16555-98-9Relevant academic research and scientific papers
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.
Convenient synthetic method for 6-substituted derivatives of 4-methylumbelliferone
Moskvina,Ishchenko,Khilya
, p. 751 - 756 (2012)
New 6-pyrazolyl-, isoxazolyl-, and pyrimidinylumbelliferones were synthesized from an analog of natural 6-acetyl-7-hydroxy-4-methylumbelliferone.
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
Substrate specificity of acetoxy derivatives of coumarins and quinolones towards Calreticulin mediated transacetylation: Investigations on antiplatelet function
Kathuria, Abha,Priya, Nivedita,Chand, Karam,Singh, Prabhjot,Gupta, Anjali,Jalal, Sarah,Gupta, Shilpi,Raj, Hanumantharao G.,Sharma, Sunil K.
, p. 1624 - 1638 (2012)
Calreticulin transacetylase (CRTAase) is known to catalyze the transfer of acetyl group from polyphenolic acetates (PA) to certain receptor proteins (RP), thus modulating their activity. Herein, we studied for the first time the substrate specificity of CRTAase towards N-acetylamino derivatives of coumarins and quinolones. This study is endowed with antiplatelet action by virtue of causing CRTAase catalyzed activation of platelet Nitric Oxide Synthase (NOS) by way of acetylation leading to the inhibition of ADP/Arachidonic acid (AA)-dependent platelet aggregation. Among all the N-acetylamino/acetoxy coumarins and quinolones screened, 7-N-acetylamino-4-methylcoumarin (7-AAMC, 17) was found to be the superior substrate to platelet CRTAase and emerged as the most promising antiplatelet agent both in vitro and in vivo. Further it caused the inhibition of cyclooxygenase-1 (Cox-1) resulting in the down regulation of thromboxane A2 (TxA2), modulation of tissue factor and the inhibition of platelet aggregation. It was also found effective in the inhibition of LPS induced pro-thrombotic conditions.
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 and photooxygenation of linear and angular furocoumarin derivatives as a hydroxyl radical source: Psoralen, pseudopsoralen, isopseudopsoralen, and allopsoralen
Elgogary, Sameh Ramadan,Hashem, Neveen Mohamed,Khodeir, Mohamed Nabeel
, p. 506 - 512 (2015/03/30)
Synthesis of linear and angular furocoumarins with new skeleton structure of potential photobiological feature interest was carried out through Williamson reaction of hydroxycoumarins with 3-chloro-2-butanone followed by cyclization with polyphosphoric acid or by heating in a strongly alkaline solution. The photooxygenation reactions of synthesized furocoumarins were performed in chloroform and in the presence of tetraphenylporphyrin as singlet oxygen sensitizer (1O2). The photooxygenation reactions afforded the photocleaved product through [2 + 2] cycloaddition and the photooxygenated products through ene reaction and [4 + 2] cycloaddition. The photoproducts were isolated and fully characterized by spectral analyses.
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.
Synthesis and antiproliferative and c-Src kinase inhibitory activities of cinnamoyl-and pyranochromen-2-one derivatives
Chand, Karam,Shirazi, Amir Nasrolahi,Yadav, Preeti,Tiwari, Rakesh K.,Kumari, Meena,Parang, Keykavous,Sharma, Sunil K.
, p. 741 - 754 (2013/08/23)
A series of 6-and 8-cinnamoylchromen-2-one and dihydropyranochromen-2-one derivatives were synthesized and their antiproliferative activities were evaluated against three human cancer cell lines, i.e., ovarian adenocarcinoma (SK-OV-3), leukemia (CCRF-CEM), and breast carcinoma (MCF-7). In general, 8-cinnamoylchromen-2-one derivatives were found to have higher antiproliferative activity against the cancer cells when compared with 6-cinnamoyl analogues. Among all of the hybrid chromen-2-one-chalcone/flavanone compounds, a 7-hydroxy-8-cinnamoylchromen-2-one derivative 35 was found to be consistently active against all the cancer cell lines and inhibited the cell proliferation of SK-OV-3, CCRF-CEM, and MCF-7 by 63%, 50%, and 43%, respectively, at a concentration of 50 μmol/L after 72 h of incubation. This compound also exhibited the highest Src kinase inhibition (IC50 = 14.5 μmol/L). Structure-activity relationship studies provided insights for designing the next generation of chromen-2-one-chalcone hybrid prototypes and the development of new leads as anticancer agents and (or) Src kinase inhibitors.
Introduction of poly(4-vinylpyridinium) perchlorate as a new, efficient, and versatile solid acid catalyst for one-pot synthesis of substituted coumarins under ultrasonic irradiation
Khaligh, Nader Ghaffari,Shirini, Farhad
, p. 26 - 31,6 (2012/12/11)
Poly(4-vinylpyridinium) perchlorate, is a supported, recyclable, eco-benign catalyst for synthesis of substituted coumarins via Pechmann reaction using ultrasound irradiation at room temperature and neat condition in high yields with short reaction times. The catalyst was studied by FT-IR, X-ray diffraction, scanning electron microscope, thermo-gravimetric and energy dispersion X-ray analyses. All the products were extensively characterized by 1H NMR, FT-IR, MS and melting point analyses. This methodology offers momentous improvements over various options for the synthesis of coumarins with regard to yield of products, simplicity in operation and green aspects by avoiding toxic catalysts and solvents. Further, the catalyst can be reused and recovered for several times without loss of activity.
Ultrasound-assisted one-pot synthesis of substituted coumarins catalyzed by poly(4-vinylpyridinium) hydrogen sulfate as an efficient and reusable solid acid catalyst
Khaligh, Nader Ghaffari
, p. 1062 - 1068 (2013/04/24)
Poly(4-vinylpyridinium) hydrogen sulfate solid acid was found to be efficient catalyst for synthesis of substituted coumarins via Pechmann reaction using ultrasound irradiation at room temperature and neat condition in high yields with short reaction times. This methodology offers momentous improvements over various options for the synthesis of coumarins with regard to yield of products, simplicity in operation and green aspects by avoiding toxic catalysts and solvents. Further, the catalyst can be reused and recovered for several times.
