scholarly journals Three Multi-Components Reaction: Synthesis and X-Ray Single-Crystal of Hydroacridinone-Based Hydrazino-S-Triazine Derivative as a New Class of Urease Inhibitor

Crystals ◽  
2019 ◽  
Vol 10 (1) ◽  
pp. 14 ◽  
Author(s):  
Assem Barakat ◽  
Saied M. Soliman ◽  
Ayman El-Faham ◽  
M. Ali ◽  
Abdullah Mohammed Al-Majid ◽  
...  
Keyword(s):  
Structural Features ◽  
Acetohydroxamic Acid ◽  
Orthorhombic Crystal System ◽  
Orthorhombic Crystal ◽  
One Pot ◽  
X Ray ◽  
New Class ◽  
Hirshfeld Surfaces ◽  
The One

The one-pot fashion of three multi-component reaction provides the desired hydroacridinone-based hydrazino-s-triazine scaffold 4. Compound 4 was crystallized in an orthorhombic crystal system and Pbca space group with a = 11.6271(2) Å, b = 18.2018(4) Å, c = 32.4721(6) Å, and α = β = γ = 90° with one formula unit per asymmetric unit and eight molecules per unit cell. Additionally, structural features, Hirshfeld surfaces, and DFT studies were also investigated. Its packing in the crystal is controlled by H…H (63.4%), O…H (12.7%), Cl…H (7.2%), N…H (4.7%), and C…H (10.2%) contacts, where the O…H and Cl…H contacts were found the strongest. In vitro urease inhibition evaluation showed that the hydroacridinone-based hydrazino-s-triazine is more active (IC50 = 17.9 ± 0.47 µM) than the standard acetohydroxamic acid (IC50 = 20.3 ± 0.43 µM).

scholarly journals Water-Soluble O-, S- and Se-Functionalized Cyclic Acetyl-triaza-phosphines. Synthesis, Characterization and Application in Catalytic Azide-alkyne Cycloaddition

Molecules ◽  
2020 ◽  
Vol 25 (22) ◽  
pp. 5479
Author(s):  
Abdallah Mahmoud ◽  
Piotr Smoleński ◽  
M. Guedes da Silva ◽  
Armando Pombeiro
Keyword(s):  
Cycloaddition Reaction ◽  
Structural Features ◽  
Water Soluble ◽  
31P Nmr Spectroscopy ◽  
The Novel ◽  
X Ray Diffraction ◽  
One Pot ◽  
Hirshfeld Surfaces ◽  
The One ◽  
High Yields

The 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane (DAPTA) derivatives, viz. the already reported 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane 5-oxide (DAPTA=O, 1), the novel 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane-5-sulfide (DAPTA=S, 2), and 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane-5-selenide (DAPTA=Se, 3), have been synthesized under mild conditions. They are soluble in water and most common organic solvents and have been characterized using 1H and 31P NMR spectroscopy and, for 2 and 3, also by single crystal X-ray diffraction. The effect of O, S, or Se at the phosphorus atom on the structural features of the compounds has been investigated, also through the analyses of Hirshfeld surfaces. The presence of 1–3 enhances the activity of copper for the catalytic azide-alkyne cycloaddition reaction in an aqueous medium. The combination of cheaply available copper (II) acetate and compound 1 has been used as a catalyst for the one-pot and 1,4-regioselective procedure to obtain 1,2,3-triazoles with high yields and according to ‘click rules’.

scholarly journals Synthesis of 1-aryl-1-phenylpropenes using an alkylation-rearrangement-methylation-isomerization one-pot reaction sequence

2011 ◽  
Vol 9 (5) ◽  
pp. 904-909 ◽  
Author(s):  
Nenad Maraš ◽  
Franc Perdih ◽  
Marijan Kočevar
Keyword(s):  
Claisen Rearrangement ◽  
Structural Features ◽  
X Ray Diffraction ◽  
Reaction Sequence ◽  
One Pot ◽  
Double Bond Migration ◽  
X Ray ◽  
Crystalline Product ◽  
Tetramethylammonium Chloride ◽  
The One

Abstract(Z/E)-1-(2-Methoxyaryl)-1-phenylpropenes have been prepared in good yields by heating a mixture of a phenolic substrate, cinnamyl chloride, tetramethylammonium chloride and K2CO3 in polyethyleneglycol at 180°C. The one-pot synthesis proceeds through four discrete reaction steps: alkylation of the phenol with cinnamyl chloride, Claisen rearrangement, O-methylation and double-bond migration. The configuration of one crystalline product was determined using a single-crystal X-ray diffraction analysis. The thermodynamic and structural features of the products were evaluated using computational chemistry techniques.

scholarly journals One-Pot Multicomponent Synthesis of Methoxybenzo[h]quinoline-3-carbonitrile Derivatives; Anti-Chagas, X-ray, and In Silico ADME/Tox Profiling Studies

Molecules ◽  
2021 ◽  
Vol 26 (22) ◽  
pp. 6977
Author(s):  
Hegira Ramírez ◽  
Katiuska Charris ◽  
Esteban Fernandez-Moreira ◽  
Benjamín Nogueda-Torres ◽  
Mario V. Capparelli ◽  
...  
Keyword(s):  
In Silico ◽  
Ammonium Acetate ◽  
Aromatic Aldehydes ◽  
Multicomponent Synthesis ◽  
Activity Profile ◽  
One Pot ◽  
X Ray ◽  
Elemental Analyses ◽  
The One

Several methoxybenzo[h]quinoline-3-carbonitrile analogs were designed and synthesized in a repositioning approach to developing compounds with anti-prostate cancer and anti-Chagas disease properties. The compounds were synthesized through a sequential multicomponent reaction of aromatic aldehydes, malononitrile, and 1-tetralone in the presence of ammonium acetate and acetic acid (catalytic). The effect of the one-pot method on the generation of the target product has been studied. The compounds were in vitro screened against bloodstream trypomastigotes of T. cruzi (NINOA and INC-5 strains) and were most effective at showing a better activity profile than nifurtimox and benznidazole (reference drugs). A study in silico on absorption, distribution, metabolism, excretion, and toxicity (ADME/Tox) profiling to help describe the molecular properties related to the pharmacokinetic aspects in the human body of these compounds was reported. In addition, X-ray data for the compound 2-Amino-5,6-dihydro-4-(3-hydroxy-4-methoxy-phenyl)-8-methoxybenzo[h]quinoline-3-carbonitrile 6 was being reported. Spectral (IR, NMR, and elemental analyses) data on all final compounds were consistent with the proposed structures.

PTSA-Catalyzed One Pot Domino Synthesis of Dihydropyrido[2,3-d]pyrimidine Derivatives and their Antimicrobial Activity

2021 ◽  
Vol 6 (3) ◽  
pp. 222-227
Author(s):  
Krishna A. Bhensdadia ◽  
Prakash L. Kalavadiya ◽  
Nilam H. Lalavani ◽  
Shipra H. Baluja
Keyword(s):  
Antimicrobial Activity ◽  
Spectral Analysis ◽  
Pyrimidine Derivatives ◽  
One Pot ◽  
In Vitro Antimicrobial Activity ◽  
Aryl Aldehydes ◽  
Three Component Reaction ◽  
The One

A novel series of dihydropyrido[2,3-d]pyrimidine derivatives were synthesized by multicomponent domino cyclization via the one-pot three component reaction of 6-amino uracil, substituted aryl aldehydes and N-methyl-1-(methylthio)-2-nitroethenamine in the presence of PTSA 10 mol% as a catalyst. The structures of these synthesized compounds were characterized by spectral analysis. Further the synthesized compounds screened for in vitro antimicrobial activity. Among all the compounds, compound 4b containing flouro substitution exhibited good inhibition against the tested species.

Alginate–copper microspheres as efficient and reusable heterogeneous catalysts for the one-pot synthesis of 4-organylselanyl-1H-pyrazoles

2020 ◽  
Vol 10 (12) ◽  
pp. 3918-3930 ◽  
Author(s):  
Jaqueline F. Souza ◽  
Thalita F. B. de Aquino ◽  
José E. R. Nascimento ◽  
Raquel G. Jacob ◽  
André R. Fajardo
Keyword(s):  
Heterogeneous Catalysts ◽  
One Pot ◽  
New Class ◽  
One Pot Synthesis ◽  
Facile Preparation ◽  
The One ◽  
Substituted Pyrazoles

This study demonstrates the facile preparation and use of alginate–Cu2+ microspheres in the catalysis of a new class of organoselenium substituted pyrazoles through one-pot reactions.

5,6,7,8-Tetrahydronaphthalen-1-amine as Precursor for Thiazolidi­nones and Benzothiazepinones: Synthesis and Atropisomeric Relationship

Synthesis ◽  
2017 ◽  
Vol 49 (23) ◽  
pp. 5167-5175 ◽  
Author(s):  
Bruna Drawanz ◽  
Georgia Zimmer ◽  
Leticia Rodrigues ◽  
Andressa Nörnberg ◽  
Manfredo Hörner ◽  
...  
Keyword(s):  
Small Difference ◽  
Mercaptoacetic Acid ◽  
X Ray Diffraction ◽  
Ring Plane ◽  
One Pot ◽  
X Ray ◽  
Nmr Techniques ◽  
The One ◽  
Electron Donating Groups ◽  
Weak Electron

The one-pot reaction of 5,6,7,8-tetrahydronaphthalen-1-amine, mercaptoacetic acid, and arenealdehydes having strong and weak electron-withdrawing groups gave the corresponding 1,3-thiazolidin-4-ones (47–70%). When arenealdehydes bearing strong and weak electron-donating groups were used as precursors, the 1,4-benzothiazepin-2-ones were obtained (30–72%) by p-TsOH catalysis. All compounds are unknown and were characterized by GC-MS and NMR techniques, and available crystals by X-ray diffraction studies. The atropisomerism phenomenon was observed in several 1,3-thiazolidin-4-ones as confirmed by VTNMR method. The Tc was established as 332 K and the energy required for the interconversion of one atrop­isomer into another is around 16.8 kcal·mol–1. Chemical quantum calculation and NOESY displayed that more stable isomer has the tetrahydro­naphthalene portion below the five-ring plane. Only a small difference between isomers (–0.21 to –0.84 kcal·mol–1) was observed by calculated energy.

Two new zinc(II) and mercury(II) complexes based on N,N′-(cyclohexane-1,2-diylidene)bis(4-fluorobenzohydrazide): synthesis, crystal structures and antibacterial activities

2020 ◽  
Vol 76 (5) ◽  
pp. 476-482
Author(s):  
Al-Ameen Bariz OmarAli ◽  
Ahmed Jasim M. Al-Karawi ◽  
Adil A. Awad ◽  
Necmi Dege ◽  
Sevgi Kansız ◽  
...  
Keyword(s):  
Organic Ligand ◽  
Antibacterial Activities ◽  
Structural Features ◽  
Bacterial Strains ◽  
Tetrahedral Geometry ◽  
X Ray ◽  
X Ray Crystallography ◽  
Growth Inhibitory ◽  
The Difference

Reaction of N,N′-(cyclohexane-1,2-diylidene)bis(4-fluorobenzohydrazide), C20H18F2N4O2, (LF ), with zinc chloride and mercury(II) chloride produced different types and shapes of neutral coordination complexes, namely, dichlorido[N,N′-(cyclohexane-1,2-diylidene)bis(4-fluorobenzohydrazide)-κ2 N,O]zinc(II), [ZnCl2(C20H18F2N4O2)], (1), and dichlorido[N,N′-(cyclohexane-1,2-diylidene)bis(4-fluorobenzohydrazide)-κ4 O,N,N′,O′]mercury(II), [HgCl2(C20H18F2N4O2)], (2). The organic ligand and its metal complexes are characterized using various techniques: IR, UV–Vis and nuclear magnetic resonance (NMR) spectroscopies, in addition to powder X-ray diffraction (PXRD), single-crystal X-ray crystallography and microelemental analysis. Depending upon the data from these analyses and measurements, a typical tetrahedral geometry was confirmed for zinc complex (1), in which the ZnII atom is located outside the bis(benzhydrazone) core. The HgII atom in (2) is found within the core and has a common octahedral structure. The in vitro antibacterial activities of the prepared compounds were evaluated against two different bacterial strains, i.e. gram positive Bacillus subtilis and gram negative Pseudomonas aeruginosa bacteria. The prepared compounds exhibited differentiated growth-inhibitory activities against these two bacterial strains based on the difference in their lipophilic nature and structural features.

scholarly journals Synthesis and characterization of novel bioactive 1,2,4-oxadiazole natural product analogs bearing the N-phenylmaleimide and N-phenylsuccinimide moieties

2013 ◽  
Vol 9 ◽  
pp. 2202-2215 ◽  
Author(s):  
Catalin V Maftei ◽  
Elena Fodor ◽  
Peter G Jones ◽  
M Heiko Franz ◽  
Gerhard Kelter ◽  
...  
Keyword(s):  
Natural Product ◽  
Synthesis And Characterization ◽  
Aminobenzoic Acid ◽  
One Pot ◽  
X Ray ◽  
X Ray Crystallography ◽  
Quisqualic Acid ◽  
Oxobutanoic Acid

Taking into consideration the biological activity of the only natural products containing a 1,2,4-oxadiazole ring in their structure (quisqualic acid and phidianidines A and B), the natural product analogs 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)pyrrolidine-2,5-dione (4) and 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)-1H-pyrrole-2,5-dione (7) were synthesized starting from 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)aniline (1) in two steps by isolating the intermediates 4-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylamino)-4-oxobutanoic acid (3) and (Z)-4-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylamino)-4-oxobut-2-enoic acid (6). The two natural product analogs 4 and 7 were then tested for antitumor activity toward a panel of 11 cell lines in vitro by using a monolayer cell-survival and proliferation assay. Compound 7 was the most potent and exhibited a mean IC50 value of approximately 9.4 µM. Aniline 1 was synthesized by two routes in one-pot reactions starting from tert-butylamidoxime and 4-aminobenzoic acid or 4-nitrobenzonitrile. The structures of compounds 1, 2, 4, 5 and 6 were confirmed by X-ray crystallography.

scholarly journals Crystal Structure, Spectral Studies, and Hirshfeld Surfaces Analysis of 5-Methyl-5H-dibenzo[b,f]azepine and 5-(4-Methylbenzyl)-5H-dibenzo[b,f]azepine

2014 ◽  
Vol 2014 ◽  
pp. 1-9
Author(s):  
Madan Kumar Shankar ◽  
Basavapattana C. Manjunath ◽  
Koravangala Shivakumar Vinay Kumar ◽  
Kudigana J. Pampa ◽  
Marilinganadoddi P. Sadashiva ◽  
...  
Keyword(s):  
Diffraction Method ◽  
Spectral Studies ◽  
Boat Conformation ◽  
Orthorhombic Crystal System ◽  
Orthorhombic Crystal ◽  
Space Group ◽  
Cell Parameters ◽  
Crystal System ◽  
Hirshfeld Surfaces ◽  
Short Contacts

The compounds, 5-methyl-5H-dibenzo[b,f]azepine (1) and 5-(4-methylbenzyl)-5H-dibenzo[b,f]azepine (2), were synthesized and characterized by spectral studies, and finally confirmed by single crystal X-ray diffraction method. The compound 1 crystallizes in the orthorhombic crystal system in Pca21 space group, having cell parameters a=11.5681 (18) Å, b=11.8958 (18) Å, c=8.0342 (13) Å, and Z=4 and V=1105.6 (3) Å3. And the compound 2 crystallizes in the orthorhombic crystal system and space group Pbca, with cell parameters a=16.5858 (5) Å, b=8.4947 (2) Å, c=23.1733 (7) Å, and Z=8 and V=3264.92 (16) Å3. The azepine ring of both molecules 1 and 2 adopts boat conformation with nitrogen atom showing maximum deviations of 0.483 (2) Å and 0.5025 (10) Å, respectively. The C–H⋯π short contacts were observed. The dihedral angle between fused benzene rings to the azepine motif is 47.1 (2)° for compound 1 and 52.59 (6)° for compound 2, respectively. The short contacts were analyzed and Hirshfeld surfaces computational method for both molecules revealed that the major contribution is from C⋯H and H⋯H intercontacts.

Sign in / Sign up

Export Citation Format

Share Document