4-aminoantipyrine Derivatives Research Articles

Synthesis, Characterization and Antimicrobial Activity of New 4-aminoantipyrine Derivatives Using Ultrasonic Mediation

تم استخدام تفاعل المباشر, ذو وعاء واحد، ثلاثي المكونات بين الألديهايدات الاروماتيه المعوضه, 2-نافثول و4- أمينو أنتيبيرين لتخليق سلسلة جديده من 4-(((2-hydroxynaphthalen-1-yl) (phenyl) methylene) amino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one (A1- A5) لقد أجريت هذا التفاعل بأستخدام كلوريد الزركونيل كمحفز فعال في حالة التشعيع بالموجات فوق الصوتية. في الحقيقة أن هذه المشتقات لديها قدره على العمل كمواد أساسية في تكوين مركبات جديده 4- (1H-naphtho [1,2-e] [1,3] oxazin-2(3H)-yl)-2-phenyl-1, 5-dimethyl-1,2-dihydro-3H-pyrazol-3-one(A6, A7 and A8). وبالمثل, تم استخدام MCRs التي أدت إلى تكوين مركب حلقي غير متجانس (1،3-نافثوكسازين( وتضمنت تفاعل 4- أمينو أنتي بييرين, و الفورمالديهايد و 2-نافثول بنسبة مول 1: 2: 1 لتكوين , 4-(1H-naphtho [1,2-e] [1,3] oxazin-2(3H)-yl)-2-phenyl-1-5 dimethyl-1,2-dihydro-3H-pyrazol-3-one (A9)1 يبدأ هذا التفاعل بأدخال نظام محفزZrOCl2-K2CO3 ويستمر من خلال التكثيف وتكوين الحلقه. ثم تحليل جميع المركبات المنتجه من خلال بيانات أطياف IR و H1 NMR و C13 NMR لتوضيح عمل هذه المركبات المميزه. باستخدام طريقة التخفيف الدقيق للمرق وطريقة نشر القرص، تم تقييم الأنشطة المضادة للبكتيريا (إيجابية الجرام وسالبة الجرام) والفطريات و مقارنة بالأدوية التقليدية (امبيسلين, سيبروفلوكساسين و اموكسيسلين). كان للمركبات المحضرة مجموعة واسعة من التأثير بقيم MIC من 200 600, و 1000ميكروغرام / مل ضد البكتيريا التي تم فحصها ، كما هو محدد بواسطة التحليل الميكروبيولوجي.

Crystal structure, Hirshfeld surface analysis, computational study and molecular docking simulation of 4-aminoantipyrine derivative

Herein, a new derivative (4APSA) has been synthesized by treating 4-aminoantipyrine with succinic anhydride at 25 °C employing glacial acetic acid as a solvent. The molecular structure of 4APSA is investigated via single crystal X-ray diffraction (XRD) analysis. Cambridge structure database CSD 2023.3.1 (updated March 2024) was used for comparison of 4APSA with the associated reported structures. The supramolecular assemblage was alleviated by several intermolecular connections. Hirshfeld surface analysis was conducted for further assessment of intermolecular interactions with respect to interatomic contacts for 4APSA and a closely associated structure having a reference code of HOMDUI. Interaction energy calculations were performed at B3LYP/6–31G(d,p) electron density level to find the type of interaction energy that had the highest contribution to the supramolecular assembly. Moreover, in-depth DFT calculations were studied at B3LYP/6-311++g(d,p) level to obtain molecular structure, Mulliken charge analysis, MEP surface, electronic properties, quantum chemical reactivity, and DOS spectrum. Strong correlations are found between theoretical and experimental structures. The ADME-T prediction was applied for the 4APSA, 4AP, and SA compounds utilizing OSIRIS DataWarrior. Docking simulation demonstrates the high tendency of 4APSA to bind with the active sites of Cannabinoid Receptor Subtype 2 (CB2R) compared to JWH-018. This finding suggested that the synthesized compound has a positive effect on the CB2R protein.

Unveiling the therapeutic potential of BAP from crystallographic analysis to protein docking and anticancer assessment in MCF-7 human breast cancer cells

The 4-aminoantipyrine derivatives comprising both N- and O-donor modes generate novel coordination assemblies which tend to exhibit anti-tumor activities. Crystallographic study of 1,5-Dimethyl-4- [(2-oxo-1,2-diphenyl ethylidene) amino]-2-phenyl-1,2-dihydro-3H-pyrazol-3-one (BAP) is reported. Hirshfeld surface analysis is employed to analyze molecular electrostatic potential, inter-molecular interaction energies, and H-bonded framework. To investigate the adaptability and specificity of BAP with different protein interactions, we ran molecular docking simulations using a single ligand and many different protein targets. In this docking study, BAP crystal was selected due to its importance in cancer research, and with the different protein targets 1TNF, 2TUN, 1TNR, 5TSW, 6GK0, 6IUL, 6 K04 and 6 K05 are included. TNF-alpha, a cytokine essential for the immune system and inflammatory reactions, is generated by activated immune cells and is crucial for preventing infections and controlling cell proliferation. TNF inhibitors have improved the treatment of various ailments. TNF-alpha dysregulation is a major area of study in immunology and immunotherapy. Dihydroorotate dehydrogenase, mitochondrial enzyme, and Natterin-like proteins are also important in epigenetics and drug development. BET family proteins, including BRD2, are crucial in disease connections, cell cycle control, and gene regulation. The Swiss ADME method, which assesses medication similarity, strongly implies that the BAP may be a potential option for the treatment of breast cancer. After screening chemical libraries, BAP was shown to be an antagonist of this protein–protein interaction. In this study, the yellow tetrazolium salt (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) evaluation on MCF-7 human breast cancer cells to investigate the feasible anticancer characteristics and cytotoxicity of the BAP complex.

Synthesis , Spectroscopic and Antibacterial Investigation of New Molecular hybridized 4-Aminoantipyrine Derivatives of pharmaceutical Interest

A new series of a hybridized 4-(N- substituted) aminoantipyrine derivatives with amide linkage backbone aminoantipyrine, series (A),compounds [13a- g] and secondary amine linkage, series(B), compounds [l4a-20a] were prepared through systematic sequence coupling reaction of 4-aminoantipyrine (4-AA) and well established active nitrogen bases moieties of phthalimide,piperidine and substituted aniline derivatives with chloroacetylchloride of actively different chlorine functions. . The antibacterial activity of some selected products was reported

Transition Metal Complexes of 4-Aminoantipyrine Derivatives and Their Antimicrobial Applications

Transition Metal Complexes of 4-Aminoantipyrine Derivatives and Their Antimicrobial Applications

SYNTHESIS, DOCKING STUDY, AND BIOLOGICAL EVALUATION OF 4-AMINOANTIPYRINE-ISONIAZID DERIVATIVES AS A HYBRID ANTIBACTERIAL AND ANALGESIC AGENTS

Background: 4-aminoantipyrine is one of the pyrazolone derivatives, it has been exposed to a large range of biological activities as an antimicrobial, analgesic, antiviral, anti-inflammatory, and anticancer compound. One of the important derivatives is the hybrid pyrazolone which includes two organic or inorganic drugs attached to give new pharmaceutical agents which may be the same or different activity from the original drugs. Aim: This research aimed to synthesize novel compounds derived from 4-aminoantipyrine and test their biological activity. Methods: Synthesis of 4-aminoantipyrine derivatives, which contain structurally two heterocyclic moieties, pyrazolone with oxadiazole, triazole, or tetrazole rings. The structures of the compounds were identified by 1H-NMR and FT-IR spectroscopy. The in vitro, developed compounds were screened for their analgesic activity and antibacterial activity against medically important gram (+) and gram (-) bacterial strains. Results: The antibacterial evaluation tests showed that some compounds gave good activity and others had no activity. The analgesic activity referred that the synthesized compounds had promising potency. The free binding energy (S) of the compounds with the protein 6B73 were ?4.90 to ?8.76 kcal/mol, whereas free energy (S) with the protein 5C1M gave ?4.94 to ?9.21 kcal/mol. Discussion: Among the tested compounds, it was found that compounds 1a, 4b, and 5a had more potent antibacterial activity. The analgesic activity showed that compounds 1b, 4b, and 5a gave the best activity using hot plate methods compared with the standard drug. On the other hand, compounds 1a, 4b, and 5b gave good activity using the writhing test method. Conclusions: Potent, good, or moderate analgesic and antibacterial agents were synthesized using simple and high-yield chemical reactions. The chemical reactions include the synthesis of hybrid antibacterial and analgesic agents using pyrazolone compounds.

Studying spectroscopic, cyclic voltammetry, and electrical properties of novel 4-amino antipyrine derivative for photonic applications

The present work aims to synthesize a new antipyrine derivative and then study its optical properties in the form of thin films with the aim of using the obtained results in the fabrication and designing of new optoelectronic devices. A N1,N3-bis(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)malonamide, dpdp novel organic compound has been successfully synthesized in dimethylformamide (DMF) medium by the chemical reaction between 4-aminoantipyrine and malonyl chloride. The obtained dpdp compound is characterized quantitatively and qualitatively by using micro elemental analysis, FTIR spectroscopy, 1H– & 13C–NMR, and thermogravimetric measurements. Two steps weight loss of 84 % (calcd. mass loss 37.25 %) is recorded in the temperature range of 25 °C to 800 °C. Thin films of the novel organic dpdp were successfully grown by the thermal evaporation technique. FSEM images show the surface topology of the as-deposited thin film which is characterized by high quality, continuous, and crystalline granular surface with an average particle size of 70 nm. The cyclic voltammetric analysis showed that the energy difference between the HOMO and LUMO equals 2.43 eV. The calculated values of the optical band gap transitions deduced from the diffuse reflectance spectra are found to be 2.27 eV, and 3.44 eV for the powder and the as-deposited dpdp thin films, respectively. The photoluminescence spectra analysis showed that the as-deposited film dpdp is characterized by a main green peak centered at 530 nm. The optical transflection spectra showed that the calculated values of the indirect optical band gap transitions are found to be 3.53 eV for the as-deposited thin film which slightly increased to 3.63 eV after annealing at 373 K and 423 K for 4 h. Spectral variations of the refractive index and the specific polarizability showed one peak around 400 nm which fades by annealing treatment at 373 K and 423 K. The dc electrical resistivity activation energy of the free charge carriers was estimated.

Gravimetric analysis and quantum chemical assessment of 4-aminoantipyrine derivatives as corrosion inhibitors

Gravimetric analysis and quantum chemical assessment of 4-aminoantipyrine derivatives as corrosion inhibitors

Design, synthesis and characterization of some novel 4-aminoantipyrine derivatives and evaluation of their activity as analgesic agents

Design, synthesis and characterization of some novel 4-aminoantipyrine derivatives and evaluation of their activity as analgesic agents

4-Aminoantipyrine Analogs as Anti-inflammatory and Antioxidant agents: Synthesis, Biological Evaluation and Molecular Docking Studies

Objectives: A novel series of 4-aminoantipyrine derivatives were designed and efficiently synthesized from Gewald, triphosgene and various substituted aromatic/ aliphatic/heterocyclic amines. Methods: The synthesized derivatives were characterized by IR, NMR, Mass and elemental analysis. The synthesized derivatives were evaluated for their anti-inflammatory activity using in vitro protein denaturation assay and antioxidant activity by using the 1,1-diphenyl-1-picrylhydrazyl free radical scavenging method. To establish the selectivity and safety profile of the drug, the most active compounds 4a and 4b were further screened for cytotoxicity against HeLa and MCF-7 cell lines using the sulforhodamine-B assay. The synthesized compounds were also analyzed for ADME properties and a docking study was done into the active site of oxidoreductase, cyclooxygenase-1 and cyclooxygenase-2 enzymes in an attempt to understand their binding mode using Auto Dock Vina. Results: Among the series Compounds 4a and 4b showed potent anti-inflammatory activity and antioxidant activity as compared with standard diclofenac and Ascorbic acid respectively. The results of in silico ADME Screening showed that compounds could be exploited as an oral drug candidate. The most prominent compound 4a and 4b showed no significant cytotoxic activity against HeLa and MCF-7 cell lines. The molecular docking study of most active compounds had shown good binding interactions against oxidoreductase, cyclooxygenase-1 and cyclooxygenase-2 enzymes. Conclusion: Results of in vitro anti-inflammatory, antioxidant activities and docking study showed that synthesized compounds had potential antiinflammatory and antioxidant activities and can be further optimized and developed as a lead compound.

Synthesis, identification of some new derivatives of 4-amino antipyrine bearing six and seven membered rings

In this paper, we consider the Synthesis of a series of various 4-amino antipyrine derivatives containing 1,3-thiazinan-4-one, 1,3-oxazinan-6-one, and 1,3-oxazepin-4,7-dione in its structure. These derivatives were obtained via cycloaddition of the methenamine group in Schiff base analog of 4-amino antipyrine with 3-mercaptopropanoic acid, 3-chloropropanoic acid, maleic and citraconic anhydride, respectively. The Schiff bases were prepared in excellent yields by condensation of 4-amino antipyrine with 3-nitro- or 3-bromobenzaldehyde in n-butanol. We characterize the desired products by C.H.N.S analysis, FT-IR, and 1HNMR spectroscopy.

Synthesis, Characterization and Antibacterial Activity Evaluation of 4-amino Antipyrine Derivatives and Their Transition Metal Complexes

Due to their importance as catalysts in many reactions and their biological activities, an interest in the synthesis and characterization of transition metal complexes containing Schiff bases is increasing. Schiff base ligands have achieved considerable attention by the scientist over the decades as potential drug agent, Azomethine linkage (-CH=N-) of Schiff base play a significant role in medical chemistry. Derivatives of Schiff bases of 4-aminoantipyrine viz, 4-(2-hydroxy-3-methoxy benzylid ene amino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one (4) and 4-((5-methylfuran-2-yl) methylene amino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one (5) and their Co (II), Ni (II), Cu (II) complexes were successfully synthesized, the Schiff bases ligand (4) and (5) were synthesized by condensation reaction. The structures of all the synthesized ligands were confirmed by using IR, UV-Visible, ¹H NMR, and ¹³C NMR. The Cu (II), Ni (II) and Co (II) complexes were confirmed by using IR and VU-Visible. The complexes are electrolytic in nature as indicated by molar conductance measurements. The data have shown that all complexes possess octahedral geometry. In-vitro antibacterial activity of all the synthesized ligands and their metal complexes were carried out by using disc diffusion method against Staphylococcus<i> aureus, Escherichia coli </i>and <i>Pseudomonas aeruginosa</i> bacterial strain. Compound Co (4) has exhibited better antibacterial activity than the standard drug against S. aureus (25 mm zone of inhibition compared to the standard antibiotic Oxacillin (23 mm zone of inhibition).

Synthesis and Biological Evaluation of 4-Aminoantipyrine Analogues.

The aim of the present study is to carry out a simple synthesis of aminoantipyrine analogues and exploration of their antibacterial, cytotoxic, and anticonvulsant potential. The compounds were characterized employing multi-spectroscopic methods. The in vitro pharmacological response of a series of bacteria was screened employing serial dilution method. The derivatives were screened against maximal electro-shock for their anticonvulsant activity. Molecular docking was carried out to optimize the interaction of the compounds with HPV16-E7 receptors. Further, the in vitro cytotoxicity was tested against human cervical cancer (SiHa) cell lines. The compounds show protection against maximal electroshock, esp. 3-nirto- and 4- methyl-3-nitrobenzamido derivatives. In addition, they reveal appreciable DNA cleavage activities and interactions with HPV16-E7 protein receptors, esp. 3,5-dinitro- and 4-methyl-3-nitrobenzamido derivatives. Furthermore, they show potent activity against cervical cancer cells (LD50 value up to 1200 in the case of 4-methyl-3-nitrobenzamido derivative and an inhibition of a maximum of ~97% of cells). The simply synthesized aminoantipyrine derivatives show a variety of biological activities like antibacterial and anticancer effects. In addition, this is the first study demonstrating that 4-aminoantipyrine derivatives show an anticonvulsant activity.

Gravimetrical and surface morphology studies of corrosion inhibition effects of a 4-aminoantipyrine derivative on mild steel in a corrosive solution

Gravimetrical and surface morphology studies of corrosion inhibition effects of a 4-aminoantipyrine derivative on mild steel in a corrosive solution

Synthesize palladium and nickel oxide nanoparticles in the presence of 4-aminoantipyrine derivative as a precursor: decolorization efficiency of methylene blue

Synthesize palladium and nickel oxide nanoparticles in the presence of 4-aminoantipyrine derivative as a precursor: decolorization efficiency of methylene blue

Synthesize palladium and nickel oxide nanoparticles in the presence of 4-aminoantipyrine derivative as a precursor: decolorization efficiency of methylene blue

Synthesize palladium and nickel oxide nanoparticles in the presence of 4-aminoantipyrine derivative as a precursor: decolorization efficiency of methylene blue

Structural and Biological Studies on Transition Metal Complexes of 4-Aminoantipyrine Derivative

Novel tetra dentate Cu(II), Ni(II), Co(II), VO(II) and Zn(II) Schiff base complexes have been synthesized from salicylidene-4-iminoantipyrine and tyrosine. The synthesized Schiff base complexes was characterized by powder X-ray diffraction studies (XRD), scanning electron microscopy (SEM), FT-IR, ESR, 1H NMR, 13C NMR, UV-vis, molar conductance and magnetic susceptibility measurements. The general formula of complexes was confirmed as [ML] type [M = Cu(II), Co(II), Zn(II), Ni(II) and VO(II); L = C27H24N4O4]. Magnetic susceptibility, IR and UV-vis, spectral data showed that all the complexes have square planar geometry except vanadyl complex which suggests square pyramidal geometry. Lower molar conductance values proved that all the chelates were non-electrolytic nature. The X-band ESR spectra of [CuL] and [VOL] complexes in DMSO solution suggest that the complexes were predominant covalent character. Powder XRD and SEM image pattern evidenced that all the compounds were crystalline in nature and their size ranges from 100-40 nm. Calf thymus DNA binding potential of [CuL] and [VOL] complexes shows that the binding occurs through intercalation mode with low binding constant. The analgesic, CNS, antiulcer and antimicrobial activities of the investigated compounds report reveals that the chelates were significant effect than free Schiff base.

Chemical Preparation of Nanostructures of Ni(II), Pd(II), and Ru(III) Oxides by Thermal Decomposition of New Metallic 4-Aminoantipyrine Derivatives. Catalytic Activity of the Oxides

This article is focused on preparation of Ni(II), Pd(II) and Ru(III) oxides in the nanoscale form from the complexes of N,N,N,N-tetradentate Schiff base with Ni(II), Pd(II) and Ru(III). The complexes have been synthesized and characterized by elemental analyses, magnetic susceptibility, molar conductivity, 1H and 13C NMR, FT-IR, UV-Vis, mass, and TG-DTG analysis. The accumulated data indicate that the central metal ion in the complexes is coordinated with four nitrogen atoms of the imino and amino groups. The complexes are characterized by a 1 : 1 metal : ligand ratio and octahedral geometry except for Pd(II) complex which has a tetradentate structure. The complexes have been used as precursors for NiO, PdO and RuO2 preparation of NPs by thermal decomposition at 600°C in the static air. Formation of the NPs is discussed in terms of FTIR, XRD, SEM, and TEM analyses data. The rate of catalytic decoloration activity of Malachite green dye under the action of metal oxides is considered. The dye has been successfully decolorized in presence of the NPs at room temperature.

New potential antitumor quinazolinones derived from dynamic 2-undecyl benzoxazinone: Synthesis and cytotoxic evaluation

Since the quinazoline and its derivatives have been considered as a novel class of cancer chemotherapeutic agents that show promising activity against different tumors, a new series of 6-iodo-2-undecylquinazolin-4(3H)-ones were prepared via reaction of 6-iodo-2-undecyl-4H-benzoxazin-4-one with nitrogen nucleophiles, namely, primary amines, 4-amino antipyrine, hydrazine hydrate, diamines, ethanol amine, and/or hydrazide derivatives and screened for their antitumor activity in vitro against a panel of three human tumor cell lines namely; hepatocellular carcinoma (liver) HepG2, colon cancer HCT-116, and mammary gland breast MCF-7. Compounds 14, 16, and 18 showed remarkable broad spectrum antitumor activity. All compounds were fully characterized by means of IR, MS, and 1H-NMR spectra.

Synthesis, Spectral Characterization and Antibacterial Investigation of Ni(II) Coordination Complexes of Macrocyclic Schiff base ligands Derived from 4-Aminoantipyrine

A series of Ni(II) complexes (NiL1-NiL5) have been synthesized from macrocyclic Schiff base ligands (L1-L5) were obtained from condensation of 4-aminoantipyrine derivative (L) with different diamines and hydrazides. All these compounds were well characterized by elemental, spectral analysis(mass, IR, 1H-NMR, electronic), magnetic suseceptibility, molar conductance and thermal studies. Macrocyclic Schiff bases are tetradentate with N4 donor system around the metal ion.Octahedral geometry have been assigned for all complexes. All ligands and complexes were examined for antibacterial activity and found that complexes were more potent when compared to ligands.