133239-50-6Relevant articles and documents
Synthesis, in vitro and in vivo antimycobacterial activities of diclofenac acid hydrazones and amides
Sriram, Dharmarajan,Yogeeswari, Perumal,Devakaram, Ruth Vandana
, p. 3113 - 3118 (2006)
Various diclofenac acid hydrazones and amides were synthesized and evaluated for in vitro and in vivo antimycobacterial activities against Mycobacterium tuberculosis. Preliminary results indicated that most of the compounds demonstrated better in vitro antimycobacterial activity (MIC: 0.0383-7.53 μM) than diclofenac (MIC: 21.10 μM) and ciprofloxacin (MIC: 9.41 μM). Among the synthesized compounds, 1-cyclopropyl-6-fluoro-8-methoxy- 7-[[N4-(2-(2-(2,6-dichlorophenylamino)phenyl)acetyl)-3-methyl]-N 1-piperazinyl]-4-oxo-1,4-dihydro-3-quinoline carboxylic acid (5d) was found to be the most active compound in vitro with MIC of 0.0383 μM and was more potent than first line antitubercular drug isoniazid (MIC: 0.1822 μM). In the in vivo animal model 5d decreased the bacterial load in lung and spleen tissues with 2.42 - and 3.66 - log 10 protections, respectively, at 25 mg/kg body weight.
Synthesis of Novel Diclofenac Hydrazones: Molecular Docking, Anti-Inflammatory, Analgesic, and Ulcerogenic Activity
Al-Dhfyan, Abdullah,Al-Omar, Mohamed A.,Al-Tuwajiri, Hanaa M.,Alsaif, Nawaf A.,Bhat, Mashooq A.,Naglah, Ahmed M.
, (2020)
This study was aimed to design novel diclofenac hydrazones having anti-inflammatory and analgesic activity with gastric sparing effect. A new series of 2-[2-(2,6-dichloroanilino)phenyl]-N'-[(substituted phenyl) methylidene] acetohydrazide derivatives (1-14) were synthesized and evaluated for their anti-inflammatory, analgesic, and ulcerogenic activity. The compounds were identified and confirmed by elemental analysis and spectral data. During anti-inflammatory activity by carrageenan-induced paw edema method, compounds (2, 3, 7, 8, 11, and 13) were found to be most promising. Compounds 3, 8, and 13 have been found to have significant analgesic activity compared to the reference drug diclofenac in analgesic activity by both the hot plate method and acetic acid-induced writhing method. The compounds which presented highly significant anti-inflammatory and analgesic activity were further tested for their ulcerogenic activity. Compounds 3 and 8 showed maximum ulcerogenic reduction activities. Compound 8 was found to have LD50 of 168 mg/kg. Compound 8 with 3,5-dimethoxy-4-hydroxyphenyl substitution was found to be the most promising anti-inflammatory and analgesic agent with gastric sparing activity. Molecular docking of compounds was performed for COX-1/COX-2 binding site. Lead compound 8 showed better binding affinities of -9.4 kJ/mol with both COX-1 and COX-2 as compared to the standard drug, diclofenac with binding affinities of -6.6 kJ/mol and -8.1 kJ/mol for COX-1 and COX-2, respectively.
Cu(II) complexes of hydrazones–NSAID conjugates: synthesis, characterization and anticancer activity
Bandyopadhyay, Parbati,Basu, Soumya,Chikate, Rajeev,Chikate, Tanmayee,Kaur, Jatinder
, p. 3186 - 3202 (2020/12/22)
The hydrazones of nonsteroidal anti-inflammatory drugs (NSAIDs) diclofenac and ibuprofen are synthesized with aldehydes of pyridine and imidazole and are characterized by 1H, 13C and mass spectroscopy. Cu(II) complexes of hydrazones constructed from these ligands possess square planar geometry for bidentate diclofenac-hydrazone and tridentate ibuprofen-hydrazone conjugates with [Cu(L)2] and [Cu(L)Cl] compositions, respectively. The observed irreversible Cu(II)/Cu(I) redox couple in the range of +0.20 to +0.61 V is due to the substantial distortion in the square-planar geometry. ESR studies indicate the appreciably covalent character within M–L bonding due to extensive delocalization of electron from d x2–-y2 orbital. The hydrazone–NSAID conjugates exhibit substantial cytotoxicity against A-549, HCT-116 and MDA-MB-231 cancer cell lines with ibuprofen-imidazole-hydrazone ligand possessing the lowest IC50 (2.26 μM) amongst the synthesized NSAID-conjugates. Interestingly, its Cu(II) complex also displays excellent anticancer activity against MDA-MB- 231 with IC50 value of 3.58 μM. Such a feature may be ascribed to the synergistic association of Cu(II)–NSAID–hydrazone linkage. Thus, conjugation of NSAID with hydrazone and its complexation with a bioactive metal ion may be regarded as a potential strategy for designing of non-platinum anticancer agents.
