2022 March - 48 articles
Reaction of 4,5-dichloro-1,2,3-dithiazolium chloride with 2-[amino(methylthio)methylene])malononitrile (1 equiv) in the presence of pyridine (2 equiv) gave (Z)-2-{[(4-chloro-5H-1,2,3-dithiazol-5-ylidene)amino](methylthio)methylene}malononitrile in 20...
Based on previously highlighted structural features, the development of highly selective 5-HT1A receptor inhibitors is closely linked to the incorporation of a 4-alkyl-1-arylpiperazine scaffold on them. In this paper, we present the synthesis of two...
This work describes the synthesis and the cytotoxic evaluation of thiophene and thienopyrimidine derivatives. The investigated compound was subjected to target prediction that indicated its high affinity to kinases and to Janus kinase 2 (JAK2) specif...
The 1,2,3-triazole ring system can be easily obtained by copper-catalyzed click reaction of azides with alkynes. 1,2,3-Triazole exhibits a myriad of biological activities, including antimalarial, antibacterial, and antiviral activities. We herein rep...
Herein we report the obtaining of 1-(3,4-dihydroquinolin-1(2H)-yl)-2- (4-isobutylphenyl)propan-1-one and its characterization. The newly obtained hybrid and its derivatives (hybrids of ibuprofen with 1,2,3,4-tetrahydroisoquinoline, and piperidine) we...
In this note we report the synthesis of a doubly acylated cis-THF-diol product synthesised in three steps by the stereoselective RuO4-catalysed oxidative cyclisation of 1,5-hexadiene, followed by benzoylation and acetylation. This substance is one of...
Potassium ion sensors are important for the study of concentration profiles in tissues. The synthesis of a cryptand suited for potassium ions and the crystal structure of it with a chelated sodium ion are presented.
Synthesis, NMR spectral data and crystal structure of 9,12-dibromo derivative of ortho-carborane are reported.
Based on the diaryl hydroxylamine scaffold, which exhibits the potential to inhibit all three enzymes of the first step of the kynurenine pathway, the main tryptophan degradation pathway in mammals, which is often activated in cancer, we report herei...
Cyclic adenosine diphosphate ribose (cADPR) is a cyclic nucleotide involved in the Ca2+ homeostasis. In its structure, the northern ribose, bonded to adenosine through an N1 glycosidic bond, is connected to the southern ribose through a pyrophosphate...
In this communication, we investigate the reaction between seleno- and thiourea, derived from N-heterocyclic carbenes, with the interhalogen iodine monochloride. The formation of all three products was confirmed by NMR spectroscopy, while single-crys...
Three novel pyrazolo[3,4-b]pyridines were synthesized via the cyclization of 5-amino-1-phenylpyrazole with the corresponding unsaturated ketone in the catalytic presence of ZrCl4. The ketones were afforded by modifying a stabilized ylide facilitated...
In this work, we describe a simple and easy synthetic approach to variously 4-aryl-2-alkylphosphonomethyl-4-oxobutanenitrile based on the reaction of aromatic aldehydes with phosphorylated Michael’s acceptors in good yields. A general mechanism...
The synthesis and structural diversification of N-heterocycles systems have attracted much attention because of their potential applications. Three 6-aryl-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde 4 derivatives, in reaction with ace...
For the first time, 5-formyl-1-(pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate was synthesized via a two-step scheme. The molecular structure of the compound was determined by a single-crystal X-ray diffraction analysis. The Hirshfeld surface analysis...
This short note describes the synthesis of an amorphous benzo[1,2,3]dithiazole chloride salt (commonly known as a ‘Herz salt’) by use of the Herz reaction. Hetero- and homolytic transformations of this species to a variety of useful adduc...
The Diels–Alder reaction of ethyl 3-(1-phenyl-1H-tetrazol-5-yl-1,2-diaza-1,3-butadiene-1-carboxylate with 2-acetyl-6-methyl-2,3-dihydro-4H-pyran (methyl vinyl ketone dimer) regioselectively afforded the corresponding 3-(tetrazol-5-yl)-hexahydro...
Treatment of N-acetylneuraminic acid with excess base in the presence of benzyl bromide gives a polyhydroxylated 1,4 lactone which after acetylation gave the title compound in 20% overall yield. The structure of the product was confirmed by single cr...
Catechols and their derivatives attract great scientific interest due to the broad spectrum of their functional properties, including complexation, redox behavior, association ability and antioxidant activity. Because of the low molecular mass and tw...
In this communication, we present the crystal structure of a secondary amine: 4-chloro-N-(1-(pyridin-2-yl)ethyl)aniline (Lb) obtained from a stepwise reduction of an imine, (E)-N-(4-chlorophenyl)-1-(pyridin-2-yl)ethan-1-imine (La) with sodium borohyd...
Copper phosphido compound Cu4(μ-PPh2)4(PtBu3)2 was synthesized by three synthetic methods and structurally characterized by X-ray diffraction and 1H, 31P, 13C and 31P HMBC NMR spectroscopy. Cu4(μ-PPh2)4(PtBu3)2 was also demonstrated to be a hyd...
1,3-Dihydro-1-{1-[4-(4-phenylpyrrolo[1,2-a]quinoxalin-3-yl)benzyl]piperidin-4-yl}-2H-benzimidazol-2-one has been synthesized through a multi-step pathway starting from commercially available 2-nitroaniline. A structure characterization of this new su...
Donor molecules of the D-π-A-π-D type structure are often used for applications in organic photovoltaics. In this communication, bromination of 4,7-di(thiophen-2-yl)-[1,2,5]thiadiazolo[3,4-d]pyridazine followed by Suzuki cross-coupling with carbazole...
6-Heteryl-5-methylthieno[2,3-d]pyrimidin-2,4(1H,3H)-diones are of great interest as the promising objects for the search of antibacterials. In this communication, we obtained 6-(imidazo[1,2-a]pyridin-2-yl)-5-methyl-3-phenylthieno[2,3-d]pyrimidine-2,4...
Here we describe the functionalization of lupulone natural compound in obtaining 3-isobutyl-5,5,7-tris(3-methylbut-2-en-1-yl)-1-phenyl-1,7-dihydro-4H-indazole-4,6(5H)-dione. The lupulone-H-indazole derivative was prepared with 75% yield through the r...
New quercetin-based derivatives are synthesized in an easily accessible one-pot manner. The method is based on the reaction of quercetin with in situ formed electrophilic N-alkoxycarbonylazolium ions. The position of the newly formed C-C bond and str...
The pharmacophore hybridization approach is widely used for the design of drug-like small molecules with anticancer properties. In the present work, a “cost-effective” approach to the synthesis of the novel non-condensed pyrazoline-bearin...
An Ag(I)formamidine cluster Ag6L16 (1) and an Ag(I)formamidine coordination polymer Ag7(L2)2 2 (L1 = N,N′-bis(2,6-disopropylphenyl) formamidine dithiocarbamate and L2 = N,N′-mesityl formamidine dithiocarbamate) have been synthesized...
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Nitroimidazoles are pharmacophoric groups responsible for important antiparasitic activity against several infectious diseases. 2-Nitroimidazoles are found in some antiparasitic drugs and are one of the main moieties responsible for the biological ac...
3-Carbamoylmethyl-Indole-1-Carboxylic Acid Ethyl Ester (an ethoxycarbonyl derivative of indole-3-acetamide) is obtained by Friedel–Crafts type cyclocondensation of γ-functionalized acetoacetamide in neat polyphosphoric acid.
We report a synthesis of 3-bromo-9-N′-(N,N-dimethylformamidino)benzanthrone in good yield by a condensation reaction of 3-bromo-9-aminobenzanthrone with dimethylformamide in the presence of phosphorous oxychloride. The structure of the synthesi...
The reaction of 4,5-dichloro-1,2,3-dithiazolium chloride with 2-(phenylsulfonyl)acetonitrile (1 equiv) in the presence of pyridine (2 equiv) gave S-(3-chloro-5-cyanoisothiazol-4-yl)benzenesulfonothioate and (Z)-2-(4-chloro-5H-1,2,3-dithiazol-5-yliden...
3,5-Dichloro-4H-1,2,6-thiadiazin-4-one reacts with benzo[d]thiazole-2-thiol (1 equiv) and triethylamine (1 equiv) to give 3-(benzo[d]thiazol-2-ylthio)-5-chloro-4H-1,2,6-thiadiazin-4-one in 71% yield. The reactivity of this compound with methoxide is...
The title epoxide was obtained by spontaneous epoxidation of the corresponding unsaturated imide in air or by peracid oxidation. Unambiguous assignment of the 1H- and 13C-NMR spectra is achieved by comparison between analogous compounds and its X-ray...
2-(2-fluoro-[1,1′-biphenyl]-4-yl)-N-(1-phenylpropan-2-yl)propanamide was synthesized by a reaction between amphetamine and flurbiprofen in high yields. The newly obtained hybrid molecule was fully analyzed and characterized via 1H, 13C, UV, IR,...
The X-ray structure of the title compound, obtained as a byproduct in a natural product synthesis, has been determined and shows an unusual pattern featuring chains of molecules with both intra- and intermolecular hydrogen bonding of the OH groups.
Michael addition–halogenation–intramolecular ring-closing (MHIRC) reactions are processes in which a halogen atom as a leaving group can attach to substrates or reactants during the reaction, which then undergoes intramolecular ring closu...
Herein, two title compounds, N-benzoyl-N′-(4′-cyanophenyl)thiourea (1) and N-(4-nitrobenzoyl)-N′-(4′-cyanophenyl)thiourea (2) were synthesized in a high yield, via different applications of aroyl isocyanate and 4-aminobenzonit...
A simple and efficient protocol for the synthesis of the previously unknown 2-(2-(4-methoxyphenyl)furo[3,2-h]quinolin-3-yl)acetic acid was elaborated. The suggested method is based on the telescoped multicomponent reaction of 8-hydroxyquinoline, 4-me...
Over the last decade, there has been an increasing effort to fight inflammatory conditions establishing new multitarget approaches. Chronic inflammation is implicated in many multifactorial diseases, constituting a great economic burden and a chronic...
Natural compounds are endowed with an intriguing variety of scaffolds, functional groups and stereochemical properties [...]
Reaction of 1-(4-(dimethylamino)phenyl)-3,5-diphenylformazane with boron trifluoride diethyl etherate (5 equiv) in the presence of triethylamine (3 equiv) in toluene medium gave “boratetrazine”—2-(4-(dimethylamino)phenyl)-3,3-difluo...
In the present work, construction of double-charged cationic amphiphilic 1,1′-{[3,5-bis(dodecyl¬oxy-carbonyl)-4-(thiophen-3-yl)-1,4-dihydropyridine-2,6-diyl]bis-(methylene)}bis(pyridin-1-ium) dibromide (7) was performed in four steps. Dodec...
The multicomponent reactions are environmentally benign synthetic methods of building-up of complex molecules and several levels of structural diversity for diverse applications. Spirooxindoles are an important synthetic target possessing extended bi...
2,6-Bis(benzo[c][1,2,5]thiadiazol-4-yl)-4H-cyclopenta[2,1-b:3,4-b’]dithiophenes are of interest for the synthesis of molecules which can be employed in optoelectronic devices. In this communication, 7,7’-(4,4-bis(2-ethylhexyl)-4H-cyclopen...
Dimethyl sulfoxide (DMSO) is widely used as a solvent in organic synthesis and in pharmacology because of its low cost, stability, and non-toxicity. Multicomponent reactions are a powerful synthetic tool for the rapid and efficient construction of co...
2-Aryl-2-(3-indolyl)acetohydroxamic acids demonstrate promising antitumor activity, but quickly metabolize in vivo via glucuronidation of hydroxamic acid residue. In an attempt to improve their pharmacokinetics, methyl esters were synthesized via a n...
