304458-95-5Relevant academic research and scientific papers
Synthesis and evaluation of biological activities of 4-cyclopropyl-5-(2-fluorophenyl) arylhydrazono-2,3-dihydrothiazoles as potent antioxidant agents
Ghanbari Pirbasti,Mahmoodi, Nosrat O.,Abbasi Shiran, Jafar
, p. 196 - 210 (2016/03/25)
A new series of 4-cyclopropyl-5-(2-fluorophenyl)arylhydrazono-2,3-dihydrothiazole derivatives was synthesized via the reaction of prepared thiosemicarbazones with 2-bromo-1-cyclopropyl-2-(2-uorophenyl)ethanone in the presence of Et3 N as a catalyst throug
Facile synthesis and biological assays of novel 2,4-disubstituted hydrazinyl-thiazoles analogs
Ghanbari Pirbasti, Fateme,Mahmoodi, Nosrat O.
, p. 497 - 506 (2016/04/20)
A convenient, one-pot multi-component synthesis of new 2,4-disubstituted hydrazinyl-thiazoles was accomplished using different aldehydes/ketones, thiosemicarbazide, and 4-methoxy phenacyl bromide in the presence of a catalytic amount of AcOH in EtOH. Prod
Efficient "on water" green route heterocyclization of thiosemicarbazones with DMAD
Singla, Rohit,Gautam, Deepika,Gautam, Poonam,Chaudhary
, p. 740 - 745 (2016/05/09)
A simple, efficient, and eco-friendly procedure for the synthesis of thiazolidin-4-one derivatives in water from cyclocondensation reaction of thiosemicarbazone derivatives and dimethylacetylene dicarboxylate (DMAD) in good yield is reported. The regiochemistry of the cyclized products is established by elemental analysis, IR, NMR, and mass spectral data. A single crystal X-ray diffraction study of a representative compound, 3f, is reported.
Small-molecule inhibitors of cathepsin L incorporating functionalized ring-fused molecular frameworks
Song, Jiangli,Jones, Lindsay M.,Chavarria, Gustavo E.,Charlton-Sevcik, Amanda K.,Jantz, Adam,Johansen, Audra,Bayeh, Liela,Soeung, Victoria,Snyder, Lindsey K.,Lade Jr., Shawn D.,Chaplin, David J.,Trawick, Mary Lynn,Pinney, Kevin G.
supporting information, p. 2801 - 2807 (2013/06/27)
Cathepsin L is a cysteine protease that is upregulated in a variety of malignant tumors and plays a significant role in cancer cell invasion and migration. It is an attractive target for the development of small-molecule inhibitors, which may prove beneficial as treatment agents to limit or arrest cancer metastasis. We have previously identified a structurally diverse series of thiosemicarbazone-based inhibitors that incorporate the benzophenone and thiochromanone molecular scaffolds. Herein we report an important extension of this work designed to explore fused aryl-alkyl ring molecular systems that feature nitrogen atom incorporation (dihydroquinoline-based) and carbon atom exclusivity (tetrahydronaphthalene-based). In addition, analogues that contain oxygen (chromanone-based), sulfur (thiochroman-based), sulfoxide, and sulfone functionalization have been prepared in order to further investigate the structure-activity relationship aspects associated with these compounds and their ability to inhibit cathepsins L and B. From this small-library of 30 compounds, five were found to be strongly inhibitory (IC50 50 = 164 nM. All of the compounds evaluated were inactive (IC50 >10,000 nM) as inhibitors of cathepsin B, thus establishing a high degree (>20-fold) of selectivity (cathepsin L vs. cathepsin B) for the most active cathepsin L inhibitors in this series.
