- Evaluation of the cell cytotoxicity and DNA/BSA binding and cleavage activity of some dioxidovanadium(V) complexes containing aroylhydrazones
-
Three dioxidovanadium(V) complexes [VO2L1-3] (1-3) [HL1 = 1-napthoyl hydrazone of 2-acetyl pyridine, HL2 = 2-furoyl hydrazone of 2-acetyl pyridine and H2L3 = isonicotinoyl hydrazone of 2-hy
- Dash, Subhashree P.,Panda, Alok K.,Pasayat, Sagarika,Majumder, Sudarshana,Biswas, Ashis,Kaminsky, Werner,Mukhopadhyay, Subhadip,Bhutia, Sujit K.,Dinda, Rupam
-
-
Read Online
- Synthesis, characterization and structural studies of diorganotin(IV) complexes with Schiff base ligand salicylaldehyde isonicotinylhydrazone
-
Eight diorganotin(IV) complexes of salicylaldehyde isonicotinylhydrazone (H2SalN) R2Sn(SalN) R = t-Bu 1, Ph 2, PhCH2 3, o-ClC6H4CH2 4, p-ClC6H 4CH2 5, m-ClC
- Yin, Han Dong,Hong, Min,Li, Gang,Wang, Da Qi
-
-
Read Online
- Antiproliferative and antioxidative effects of novel hydrazone derivatives bearing coumarin and chromene moiety
-
[InlineMediaObject not available: see fulltext.] A series of new hybrid molecules with a hydrazone fragment were synthesized and characterized by Fourier transform-infrared spectroscopy, nuclear magnetic resonance, mass spectrometry, and elemental analysi
- Angelova, Violina T.,Vassilev, Nikolay G.,Nikolova-Mladenova, Boryana,Vitas, Jasmina,Malba?a, Radomir,Momekov, Georgi,Djukic, Mirjana,Saso, Luciano
-
-
Read Online
- Field enhanced thermally activated mechanism in a square Dy4 aggregate
-
A rare μ4-OH centred square Dy4 aggregate displays a field enhanced thermally activated mechanism with 3-fold increase in the single-molecule magnetic relaxation barrier upon application of an optimal field. The Royal Society of Chem
- Xue, Shufang,Zhao, Lang,Guo, Yun-Nan,Chen, Xiao-Hua,Tang, Jinkui
-
-
Read Online
- The interaction of pyridoxal isonicotinoyl hydrazone (PIH) and salicylaldehyde isonicotinoyl hydrazone (SIH) with iron
-
The interaction of pyridoxal isonicotinoyl hydrazone (PIH) and salicylaldehyde isonicotinoyl hydrazone (SIH), two important biologically active chelators, with iron has been investigated by spectrophotometric methods. High iron(III) affinity constants were determined for PIH, logβ2 = 37.0 and SIH, logβ2 = 37.6. The associated redox potentials of the iron complexes were determined using cyclic voltammetry at pH 7.4 as + 130 mV (vs normal hydrogen electrode, NHE) for PIH and + 136 mV(vs NHE) for SIH. These redox potentials are much higher than those corresponding to iron chelators in clinical use, namely deferiprone, ? 620 mV; desferasirox, ? 600 mV and desferrioxamine, ? 468 mV. Although the positive redox potentials of SIH and PIH are similar to that of EDTA, namely + 120 mV, the iron complexes of these two hydrazone chelators, unlike the iron complex of EDTA, do not redox cycle in the presence of vitamin C. These properties render PIH and SIH as excellent scavengers of iron, under biological conditions. Both SIH and PIH scavenge mononuclear iron(II) and iron(III) rapidly. These fast kinetic properties of the hydrazone-based chelators provide a ready explanation for the adoption of SIH in fluorescence-based methods for the quantification of cytosolic iron(II).
- Chen, Yu-Lin,Kong, Xiaole,Xie, Yuanyuan,Hider, Robert C.
-
-
Read Online
- Biochemical relevance of Cr(III) complexes of isoniazid: synthesis, characterization, DFT, antibacterial screening, antioxidant activity and glucose-lowering effect in STZ-induced diabetic rats
-
Molecular mechanism suggests that the incorporation of an antioxidant organic moiety to chromium will be a sound strategy for the synthesis of safer and more effective hypoglycemic compounds. Two Schiff base ligands were derived by condensation of isonico
- Shukla, Satyendra N.,Gaur, Pratiksha,Jhariya, Sangeeta,Chaurasia, Bhaskar,Vaidya, Preeti,Azam, Mohammad
-
-
Read Online
- The hydrolytic susceptibility of prochelator BSIH in aqueous solutions
-
The prochelator BSIH ((E)-N′-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylidene)isonicotinohydrazide) contains a boronate group that prevents metal coordination until reaction with peroxide releases the iron chelator SIH ((E)-N′-(2-hydroxybenzyli
- Wang, Qin,Franz, Katherine J.
-
-
Read Online
- A novel 2D vanadium(V)-isonicotinohydrazide coordination polymer, C 15H16AgN4O8V: Synthesis, structure, catalytic activity and DFT calculation
-
A novel two-dimensional 3d-4d transition metal-based coordination polymer [VO(OCH3)(OHCH3)(L)Ag(NO3)]∞ (1) has been synthesized and characterized by single crystal X-ray diffraction and fluorescence spectroscopy
- Monfared, Hassan Hosseini,Alavi, Sohaila,Farrokhi, Afsaneh,Vahedpour, Morteza,Mayer, Peter
-
-
Read Online
- Spectroscopic, molecular docking and structural activity studies of (E)-N′-(substituted benzylidene/methylene) isonicotinohydrazide derivatives for DNA binding and their biological screening
-
Acid catalyzed condensation of isoniazid with a number of suitably substituted aromatic and heterocyclic aldehydes was carried out in dry ethanol to afford the title (E)-N′-(substituted benzylidene/methylene) isonicotinohydrazides (SF 1 – SF 4) in good yi
- Arshad, Nasima,Perveen, Fouzia,Saeed, Aamer,Channar, Pervaiz Ali,Farooqi, Shahid Iqbal,Larik, Fayaz Ali,Ismail, Hammad,Mirza, Bushra
-
-
Read Online
- A pro-chelator triggered by hydrogen peroxide inhibits iron-promoted hydroxyl radical formation
-
The synthesis and structural characterization of a new pro-chelating agent, isonicotinic acid [2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzylidene]-hydrazide (BSIH), are presented. BSIH only weakly interacts with iron unless hydrogen peroxide (H
- Charkoudian, Louise K.,Pham, David M.,Franz, Katherine J.
-
-
Read Online
- N-acylhydrazones confer inhibitory efficacy against New Delhi metallo-β-lactamase-1
-
The expression of β-lactamases, especially metallo-β-lactamases (MβLs) in bacteria is one of the main causes of drug resistance. In this work, an effective N-acylhydrazone scaffold as MβL inhibitor was constructed and characterized. The biological activity assays indicated that the synthesized N-acylhydrazones 1–11 preferentially inhibited MβL NDM-1, and 1 was found to be the most effective inhibitor with an IC50 of 1.2 μM. Analysis of IC50 data revealed a structure–activity relationship, which is that the pyridine and hydroxylbenzene substituents at 2-position improved inhibition of the compounds on NDM-1. ITC and enzyme kinetics assays suggested that it reversibly and competitively inhibited NDM-1 (Ki = 0.29 ± 0.05 μM). The synthesized N-acylhydrazones showed synergistic antibacterial activities with meropenem, reduced 4–16-fold MIC of meropenem on NDM-1- producing E. coli BL21 (DE3), while 1 restored 4-fold activity of meropenem on K. pneumonia expressing NDM-1 (NDM-K. pneumoniae). The mice experiments suggested that 1 combined meropenem to fight against NDM-K. pneumoniae infection in the spleen and liver. Cytotoxicity assays showed that 1 and 2 have low cytotoxicity. This study offered a new framework for the development of NDM-1 inhibitors.
- Gao, Han,Li, Jia-Qi,Kang, Peng-Wei,Chigan, Jia-Zhu,Wang, Huan,Liu, Lu,Xu, Yin-Sui,Zhai, Le,Yang, Ke-Wu
-
-
- Promising Ag(I) complexes with N-acylhydrazones from aromatic aldehydes and isoniazid against multidrug resistance in tuberculosis
-
In the present work, synthesis, characterization and antitubercular assays of N-acylhydrazones derivatives and their corresponding silver(I) complexes are described. The compounds were characterized by elemental analysis, IR and NMR spectroscopic measurem
- dos Santos, Paulo Victor P.,Ribeiro, Camila M.,Pavan, Fernando R.,Corbi, Pedro P.,Bergamini, Fernando R.G.,Carvalho, Marcos A.,D'Oliveria, Kaique A.,Cuin, Alexandre
-
-
- Acylhydrazones as isoniazid derivatives with multi-target profiles for the treatment of Alzheimer's disease: Radical scavenging, myeloperoxidase/acetylcholinesterase inhibition and biometal chelation
-
Acylhydrazones 1a-o, derived from isoniazid, were synthesized and evaluated for Myeloperoxidase (MPO) and Acetylcholinesterase (AChE) inhibition, as well as their antioxidant and metal chelating activities, with the purpose of investigating potential multi-target profiles for the treatment of Alzheimer's disease. Synthesized compounds were tested using the 2,2-diphenyl-2-picrylhydrazyl (DPPH) method and 1i, 1j and 1 m showed radical scavenging ability. Compounds 1b, 1 h, 1i, 1 m and 1o inhibited MPO activity (10 μM) at 96.1 ± 5.5%, 90 ± 2.1%, 100.3 ± 1.7%, 80.1 ± 9.4% and 82.2 ± 10.6%, respectively, and only compound 1 m was able to inhibit 54.2 ± 1.7% of AChE activity (100 μM). Docking studies of the most potent compound 1 m were carried out, and the computational results provided the theoretical basis of enzyme inhibition. Furthermore, compound 1 m was able to form complexes with Fe2+ and Zn2+ ions in a 2:1 ligand:metal ratio according to the Job Plot method.
- Henriques, Ruan Roberto,Junior, Marcos Antonio de Abreu Lopes,Nogueira, Thayssa Lisboa do Couto,Romeiro, Nelilma Correia,Silva, Leandro Louback da,Farias, André Borges,Quimas, Jo?o Victor Fernandes,Santos, Daniela Corrêa,Souza, Andréa Luzia Ferreira de
-
-
- Composition and Structure of Complexes Formed in GeCl4–2-Hydroxybenzene(2-hydroxynaphthaline-1)carbaldehyde Isonicotinoylhydrazone–ZnCl2–Methanol
-
Abstract: Tetrachlorozincates [Ge(LH)2][ZnCl4]?CH3OH were isolated for the first time from isonicotinoylhydrazone 2-hydroxybenzene (2-hydroxynaphyl-1)carbaldehyde (H2L)–GeCl4–ZnCl2–CH3
- Shmatkova,Seifullina,Skorokhod,Morozov,Popov,Gazieva
-
p. 2323 - 2327
(2021/02/12)
-
- BF3-Etherate-catalyzed tandem reaction of 2-formylarylketones with electron-rich arenes/heteroarenes: An assembly of isobenzofurans
-
An efficient and BF3·Et2O-catalyzed chemoselective synthesis of diversified 1,3-diarylisobenzofuran in a high yield has been described. The reaction proceeds through sequential hydroarylation-cyclization between 2-formylarylketones and electron-rich arenes/heteroarenes. Advantageous features of the developed methodology include operational simplicity, a broad substrate scope, and applicability towards gram scale synthesis. The utility of isobenzofuran derivatives as the diene was extended to the synthesis of [4+2] cyclo-adducts with DMAD and the synthesis of 1,2-dicarbonylarenes in good yields.
- Mishra, Pawan K.,Kumar, Ankit,Verma, Akhilesh K.
-
supporting information
p. 6122 - 6125
(2020/06/18)
-
- Design and Synthesis of 5-Oxoimidazolidine Derivatives in Search of Potent Antitubercular and Antifungal agents
-
5-Oxoimidazolidines are significant outfits because of their impending biological activity and also because of their resourcefulness as synthons in organic revolutions. The designed library was docked against the crystal structure of Mycobacterium tuberculosis enoyl reductase (2B35) and crystal structure of flavohemoglobin (3OZU) to know the best fit molecule. The ADMET parameters revealed that the compounds have synthetic acceptability and leadlikeness. Accordingly, the selected 5-oxoimidazolidines (S1-8 and A1-8) were synthesized from carbohydrazides (1a-h) and characterized by spectral data. Further, these compounds were screened against M. tuberculosis H37RV by microplate Alamar Blue assay method. The compound S3 showed minimum inhibitory concentration at 6.25 μg/mL, while the antifungal screening demonstrated S1 as a promising lead with the corresponding zone of inhibitions of 22 mm and 18 mm against Aspergillus niger and Candida albicans.
- Singirisetty, Triveni,Chilamakuru, Naresh Babu,Peraman, Ramalingam,Mallela, Vijaya Jyothi,Sana, Maheswari P.,Begum, Inthiyaz
-
p. 441 - 451
(2021/02/02)
-
- Harnessing the reactivity of Ortho-formyl-arylketones: Base-promoted regiospecific synthesis of functionalized isoquinolines
-
An efficient and base-mediated one-pot regiospecific synthesis of structurally diversified isoquinolines and benzo[h] isoquinolines from easily accessible ortho-formyl-arylketones and aryl/(het)arylmethanamines has been described. Challenging 3-alkynyl/alkenyl isoquinolines and bis-isoquinolines were easily attained through this developed chemistry, which can be further used for various organic transformations. Operational simplicity, high atom-economy, broad substrate scope, functional group tolerance and applicability towards large scale synthesis are the advantageous features of this developed methodology.
- Mishra, Pawan K.,Verma, Shalini,Kumar, Manoj,Kumar, Ankit,Verma, Akhilesh K.
-
p. 8278 - 8281
(2019/07/16)
-
- HINOKITIOL ANALOGUES, METHODS OF PREPARING AND PHARMACEUTICAL COMPOSITIONS THEREOF
-
Disclosed are analogues of hinokitiol, methods for preparing them, and pharmaceutical compositions thereof. Also disclosed are methods for their use in treating iron-related diseases.
- -
-
Page/Page column 197
(2019/11/04)
-
- Comparative studies on conventional and solvent-free synthesis toward hydrazones: Application of PXRD and chemometric data analysis in mechanochemical reaction monitoring
-
Synthesis of hydrazones was performed via both conventional and solvent-free routes using the corresponding hydrazide (isonicotinic hydrazide, nicotinic hydrazide, 2-aminobenzhydrazide or 4-aminobenzhydrazide) and appropriate aldehyde (salicylaldehyde, 3-
- Pisk, Jana,Hrenar, Tomica,Rub?i?, Mirta,Pavlovi?, Gordana,Damjanovi?, Vladimir,Lovri?, Jasna,Cindri?, Marina,Vrdoljak, Vi?nja
-
p. 1804 - 1817
(2018/04/03)
-
- C-Se cross-coupling of arylboronic acids and diphenyldiselenides over non precious transition metal (Fe, Cu and Ni) complexes
-
Various tetradentate and tridentate ligands such as salophane, bishydrazone, bisbenzimidazolyl pyridine and isonicotinohydrazide have been prepared. Transition metal complexes of these ligands with Cu, Ni and Fe have been further synthesized and characterized by UV–vis, IR, NMR and CHN analysis. Catalytic activity of the metal complexes was tested for the cross coupling of diarylchalcogenide with arylboronic acid in DMSO as solvent in presence of a base. These non-precious metal complexes catalysed cross coupling reactions smoothly in shorter reaction time compared to earlier reports with comparable yields.
- Sahani, Amber J.,Jayaram, Radha V.,Burange, Anand S.
-
-
- Designing salicylaldehyde isonicotinoyl hydrazones as Cu(II) ionophores with tunable chelation and release of copper for hitting redox Achilles heel of cancer cells
-
Higher levels of copper, reduced glutathione (GSH) and reactive oxygen species (ROS) observed in cancer cells than in normal cells, favor the idea of developing copper ionophores as prooxidative anticancer agents (PAAs) to hit the altered redox homeostasi
- Ji, Yuan,Dai, Fang,Zhou, Bo
-
p. 215 - 226
(2018/10/02)
-
- Antimicrobial activities of synthetic arylidine nicotinic and isonicotinic hydrazones
-
Background: Despite availability of variety of antibacterial agents, re-emergance of pathogenic bacteria is still a serious medical concern. Identification of new, safer, and selective antibacterial agents is the key interest in the medicinal chemistry research. Methods: A library of synthetic arylidene nicotinic and isonicotinic hydrazones (1-63) were investigated for antimicrobial activities. Results: A number of derivatives showed significant to moderate antimicrobial activities against Gram positive and Gram negative bacterial cultures. Few compounds also showed antifungal activity against fungal cultures. Minimum Inhibitory Concentration (MIC) was calculated for the most active compounds 1, 7, 11, 19, 34, 46, 50, 51, and 55 against gram positive and gram negative cultures. Conclusion: Newly identified compounds may serve as lead for future research in order to get the more powerful antibacterial agents.
- Hayat, Muhammad,Khan, Khalid Mohammed,Saeed, Sumayya,Salar, Uzma,Khan, Momin,Baig, Taimoor,Ahmad, Aqeel,Parveen, Shahnaz,Taha, Muhammad
-
p. 1057 - 1067
(2018/10/31)
-
- Xanthine oxidase inhibitory activity of nicotino/isonicotinohydrazides: A systematic approach from in vitro, in silico to in vivo studies
-
Change in life style and eating habits has led to an increased prevalence of hyperuricemia worldwide. The role of hyperuricemia is no more restricted to gout, but it has a central role in progression of CVD, hypertension, metabolic syndrome, and arthritis
- Zafar, Humaira,Hayat, Muhammad,Saied, Sumayya,Khan, Momin,Salar, Uzma,Malik, Rizwana,Choudhary, M. Iqbal,Khan, Khalid Mohammed
-
p. 2351 - 2371
(2017/04/03)
-
- Isonicotinohydrazones as inhibitors of alkaline phosphatase and ecto-5′-nucleotidase
-
A series of isonicotinohydrazide derivatives was synthesized and tested against recombinant human and rat ecto-5′-nucleotidases (h-e5′NT and r-e5′NT) and alkaline phosphatase isozymes including both bovine tissue-non-specific alkaline phosphatase (b-TNAP)
- Channar, Pervaiz Ali,Shah, Syed Jawad Ali,Hassan, Sidra,Nisa, Zaib un,Lecka, Joanna,Sévigny, Jean,Bajorath, Jürgen,Saeed, Aamer,Iqbal, Jamshed
-
p. 365 - 370
(2017/04/03)
-
- Pharmaceutical salts of biologically active hydrazone compound salinazid: Crystallographic, solubility, and thermodynamic aspects
-
The crystal structures of salts of the active pharmaceutical ingredient (API) called salinazid with dicarboxylic acids and acesulfame were determined by single-crystal X-ray diffraction method. The crystals contain hydrogen bond motifs of different structure and complexity, the energies of which were estimated by using the quantum theory of atoms in molecules and crystals (QTAIMC) methodology. It was found that the driving force for facile the oxalate and malate salts formation is the bifurcated N+-H···O- and N+-H···O hydrogen bond synthon, while salinazid malonate is mainly stabilized via a "classic" pyridinium-carboxylate heterosynthon. The oxalate and acesulfame salts of salinazid were found to be stable during aqueous dissolution experiments, providing a substantial solubility improvement compared to pure API (33 and 18 times, respectively). However, the malonate and malate salts dissolved incongruently and rapidly underwent a solution-mediated transformation to form pure salinazid. Based on the solubility data of the stable salts and of the pure components, the Gibbs free energy of the salts formation were calculated to be -21.2 kJ·mol-1 for salinazid oxalate and -22.6 kJ·mol-1 for salinazid acesulfame.
- Surov, Artem O.,Voronin, Alexander P.,Simagina, Anna A.,Churakov, Andrei V.,Perlovich, German L.
-
p. 2605 - 2617
(2016/06/01)
-
- Eco-friendly and highly efficient synthesis, including multigram synthesis, of aldehyde isonicotinoyl hydrazones using sonochemistry
-
Background: The isoniazid has been a key compound in first-line tuberculosis (TB) treatment, usually in combination with other drugs. Following on from the use of isoniazid itself, various derivatives of isoniazid have also been investigated as anti-TB ag
- Da Silveira Pinto, Ligia S.,De Souza, Marcus V. N.,Da Silva, Emerson T.,Kaiser, Carlos R.,Wardell, Solange M.S.V.,Wardell, James L.
-
p. 585 - 590
(2016/12/18)
-
- Endothelium dependent and independent mechanisms of vasorelaxant activity of synthesized 2,5-disubstituted-1,3,4-oxadiazole derivatives in rat thoracic aorta-ex vivo and molecular docking studies
-
Background: Vasoconstriction is a major pathological feature of cardiovascular diseases involving endothelium dependent and independent mechanisms. Oxadiazole moiety appeared to be effective in various pathologies. Objective: The aim of the study was to s
- Attari, Zenab,Mudgal, Jayesh,Nayak, Pawan G.,Krishnadas, Nandakumar,Rajappan, Revathi,Gopalan Kutty
-
p. 441 - 450
(2016/05/19)
-
- Synthesis and luminescence properties of salicylaldehyde isonicotinoyl hydrazone derivatives and their europium complexes
-
Four novel salicylaldehyde isonicotinoyl hydrazone derivatives and their corresponding europium ion complexes were synthesized and characterized, while the luminescence properties and the fluorescence quantum yields of the target complexes were investigated. The results indicated that the ligands favored energy transfers to the emitting energy level of europium ion, and four target europium complexes showed the characteristic luminescence of central europium ion. Besides the luminescence intensity of the complex with methoxy group, which possessed the highest fluorescence quantum yield (0.522), was stronger than that of other complexes. Furthermore, the electrochemical properties of the target complexes were further investigated by cyclic voltammetry, the results indicated that the highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO) energy levels and the oxidation potential of the complexes with electron donating group increased, however, that of the complexes with accepting electron group decreased.
- Shan, Wenfei,Liu, Fen,Liu, Jiang,Chen, Yanwen,Yang, Zehui,Guo, Dongcai
-
p. 100 - 107
(2015/12/08)
-
- MFA zeotype catalyst: A greener approach for the synthesis of INH azomethine scaffolds
-
Herein, we are reporting the green and efficient synthesis of some pharmacologically important azomethine derivatives of isoniazide (INH) using Modified Fly Ash (MFA) as an excellent zeotic solid acid catalyst. The catalyst, by virtue of its terminal hydr
- Raghuvanshi, Devendra S.,Mahulikar, Pramod P.,Meshram, Jyotsna S.
-
p. 48071 - 48078
(2015/06/16)
-
- Potent antimicrobial agents against azole-resistant fungi based on pyridinohydrazide and hydrazomethylpyridine structural motifs
-
Abstract Schiff base derivatives have recently been shown to possess antimicrobial activity, and these derivatives include a limited number of salicylaldehyde hydrazones. To further explore this structure-activity relationship between salicylaldehyde hydrazones and antifungal activity, we previously synthesized and analyzed a large series of salicylaldehyde and formylpyridinetrione hydrazones for their ability to inhibit fungal growth of both azole-susceptible and azole-resistant species of Candida. While many of these analogs showed excellent growth inhibition with low mammalian cell toxicity, their activity did not extend to azole-resistant species of Candida. To further dissect the structural features necessary to inhibit azole-resistant fungal species, we synthesized a new class of modified salicylaldehyde derivatives and subsequently identified a series of modified pyridine-based hydrazones that had potent fungicidal antifungal activity against multiple Candida spp. Here we would like to present our synthetic procedures as well as the results from fungal growth inhibition assays, mammalian cell toxicity assays, time-kill assays and synergy studies of these novel pyridine-based hydrazones on both azole-susceptible and azole-resistant fungal species.
- Backes, Gregory L.,Jursic, Branko S.,Neumann, Donna M.
-
p. 3397 - 3407
(2015/08/03)
-
- Synthesis and Performance of a Biomimetic Indicator for Alkylating Agents
-
4-(4-Nitrobenzyl)pyridine (NBP) is a colorimetric indicator compound for many types of carcinogenic alkylating agents. Because of the similar reactivity of NBP and guanine in DNA, NBP serves as a DNA model. NBP assays are used in the toxicological screeni
- Provencher, Philip A.,Love, Jennifer A.
-
p. 9603 - 9609
(2015/10/12)
-
- Benzaldehyde Schiff bases regulation to the metabolism, hemolysis, and virulence genes expression in vitro and their structure-microbicidal activity relationship
-
There is an urgent need to develop new antibacterial agents because of multidrug resistance by bacteria and fungi. Schiff bases (aldehyde or ketone-like compounds) exhibit intense antibacterial characteristics, and are therefore, promising candidates as antibacterial agents. To investigate the mechanism of action of newly designed benzaldehyde Schiff bases, a series of high-yielding benzaldehyde Schiff bases were synthesized, and their structures were determined by NMR and MS spectra data. The structure-microbicidal activity relationship of derivatives was investigated, and the antibacterial mechanisms were investigated by gene assays for the expression of functional genes in vitro using Escherichia coli, Staphylococcus aureus, and Bacillus subtilis. The active compounds were selective for certain active groups. The polar substitution of the R2 group of the amino acids in the Schiff bases, affected the antibacterial activity against E. coli and S. aureus; specific active group at the R3 or R4 groups of the acylhydrazone Schiff bases could improve their inhibitory activity against these three tested organisms. The antibacterial mechanism of the active benzaldehyde Schiff bases appeared to regulate the expression of metabolism-associated genes in E. coli, hemolysis-associated genes in B. subtilis, and key virulence genes in S. aureus. Some benzaldehyde Schiff bases were bactericidal to all the three strains and appeared to regulate gene expression associated with metabolism, hemolysis, and virulence, in vitro. The newly designed benzaldehyde Schiff bases possessed unique antibacterial activity and might be potentially useful for prophylactic or therapeutic intervention of bacterial infections.
- Xia, Lei,Xia, Yu-Fen,Huang, Li-Rong,Xiao, Xiao,Lou, Hua-Yong,Liu, Tang-Jingjun,Pan, Wei-Dong,Luo, Heng
-
-
- Heteroleptic binuclear copper(I) complexes bearing bis(salicylidene)hydrazone ligands: Synthesis, crystal structure and application in catalytic N-alkylation of amines
-
A new series of heteroleptic binuclear Cu(I) bis(salicylidene)hydrazone complexes (1-4) bearing triphenylphospine coligands have been synthesized from the reactions of copper(II) precursor complex [CuCl2(PPh3)2] with oxadiazole compounds A-D, respectively. It has been observed that the oxadiazole compounds undergo ring cleavage with in situ reduction of Cu(II) ion, during the formation of complexes (1-4). The oxadiazoles (A-D) and the Cu(I) complexes (1-4) have been characterized by analytical and spectroscopic methods. Single crystal X-ray diffraction study of complex 2 has revealed a distorted tetrahedral geometry around each Cu(I) center. Catalytic efficiency of the new complexes on the N-alkylation of amines using alcohols was studied under optimized conditions. The new complexes have also been tested for their catalytic activity towards the direct N-alkylation of 2-nitropyridine.
- Prakash, Govindan,Nirmala, Muthukumaran,Ramachandran, Rangasamy,Viswanathamurthi, Periasamy,Malecki, Jan Grzegorz,Sanmartin, Jesus
-
-
- Ruthenium(II) bis(hydrazone) complexes derived from 1,3,4-oxadiazoles: Synthesis, crystal structure and catalytic application in N-alkylation reactions
-
1,3,4-Oxadiazoles (A-C) were derived via a series of reactions between isoniazid and salicylaldehydes. While reacting the oxadiazoles with [RuHCl(CO)(PPh3)3] in the presence of NaOH, mononuclear ruthenium(II) complexes bearing 'salen' type N,N′-bis(salicylidene)hydrazone ligands (1-3) were obtained. The oxadiazoles and ruthenium(II) complexes were characterized by analytical and spectral methods. The single crystal XRD analyses of complexes 1 and 2 suggested an octahedral geometry around ruthenium(II) ions in which the bis(hydrazone) act as mononegative bidentate ligands. It was also observed that the presence of an intramolecular hydrogen bonding between the hydroxyl proton and one of the azomethine nitrogens in all the complexes. Further, the complexes were proved as versatile catalysts for the N-alkylation of amines with alcohols under optimized reaction conditions.
- Prakash, Govindan,Ramachandran, Rangasamy,Nirmala, Muthukumaran,Viswanathamurthi, Periasamy,Sanmartin, Jesus
-
supporting information
p. 203 - 210
(2015/01/30)
-
- Syntheses and structural investigation of some alkali metal ion-mediated LVVO2- (L2- = tridentate ONO ligands) species: DNA binding, photo-induced DNA cleavage and cytotoxic activities
-
Eight alkali metal ion-mediated dioxidovanadium(v), [{VVO 2L1-6}A(H2O)n]∝, complexes for A = Li+, Na+, K+ and Cs +, containing tridentate aroylhydrazonate ligands coordinating via ONO donor atoms, are described. All the synthesised ligands and the metal complexes were successfully characterised by elemental analysis, IR, UV-Vis and NMR spectroscopy. X-ray crystallographic investigation of 3, 5-7 shows the presence of distorted NO4 coordination geometries for LVO 2- in each case, and varying μ-oxido and/or μ-aqua bridging with interesting variations correlated with the size of the alkali metal ions: with small Li+, no bridging-O is found but four ion aggregates are found with Na+, chains for K+ and finally, layers for Cs+. Two (5) or three-dimensional (3, 6 and 7) architectures are consolidated by hydrogen bonding. The dioxidovanadium(v) complexes were found to exhibit DNA binding activity due to their interaction with CT-DNA by the groove binding mode, with binding constants ranging from 103 to 104 M-1. Complexes 1-8 were also tested for DNA nuclease activity against pUC19 plasmid DNA which showed that 6 and 7 had the best DNA binding and photonuclease activity; these results support their good protein binding and cleavage activity with binding constants ranging from 104 to 105 M-1. Finally, the in vitro antiproliferative activity of all complexes was assayed against the HeLa cell line. Some of the complexes (2, 5, 6 and 7) show considerable activity compared to commonly used chemotherapeutic drugs. The variation in cytotoxicity of the complexes is influenced by the various functional groups attached to the aroylhydrazone derivative.
- Dash, Subhashree P.,Panda, Alok K.,Pasayat, Sagarika,Dinda, Rupam,Biswas, Ashis,Tiekink, Edward R. T.,Patil, Yogesh P.,Nethaji,Kaminsky, Werner,Mukhopadhyay, Subhadip,Bhutia, Sujit K.
-
p. 10139 - 10156
(2014/06/24)
-
- Solvent-free and catalysis-free approach to the solid state in situ growth of crystalline isoniazid hydrazones
-
The isonicotinoylhydrazones and their coordination compounds have antibacterial, antifungal, antitubercular, antitumor, and anticonvulsant activities. A typical method employed in the preparation of isonicotinoylhydrazones involves the usage of the volati
- Trzesowska-Kruszynska, Agata
-
p. 3892 - 3900
(2013/09/24)
-
- DNA binding, antitumor activities, and hydroxyl radical scavenging properties of novel oxovanadium(IV) complexes with substituted isoniazid
-
Four novel oxovanadium(IV) complexes-[VO(PAHN)(phen)] (1; PAHN is 4-pyridinecarboxylic acid, 2-[(2-hydroxy)-1-naphthalenylene] hydrazide, phen is 1,10-phenanthroline), [VO(PAHN)(bpy)] (2; bpy is 2,2′- bipyridine), [VO(PAH)(phen)] (3; PAH is 4-pyridinecarb
- Liao, Xiangwen,Lu, Jiazheng,Ying, Peng,Zhao, Ping,Bai, Yinliang,Li, Wenjie,Liu, Mingpei
-
p. 975 - 984
(2014/01/23)
-
- Studies on complexes of copper and nickel with a Schiff base derived from salicylaldehyde and isonicotinoyl hydrazide
-
A series of transition metal complexes with formulae [M(SIH)(H 2O)n]2, where Mn+ = Cu 2+/Ni2+, n = 2 and SIH = salicylideneisonicotinoylhydrazone, are synthesized by the condensation of sal
- Kar,Das,Panda,Behera,Biswal,Panda
-
p. 1641 - 1646
(2013/08/24)
-
- Synthesis, characterization and pharmacological evaluation of (E)-N′-(substituted-benzylidene)isonicotinohydrazide derivatives as potent anticonvulsant agents
-
A series of (E)-N′-(substituted-benzylidene)isonicotinohydrazide derivatives were synthesized by coupling it with different substituted aldehydes, acetophenone, and benzophenones in presence of absolute ethanol along with catalytic amount of glacial aceti
- Malhotra, Manav,Monga, Vikramdeep,Sharma, Sagun,Jain, Jainendra,Samad, Abdul,Stables, James,Deep, Aakash
-
p. 2145 - 2152
(2012/11/07)
-
- Isonicotinic acid hydrazide derivatives: Synthesis, antimicrobial activity, and QSAR studies
-
A series of isonicotinic acid hydrazide derivatives (1-19) was synthesized and tested in vitro for antimycobacterial activity against Mycobacterium tuberculosis and antimicrobial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Candida albicans, and Aspergillus niger and the results indicated that the compounds with OH, SCH3, and OCH 3 groups were found to be active against the tested strains. None of the test compounds were active against a broad variety of RNA and DNA viruses at subtoxic concentrations, except 8, that showed some selective anti-reovirus-1 activity. The multi-target QSAR models were found to be effective in predicting the antimicrobial activity of the isoniazid derivatives and indicated the importance of nuclear repulsion energy (Nu.E) in explaining the antimicrobial activity of isoniazid derivatives. The developed QSAR models were validated using the external test set of synthesized derivatives. Springer Science+Business Media, LLC 2011.
- Judge, Vikramjeet,Narasimhan, Balasubramanian,Ahuja, Munish,Sriram, Dharmarajan,Yogeeswari, Perumal,De Clercq, Erik,Pannecouque, Christophe,Balzarini, Jan
-
p. 1451 - 1470
(2012/09/22)
-
- Synthesis, characterization and antiamoebic activity of some hydrazone and azole derivatives bearing pyridyl moiety as a promising heterocyclic scaffold
-
In an effort to develop effective antiamoebic agents, some hydrazones and azoles containing pyridyl moiety were synthesized and screened for in vitro antiamoebic activity against HM1:IMSS strain of Entamoeba histolytica. Among all the compounds, only five compounds (1, 3, 5, 9 and 11) were found to be better inhibitors of growth of E. histolytica than the reference drug metronidazole. The cytotoxic studies of these compounds on human breast cancer MCF-7 cell line revealed that all the compounds were low-cytotoxic in the concentration range of 2.5-250 μM.
- Siddiqui, Shadab Miyan,Salahuddin, Attar,Azam, Amir
-
experimental part
p. 411 - 416
(2012/04/04)
-
- Thiazolidin-4-one, azetidin-2-one and 1,3,4-oxadiazole derivatives of isonicotinic acid hydrazide: Synthesis and their biological evaluation
-
A series of thiazolidin-4-one (2a-h; 3a-h), azetidin-2-one (4a-h) and 1,3,4-oxadiazole (5a-h) derivatives of isoninicotinic acid hydrazide (INH) were synthesized in order to obtain new compounds with potential anti-inflammatory, analgesic, ulcerogenic and
- Gilani, Sadaf J.,Khan, Suroor A.,Alam, Ozair,Singh, Vijender,Arora, Alka
-
experimental part
p. 1057 - 1067
(2012/02/05)
-
- Ruthenium(II) hydrazone Schiff base complexes: Synthesis, spectral study and catalytic applications
-
Ruthenium(II) hydrazone Schiff base complexes of the type [RuCl(CO)(B)(L)] (were B = PPh3, AsPh3 or Py; L = hydrazone Schiff base ligands) were synthesized from the reactions of hydrazone Schiff base ligand (obtained from isonicotinoylhydrazide and different hydroxy aldehydes) with [RuHCl(CO)(EPh3)2(B)] (where E = P or As; B = PPh 3, AsPh3 or Py) in 1:1 molar ratio. All the new complexes have been characterized by analytical and spectral (FT-IR, electronic, 1H, 13C and 31P NMR) data. They have been tentatively assigned an octahedral structure. The synthesized complexes have exhibited catalytic activity for oxidation of benzyl alcohol to benzaldehyde and cyclohexanol to cyclohexanone in the presence of N-methyl morpholine N-oxide (NMO) as co-oxidant. They were also found to catalyze the transfer hydrogenation of aliphatic and aromatic ketones to alcohols in KOH/Isopropanol.
- Manikandan,Viswanathamurthi,Muthukumar
-
experimental part
p. 297 - 303
(2011/12/13)
-
- ROS-SENSITIVE IRON CHELATORS AND METHODS OF USING THE SAME
-
The present invention provides compounds of Formula (I): along with compositions containing the same and methods of use thereof in treating oxidative stress.
- -
-
Page/Page column 10
(2010/02/16)
-
- 1-Malonyl-1,4-dihydropyridine as a novel carrier for specific delivery of drugs to the brain
-
A group of 1-malonyl-1,4-dihydropyridine derivatives were synthesized as novel carrier systems for site-specific and sustained drug delivery to the brain. Such carriers are expected to be stable against air oxidation due to the presence of the carbonyl group close to nitrogen of the dihydropyridine. These carrier systems were attached to a group of different aldehydes to afford novel quaternary pyridinium derivatives 9a-e, 11a-d, 13 and 18a-b. Reduction of the prepared quaternary pyridinium derivatives with sodium dithionite afforded a novel group of 1-malonyl-1,4-dihydropyridine chemical delivery systems (CDSs) 10a-e, 12a-d, 14 and 19a-b. The synthesized 1-malonyl-1,4-dihydropyridine CDSs were subjected to various chemical and biological investigations to evaluate their ability to cross the blood-brain barrier, and to be oxidized biologically into their corresponding quaternary derivatives. The in vitro oxidation studies showed that most of the 1-malonyl-1,4-dihydropyridine CDSs could be oxidized into their corresponding quaternary derivatives at an adequate rate. The in vivo studies showed that compounds 10c and 14 were able to cross the blood-brain barrier at detectable concentrations. Moreover, the pyridinium quaternary intermediates 9a, 9c, 13, 18a and their corresponding dihydro derivatives 10a, 10c, 14 and 19a were screened for their antidepressant activity using tail suspension behavioral despair test compared to imipramine as a reference at a dose level of 10 mg/kg. The results indicated that compounds 13, 14 and 19a induced remarkable antidepressant activity comparable to imipramine. Compounds 10a, 10c and 18a exhibited good antidepressant activity, their activities nearly equal to 92.8%, 86.7% and 90.20% of the activity of imipramine, respectively. The other derivatives 9a and 9c exhibited moderate antidepressant activity compared with imipramine.
- Hassan, Heba A.,Abdel-Aziz, Mohamed,Abuo-Rahma, Gamal El-Din A.A.,Farag, Hassan H.
-
experimental part
p. 1681 - 1692
(2009/08/07)
-
- Microwave-assisted, solvent-free, parallel syntheses and elucidation of reaction mechanism for the formation of some novel tetraaryl imidazoles of biological interest
-
The microwave assisted, solvent free, parallel syntheses of title compounds is described in this protocol. Twelve new tetraaryl imidazoles, which are incorporated with the chemotherapeutic pharmaco- phores, have been synthesized by adopting one pot multic
- Kumar, B. R. Prashantha,Sharma, Gyanendra Kumar,Srinath,Noor, Mohamed,Suresh,Srinivasa
-
experimental part
p. 278 - 284
(2009/07/05)
-
- Synthesis and antimycobacterial activity of a novel series of isonicotinylhydrazide derivatives
-
A novel series of 14 new isonicotinyl hydrazide derivatives 2a-g, 3a-g containing a 4-thiazolidinone / 2-azetidinone nucleus were synthesized by reacting N9-substituted arylidene / heteroarylidene isonicotinyl hydrazide 1a-g with thioglycollic acid in the presence of dry benzene and with chloroacetyl chloride in the presence of triethylamine, respectively. Structures of all newly synthesized compounds were characterized on the basis of elemental analyses and spectral data (IR and 1H-NMR). All the title compounds were tested for their in-vitro antimycobacterial activity against Mycobacterium tuberculosis H 37Rv using Alamar-Blue susceptibility test, and the activity is expressed as the minimum inhibitory concentration (MIC) in μg/mL. Among the series, compounds 2b, 2g, 3b, and 3g displayed an encouraging antimycobacterial activity profile as compared to that of the reference drugs isoniazid / rifampicin.
- Jaju, Sandip,Palkar, Mahesh,Maddi, Veeresh S.,Ronad, Pradeepkumar,Mamledesai, Shivalingarao,Satyanarayana, Darbhamulla,Ghatole, Mangala
-
experimental part
p. 723 - 731
(2010/05/02)
-
- Polystyrene-supported iodobenzene diacetate (PSIBD)-mediated synthesis of 1,2-diacylbenzenes from 2-hydroxyaryl aldehyde/ketone acylhydrazones
-
Synthesis of some new 1,2-diacylbenzenes is described by the oxidation of 2-hydroxyaryl aldehyde/ketone acylhydrazones using polystyrene-supported iodobenzene diacetate (PSIBD) in good yield. Copyright Taylor & Francis Group, LLC.
- Kumar, Sunil,Kumar, Devinder
-
p. 3683 - 3699
(2008/12/23)
-
- Hydrogen peroxide triggered prochelator activation, subsequent metal chelation, and attenuation of the fenton reaction
-
(Chemical Equation Presented) Fenton antidote: The prochelator 2-boronobenzaldehyde isonicotinoyl hydrazone (SIH-B) reacts with H 2O2 to yield the active chelator salicylaldehyde isonicotinoyl hydrazone (SIH), which sequesters copper
- Wei, Yibin,Guo, Maolin
-
p. 4722 - 4725
(2008/02/10)
-
- Mechanistic differences between in vitro assays for hydrazone-based small molecule inhibitors of anthrax lethal factor
-
A systematically generated series of hydrazones were analyzed as potential inhibitors of anthrax lethal factor. The hydrazones were screened using one UV-based and two fluorescence-based in vitro assays. The study identified several inhibitors with IC50 values in the micromolar range, and importantly, significant differences in the types of inhibition were observed with the different assays.
- Hanna, M. Leslie,Tarasow, Theodore M.,Perkins, Julie
-
-
