scholarly journals Synthesis of Anti-Inflammatory Spirostene-Pyrazole Conjugates by a Consecutive Multicomponent Reaction of Diosgenin with Oxalyl Chloride, Arylalkynes and Hydrazines or Hydrazones

Molecules ◽  
2021 ◽  
Vol 27 (1) ◽  
pp. 162
Author(s):  
Maksim E. Mironov ◽  
Sergey A. Borisov ◽  
Tatyana V. Rybalova ◽  
Dmitry S. Baev ◽  
Tatyana G. Tolstikova ◽  
...  
Keyword(s):  
Oxalyl Chloride ◽  
Diclofenac Sodium ◽  
One Pot ◽  
Consecutive Reaction ◽  
Covalent Bonds ◽  
X Ray ◽  
Kelch Domain ◽  
Anti Inflammatory ◽  
New Compounds ◽  
Synthetic Application

Steroid sapogenin diosgenin is of significant interest due to its biological activity and synthetic application. A consecutive one-pot reaction of diosgenin, oxalyl chloride, arylacetylenes, and phenylhydrazine give rise to steroidal 1,3,5-trisubstituted pyrazoles (isolated yield 46–60%) when the Stephens–Castro reaction and heterocyclization steps were carried out by heating in benzene. When the cyclization step of alkyndione with phenylhydrazine was performed in 2-methoxyethanol at room temperature, steroidal α,β-alkynyl (E)- and (Z)-hydrazones were isolated along with 1,3,5-trisubstituted pyrazole and the isomeric 2,3,5-trisubstituted pyrazole. The consecutive reaction of diosgenin, oxalyl chloride, phenylacetylene and benzoic acid hydrazides efficiently forms steroidal 1-benzoyl-5-hydroxy-3-phenylpyrazolines. The structure of new compounds was unambiguously corroborated by comprehensive NMR spectroscopy, mass-spectrometry, and X-ray structure analyses. Performing the heterocyclization step of ynedione with hydrazine monohydrate in 2-methoxyethanol allowed the synthesis of 5-phenyl substituted steroidal pyrazole, which was found to exhibit high anti-inflammatory activity, comparable to that of diclofenac sodium, a commercial pain reliever. It was shown by molecular docking that the new derivatives are incorporated into the binding site of the protein Keap1 Kelch-domain by their alkynylhydrazone or pyrazole substituent with the formation of more non-covalent bonds and have higher affinity than the initial spirostene core.

scholarly journals Funktionalisierte tripod-Liganden mit Neopentan-Grundgerüst: Umsetzung von HOCH2C(CH2PR2)3 mit Elektrophilen / Functionalized tripod-Ligands with N eopentane Fram ew ork: R eaction of HOCH2C(CH2PR2)3 with Electrophiles

1995 ◽  
Vol 50 (9) ◽  
pp. 1287-1306 ◽  
Author(s):  
Thomas Seitz ◽  
Alexander Asam ◽  
Gottfried Hüttner ◽  
Olaf Walter ◽  
Laszlo Zsolnai
Keyword(s):  
Hydroxy Group ◽  
Analytical Techniques ◽  
One Pot ◽  
X Ray ◽  
One Pot Synthesis ◽  
Tripod Ligands ◽  
Esterification Reactions ◽  
New Compounds

AbstractSeveral ways to functionalize hydroxy-tripod-ligands (HOCH2C(CH2PR2)3) by activation with electrophiles are presented. The use of carboxylic halides and anhydrides is shown to be generally successful for esterification reactions in a one-pot synthesis starting from the oxetanes O(CH2)2C(CH2PR2)2. Facial coordinaton of the related esters towards iron(II) and molybdenum(O) can be achieved depending on the nature of the phosphane donor groups. If methyliodide or trimethylsilylchloride are used as electrophiles in order to functionalize the hydroxy group in HOCH2C(CH2PR2)3, it is necessary to proctect the phosphane groups by formation of the tris-borane adduct. All new compounds have been fully characterized by the usual analytical techniques as well as by X-ray analyses on selected examples.

Catalyst-Free One-Pot Synthesis of Chromeno-Imidazo-Pyridinones by an Aza-Michael Addition/Rearrangement/Heterocyclization Tandem Reaction

Synlett ◽  
2018 ◽  
Vol 29 (11) ◽  
pp. 1437-1440 ◽  
Author(s):  
Oualid Talhi ◽  
Norah Bennamane ◽  
Artur Silva ◽  
Houria Lakhdari ◽  
Ridha Hassaine ◽  
...  
Keyword(s):  
Michael Addition ◽  
Room Temperature ◽  
Addition Reaction ◽  
2D Nmr ◽  
X Ray Diffraction ◽  
One Pot ◽  
X Ray ◽  
Catalyst Free ◽  
One Pot Synthesis ◽  
New Compounds

A one-pot synthesis of a novel series of chromeno-imidazo-pyridinone derivatives from 3-[(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl]chromones and ethane-1,2-diamine at room temperature under catalyst-free conditions has been successfully developed. This approach involves a tandem aza-Michael addition reaction, a chromone-to-chromanone rearrangement, and a heterocyclization sequence, leading to chromeno-imidazo-pyridinone polyheterocycles. The structure and absolute configurations of the new compounds were elucidated by a combination of 1D- and 2D-NMR analyses and single-crystal X-ray diffraction.

scholarly journals One-pot activation–alkynylation–cyclization synthesis of 1,5-diacyl-5-hydroxypyrazolines in a consecutive three-component fashion

2019 ◽  
Vol 15 ◽  
pp. 1360-1370 ◽  
Author(s):  
Christina Görgen ◽  
Katharina Boden ◽  
Guido J Reiss ◽  
Walter Frank ◽  
Thomas J J Müller
Keyword(s):  
Nmr Spectroscopy ◽  
Oxalyl Chloride ◽  
Cyclization Reaction ◽  
One Pot ◽  
X Ray

A consecutive three-component activation–alkynylation–cyclization reaction of (hetero)aryl glyoxylic acids, oxalyl chloride, arylacetylenes, and hydrazides efficiently forms 1,5-diacyl-5-hydroxypyrazolines in moderate to good yields. The structures were unambiguously corroborated by comprehensive NMR spectroscopy and X-ray structure analyses of selected derivatives.

Water Promoted One-pot Three-Step Synthesis of Novel N-Saccharin Isoxazolines/Isoxazoles Using KI/Oxone Under Ultrasonic Activation

2019 ◽  
Vol 23 (11) ◽  
pp. 1270-1281 ◽  
Author(s):  
Hamza Tachallait ◽  
Mohsine Driowya ◽  
Eleuterio Álvarez ◽  
Rachid Benhida ◽  
Khalid Bougrin
Keyword(s):  
Cycloaddition Reaction ◽  
Hydroxylamine Hydrochloride ◽  
Spectroscopic Techniques ◽  
X Ray Diffraction ◽  
Ultrasonic Activation ◽  
One Pot ◽  
Ultrasonic Probe ◽  
X Ray ◽  
X Ray Crystallography ◽  
New Compounds

A green and efficient regioselective protocol was developed for the preparation of novel isoxazolines and isoxazoles of N-saccharin derivatives via the water-promoted cycloaddition reaction of nitrile oxides with alkenes and alkynes. It is noteworthy that KI/Oxone/water-promoted one-pot three-component reactions of aldehyde, hydroxylamine hydrochloride, and alkene or alkyne were observed to be very satisfactory. The synthesis of all adducts (4a-j/5a-j) has been carried out by this method with high to excellent yields (70-95%) at 25°C within 30 min, using ultrasonic probe. All the new compounds were thoroughly characterized by spectroscopic techniques and also 5b, 5c and 5f were structurally identified by single-crystal X-ray diffraction methods. X-ray crystallography structure analysis clearly supported the regioselectivity of the cycloaddition reaction.

scholarly journals Synthesis and Anti-inflammatory Activity of Some Novel 2,4-Diaryl-3,5-bis(arylimino)-1,2,4-thiadiazolidine Derivatives

2009 ◽  
Vol 6 (2) ◽  
pp. 495-503 ◽  
Author(s):  
P. Venkatesh ◽  
S. N. Pandeya
Keyword(s):  
Diclofenac Sodium ◽  
Inflammatory Activity ◽  
Second Step ◽  
Paw Edema ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
Methoxy Groups ◽  
Anti Inflammatory ◽  
Sar Study ◽  
New Compounds

A series of some novel 2,4-diaryl-3,5-bis(arylimino)-1,2,4-thiadiazolidine derivatives were synthesized and evaluated for anti-inflammatory activity. In the SAR study, the phenyl ring on 3 and 4 position of 1,2,4-thiadiazolidine ring substituted with chloro, nitro and methoxy groups showed better activity. The title compounds were synthesized from two steps; the first step involved the synthesis of diaryl substituted thioureas then, it was cyclised to give the 1,2,4-thiadiazole system in the presence of oxidizing agent (hydrogen peroxide and concentrated hydrochloric acid) in the second step. The purity of the synthesized compounds were judged by their C, H and N analysis and the structure was analyzed on the basis of IR, H1NMR, C13NMR and Mass spectral data. The anti-inflammatory activity of new compounds was determined by λ-Carrageenan induced mice paw edema method using diclofenac sodium as a standard. Among the compounds tested four compounds, B2 (2,4-diphenyl-3,5-bis(3-nitrophenylimino)-1,2,4-thiadiazolidine), B4 (2,4-diphenyl-3,5-bis(3-chlorophenylimino)-1,2,4-thiadiazolidine), B6 (2,4-diphenyl-3,5-bis(4-methoxyphenylimino)-1,2,4-thiadiazolidine) and B7 (2,4-diphenyl-3,5-bis (2-methoxyphenylimino)-1,2,4-thiadiazolidine) were the most active compounds in these series.

A Facile One-Pot Synthesis of 3-Methylbenzisoxazoles via a Key Intermediate of ortho-Ethoxyvinyl Nitroaryls by Domino Rearrangement and Their Anti- Inflammatory Activity

2020 ◽  
Vol 16 (8) ◽  
pp. 1161-1165
Author(s):  
Bashetti Nagaraju ◽  
Jagarlapudi V. Shanmukhakumar ◽  
Nareshvarma Seelam ◽  
Tondepu Subbaiah ◽  
Bethanamudi Prasanna
Keyword(s):  
Stannous Chloride ◽  
Biologically Active ◽  
Inflammatory Activity ◽  
Albino Rats ◽  
One Pot ◽  
Simple Method ◽  
Standard Drug ◽  
Entire Study ◽  
One Pot Synthesis ◽  
Anti Inflammatory

Background: Recently, there has been a lot of scientific interest in exploring the syntheses of oxygen and nitrogen-containing heterocyclic compounds due to their pharmacological activities. In addition, benzisoxazoles play a very important role in organic synthesis as key intermediates. Objective: In this paper, we focused on developing a novel synthetic route for biologically active arylisoxazoles under normal conditions, and simplified it to get high purities and yields, and also reported their anti-inflammatory activities. Method: An efficient and simple method has been explored for the synthesis of novel 3-methyl arylisoxazoles from o-nitroaryl halides via o-ethoxyvinylnitroaryls, using dihydrated stannous chloride (SnCl2.2H2O) in MeOH / EtOAc (1:1) via Domino rearrangement in one pot synthesis. Result: We synthesized novel 3-methylarylisoxazoles from o-nitroarylhalides via o-ethoxyvinylnitroaryls, using dihydrated stannous chloride (SnCl2.2H2O) in MeOH / EtOAc (1:1) via domino rearrangement. In this reduction, nitro group and ethoxy vinyl group change to the functional acyl ketones, followed by hetero cyclization. Here, the reaction proceeds without the isolation of intermediates like 2-acylnitroarenes and 2- acylanilines. All the synthesized compounds were completely characterized by the NMR and mass spectra. The compounds were also explored for their anti-inflammatory activity by carrageenan-induced inflammation in the albino rats (150-200 g) of either sex used in this entire study with the use of Diclofenac sodium as the standard drug. The initial evaluations identified leading targets with good to moderate anti-inflammatory activity. Conclusion: A simple, one-pot and convenient method has been explored for the synthesis of novel 3- methylarylisoxazoles with high purity and reaction yields. All the compounds 3a, 3c, 3d, 3f, 3g and 3h exhibited 51-64% anti-inflammatory activities.

One-pot Synthesis of Pyrazolone Sulfones by Iodine-catalyzed Sulfenylation of Pyrazolones with Aryl Sulfonyl Hydrazides Followed by Oxidation in Water

2018 ◽  
Vol 15 (3) ◽  
pp. 380-387
Author(s):  
Xia Zhao ◽  
Xiaoyu Lu ◽  
Lipeng Zhang ◽  
Tianjiao Li ◽  
Kui Lu
Keyword(s):  
Double Bond ◽  
Efficient Method ◽  
Room Temperature ◽  
Sulfonyl Chloride ◽  
Antibacterial Activities ◽  
Oxidation Reactions ◽  
Reaction Conditions ◽  
One Pot ◽  
X Ray ◽  
Amide Form

Aim and Objective: Pyrazolone sulfones have been reported to exhibit herbicidal and antibacterial activities. In spite of their good bioactivities, only a few methods have been developed to prepare pyrazolone sulfones. However, the substrate scope of these methods is limited. Moreover, the direct sulfonylation of pyrazolone by aryl sulfonyl chloride failed to give pyrazolone sulfones. Thus, developing a more efficient method to synthesize pyrazolone sulfones is very important. Materials and Method: Pyrazolone, aryl sulphonyl hydrazide, iodine, p-toluenesulphonic acid and water were mixed in a sealed tube, which was heated to 100°C for 12 hours. The mixture was cooled to 0°C and m-CPBA was added in batches. The mixture was allowed to stir for 30 min at room temperature. The crude product was purified by silica gel column chromatography to afford sulfuryl pyrazolone. Results: In all cases, the sulfenylation products were formed smoothly under the optimized reaction conditions, and were then oxidized to the corresponding sulfones in good yields by 3-chloroperoxybenzoic acid (m-CPBA) in water. Single crystal X-ray analysis of pyrazolone sulfone 4aa showed that the major tautomer of pyrazolone sulfones was the amide form instead of the enol form observed for pyrazolone thioethers. Moreover, the C=N double bond isomerized to form an α,β-unsaturated C=C double bond. Conclusion: An efficient method to synthesize pyrazolone thioethers by iodine-catalyzed sulfenylation of pyrazolones with aryl sulfonyl hydrazides in water was developed. Moreover, this method was employed to synthesize pyrazolone sulfones in one-pot by subsequent sulfenylation and oxidation reactions.

scholarly journals Facile Bio-Fabrication of Ag-Cu-Co Trimetallic Nanoparticles and Its Fungicidal Activity against Candida auris

2021 ◽  
Vol 7 (1) ◽  
pp. 62 ◽  
Author(s):  
Majid Rasool Kamli ◽  
Vartika Srivastava ◽  
Nahid H. Hajrah ◽  
Jamal S. M. Sabir ◽  
Khalid Rehman Hakeem ◽  
...  
Keyword(s):  
Electron Microscopy ◽  
Antimicrobial Properties ◽  
Bloodstream Infections ◽  
Multidrug Resistant ◽  
Biologically Active ◽  
Phase Cell ◽  
Candida Auris ◽  
Medical Problems ◽  
One Pot ◽  
X Ray

Candida auris is an emergent multidrug-resistant pathogen that can lead to severe bloodstream infections associated with high mortality rates, especially in hospitalized individuals suffering from serious medical problems. As Candida auris is often multidrug-resistant, there is a persistent demand for new antimycotic drugs with novel antifungal action mechanisms. Here, we reported the facile, one-pot, one-step biosynthesis of biologically active Ag-Cu-Co trimetallic nanoparticles using the aqueous extract of Salvia officinalis rich in polyphenols and flavonoids. These medicinally important phytochemicals act as a reducing agent and stabilize/capping in the nanoparticles’ fabrication process. Fourier Transform-Infrared, Scanning electron microscopy, Transmission Electron Microscopy, Energy dispersive X-Ray, X-ray powder diffraction and Thermogravimetric analysis (TGA) measurements were used to classify the as-synthesized nanoparticles. Moreover, we evaluated the antifungal mechanism of as-synthesized nanoparticles against different clinical isolates of C. auris. The minimum inhibitory concentrations and minimum fungicidal concentrations ranged from 0.39–0.78 μg/mL and 0.78–1.56 μg/mL. Cell count and viability assay further validated the fungicidal potential of Ag-Cu-Co trimetallic nanoparticles. The comprehensive analysis showed that these trimetallic nanoparticles could induce apoptosis and G2/M phase cell cycle arrest in C. auris. Furthermore, Ag-Cu-Co trimetallic nanoparticles exhibit enhanced antimicrobial properties compared to their monometallic counterparts attributed to the synergistic effect of Ag, Cu and Co present in the as-synthesized nanoparticles. Therefore, the present study suggests that the Ag-Cu-Co trimetallic nanoparticles hold the capacity to be a lead for antifungal drug development against C. auris infections.

scholarly journals Fusarins G–L with Inhibition of NO in RAW264.7 from Marine-Derived Fungus Fusarium solani 7227

Marine Drugs ◽  
2021 ◽  
Vol 19 (6) ◽  
pp. 305
Author(s):  
Guangyuan Luo ◽  
Li Zheng ◽  
Qilin Wu ◽  
Senhua Chen ◽  
Jing Li ◽  
...  
Keyword(s):  
Fusarium Solani ◽  
2D Nmr ◽  
Inflammatory Activity ◽  
Raw264.7 Cells ◽  
Spectroscopic Methods ◽  
X Ray ◽  
X Ray Crystallography ◽  
Structure Activity ◽  
Ic50 Values ◽  
New Compounds

Six new fusarin derivatives, fusarins G–L (1–6), together with five known compounds (5–11) were isolated from the marine-derived fungus Fusarium solani 7227. The structures of the new compounds were elucidated by means of comprehensive spectroscopic methods (1D and 2D NMR, HRESIMS, ECD, and ORC) and X-ray crystallography. Compounds 5–11 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide, with IC50 values ranging from 3.6 to 32.2 μM. The structure–activity relationships of the fusarins are discussed herein.

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