Synthesis of 3,3,3-trifluoroethyl isocyanate, carbamate and ureas. Anticancer activity evaluation of N-(3,3,3-trifluoroethyl)-N′-substituted ureas

Luzina, Elena L.; Popov, Anatoliy V.

doi:10.1016/j.jfluchem.2015.06.005

Cited by 11 publications

(3 citation statements)

References 43 publications

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“…These disciplines vary from pharmacology [4–6] to molecular imaging [7, 8], the latter of which includes a promising new technique known as Cerenkov imaging [9–12]. Our fluorine-related research is focused on the synthesis of novel potential anticancer drugs [13–18] and the development of 18 F-labeled Cerenkov imaging agents [19–23]. Recently, we reported that direct electrophilic fluorination with dilute fluorine gas under acidic conditions is a useful method for labeling of triarylmethane-based pH indicators with the positron emitting isotope 18 F [19–21] for in vivo pH measurement [22] by a combination of optical Cerenkov imaging and nuclear positron emission tomography (PET).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of pH indicators for Cerenkov imaging by electrophilic substitution of bromine by fluorine in an aromatic system

Kachur

Arroyo

Bryan

et al. 2017

Journal of Fluorine Chemistry

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Direct electrophilic fluorination using molecular fluorine gas is used in organic synthesis to create novel fluorine-containing compounds with potential beneficial activity that could not be obtained by nucleophilic substitution. In this paper, we report a novel electrophilic substitution of bromine by fluorine in an aromatic system. The mechanism of this type of fluorination was explored using the reaction between bromothymolsulfonphthalein (Bromothymol Blue) and dilute fluorine gas under acidic conditions. Substitution occurs in the bromine atoms located in the ortho-position relative to the hydroxyl group. A similar electrophilic fluorination of thymolsulfonphthalein (Thymol Blue) leads to a substitution of hydrogen atoms in the same position (ortho to hydroxyl). NMR spectroscopy was used to confirm the fluorination sites. NMR spectra of thymolsulfonphthalein and its derivatives under basic conditions can be explained by considering the absence of resonance between the two phenolic rings. Both dibromothymol blue and fluorobromothymol blue revealed intermolecular attenuate Cerenkov radiation selectively near their maximum absorbance in a pH dependent manner.

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Section: Introductionmentioning

confidence: 99%

Synthesis of pH indicators for Cerenkov imaging by electrophilic substitution of bromine by fluorine in an aromatic system

Kachur

Arroyo

Bryan

et al. 2017

Journal of Fluorine Chemistry

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“…According to a COMPARE analysis [38] of microarray-based transcriptome-wide mRNA expressions, 21 genes were found to be significantly correlated with the response of 60 tumor cell lines to cantharidin. Some researchers screened their synthetic compounds against human cancer cell lines and used a COMPARE analysis to evaluate the anticancer activity and predict the probable mechanism [27,39,40,41,42]. Therefore, the following studies examined the possible mechanism using a standard NCI-60 test and COMPARE analysis of 5a .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Canthardin Sulfanilamides and Their Acid Anhydride Analogues via a Ring-Opening Reaction of Activated Aziridines and Their Associated Pharmacological Effects

et al. 2016

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Abstract:The cantharidinimide derivatives, 5a-h, including sulfanilamides containing pyrimidyl, pyrazinyl, hydrogen, thiazolyl, and oxazolyl groups were synthesized.Modification of cantharidinimide by means of the reaction of activated aziridine ring opening led to the discovery of a novel class of antitumor compounds. The analogues 10i-k, 11l-n, 12o-p, and 16q-s were obtained from treating cantharidinimide 6 and analogues (7, 8, and 13) with activated aziridines, which produced a series of ring-opened products including normal and abnormal types. Some of these compounds showed cytotoxic effects in vitro against HL-60, Hep3B, MCF7, and MDA-MB-231 cancer cells. The most potent cytostatic compound, N-cantharidinimido-sulfamethazine (5a), exhibited anti-HL-60 and anti-Hep3B cell activities. Two compounds 5g and 5h displayed slight effects on the Hep3B cell line, while the other compounds produced no response in these four cell lines.

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“…Recently, urea derivatives obtained from sulfamethoxazole (SMX) 1 have been proposed as potential inhibitors of human carbonic anhydrases [ 11 ], anticancer [ 12 , 13 ], and antimicrobial agents [ 14 , 15 ]. Importantly, we reported the synthesis and antimicrobial activity of nine sulfamethoxazole-based ureas and corresponding cyclic analogues, imidazolidine-2,4,5-triones.…”

Section: Introductionmentioning

confidence: 99%

Novel Sulfamethoxazole Ureas and Oxalamide as Potential Antimycobacterial Agents

2017

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Infections caused by Mycobacterium tuberculosis (Mtb.) and nontuberculous mycobacteria (NTM) are considered to be a global health problem; current therapeutic options are limited. Sulfonamides have exhibited a wide range of biological activities including those against mycobacteria. Based on the activity of 4-(3-heptylureido)-N-(5-methylisoxazol-3-yl)benzenesulfonamide against NTM, we designed a series of homologous sulfamethoxazole-based n-alkyl ureas (C1–C12), as well as several related ureas and an oxalamide. Fifteen ureas and one oxalamide were synthesized by five synthetic procedures and characterized. They were screened for their activity against Mtb. and three NTM strains (M. avium, M. kansasii). All of them share antimycobacterial properties with minimum inhibitory concentration (MIC) values starting from 2 µM. The highest activity showed 4,4′-[carbonylbis(azanediyl)]bis[N-(5-methylisoxazol-3-yl)benzenesulfonamide] with MIC of 2–62.5 µM (i.e., 1.07–33.28 µg/mL). Among n-alkyl ureas, methyl group is optimal for the inhibition of both Mtb. and NTM. Generally, longer alkyls led to increased MIC values, heptyl being an exception for NTM. Some of the novel derivatives are superior to parent sulfamethoxazole. Several urea and oxalamide derivatives are promising antimycobacterial agents with low micromolar MIC values.

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Synthesis of 3,3,3-trifluoroethyl isocyanate, carbamate and ureas. Anticancer activity evaluation of N-(3,3,3-trifluoroethyl)-N′-substituted ureas

Cited by 11 publications

References 43 publications

Synthesis of pH indicators for Cerenkov imaging by electrophilic substitution of bromine by fluorine in an aromatic system

Synthesis of pH indicators for Cerenkov imaging by electrophilic substitution of bromine by fluorine in an aromatic system

Synthesis of Canthardin Sulfanilamides and Their Acid Anhydride Analogues via a Ring-Opening Reaction of Activated Aziridines and Their Associated Pharmacological Effects

Novel Sulfamethoxazole Ureas and Oxalamide as Potential Antimycobacterial Agents

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