various bacterial and fungal strains and proved to be active at low concentrations against Gram-positive and Gram-negative bacteria as well as fungi. These compounds were prepared by the reaction of 2-((4-ethylphenoxy) methyl)benzoyl isothiocyanate with various primary aromatic amines, and were characterised by melting point and solubility. The structures were identified by elemental analysis, 1H and 13C NMR, and IR spectral data. The level of antimicrobial activity of the new 2-((4-ethylphenoxy)methyl) benzoylthiourea derivatives was dependent on the type, number and position of the substituent on the phenyl group attached to thiourea nitrogen. The iodine and nitro substituents favoured the antimicrobial activity against the Gram-negative bacterial strains, while the highest inhibitory effect against Gram-positive and fungal strains was exhibited by compounds with electron-donating substituents such as the methyl and ethyl groups.
New 2-(4-ethyl-phenoxymethyl)benzoic acid thioureides. Synthesis, spectral analyses and microbiological assays
Limban, Carmen,Missir, Alexandru-Vasile,Chirita, Ileana Cornelia,Nitulescu, George Mihai,Draghici, Constantin,Caproiu, Miron T.,Chifiriuc, Mariana Carmen,Dracea, Olguta Nicoleta
experimental part, p. 637 - 642 (2010/07/05)
We present in this paper the synthesis of new thioureides of the 2-(4-ethyl-phenoxymethyl)benzoic acid performed by the addition of various primary aromatic amines to the 2-(4-ethyl-phenoxymethyl)benzoyl isothiocyanate. We established the best reaction conditions in order to obtain with good yields high pure compounds. The chemical structure and the purity of the new compounds were confirmed by 1H-NMR, 13C-NMR, FT-IR spectra and using elemental analysis. The obtained substances were tested by qualitative and quantitative methods on various microbial and fungal strains and proved to be active at low concentrations both on gram positive, gram negative bacteria and fungi being a possible future therapeutical solution.
Amide derivatives and nociceptin antagonists
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, (2008/06/13)
The present invention relates to a compound of the formula [1′] wherein R2is lower alkyl optionally substituted by hydroxy, amino and the like, ring B is phenyl, thienyl and the like, E is a single bond, —O—, —S— and the like, ring G is aryl, heterocyclic group and the like, R5is halogen atom, hydroxy, lower alkyl optionally substituted by halogen atom etc., and the like, t is 0 or an integer of 1 to 5, when t is an integer of 2 to 5, each R5may be the same or different, m is 0 or an integer of 1 to 8, and n is 0 or an integer of 1 to 4, and a nociceptin antagonist containing compound [1′] as an active ingredient. The compound [1′] shows, due to nociceptin antagonistic action, analgesic effect against sharp pain such as postoperative pain and the like. The present invention also relates to the use of certain amide derivative inclusive of compound [1′] as a nociceptin antagonist or analgesic.
4-Aminoquinolines: Novel nociceptin antagonists with analgesic activity
Shinkai,Ito,Iida,Kitao,Yamada,Uchida
, p. 4667 - 4677 (2007/10/03)
Small-molecule nociceptin antagonists were synthesized to examine their therapeutic potential. After a 4-aminoquinoline derivative was found to bind with the human ORL1 receptor, a series of 4-aminoquinolines and related compounds were synthesized and their binding was evaluated. Elucidation of structure - Activity relationships eventually led to the optimum compounds. One of these compounds, N-(4-amino-2-methylquinolin-6-yl)-2-(4-ethylphenoxymethyl)benzamide hydrochloride (11) not only antagonized nociceptin-induced allodynia in mice but also showed analgesic effect in a hot plate test using mice and in a formalin test using rats. Its analgesic effect was not antagonized by the opioid antagonist naloxone. These results indicate that this nociceptin antagonist has the potential to become a novel type of analgesic that differs from μ-opioid agonists.
