scholarly journals Synthesis, X-ray Single Crystal, Conformational Analysis and Cholinesterase Inhibitory Activity of a New Spiropyrrolidine Scaffold Tethered Benzo[b]Thiophene Analogue

Crystals ◽  
2020 ◽  
Vol 10 (2) ◽  
pp. 120 ◽  
Author(s):  
Assem Barakat ◽  
Saied M. Soliman ◽  
Saeed Alshahrani ◽  
Mohammad Shahidul Islam ◽  
M. Ali ◽  
...  
Keyword(s):  
Single Crystal ◽  
Inhibitory Activity ◽  
Chemical Yield ◽  
Moderate Activity ◽  
One Pot ◽  
Topology Analysis ◽  
Standard Drug ◽  
X Ray ◽  
Cholinesterase Inhibitory Activity ◽  
Bond Network

Described herein is a one-pot protocol for the synthesis of a substituted spiropyrrolidine scaffold tethered benzo[b]thiophene analogue from (E)-3-(benzo[b]thiophen-2-yl)-1-(4-fluoro- phenyl)-prop-2-en-1-one. The described protocol has the advantage of the high purity of the cyclized adduct and high chemical yield. To assign the chemical structure, different spectrophotometric tools have been applied, including 1H-NMR, 13C-NMR, FTIR, and the X-ray single crystal technique. The X-ray structure showed that the studied compound exist in two disordered parts with equal partial occupancies. The energies of the two conformers were found to be very similar and not exceed 1 kcal/mol, which justifies their coexistence in the crystal with equal percentage. The molecular packing in the crystal was analyzed using Hirshfeld topology analysis. The packing described as two dimensional hydrogen bond network extended along the ac-plane in both conformers but the intermolecular interactions included in each conformer are not similar. The synthesized spiropyrrolidine scaffold tethered benzo[b]thiophene analogue was examined against cholinesterase inhibitory activity and show moderate activity compared to standard drug galantamine.

scholarly journals Three-Component Access to Functionalized Spiropyrrolidine Heterocyclic Scaffolds and Their Cholinesterase Inhibitory Activity

Molecules ◽  
2020 ◽  
Vol 25 (8) ◽  
pp. 1963 ◽  
Author(s):  
Sarra Boudriga ◽  
Saoussen Haddad ◽  
Vikneswaran Murugaiyah ◽  
Moheddine Askri ◽  
Michael Knorr ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Cycloaddition Reaction ◽  
Docking Study ◽  
X Ray Diffraction ◽  
Molecular Docking Study ◽  
Reaction Conditions ◽  
One Pot ◽  
X Ray ◽  
Cholinesterase Inhibitory Activity ◽  
Ache Inhibitory Activity

A novel one-pot [3+2]-cycloaddition reaction of (E)-3-arylidene-1-phenyl-succinimides, cyclic 1,2-diketones (isatin, 5-chloro-isatin and acenaphtenequinone), and diverse α-aminoacids such as 2-phenylglycine or sarcosine is reported. The reaction provides succinimide-substituted dispiropyrrolidine derivatives with high regio- and diastereoselectivities under mild reaction conditions. The stereochemistry of these N-heterocycles has been confirmed by four X-ray diffraction studies. Several synthetized compounds show higher inhibition on acetylcholinesterase (AChE) than butyrylcholinesterase (BChE). Of the 17 synthesized compounds tested, five exhibit good AChE inhibition with IC50 of 11.42 to 22.21 µM. A molecular docking study has also been undertaken for compound 4n possessing the most potent AChE inhibitory activity, disclosing its binding to the peripheral anionic site of AChE enzymes.

scholarly journals One-pot tandem cyclization of enantiopure asymmetric cis-2,5-disubstituted pyrrolidines: Facile access to chiral 10-heteroazatriquinanes

2013 ◽  
Vol 9 ◽  
pp. 265-269 ◽  
Author(s):  
Ping-An Wang ◽  
Sheng-Yong Zhang ◽  
Henri B Kagan
Keyword(s):  
Single Crystal ◽  
Diffraction Analysis ◽  
Single Crystal Diffraction ◽  
One Pot ◽  
X Ray ◽  
Tandem Cyclization

A series of chiral 10-heteroazatriquinanes were synthesized from enantiopure asymmetric cis-2,5-disubstituted pyrrolidines through a one-pot tandem cyclization procedure. The structures and configurations of these new chiral 10-heteroazatriquinanes are confirmed by X-ray single-crystal diffraction analysis.

Reactions of Methyl Ketones and (Hetero)arylcarboxamides with N,N-Dimethylacetamide Dimethyl Acetal. A Simple Metal-Free Synthesis of 2,4,6-Trisubstituted Pyridines

2015 ◽  
Vol 68 (2) ◽  
pp. 184 ◽  
Author(s):  
Benjamin Prek ◽  
Uroš Grošelj ◽  
Marta Kasunič ◽  
Silvo Zupančič ◽  
Jurij Svete ◽  
...  
Keyword(s):  
Microwave Irradiation ◽  
Single Crystal ◽  
Ammonium Acetate ◽  
Dimethyl Acetal ◽  
Methyl Ketones ◽  
Closed Vessel ◽  
Simple Metal ◽  
One Pot ◽  
X Ray ◽  
Metal Free

Two metal-free syntheses of 2,4,6-trisubstituted pyridines 10a–m and 16a–j are described. N,N,6-Trimethyl-4-(substituted)pyridin-2-amines 10 were prepared from aryl or heteroaryl methyl ketones which were transformed with N,N-dimethylacetamide dimethyl acetal (DMADMA) into enaminones 4a–m, followed by treatment with ammonium acetate to give (Z)-3-amino-1-(substituted)but-2-en-1-ones 5a–m. These were treated with DMADMA under microwave irradiation in a closed vessel at 130°C, to give via intermediates 7–9 the final products 10a–m. N2,N2,N4,N4-Tetramethyl-6-(substituted) pyridine-2,4-diamines 16a–j were prepared in a one-pot synthesis from the corresponding carboxamides 11a–j by treatment with an excess of DMADMA in a closed vessel under microwave irradiation to give via intermediates 12a–j to 15a–j the final products 16a–j. X-Ray single crystal diffractometry studies of the enaminones 5c, 5g, 5i, 5j, and 5m and 2,4,6-trisubstituted pyridines 16a, 16b, 16g, 16i, and 16j were consistent with the expected structures.

scholarly journals Synthesis, Crystal Structure, and Biological Activity ofcis/transAmide Rotomers of (Z)-N′-(2-Oxoindolin-3-ylidene)formohydrazide

2014 ◽  
Vol 2014 ◽  
pp. 1-7 ◽  
Author(s):  
Hatem A. Abdel-Aziz ◽  
Hazem A. Ghabbour ◽  
Wagdy M. Eldehna ◽  
Maha M. Qabeel ◽  
Hoong-Kun Fun
Keyword(s):  
Crystal Structure ◽  
Human Tumor ◽  
Cancer Cell Line ◽  
Monoclinic Space Group ◽  
Moderate Activity ◽  
Standard Drug ◽  
X Ray ◽  
H Nmr ◽  
Mcf 7

(Z)-N′-(2-Oxoindolin-3-ylidene)formohydrazide (2) was synthesized by the reaction of (Z)-3-hydrazonoindolin-2-one (1) with formic acid under reflux. The structure of2was characterized by IR, Mass,1H NMR, and X-ray crystal structure determination. Interestingly, compound2appeared in DMSO-d6ascisandtransamide rotomers in 25% and 75%, respectively. The X-ray analysis showed theZgeometrical isomer of2around –C=N– forcisandtransamide rotomers. The crystal of2belongs to monoclinic, space groupP21/c, witha=4.5206(1) Å,b=22.4747(7) Å,c=17.3637(5) Å,β=103.752(1)°,Z=8,V=1713.57(8) Å3,Dc=1.467 Mg m−3,μ=0.11 mm−1,F(000)=784,R=0.047, andwR=0.123for 3798 observed reflections withI>2σ(I). Compound2exhibited a moderate activity in its antimicrobial evaluation againstE. coliandP. aeruginosaand a good activity againstS. aureusclose to that of the standard drug ciprofloxacin. Thein vitroanticancer activity of2was evaluated against two human tumor cell lines, namely, HepG2 hepatocellular carcinoma and MCF-7 breast cancer. HepG2 cancer cell line was more susceptible to compound2than MCF-7.

scholarly journals Allenylphosphine oxides as simple scaffolds for phosphinoylindoles and phosphinoylisocoumarins

2014 ◽  
Vol 10 ◽  
pp. 996-1005 ◽  
Author(s):  
G Gangadhararao ◽  
Ramesh Kotikalapudi ◽  
M Nagarjuna Reddy ◽  
K C Kumara Swamy
Keyword(s):  
Single Crystal ◽  
Trifluoroacetic Acid ◽  
One Pot ◽  
X Ray ◽  
X Ray Crystallography ◽  
Reaction Proceeds ◽  
Propargyl Alcohols

A range of phosphinoylindoles was prepared in one-pot from functionalized propargyl alcohols and a suitable P(III) precursor via a base-mediated reaction. The reaction proceeds via the intermediacy of allenylphosphine oxides. Similarly, phosphinoylisocoumarins were prepared from allenylphosphine oxides in a trifluoroacetic acid-mediated reaction; the latter also acts as a solvent. Interestingly, in the presence of wet trifluoroacetic acid, in addition to phosphinoylisocoumarins, phosphorus-free isocoumarins were also obtained. Key products were characterized by single crystal X-ray crystallography.

Synthesis of 2-(2-Aminophenyl)-4-arylquinazoline Derivatives by Reaction of 2-Aminoarylbenzimidamides with Isatoic Anhydride

2009 ◽  
Vol 64 (8) ◽  
pp. 945-951 ◽  
Author(s):  
Kamal M. El-Shaieb ◽  
Peter G. Jones
Keyword(s):  
Single Crystal ◽  
Structure Analysis ◽  
High Yield ◽  
Isatoic Anhydride ◽  
Reaction Conditions ◽  
One Pot ◽  
X Ray ◽  
Neutral Reaction

A series of 2-(2-aminophenyl)-4-arylquinazoline derivatives (5a - j), with various 4-substituents, have been synthesized by one-pot cyclization in 66 - 79% yield by heating 2-aminoarylbenzimidamides 3a - j with isatoic anhydride (4). The high yield and simplified workup procedure, in addition to the neutral reaction conditions, are the main advantages of our approach. The structure of the product 5e was further confirmed by single-crystal X-ray structure analysis

scholarly journals Secondary Metabolites with α-Glucosidase Inhibitory Activity from the Mangrove Fungus Mycosphaerella sp. SYSU-DZG01

Marine Drugs ◽  
2019 ◽  
Vol 17 (8) ◽  
pp. 483 ◽  
Author(s):  
Pei Qiu ◽  
Zhaoming Liu ◽  
Yan Chen ◽  
Runlin Cai ◽  
Guangying Chen ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Secondary Metabolites ◽  
Single Crystal ◽  
Absolute Configuration ◽  
Inhibitory Activity ◽  
Spectroscopic Data ◽  
X Ray Diffraction ◽  
X Ray ◽  
Ic50 Values ◽  
New Metabolites

Four new metabolites, asperchalasine I (1), dibefurin B (2) and two epicoccine derivatives (3 and 4), together with seven known compounds (5–11) were isolated from a mangrove fungus Mycosphaerella sp. SYSU-DZG01. The structures of compounds 1–4 were established from extensive spectroscopic data and HRESIMS analysis. The absolute configuration of 1 was deduced by comparison of ECD data with that of a known structure. The stereostructures of 2–4 were further confirmed by single-crystal X-ray diffraction. Compounds 1, 8 and 9 exhibited significant α-glucosidase inhibitory activity with IC50 values of 17.1, 26.7 and 15.7 μM, respectively. Compounds 1, 4, 6 and 8 showed antioxidant activity by scavenging DPPH· with EC50 values ranging from 16.3 to 85.8 μM.

Two Zr−based heterometal−organic frameworks for efficient CO2 reduction under visible light

CrystEngComm ◽  
2021 ◽  
Author(s):  
Ying Wang ◽  
Yao-mei Fu ◽  
Si-qi You ◽  
xuexin Li ◽  
Xinlong Wang ◽  
...  
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Single Crystal ◽  
Diffraction Analysis ◽  
Co2 Reduction ◽  
X Ray Diffraction ◽  
Transition Metal Cations ◽  
One Pot ◽  
X Ray ◽  
Secondary Building Units

Two new zirconium−based heterometal−organic frameworks, Zr3CP3−Mn (1) and Zr3CP3−Ni (2) constructed from [Cp3Zr3(μ3−O)(μ2−OH)3(IN)3] secondary building units and transition metal cations, were successfully synthesized through one−pot method. Single-crystal X-ray diffraction analysis...

Syntheses and molecular structures of some di(amidino)monosilanes

2021 ◽  
Vol 44 (1) ◽  
pp. 228-238
Author(s):  
Markus Bös ◽  
Marcus Herbig ◽  
Uwe Böhme ◽  
Edwin Kroke
Keyword(s):  
Raman Spectroscopy ◽  
Single Crystal ◽  
High Field ◽  
Structural Features ◽  
Molecular Structures ◽  
X Ray Diffraction ◽  
One Pot ◽  
X Ray ◽  
Field Shift ◽  
Nmr Signals

Abstract The syntheses of three different amidinosilanes of the type Me2Si[N=C(Ph)R]2 with R = pyrrolidino, morpholino, and diethylamino and one derivative with the composition R2Si[N=C(Ph)R]2 with R = morpholino are reported. These compounds were prepared in one-pot syntheses including three consecutive steps. All products are analysed by single crystal X-ray diffraction, NMR, and Raman spectroscopy. The Si–N=C–N units of these compounds show characteristic structural features and cause a significant high field shift of the 29Si NMR signals.

Synthesis and Biological Activity of Some 17a-Substituted Homolactones of Androst-5-ene Derivatives

2005 ◽  
Vol 70 (9) ◽  
pp. 1387-1396 ◽  
Author(s):  
Katarina M. Penov Gaši ◽  
Srdjan Z. Stojanović ◽  
Marija N. Sakač ◽  
Evgenija A. Djurendić ◽  
János J. Csanádi ◽  
...  
Keyword(s):  
Biological Activity ◽  
Structural Analysis ◽  
Ethylene Glycol ◽  
Structure Analysis ◽  
Inhibitory Activity ◽  
Potassium Hydroxide ◽  
One Pot ◽  
X Ray ◽  
Starting Compound

Some new 17a-homolactones were prepared from 3β-hydroxy-16-(hydroxyimino)androst-5-en-17-one (1) as a starting compound, which was transformed first to the corresponding 17α-phenyl and 17α-benzyl derivatives 2 and 3. The structure of compound 3 was confirmed by X-ray structure analysis. Beckmann fragmentation of compounds 2 and 3 yielded 16,17-seco-cyano ketones 4-7, whose reduction with NaBH4 gave 16,17-seco-cyano alcohols 8-11, whereby the structure of compound 7 was established by X-ray structural analysis. Compounds 8-11 served as the starting compounds for obtaining lactones 12 and 13 in a reaction with potassium hydroxide in ethylene glycol. One-pot procedures were also developed for preparing 17a-homolactones 12, 13 and 16 from the hydroxyimino alcohols 2, 3 and 14. Compounds 12 and 13 showed an inhibitory activity against the enzyme aromatase (63 and 59%, respectively).

Sign in / Sign up

Export Citation Format

Share Document