A series of 3,4-dihydro-4,6-diaryl-2-pyrimidinethiones was obtained using a three-component reaction and their modifiaction with dimethyl chloroethynylphosphonate was performed. It was shown that the phosphonylation reaction occurs under mild conditions and chemo- and regioselectively leads to bicyclic products, namely dimethyl 5,7-diaryl-5H-thiazolo[3,2-a]pyrimidine-3...
4-Methyl-6-pyrazolyl-2-chloronicotinonitriles were synthesized by the reaction of 6-hydrazino-4-methyl-2-chloronicotinonitriles with 1,3-diketones. Upon treatment with hydrazine and methylhydrazine, 4-methyl-6-pyrazolyl-2-chloronicotinonitriles were converted into the corresponding 3-amino-4-methyl-6-pyrazolyl-1H-pyrazolo[3,4-b]pyridines. A similar reaction involving 1,1...
New morpholinium surfactants with a carbamate fragment between the amphiphile head group and its hydrophobic tail (CnMB-carb, where n = 8, 10, 12, 14, 16) were synthesized. The cmc values obtained by tensiometry for dodecyl, tetradecyl, and hexadecyl homologues are 3–4 times lower than those of 4-alkyl-4-methylmorpholinium bromides. The introduction of a carbamate fragment can be...
A new nanocarrier was developed for the delivery of an antidote for poisoning with organophosphorus compounds. The nanocarrier acts as an artificial esterase, hydrolyzing acetylcholine and releasing the antidote (atropine) when acetylcholine level is high. The nanocarrier was made using histidine-containing resorcinarene as a building block. Histidine-resorcinarene was...
Distally substituted bis-1,3-diketone derivatives of calix[4]arene were synthesized, in which chelate groups are attached via a carbonyl carbon atom to the p-positions of phenolic fragments of a macrocycle fixed in 1,3-alternate isomeric form. 1,3-Diketone derivatives were obtained by acylation of magnesium enolate of a calix[4]arene ketone with 1-benzoylbenzotriazoles. In the...
Iodination of 2-(4-arylthiazole-2-yl)acetonitriles in DMF proceeds with the formation of previously undescribed 2,3-bis(4-aryl-1,3-thiazole-2-yl)but-2-enedicarbonitriles as a mixture of E- and Z-isomers. The latter were alternatively prepared by the reaction of cyanothioacetamide, α-bromoketones and iodine in DMF. Structure of the key compounds was proven by means of single...
Eleven copper(I) halide complexes [CuX(CNR)3] (X = Cl, Br; R = C6H3-2,6-Cl2, C6H3-2-Cl-6-Me, C6H3-2,6-Br2, C6H3-2-Br-6-Me; X = I, R = C6H3-2,6-Cl2, C6H3-2-Cl-6-Me, C6H3-2-Br-6-Me) bearing halogen-functionalized aromatic isocyanide ligands were synthesized. The compounds were characterized by atomic emission spectroscopy (Cu), IR, 1H NMR spectroscopy and high-resolution mass...
Multicomponent condensation of cyanothioacetamide, carbonyl compounds, enamines and alkylating reagents initiated by the Knoevenagel reaction led to the formation of 2-thionicotinonitriles. The molecular and crystal structure of the prepared products was studied by single crystal X-ray diffraction method.
A method for producing a number of (E)-1-aryl-3-nitroprop-2-en-1-ones based on a synthetic condensation–dehydration strategy has been optimized. New (Z)-1-aryl-3-bromo-3-nitroprop-2-en-1-ones have been synthesised from (E)-1-aryl-3-nitroprop-2-en-1-ones using halogenation-dehydrohalogenation strategy to (E)-1-aryl-3-nitroprop-2-en-1-ones. The fine structure of nitro- and...
A three-stage method was proposed for the synthesis of (1S)-(+)-camphor-10-sulfonic acid, (+)-ketopinic and (–)-camphanic acids esters containing a saturated nitrogen-containing heterocycle. It was found that (1S)-(+)-camphor-10-sulfonic acid esters undergo destruction with elimination of the sulfonic acid group in substitution reactions involving nitrogen-containing heterocycles...
A three-stage method was proposed for the synthesis of new 4-[4-(2-azolylethyl)piperazine-1-yl]-N-aryl-5H-1,2,3-dithiazole-5-imines. This approach includes the reaction of Appel salt with anilines to produce 1,2,3-dithiazole-5-imines, which were converted into 4-[(4-chloroethyl)piperazine-1-yl]-5H-1,2,3-dithiazole-5-imines, alkylating azoles at the final stage. The high...
Multicomponent condensation of alkylating reagents with carbonyl compounds functionalized by CH-acids is initiated by the Knoevenagel reaction and leads to the formation of substituted pyridines, thienopyridines, pyridothienopyridines, and pyrimidothienopyridopyrimidines. The structure of the key products was studied by the X-ray diffraction method.
Recent publications on direct reactions of elemental phosphorus with organic halides (alkyl bromides, aryl (and hetaryl) halides, and aryl (and hetaryl) methyl halides) in the presence of superbasic and micellar catalysts are considered. The development of effective, technologically and environmentally acceptable methods for obtaining alkyl(and benzyl)-H-phosphinic and...
The activation of Hh pathway demonstrates therapeutic potential for many diseases. Smo is the main target for the development of Hh pathway modulators. However, compared with Smo antagonist, the development of Smo agonists is lagging behind. Based on our previous work, a series of vismodegib derivatives were designed and synthesized, and their potential to activate the Hh pathway...