Nian Yu Huang

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

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. The in vitro anti-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 of 2-Alkylamino/Alkoxy-3-Arylthieno[3,2-d]Pyrimidin-4(3H)-One Derivatives

The title compounds 2-alkylamino/alkoxy-3-arylthieno [3,2-pyrimidin-4(3H)-ones were synthesized by base catalytic reactions of primary amines or alcohols with carbodiimides,which were obtained from the aza-wittig reaction of iminophosphorane 2 and arylisocyanates.The conditions of cyclization and spectral properties were researched.

Synthesis and Structure Elucidation of Novel Oxime Ether Type H/K+-ATPase Inhibitors

Six 6,6-dimethyl-2-phenyl-6,7-dihydrobenzofuran-4(5H)-one oxime derivatives were synthesized, characterized and evaluated as potential anti-ulcer agents. Most of the target compounds exhibited better H+/K+-ATPase inhibitory activity than commercial revaprazan, and both of the two O-propyl oxime ethers displayed the most potent activities with IC50˰̵̱̼͆̓ͅ˰̵̼̓̓˰̸̱̈́̾˰́̀˰μ̝˾ These compounds could be potentially used for the treatment of ulcer disease.

Synthesis and In Vitro Anti-Inflammatory Activity of Pyrrolo[1,2-A]pyrazines via Pd-Catalyzed Intermolecular Cyclization Reaction

Pyrrolo [1,2-a] pyrazine possessed widely bioactivities due to its particular structure. In this work, three pyrrolo [1,2-a] pyrazines derivatives were synthesized from the 2-bromo-5-methoxypyrazine and propargyl amines or ethers through the Pd-catalyzed intermolecular cycloisomerization strategy. Their structures were characterized by NMR, IR, EI-MS and elemental analysis, and all of them exhibited moderate in vitro anti-inflammatory effects with the inhibitions of 43-59% against IL-6 at 50 μM. The compound 3c revealed relatively good anti-inflammatory activities. The bioactive pyrrolo [1,2-a] pyrazines might be potentially used as anti-inflammatory agents.

Synthesis, Structure and Gastric H+/K+-ATPase Inhibitory Activities of Bisabolonalone Hydrazone Carboxamides

Five novel bisabolonalone hydrazone carboxamides were synthesized as potential anti-ulcer agents. Their structures were characterized by NMR, IR and ESI-MS. All of the compounds possessed the better H+/K+-ATPase inhibitory activity than the commercial omeprazole with the IC50 of 18~68 μM in vitro. These compounds could be potentially use for the treatment of ulcer related diseases.

The Direct Carboxylation of Terminal Alkynes with Carbon Dioxide Using Copper-Conjugated Microporous Polymer as Catalyst

A Cu-conjugated microporous polymer catalyst (CMP-Cu) was designed and prepared via Sonogashira-Hagihara cross-coupling of 3,8-dibromo-1,10-phenanthroline with 1,3,5-triethyny benzene in toluene. The CMP-Cu showed a catalytic activity for direct carboxylation of terminal alkynes with CO2 in the presence of K2CO3/Cs2CO3 at mild conditions. Several propiolic acids (such as 3-phenylpropiolic acid, 3-(4-nitrophenyl)propiolic acid and 4,4-dimethyl-2-pentynoic acid) have been prepared in a simple and feasible method at room temperature and atmospheric pressure. This catalyst is attractive for CO2 transformation.

Structure-Based Virtual Screening of Compound Library for Anti-Estrogen Breast Cancer Candidates

We reported a structure-based virtual screening of acompound library derived from 3-acyl-5-hydroxybenzofurans to develop potentialdrugs for treating breast cancer. A library of 160,000 compounds was generatedand screened based on the G-score between ligands and receptor ERα. The topstructures were further analyzed to evaluate the receptor-ligand bindinginteractions. By comparing the binding characteristics and docking scoringvalues to the existing ERα analogues, we determined top 200 compounds aspotential drug candidates for breast cancer.

Facile Synthesis, Characterization and Anti-Inflammatory Effect of 3-Aminoindolizine Derivatives

Four 3-aminoindolizines were synthesized from the substituted 2-bromopyridines and propargyl amines with the aim of obtaining potential anti-inflammatory compounds, which were characterized by NMR, IR, ESI-MS and elemental analysis. Their biological activities were evaluated by the bacterial lipopolysaccharide (LPS) stimulation of mouse cells in the RAW264.7 inflammation model. The target compounds 4a-4d revealed moderate anti-inflammatory effects with the inhibitions of 45%~61% at 50 μM. The bioactive 3-aminoindolizines might be used for further optimization as potential anti-inflammatory drugs.

Study on Biomaterials of Anti-Gastric Trametenolic Acid B Semi-Synthetic Derivatives

Discovery of bioactive ingredients from plants and fungi is always the hot spots in medicinal chemistry. The trametenolic acid B was a bioactive lanostane-type triterpenoid in Trametes lactinea (Berk.) Pat. In this work, four semi-synthetic derivatives were synthesized, characterized and evaluated the anti-gastric cancer activities against HGC-27 cells with the aim of obtaining better anti-tumor agents. The compounds 2a and 3b possessed good anti-proliferative effects under normal physiological conditions, and their anti-cancer effects increased as the pH decrease to 5.5 with the IC50 of 17.55 and 10.63 μM, respectively. These compounds might be further developed as anti-gastric cancer drugs.

Synthesis and Anti-Inflammatory Activity of 3-Aryloxylindolizine Derivatives via Sonogashira Coupling/5-endo-trig Cycloisomerization Domino Strategy

With the aim of obtaining potential IL-6 inhibitor for the treatment of rheumatoid arthritis, four 3-aryloxylindolizine derivatives were synthesized from the 2-bromopyridine and aryl propargyl ether through the Sonogashira coupling/5-endo-trig cycloisomerization domino strategy. These compounds were characterized by NMR, IR, EI-MS and elemental analysis. Their biological activities were evaluated by the bacterial lipopolysaccharide (LPS) stimulation of mouse cells on the RAW264.7 inflammation model. All the compounds revealed good anti-inflammatory activities with the inhibitions of 71~82% against IL-6 at 100 μM. The bioactive 3-aryloxylindolizines might be used as potential anti-inflammatory drugs.