55329-63-0

Upstream product

• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 107-08-4 1-iodo-propane 
• 106-94-5 propyl bromide 

Downstream Products

• 86100-84-7 4,4'-dipropoxy-2,2'-dihydroxy-α,α'-dimethylbenzalazine 
• 877129-51-6 2-ethyl-5-propoxy-phenol 
• 109615-25-0 1-(2-hydroxy-4-propoxy-phenyl)-3-piperidino-propan-1-one; hydrochloride 

Relevant academic research and scientific papers

Design, synthesis and QSAR study of 2′-hydroxy-4′-alkoxy chalcone derivatives that exert cytotoxic activity by the mitochondrial apoptotic pathway

Eleven 4′-alkoxy chalcones were synthesized and biologically evaluated for their antiproliferative activity against four human tumor cell lines (PC-3, MCF-7, HF-6, and CaSki). Compounds 3a-3d and 3f were selective against PC-3, with IC50 values ranging from 8.08 to 13.75 μM. In addition, chalcones 3a-3c did not affect the normal fibroblasts BJ cells. The most active and selective compounds were further evaluated for their effect on the progression of cell cycle in PC-3 cells, and chalcones 3a and 3c induced a G2/M phase arrest. Furthermore, it was found that these three chalcones induced the mitochondrial apoptotic pathway by regulating Bax and Bcl-2 transcripts and by increasing caspase 3/7 activation. Otherwise, the QSAR model indicates that the double bond of the α,β-unsaturated carbonyl, as well as the planar structure geometry, are important to the biological activity of the synthetized chalcones. Based on these studies, it was concluded that withdrawing substituents in ring A, decrease the antiproliferative activity. This is related to the possible mechanism of action of these compounds, where a Michael addition needs to take place in order to be a potent anticancer agent.

The π-π interactions enhanced in salicylaldimines and salicylaldazines

Four new series of salicylaldazines 1 and salicylaldimines 2-4 were prepared, characterized and their mesomorphic properties were studied. The structures of all compounds were identified and confirmed by spectroscopic techniques such as 1H, 13C NMR, MS and elemental analysis. Three single crystallographic structures of compounds 1a (n=3, 6) and 2 (n=3) were determined by X-ray analysis in order to correlate the molecular structures with the formation of mesophases. Crystallographic data indicated that the better mesomorphic properties might be controlled by CH-π, π-π or/and H-bonds in such system. Except for crystalline compounds 4, all other compounds 1-3 showed mesomorphic behavior of nematic, smectic A or/and smectic C phases, which were characterized by differential scanning calorimetry, optical polarizing microscope and X-ray diffraction experiments. All compounds 1-4 showed yellow-green photoluminescence in THF occurred at 519-521 nm.

Natural Products as Sources of New Fungicides (I): Synthesis and Antifungal Activity of Acetophenone Derivatives Against Phytopathogenic Fungi

Several series of 45 acetophenone derivatives bearing various alkyl or benzyl substituents were conveniently synthesized and their structures characterized by 1H and 13C NMR spectroscopy, HRMS and single-crystal X-ray analysis. Their in vitro antifungal activities against a panel of phytopathogenic fungi were evaluated by mycelial growth rate assay. Of them, 12 derivatives (e.g., 3a-c, 4c and 4e) exhibited more potent antifungal effects on some phytopathogens than a commercial fungicide hymexazol as positive control. In particular, compound 3b with IC50 values of 10-19μg/mL was found to be the most active in this series and might be a potential lead structure for further optimization. The preliminary structure-activity relationship (SAR) studies of a series of acetophenones are also discussed. A series of acetophenone derivatives have been synthesized and tested for their antifungal activities. Of them 12 derivatives exhibited more potent antifungal effects on some phytopathogens than a positive control hymexazol. Especially, compound 3b (IC50=10-19μg/mL) was found to be the most active and might be a potential lead structure. The SAR of these acetophenones is also discussed.

INHIBITORS OF HEPATITIS C VIRUS RNA-DEPENDENT RNA POLYMERASE, AND COMPOSITIONS AND TREATMENTS USING THE SAME

The present invention provides compounds of formula (4), and their pharmaceutically acceptable salts and solvates, which are useful as inhibitors of the Hepatitis C virus (HCV) polymerase enzyme and are also useful for the treatment of HCV infections in HCV-infected mammals. The present invention also provides pharmaceutical compositions comprising compounds of formula (4), their pharmaceutically acceptable salts and solvates. Furthermore, the present invention provides intermediate compounds and methods useful in the preparation of compounds of formula (4).

Structure-activity relationships of a novel class of endothelin-A receptor antagonists and discovery of potent and selective receptor antagonist, 2-(benzo[1,3]dioxol-5-yl)-6-isopropyloxy-4- (4-methoxyphenyl)-2H-chromene-3-carboxylic acid (S-1255). 1. Study on structure-activity relationships and basic structure crucial for ETA antagonism

A novel series of endothelin-A (ETA) selective receptor antagonists having a 2H-chromene skeleton are described. A lead compound, 2-(benzo[1,3] dioxol-5-yl)-2H-chromene-3-carboxylic acid (3), was found by modifications of our own angiotensin II antagonist. A structure-activity relationship (SAR) study of 3 reveals that the structural requirements essential for potent and selective ETA receptor binding affinity are the m,p-methylenedioxyphenyl, carboxyl, and isopropoxy groups at the 2-, 3-,and 6-positions, respectively, on the (R)-2H-chromene skeleton. The substituent at the 4-position is also important for improving the activity, and various hydrophobic functional groups of 6-9 ? such as liner, branched, and cyclic aliphatic groups, unsubstituted and substituted aryl groups, and even halogen atoms were acceptable. These results suggest that (R)-2-(benzo[1,3]dioxol-5-yl)-6-isopropoxy-2H-chromene-3-carboxylic acid, formula 108, is the crucial basic structure to be recognized by the ETA receptor. The most potent compound is (R)-48 (S-1255), which binds to the ETA receptor with an IC50 value of 0.19 nM and is 630-fold selective for the ETA receptor than for the ETB receptor. This compound has 55% oral bioavailability in rats. On the basis of the SAR, the roles of each substituent in the receptor binding are discussed.

SYNTHESIS AND MESOMORPHIC PROPERTIES OF THREE HOMOLOGOUS SERIES OF 4,4 prime -DIALKOXY- alpha , alpha prime -DIMETHYLBENZALAZINES.

Three homologous series of alpha , alpha prime -dimethylbenzalazines have been synthesized: 4,4 prime -dialkoxy- alpha , alpha prime -dimethylbenzalazines, 4,4 prime -dialkoxy-2,2 prime -dihydroxy- alpha , alpha prime -dimethylbenzalazines, and 4,4 prime -dialkoxy-2-hydroxy- alpha , alpha prime -dimethylbenzalazines. The influence of molecular structure on the mesomorphic properties was studied. Mesomorphic properties and phase transitions were determined using a polarizing hot-stage microscope and a differential scanning calorimeter. The introduction of one or two hydroxyl groups in position 2- or 2-and 2 prime -of the aromatic rings (4,4 prime -dialkoxy-2-hydroxy- alpha , alpha prime -dimethylbenzalazines and 4,4 prime -dialkoxy-2,2 prime -dihydroxy- alpha , alpha prime -dimethylbenzalazines respectively) gives molecules with an excellent mesogenic quality, and all the prepared compounds of these series exhibit mesomorphism. Compounds of the series with two hydroxyl groups exhibit smectic polymorphism which is not so in the case of the compounds of the other series. The melting temperatures are systematically lower for the 4,4 prime -dialkoxy-2-hydroxy- alpha , alpha prime -dimethylbenzalazines than for the other two series.