61499-10-3

Usage

Uses

4-Phenylbutyl isothiocyanate is an inducer of Phase II detoxifying enzymes.

InChI:InChI=1/C11H13NS/c13-10-12-9-5-4-8-11-6-2-1-3-7-11/h1-3,6-7H,4-5,8-9H2

Upstream product

• 463-71-8 thiophosgene 
• 13214-66-9 4-phenyl-1-butylamine 
• 96989-50-3 di-2-pyridyl thionocarbonate 
• 75-15-0 carbon disulfide 

Downstream Products

• 1228116-75-3 (Z)-2-isopropylimino-3-(4-phenyl-butyl)-thiazolidin-4-one 
• 1489288-30-3 1-(4-chlorophenoxyacetyl)-4-phenylbutyl-thiosemicarbazide 

Relevant academic research and scientific papers

Enantioselective synthesis of 3,5-disubstituted thiohydantoins and hydantoins

A mild method to convert optically pure amino acid thiourea and urea derivatives to thiohydantoins and hydantoins, respectively, is described. It provides an efficient way to realize enantioselective synthesis of thiohydantoins and hydantoins with good to high isolated yields and enantiomeric purities. We found that the enantiomeric purities were highly dependent on the reaction conditions including bases, solvents, and temperature.

Aggrecanase-2 inhibitors based on the acylthiosemicarbazide zinc-binding group

Osteoarthritis is a disabling disease characterized by the articular cartilage breakdown. Aggrecanases are potential therapeutic targets for the treatment of this pathology. At the starting point of this project, an acylthiosemicarbazide was discovered to inhibit aggrecanase-2. The acylthiosemicarbazide Zn binding group is also a convenient linker for library synthesis. A focused library of 920 analogs was thus prepared and screened to establish structure-activity relationships. The modification of the acylthiosemicarbazide was also explored. This strategy combining library design and discrete compounds synthesis yielded inhibitor 35, that is highly selective for aggrecanases over a panel of metalloproteases and inhibits the degradation of native fully glycosylated aggrecan. A docking study generated binding conformations explaining the structure-activity relationships.

Synthesis and anticancer activity comparison of phenylalkyl isoselenocyanates with corresponding naturally occurring and synthetic isothiocyanates

Synthesis and identification of novel phenylalkyl isoselenocyanates (ISCs), isosteric selenium analogues of naturally occurring phenylalkyl isothiocyanates (ITCs), as effective cytotoxic and antitumor agents are described. The structure - activity relationship comparison of ISCs with ITCs and effect of the increasing alkyl chain length in inhibiting cancer cell growth were evaluated on melanoma, prostate, breast, glioblastoma, sarcoma, and colon cancer cell lines. IC50 values for ISC compounds were generally lower than their corresponding ITC analogues. Similarly, in UACC 903 human melanoma cells, the inhibition of cell proliferation and induction of apoptosis were more pronounced with ISCs compared to ITCs. Further, ISCs and ITCs effectively inhibited melanoma tumor growth in mice following intraperitoneal xenograft. A similar reduction in tumor size was observed at 3 times lower doses of ISCs compared to corresponding ITCs.