Dong-Soo Shin

Synthesis and structure-activity relationships of novel 1-arylmethyl-3-aryl-1H-pyrazole-5-carbohydrazide hydrazone derivatives as potential agents against A549 lung cancer cells.

A series of novel 1-arylmethyl-3-aryl-1H-pyrazole-5-carbohydrazide hydrazone derivatives were synthesized and the effects of all the compounds on A549 cell growth were investigated. The results showed that all compounds had almost inhibitory effects on the growth of A549 cells. The study on structure-activity relationships and prediction of lipophilicities of compounds showed that compounds with LogP values in the range of 4.12-6.80 had inhibitory effects on the growth of A549 cells, and among of them the hydrazone derived from salicylaldehyde had much more inhibitory effects.

Novel conversion of epoxides to one carbon homologated allylic alcohols by dimethylsulfonium methylide

Abstract The reaction of excess of dimethylsulfonium methylide with terminal, allylic, or benzylic epoxides affords good to excellent yields of one carbon homologated allylic alcohols.

Synthesis and preliminary biological evaluation of novel pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives as potential agents against A549 lung cancer cells.

A series of novel pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives were synthesized by the reaction of ethyl 3-aryl-1-(2-bromoethyl)-1H-pyrazole-5-carboxylate and amine in the general heating condition and microwave-assisted condition. The structures of the compounds were determined by IR, (1)H NMR and mass spectroscopy, in addition, representative single-crystal structures were characterized by using X-ray diffraction analysis. Preliminary biological evaluation showed that the compounds could inhibit the growth of A549 cells in dosage- and time-dependent manners. The study on structure-activity relationships showed that compounds with 4-chlorophenyl group at pyrazole moiety, such as 5-benzyl-2-(4-chlorophenyl)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one (3o) had much more inhibitory effects. Compound 3o was the most effective small molecule in inhibiting A549 cell growth and might perform its action through modulating autophagy.

Triphenylphosphine hydrobromide: A mild and efficient catalyst for tetrahydropyranylation of tertiary alcohols

Abstract Triphenylphosphine hydrobromide is a convenient and highly effective catalyst for tetrahydropyranylation of tertiary alcohols with dihydropyran in dichloromethane at ambient temperature.

Benzimidazole bearing oxadiazole and triazolo-thiadiazoles nucleus: Design and synthesis as anticancer agents

Two new series of benzimidazole bearing oxadiazole[1-(1H-benzo[d]imidazol-2-yl)-3-(5-substituted-1,3,4-oxadiazol-2-yl)propan-1-ones (4a-l)] and triazolo-thiadiazoles[1-(1H-benzo[d]imidazol-2-yl)-3-(6-(substituted)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-yl)propan-1-one (7a-e)] have been synthesized successfully from 4-(1H-benzo[d]imidazol-2-yl)-4-oxobutanehydrazide (3) with an aim to produce promising anticancer agents. In vitro anticancer activities of synthesized compounds were screened at the National Cancer Institute (NCI), USA, according to their applied protocol against full NCI 60 human cell lines panel; results showed good to remarkable anticancer activity. Among them, compound (4j, NCS: 761980) exhibited significant growth inhibition and further screened at 10-fold dilutions of five different concentrations (0.01, 0.1, 1, 10 and 100 μM) with GI(50) values ranging from 0.49 to 48.0 μM and found superior for the non-small cell lung cancer cell lines like HOP-92 (GI(50) 0.49, TGI 19.9,LC(50) >100 and Log(10)GI(50) -6.30, Log(10)TGI -4.70, Log(10)LC(50) >-4.00).

Synthesis of novel ribavirin hydrazone derivatives and anti-proliferative activity against A549 lung cancer cells.

A series of novel ribavirin hydrazone derivatives were synthesized by the reaction of ribavirin hydrazone with benzaldehyde or acetophenone derivatives. The structures of the compounds were determined by IR, (1)H NMR, and HRESIMS. Preliminary biological evaluation showed that one compound (7h) inhibits the growth of A549 cells at 20microM.

Synthesis, single-crystal characterization and preliminary biological evaluation of novel ferrocenyl pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives.

A series of novel ferrocenyl pyrazolo[1,5-a]pyrazin-4(5H)-one derivatives was synthesized and characterized by 1H NMR, 13C NMR, IR, HRMS and X-ray diffraction analysis. Preliminary evaluation of biological applications showed that the compounds 6c and 6f inhibit the growth of A549 cells in dosage-dependent manners through cell cycle arrest.

5-Alkyl-2-ferrocenyl-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one derivatives inhibit growth of lung cancer A549 cell by inducing apoptosis

we found that 5-alkyl-2-ferrocenyl-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one derivatives 8d, 8e and 8f could effectively induce apoptosis in A549 lung cancer cells and elevate the levels of integrin beta4 and ROS. The data suggested that these compounds might be promising agents for the cancer therapy, and these compounds would be useful tools for further investigate the functions of integrin beta4 in regulation of the cancer cell apoptosis.

Sulfur ylide vinylation of halides and mesylates

Abstract One-carbon homologation of benzylic, allylic, propargylic and primary halides or mesylates with dimethylsulfonium methylide affords terminal olefins in good to excellent yields.

Controllable synthesis of uniform CaMoO4:Eu3+,M+ (M = Li, Na, K) microspheres and optimum luminescence properties

High-quality and monodisperse CaMoO4:Eu3+,M+ (M = Li, Na, K) microspheres have been synthesized with the assistance of poly-(diallyldimethylammonium chloride) (PDDA) via a facile coprecipitation hydrothermal route. X-ray diffraction (XRD), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDS), transmission electron microscopy (TEM), thermogravimetric analysis (TGA), X-ray photoelectron spectroscopy (XPS), as well as photoluminescence (PL) spectroscopy are used to characterize the resulting samples. The results show that the CaMoO4:Eu3+,M+ (M = Li, Na, K) can be directly indexed to a tetragonal CaMoO4 phase with high purity. A series of controlled experiments indicate that PDDA as a shape modifier introduced into the reaction system plays a critical role in the morphology of the final products. Furthermore, the shape and size of the products can be further manipulated by adjusting the concentration of PDDA and pH values in the initial solution. The prepared microspheres are stable at a suitable annealing temperature. The possible formation mechanism for these microspheres is presented. Additionally, the PL properties of CaMoO4:Eu3+,M+ (M = Li, Na, K) were investigated in detail. The results reveal that the red emission peak intensities of CaMoO4:Eu3+,Li+ and CaMoO4:Eu3+,Na+ are higher than that of CaMoO4:Eu3+,K+. The particle size and shape have a remarkable effect on the photoluminescence properties of the phosphor. The luminescence intensity is observably enhanced with increasing of the annealing temperature due to eliminating PDDA and/or H2O present in the samples and to the improved crystal quality.