16555-98-9Relevant articles and documents
3,4-Dihydro-3,4,6-trimethyl-2H,8H-pyrano-[3,2g]-1,3-benzoxazin-2,8-dione, a potential fluorogenic reporter group reagent for esterases - Synthesis and interaction with chymotrypsin
Kitson, Trevor M.,Freeman, Graham H.
, p. 273 - 282 (2000)
The synthesis of a novel "reporter group" reagent - 3,4-dihydro-3,4,6-trimethyl-2H,8H-pyrano-[3,2g]-1,3-benzoxazin-2,8-dione (DTPBD) - is described. This compound has a cyclic carbamate functionality and thus, like the previously used 3,4-dihydro-3-methyl-6-nitro-2H-1,3-benzoxazin-2-one (DMNB), has the potential to label an esterase such as chymotrypsin. In so doing, DTPBD would incorporate into the protein a covalently linked 4-methylumbelliferone derivative, thus providing a sensitive reporter group that is both chromophoric and fluorescent. Experiments show that DTPBD reacts with chymotrypsin in the predicted manner, except that the labeling process is freely reversible (unlike the case with DMNB). 4-Methylumbelliferyl acetate (which is structurally closely related to DTPBD) is a good substrate for chymotrypsin. The rate of acylation of the enzyme is about an order of magnitude faster than with p-nitrophenyl acetate (which in turn is structurally related to DMNB), an unexpected observation in view of the relative leaving-group abilities of the groups concerned. The results suggest that these various modifiers and substrates show subtle but significant differences in the way they position themselves in chymotrypsin's binding site.
Synthesis of novel coumarin appended bis(formylpyrazole) derivatives: Studies on their antimicrobial and antioxidant activities
Nagamallu, Renuka,Srinivasan, Bharath,Ningappa, Mylarappa B.,Kariyappa, Ajay Kumar
, p. 690 - 694 (2016)
A series of novel coumarin pyrazole hybrids of biological interest were synthesized from the hydrazones, carbazones and thiocarbazones via Vilsmeier Haack formylation reaction. These intermediates and formyl pyrazoles were evaluated for antimicrobial and
Design, synthesis, and biological activity of Schiff bases bearing salicyl and 7-hydroxycoumarinyl moieties
Hejchman, El?bieta,Kruszewska, Hanna,Maciejewska, Dorota,Sowirka-Taciak, Barbara,Tomczyk, Magdalena,Sztokfisz-Ignasiak, Alicja,Jankowski, Jan,M?ynarczuk-Bia?y, Izabela
, p. 255 - 266 (2019/01/16)
Abstract: 18 (11 novel) Schiff bases, derivatives of salicylaldehyde, 2-hydroxyacetophenone, and 6-acetyl-, 8-acetyl-, and 8-formyl-7-hydroxy-4-methylcoumarin were synthesized and characterized by their spectral studies. 6-Acetyl-7-hydroxy-4-methylcoumarin was prepared by novel method under microwave assistance. These Schiff bases were evaluated for antibacterial activities against 12 bacterial and six fungi strains in vitro. N-(3,5-Dichloro-2-hydroxybenzylidene)-4-aminobenzenesulfonic acid sodium salt proved to be the most active against Staphylococcus aureus and MRSA strains (MIC 0.0194?μmol/cm3). The substitution pattern, two chlorine atoms in the salicylidene ring and the SO3Na group, is probably the most beneficial for the activity against Gram-(+) bacteria strains. All Schiff bases were evaluated for cancer efficacy against CFPAC-1 and HeLa cell cultures originating from human pancreas cancer or human cervical cancer. Schiff bases derived from salicylaldehyde are highly effective in pancreas and cervical cancer cells; however, they demonstrate also substantial toxicity towards NIH3T3 cells. Derivatives of coumarin contain three highly selective compounds: 7-hydroxy-8-[(4-methoxyphenylimino)methyl]-4-methyl-2H-chromen-2-one, N-[(7-hydroxy-4-methyl-2-oxo-2H-chromen-8-yl)methylene]-4-aminobenzenesulfonic acid sodium salt, and 7-hydroxy-8-[1-(4-hydroxyphenylimino)ethyl]-4-methyl-2H-chromen-2-one suggesting more promising potential of the second group of substances.
Synthesis of two-photon active cinnamoyl coumarins for high-contrast imaging of cancer cells and their photophysical characterization
Yadav, Preeti,Satapathi, Soumitra,Kumari, Meena,Chaturvedi, Akanksha,Li, Lian,Samuelson, Lynne A.,Kumar, Jayant,Sharma, Sunil K.
, p. 39 - 45 (2014/04/03)
A series of two-photon (TP) active 4-dimethylaminocinnamoyl coumarins were synthesized. These compounds exhibit red shift in absorption and considerable Stokes shift in emission spectra in comparison to the parent coumarin. Large TP absorption cross-sections were measured for all the coumarins in dilute solutions. A correlation between the chemical structure and TP characteristics was established. TP confocal microscopy revealed that these coumarin derivatives can be internalized by cancer cells rendering them a potential candidate as a label in TP confocal imaging.