Synthesis and In Vitro Anti-Ulcer Effect of Triazolo-Methyl Tetrahydrobenzofuran Oxime Ether Derivatives

2013 ◽  
Vol 746 ◽  
pp. 35-39 ◽  
Author(s):  
Hu Biao Fang ◽  
Lei Jin ◽  
Cheng Qiao Cao ◽  
Hua Jun Luo ◽  
Nian Yu Huang
Keyword(s):  
Elemental Analysis ◽  
Cycloaddition Reaction ◽  
Inhibitory Effect ◽  
Dipolar Cycloaddition ◽  
Reaction Sequence ◽  
Oxime Ether ◽  
Esi Ms ◽  
Mild Conditions ◽  
Activity Evaluation

The triazolo-methyl tetrahydrobenzofuran oxime ether isomers were prepared through Cu (II)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction in a high-yielding three-step reaction sequence under mild conditions. All of the intermediates and target compounds were characterized by NMR, IR, ESI-MS and elemental analysis. Thein vitroanti-ulcer activity evaluation indicated the (Z)-oxime isomer of triazolo-methyl tetrahydrobenzofuran oxime ether exhibited most potent H+/K+-ATPase inhibitory effect with the IC50˰̵̱̼͆ͅ˰̶̿˰̅˾́̅˰μ̝˾ These compounds could be potentially used as anti-ulcer agents for the treatment of acid related diseases.

Synthesis and H+/K+-ATPase Inhibitory Activity of 2-Phenyl-6,7-Dihydrobenzofuran-4(5H)-one Oxime Ether Derivatives

2013 ◽  
Vol 634-638 ◽  
pp. 1192-1195 ◽  
Author(s):  
Hu Biao Fang ◽  
Lei Jin ◽  
Wei Chen Zai ◽  
Yu Rong Song ◽  
Jun Zhi Wang ◽  
...  
Keyword(s):  
Atpase Activity ◽  
Elemental Analysis ◽  
Inhibitory Activity ◽  
Inhibitory Effect ◽  
Oxime Ether ◽  
Esi Ms ◽  
Activity Evaluation

Three pairs of 2-phenyl-6,7-dihydrobenzofuran-4(5H)-one oxime and corresponding oxime ether isomers were synthesized and separated as potential anti-ulcer agent. Their structures were characterized by NMR, IR, ESI-MS and elemental analysis. Preliminarily H+/K+-ATPase activity evaluation indicated that all the target compounds had a better inhibitory effect than the commercial omeprazole with the IC50 of 2.0~30.0 μM.

Synthesis and In Vitro Anti-Ulcer Effect of Bisabolangelone Oxime Ether Derivatives

2013 ◽  
Vol 781-784 ◽  
pp. 1122-1125
Author(s):  
Fang Fang Wu ◽  
Yu Rong Song ◽  
Jiao Yu Zhang ◽  
Lei Chen ◽  
Jun Zhi Wang
Keyword(s):  
Atpase Activity ◽  
Oxime Ether ◽  
Esi Ms ◽  
Activity Evaluation ◽  
Inhibitory Activities

Four bisabolangelone oxime ether derivatives were synthesized and separated as potential anti-ulcer agents. Their structures were characterized by NMR, IR and ESI-MS. Preliminarily H+/K+-ATPase activity evaluation indicated that all the target oxime ethers exhibited the better H+/K+-ATPase inhibitory activities than the commercial omeprazole with the IC50of 17~46 μM. These compounds might be used as potential anti-ulcer agents in the treatment of acid-related diseases.

Synthesis and Characterization of Triazole-Linked Bistetrahydrobenzofuran Derivatives as Anti-Ulcer Agents

2014 ◽  
Vol 997 ◽  
pp. 128-131
Author(s):  
Quan Li Yang ◽  
Chun Xue Chen ◽  
Wu Li ◽  
Wan Liu ◽  
Hu Biao Fang ◽  
...  
Keyword(s):  
Elemental Analysis ◽  
Click Reaction ◽  
Bioactive Compound ◽  
Inhibitory Effect ◽  
Synthesis And Characterization ◽  
Mild Conditions ◽  
Inhibitory Activities ◽  
High Yields

A pair of triazole-linked bistetrahydrobenzofuran derivatives were prepared in high yields through Cu (II)-catalyzed click reaction under mild conditions. All of the intermediates and target compounds were characterized by NMR, IR, ESI-MS and elemental analysis. Thein vitroH+/K+-ATPase inhibitory effect for the target compounds were also evaluated by MTT methods, and the (E)-isomer of the bistetrahydrobenzofurans exhibited the better H+/K+-ATPase inhibitory activities than the commercial omeprazole with the IC50of 37.90 μM. The bioactive compound might be potentially used as anti-ulcer agents in the treatment of acid-related diseases.

New Pyrrolo[1,2-b]pyridazine Derivatives by 1,3-Dipolar Cycloaddition of Mesoionic Oxazolopyridazinone

2008 ◽  
Vol 59 (11) ◽  
Author(s):  
Miron Teodor Caproiu ◽  
Florea Dumitrascu ◽  
Mino R. Caira
Keyword(s):  
Nmr Spectroscopy ◽  
Elemental Analysis ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Pyridazine Derivatives ◽  
New Compounds

New pyrrolo[1,2-b]pyridazine derivatives 8a-f were synthesized by 1,3-dipolar cycloaddition reaction between mesoionic 1,3-oxazolo[3,2-b]pyridazinium-2-oxides and diethyl or diisopropyl acetylenedicarboxylate as alkyne dipolarophiles. The structures of the new compounds were assigned by elemental analysis and NMR spectroscopy.

scholarly journals Synthesis, Characterization, and Antibacterial Activity of Diethyl 1-((4-Methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl)-1H-1,2,3-triazole-4,5-dicarboxylate

2017 ◽  
Vol 2017 ◽  
pp. 1-6 ◽  
Author(s):  
S. Boukhssas ◽  
Y. Aouine ◽  
H. Faraj ◽  
A. Alami ◽  
A. El Hallaoui ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Cycloaddition Reaction ◽  
Bactericidal Effect ◽  
High Yield ◽  
Dipolar Cycloaddition ◽  
Gram Negative Bacteria ◽  
X Ray ◽  
X Ray Crystallography ◽  
Gram Positive Bacteria

The compound, diethyl 1-((4-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl)-1H-1,2,3-triazole-4,5-dicarboxylate 2, was synthesized in high yield, through 1,3-dipolar cycloaddition reaction of 4-(azidomethyl)-4-methyl-2-phenyl-4,5-dihydrooxazole and diethyl but-2-ynedioate in the absence of a solvent. The structure of the synthesized compound was established on the basis of NMR spectroscopy (1H, 13C), X-ray crystallography, and MS data. The prepared compound was also tested in vitro for its antibacterial activity against Gram-positive bacteria (Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli). The calculation of MBC/MIC ratio showed that this triazole derivative 2 had a bactericidal effect on the two strains tested.

CuI-Catalyzed [3+2] Cycloaddition of Hindered Vinylidenebisphosphonates (VBP) with Azomethine Imines for Highly Regioselective Access to Dinitrogen-Heterobicycle-Containing Bisphosphonates

Synthesis ◽  
2018 ◽  
Vol 50 (13) ◽  
pp. 2601-2607
Author(s):  
Zhongxiang Zhu ◽  
Qinghe Wang ◽  
Dulin Kong ◽  
Tiao Huang ◽  
Mingshu Wu
Keyword(s):  
Biological Activity ◽  
Low Cost ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Atom Economy ◽  
Mild Conditions ◽  
Synthetic Strategy ◽  
Fused Heterocycles ◽  
Azomethine Imines ◽  
High Stereoselectivity

A concise, atom-economic, and highly regioselective synthetic strategy for the construction of several dinitrogen-fused heterocycles bearing bisphosphonates by 1,3-dipolar cycloaddition reaction of azomethine imines with tetraethyl vinylidene-1,1-bisphosphonate in the presence of CuI in toluene media has been developed. The targeted compounds were obtained in good yields and with excellent regioselectivity. This method for the synthesis of gem-bisphosphonates (BPs) is particularly attractive due to features such as low cost, mild conditions, atom economy, high stereoselectivity, and potential biological activity of the product.

Synthesis of novel dispiropyrrolothiazoles by three-component 1,3-dipolar cycloaddition and evaluation of their antimycobacterial activity

RSC Advances ◽  
2014 ◽  
Vol 4 (103) ◽  
pp. 59462-59471 ◽  
Author(s):  
Saoussen Haddad ◽  
Sarra Boudriga ◽  
François Porzio ◽  
Armand Soldera ◽  
Moheddine Askri ◽  
...  
Keyword(s):  
Mycobacterium Tuberculosis ◽  
Dft Calculations ◽  
Cycloaddition Reaction ◽  
Antimycobacterial Activity ◽  
Dipolar Cycloaddition

A series of dispiropyrrolothiazoles derivatives has been synthesized screenedin vitroagainstMycobacterium tuberculosisH37Rv. The observed regio- and stereoselectivity of the cycloaddition reaction has been rationalized by DFT calculations.

scholarly journals Synthesis of spiro-3H-indazoles via 1,3-dipolar cycloaddition of arynes with 6-diazocyclohex-2-en-1-one derivatives and fused-2H-indazoles by subsequent rearrangement

RSC Advances ◽  
2017 ◽  
Vol 7 (85) ◽  
pp. 54087-54090 ◽  
Author(s):  
Bin Cheng ◽  
Bian Bao ◽  
Bing Zu ◽  
Xiaoguang Duan ◽  
Shengguo Duan ◽  
...  
Keyword(s):  
Carbonyl Group ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Mild Conditions

Rare spiro-3H-indazoles bearing a carbonyl group adjacent to the spirocyclic quarternary carbon were prepared via 1,3-dipolar cycloaddition reaction of arynes with 6-diazocyclohex-2-en-1-one derivatives under mild conditions.

scholarly journals Diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate

Molbank ◽  
10.3390/m1167 ◽  
2020 ◽  
Vol 2020 (4) ◽  
pp. M1167
Author(s):  
Serigne Abdou Khadir Fall ◽  
Saïd Achamlale ◽  
Younas Aouine ◽  
Asmae Nakkabi ◽  
Hassane Faraj ◽  
...  
Keyword(s):  
Infrared Spectroscopy ◽  
Elemental Analysis ◽  
Cycloaddition Reaction ◽  
2D Nmr ◽  
Solvent Mixture ◽  
Sodium Ascorbate ◽  
Dipolar Cycloaddition ◽  
Sulfate Pentahydrate ◽  
Copper Sulfate Pentahydrate

The title compound, diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate, was synthesized with excellent yield and high regioselectivity through 1,3-dipolar cycloaddition reaction between the α-azido diethyl amino methylphosphonate and the heterocyclic alkyne, 9-(prop-2-yn-1-yl)-9H-carbazole. The cyclization reaction by “click chemistry” was carried out in a water/ethanol solvent mixture (50/50), in the presence of copper sulfate pentahydrate and catalytic sodium ascorbate. The characterization of the structure of the resulting 1,4-regioisomer was performed by 1D and 2D-NMR experiments, infrared spectroscopy, and elemental analysis.

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