Synthesis and antimicrobial activity of fused isatin and diazepine derivatives derived from 2-acetyl benzofuran

Acetyl benzofurans 1a, 1b reacted with isatins 2a–2f in the presence of pyridine to give corresponding 3-[2-(1-benzofuran-2-yl)-2-oxoethyl]-3-hydroxy-1,3-dihydro-2H-indol-2-one derivatives 3a–3l. Dehydration of the latter in acidic media led to the corresponding α,β-unsaturated ketones 4a–4l. The structures of newly synthesized compounds 3a–3l and 4a–4l were established on the basis of analytical and spectral data. The synthesized compounds were screened for their antibacterial and antifungal activities. Compounds 5d, 5f, and 5h displayed excellent antimicrobial activity. The synthesized compounds were studied for docking on the enzyme, Glucosamine-6-phosphate Synthase.     

Synthesis and in vitro cytotoxic evaluation of some novel hexahydroquinoline derivatives containing benzofuran moiety

A series of new ethyl 4-(2-(benzofuran-2-yl)-4-substituted-1,4,5,6,7,8-hexahydroquinolin-1-yl)-benzoate 3a–c was synthesized by Michael condensation of benzofuran chalcones 1a–c and cyclohexanone to give 2-(2-benzofuranyl)-4-substituted-5,6,7,8-tetrahydro-4-H -chromene 2a–c, followed by reaction of the latter with ethyl 4-aminobenzoate. Condensation of 3a–c with different amines afforded the corresponding amides 4a–e. On the other hand, upon treatment compounds 3a–c with hydrazine hydrate gave the benzohydrazide derivatives 5a–c. The reaction of compounds 5a–c with different thio/isocyanate gave the corresponding thiosemicarbazide and semicarbazide derivatives 6a–c. Meanwhile compounds 5a–c were reacted with ethyl cyanoacetate and different β-dicarbonyl compounds such as acetyl acetone, ethyl acetoacetate, and diethyl malonate to afford pyrazolyl derivatives 7a, b; 8a, b; 9a, b; and 10a–c, respectively. Moreover, 5a–c were reacted with carbon disulfide to synthesize the corresponding oxadiazolyl derivatives 11a–c, while their condensation with different aromatic aldehydes gave the corresponding Schiff bases 12a–d. Cytotoxic evaluation of some of the newly synthesized compounds against human hepatocellular carcinoma cell lines (HepG-2) revealed that the tested compounds produce promising inhibitory effect against the growth of HepG-2 cells with IC₅₀ values ranged from 11.9 to 19.3 µg/mL.     

Microwave in glycosylation reaction: design,and synthesis of highly substituted nicotinonitrile nucleosides

An efficient and rapid regiospecific approach for the synthesis of cyclic and acyclic nucleosides of 2-oxonicotinonitriles was performed. Whereas, glycosylation of 2-oxonicotinonitriles 1a, b with peracetylated sugars (namely, peracetylated glucose, galactose and ribose) under MWI tolerated exclusively the desired N-nucleosides 2a, b, 4a, b and 6a, b in significant yields (75–86%) and in short reaction time (5–7 min.). The same products were obtained under the conventional conditions, using halo-sugar with low yields in hard conditions. Similarly, the acyclic nucleosides 8a, b and 9a, b were obtained under MWI and conventional conditions via reaction of 1a, b with 4-bromo butyl acetate and 2-acetoxyethoxymethyl bromide. Finally, deprotection of the latter blocked N-nucleosides was performed via treatment with aqueous methanolic solution containing a catalytic amount of triethyl amine to give the desired free nucleosides 3a, b, 5a, b, 7a, b, 10a, b and 11a, b, respectively. The free nucleosides (3a, b, 5a, b, 7a, b and 11a, b) were evaluated against Gram (+?ve) bacteria, Gram (–ve) bacteria and one pathogenic Fungi namely, Aspergillus flavus. Good results were obtained for compounds 7a, b and 11a, b compared with the used standard drugs (Cefotaxime and Dermatin).

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Syntheses,crystal structures,and properties of two supramolecules based on methoxyphenyl imidazole dicarboxylates

Two cobalt(II) and cadmium(II) complexes, [Co(H₂DMOPhIDC)₂(H₂O)₂] ? 2H₂O (H₃DMOPhIDC = 2-(3,4-dimethoxyphenyl)-1H-imidazole-4,5-dicarboxylic acid) (I), [Cd(H₂MOPhIDC)₂-(Phen)] ? C₂H₅OH (H₃MOPhIDC = 2-(3-dimethoxyphenyl)-1H-imidazole-4,5-dicarboxylic acid, Phen = 1,10-phenanthroline) (II), have been hydro(solvo)thermally synthesized by employing two kinds of organic ligands, H₃DMOPhIDC or H₃MOPhIDC, respectively. The molecular structures of I and II have been characterized by IR spectra, elemental analyses and single-crystal X-ray diffraction (CIF files CCDC nos. 935845 (I), 935846 (II)). Both complexes show three-dimensional supramolecular structures supported by intermolecular H-bonds. Furthermore, the thermogravimetric and photoluminescent properties of two complexes have been investigated as well.     

Photophysical properties of aqueous solutions of a styryl dye in the presence of cucurbit[<Emphasis Type="Italic">n</Emphasis>]uril (<Emphasis Type="Italic">n</Emphasis> = 5, 6, 8)

Photophysical properties of aqueous solutions of the styryl dye 4-[(E)-2-(3,4-dimethoxyphenyl)-1-ethylpyridinium] perchlorate (1) in the presence of cucurbit[n]urils (CB[n]; n = 5, 6, 8) have been studied by fluorescent spectroscopy methods. The fluorescence intensity of a 10^–6 mol L^–1 solution of 1 increases by a factor of 12.6 upon the formation of 1 : 1 inclusion complexes with CB[6] or 1.3 in complexes with CB[8]. Upon the formation of inclusion complexes, the average lifetime of the electronically excited state of 1 increases to about 1 ns for both CB[6] and CB[8]. On the basis of fluorescence anisotropy measurements, the rotational relaxation times were estimated to be 408, 314, and 183 ps for the complexes with CB[6], CB[8], and for unbound 1, respectively. Using the fluorescence titration method developed for the case of poorly soluble cavitands, the binding constant of 1 with CB[6] was determined to be 1.1 × 10⁵ L mol^–1. The addition of CB[5] does not lead to changes in the photophysical properties of a solution of 1, indicating the absence of complexes between CB[5] and 1. It has been found on the basis of the experimental data that the fluorescence rate constant of 1 decreases about twice in the complex with CB[8], but doubles in the complex with CB[6].     

Cyclization of pyrazolones: novel synthesis of pyrano,pyrido, pyrimido and spiropyrazole derivatives

Depending on the reaction conditions, two alternative cyclizations are possible for [3?+?3] cyclocondensation of pyrazolone derivative 1a and ethyl cyanoacetate of type pyrano [2,3-c] pyrazol-6(1H)-one 2 and pyrano [2,3-c] pyrazol-4(1H)-one 3. Keeping of enaminic system 3 and benzylidene malononitrile in the presence of catalytic amount of trimethylamine resulted in pyridine cyclization affording pyrazolopyranopyridine derivative 4, not 5. The pyrazolone derivative 6a was obtained as a result of the acid-mediated addition reaction between compound 1a, urea and/or ammonium thiocyanate. In addition, the bispyrazolone of type 6b was obtained from the condensation reaction of urea and pyrazolone derivative. The spiro compound 7 was obtained from the double-addition reaction of pyrazolone to cinnamoyl isothiocyanate. A one-pot three-component condensation of a 3-hydroxybenzaldehyde, pyrazolone 1a, urea and/or thiourea under Biginelli conditions resulted in tetrahydropyrazolo pyrimidine derivatives 8a and 8b, respectively. The acid-mediated reaction of benzaldehyde and pyrazolone derivative 1a in the presence of Ac₂O yielded styrylpyrazole derivative 9. The polyfunctionalized product 9 reacted with hydrazine to furnish pyrazolotriazoloe of type 10. Treatment of styrylpyrazole derivative 9 with aniline furnished the aniline derivative 11 and none of the expected polyheterocyclic derivative 12 was obtained. Compound 9 undergoes pyridine cyclization to produce 13 under the effect of urea. N-phenyl pyrazolone converted into pyrano-dipyrazolone derivative 14. Pyran of type 14 underwent a ring transformation upon treatment with urea and/or thiourea to give the same dipyrazolo pyrimidine derivative 15. The newly synthesized compounds were characterized by FT-IR, ¹H-NMR, ¹³C-NMR, ESI/LC-MS and elemental analysis.     

Electrochemical behavior and in-vitro antimicrobial screening of some thienylazoaryls dyes

Background

A series of recently reported phenolic azo dyes 7a–e were prepared by coupling the thienyl diazonium sulfate of 3-Amino-4H-benzo[f]thieno[3,4-c](2H)chromen-4-one with selected diversely substituted phenolic and naphtholic derivatives. These compounds were evaluated for their antibacterial and antifungal activities. Furthermore their voltammetric behavior was compared at a glassy carbon electrode.

Results

The voltammetric behavior of the five recently reported azo dyes has been compared at a glassy carbon electrode. It is shown that the azo dyes 7a–e with a hydroxyl group in the ortho position with respect to the azo bridge give rise to well defined, irreversible peaks for the oxidation and reduction process within a pH range of 2–7. The mechanisms of electrochemical oxidation of compound 7a–c and 7e are proposed. For the hydroxyl-substituted dyes, re-oxidation peaks were obtained in the subsequent scan. The antimicrobial activities of the reported compounds 7a–e along with the entire precursors 1–4 and 6a–e were performed against selected bacterial and fungal species and their activities compared to those of nystatin, griseofulvin and ciprofloxacin used as reference drugs.

Conclusions

The present study showed significant antimicrobial activity of compounds 6d, 7a and 7c,e against the tested microorganisms; this result confirms the antimicrobial potency of azo compounds and some of their precursors.

     

Synthesis,antibacterial activity,and fluorescence properties of a novel series from [2,4-dioxochromen-3(4<Emphasis Type="Italic">H</Emphasis>)methyl]amino acid

A new solvent-free method for synthesis of starting compounds 2,4-dioxochromen-3(4H)methyl amino acetic acid derivatives 1a–e via a green approach is reported. Also, the behavior of compound 1a towards various nitrogen nucleophiles such as primary amines, hydrazine hydrate, and hydroxylamine hydrochloride to give corresponding compounds 2–4 was studied. Furthermore, chlorination of compound 1a using a mixture of PCl₅/POCl₃ to yield acid chloride derivative 5 and the reaction of the latter compound 5 with various amino acids to obtain dipeptide compounds 6a–e are described. Moreover, cyclization of compound 1a in alkaline medium to afford dihydrochromeno[3,4-c]pyrrole-1-carboxylic acid 7 and cyclization of 6b in acidic medium, namely Ac₂O, to yield piperazine derivative 8 are reported. Also, reaction of compound 1a with maleic anhydride in dioxane to afford Diels–Alder adduct 9, which posteriorly reacted with hydrazine hydrate to give 10, was investigated. Most of the newly synthesized compounds were screened against Gram-positive and Gram-negative bacteria, with compound 5 exhibiting the maximum inhibition zone towards all four types of bacteria. In addition, the absorption and fluorescence emission of some of the substituted coumarins were studied in dioxane, revealing that the substituents altered both the absorption and fluorescence emission maxima.     

Exploring the impacts of the vinylogous anomeric effect on the synchronous early and late transition states of the hydrogen molecule elimination reactions of cis-3,6-dihalocyclohexa-1,4-dienes

LC-ωPBE, B3LYP, and M06-2X methods with the 6–311+G** basis set on all atoms and natural bond orbital (NBO) interpretation were performed to investigate the roles and contributions of the effective factors on the potential energy surfaces of the hydrogen molecule elimination reactions of cyclohexa-1,4-diene (1) and its cis-3,6-dihalo derivatives [halogen=F (2), Cl (3), Br (4)] to hydrogen molecule and their corresponding aromatic rings. The ring puckering in compound 2 (which results from the repulsive electrostatic interactions between the natural bond orbital dipole moments of two C-F bonds) shortens the allylic hydrogen atoms’ distance, leading to the smaller barrier height in compound 2 compared to that in compound 1. The barrier heights of the hydrogen molecule elimination reactions increase from compounds 2 to 4 while their corresponding exothermic characters decrease. The variations of the advancements of transition state structures (δB _av) reveal that the hydrogen molecule elimination reactions of compounds 2–4 do not obey the Hammond-Leffler postulate. In compound 2, the ring puckering shortens the allylic hydrogen distance (d _H8-H10) while d _H8-H10 values increase going from compounds 2 to 4, leading to the increase of their corresponding hydrogen molecule elimination reactions barrier heights. Interestingly, the variations of the vinylogous hyperconjugative anomeric effects justify the directions of the rings puckering going from compounds 2 to 4. The increase of the activation exchange components [PETR _(TS)-PETR _(GS)] going from compounds 2 to 4 correlates well with their corresponding hydrogen molecule elimination process barrier heights.     

Low-melting molecular complexes: Part VII. 2,3-, 2,5- and 3,4-hexanediones and their molecular complexes with chloroform

Crystals of three isomeric 2,3-, 2,5- and 3,4-hexanediones 1–3 and of molecular complexes (1:2) of 2 and 3 with chloroform (4 and 5) were grown by in situ cryocrystallisation and characterised by single-crystal X-ray crystallography. The intermolecular interactions and packing motifs were examined using the analysis of pairwise energies of intermolecular interactions. The method has revealed the importance of carbonyl…carbonyl interactions in the structures 1, 3 and 4 and the relatively weaker halogen bonds in the structures 4 and 5.     

Solution and solid-state studies of a new supramolecular proton transfer salt and its VO<Subscript>2</Subscript> complex constructed with chelidamic acid and 3,4-diaminopyridine

The proton transfer compound (Hdap)(chelH)·2H₂O (1) and its related anionic complex (Hdap) [VO₂(chel)] (2), where chelH₂ = 4-hydroxypyridine-2,6-dicarboxylic acid (chelidamic acid) and dap = 3,4-diaminopyridine, were synthesized and characterized by elemental analysis, spectroscopy (IR, UV–Vis), thermal (TG/DTG) analysis and single-crystal X-ray diffraction. Compound 1 resulted from proton transfer between chelH₂ and dap in aqueous solution. In 1, two carboxylic acids of chelH₂ were deprotonated and the protons transferred to the nitrogen atoms of one chelidamate anion and one dap moiety. Compound 2 resulted from complexation of 1 and vanadyl sulfate. In the crystal structure of 2, the metal ion is five coordinated by one tridentate ligand (chel)^2? and two O^2? anions, with (Hdap)⁺ as a counter cation. In both structures, a complicated hydrogen-bonding network accompanied with π–π, C–O···π and C–H···π stacking interactions leads to formation of a 3D supramolecular network. In the following, solution studies have been performed by means of pH potentiometric titrations method as a power technique. This method was used for determination of protonation constants of chelH₂ and dap in their probable protonated forms and for calculation of equilibrium constants for the chelH₂–dap proton transfer system and the stoichiometry and stability constants of binary and ternary complexes of this system with VO²⁺ ion in aqueous solution. The stoichiometries of the most complex species in solution were compared with the corresponding crystalline complexes in the solid state.     

Molecular modeling and cyclization reactions of 2-(4-oxothiazolidine-2-ylidene) acetonitrile

Diazotization of 2-(4-oxothiazolidine-2-ylidene) acetonitrile 1 with aryl diazonium chloride derivatives afforded 4-thiazolidinones 2a, b, whereas 3a, b derivatives produced through reaction of arylcarbonohydrazonoyl dicyanide with thioglycolic acid. Cyclization of 2a with aromatic aldehydes and malononitrile gave the expected substituted thiazolo [3,2-a] pyridines 4a, b. The reaction of 1 with anthraldehyde (1:1 molar ratio) gave the expected 4,5-dihydro-4-oxothiazole derivatives 5 which condensed with other mole p-chlorobenzaldehyde and gave the corresponding bisarylidine derivative 6. Thiazolo [3,2-a] pyridine enaminonitrile derivative 7 produced through addition of malononitrile to bisarylidine 6. Also, compound 7 reacted with other mole of malononitrile and furnished thiazolo [3,2-a] pyridine 12, furthermore, compound 7 refluxed with phenyl hydrazine, thiourea, and formic acid, to form the corresponding thiazolo [3,2-a] pyridines 13, 15 and 17, respectively. Also, compound 1 reacted with phNCS in presence of KOH and afforded 19. The molecular modeling of the synthesized compounds has been drawn and their molecular parameters were calculated. Also, valuable information is obtained from calculation of the molecular parameters including electronegativity, net dipole moment of the compounds, total energy, electronic energy, binding energy, electrophilicity index, HOMO and LUMO energy.     

Amine electrosynthesis from 1-ethyl-4-nitro-3-cyanopyrazole

Polarography and preparative electrolysis are used to show that the electrochemical behavior of 1-ethyl-4-nitro-3-cyanopyrazole (1) in acidic aqueous-alcoholic solutions resembles the behavior of nitrobenzene. By varying the parameters of the electroreduction (ER) of compound 1, one can obtain either 1-ethyl-4-amino-3-cyanopyrazole (2) or 1-ethyl-4-amino-3-cyano-5-chloropyrazole (3). Compound 2 is formed during the ER of compound 1 in the presence of a mediator (titanium(III)) at temperatures below 10°C. Compound 3 is produced by the direct reduction of compound 1 on a lead electrode (30% ethanol, 10% HCl). The yield of amine chlorohydrates 2 and 3 is 56 and 92%, respectively. The mediated ER of compound 1 at catholite temperatures higher than 10°C yields a mixture of compounds 2 and 3; the proportion of the latter increases with temperature to become the major product at 60°C. Compound 3 is formed due to the rearrangement of the hydroxylamine derivative produced by the ER of compound 1, followed by the substitution of chlorine for the hydroxy group.     

Spectroscopic characterizations,X-ray studies,and electronic circular dichroism calculations of two alkaloid triterpenoids

Two alkaloid triterpenoids formulated as C₂₆H₃₅NO₃ (1) and C₃₀H₄₅NO₂ (2) were isolated from the timer tree Aphanamixis grandifolia. The structure of 1 and 2 was determined by IR, HRESIMS, 1D, and 2D-NMR. Compound 1 was confirmed by X-ray single crystal diffraction. Compound 1 crystallizes in the monoclinic, space group C₂ with unit cell parameters a = 53.195(4) Å, b = 7.6339(8) Å, c = 11.202(2) Å, β = 94.6520(2)°. Intermolecular hydrogen bonding and π–π stacking were presented in the molecular packing of 1. The absolute configurations of 1 and 2 were established by comparison of experimental circular dichroism properties with their electronic circular dichroism predicted by molecular modeling DFT calculations.     

Synthesis and anticancer activities of 1,4-phenylene-bis-<Emphasis Type="Italic">N</Emphasis>-acetyl- and <Emphasis Type="Italic">N</Emphasis>-phenylpyrazoline derivatives

Novel 1,4-phenylene-bis-N-acetyl- (3a–h) and bis-N-phenylpyrazoline derivatives (4a–h) were obtained by addition of hydrazine hydrate and phenylhydrazine to bis-chalcone derivatives (1a–h) in acetic acid and acetic acid/ethanol for 4 and 8 h in reflux conditions, respectively. The structures of the obtained bis-N-acetylpyrazoline and bis-N-phenylpyrazoline derivatives were characterized by nuclear magnetic resonance (NMR) and infrared (IR) spectroscopic methods and elemental analysis. Compounds 3a–h and 4a–h were investigated to evaluate their anticancer activities against C6 (rat brain tumor cells) and HeLa (human uterus carcinoma) in vitro using a dose-dependent assay from 5 to 100 μM with 5-fluorouracil (5-FU) as standard anticancer drug. Compound 3a showed higher cell-selective activity compared with 5-FU against HeLa cells. Compounds 3a–h (except 3d) were shown to have better activities than 5-FU against both cells, particularly at high concentration. Compound 4c showed higher cell-selective activity compared with 5-FU against C6 cells. Compound 3a may be particularly promising as an anticancer drug against HeLa cells.     

The influence of the negative hyperconjugation is relevant for the analysis of the π-π<Superscript>*</Superscript> conjugation with the mono-substitution and di-substitution of H<Subscript>2</Subscript>C= by O= and/or HN= in <Emphasis Type="Italic">trans</Emphasis>-buta-1,3-diene?

We have studied prop-2-en-1-imine (1), prop-2-enal (2), ethane-1,2-diimine (3), ethanedial (4), and 2-iminoacetaldehyde (5) to investigate the influence of the negative hyperconjugation in π-π^* interaction with the substitution of =CH₂ by =NH and/or =O in trans-buta-1,3-diene (6). The analyzes of the π-π^* interaction performed from evaluation of the π molecular orbital diagrams and electron localization function method demonstrated, that compared to 6, the substituted compounds 1-5 presented lower electron conjugation, especially in the structures bearing =O. The geometric parameters, natural bond orders, and topological analysis realized by quantum theory of atoms in molecules method indicated a predominant C-C and C=C character for the simple and double C-C bonds in the substituted compounds, 1-5, as compared to 6. Compound 4 had the highest enthalpy of formation, which reflected the lowest π-π^* interaction, maintained by the two =O conjugated groups. The natural bond orbital (NBO) and natural resonance theory (NRT) methods revealed that the π-π^* electron delocalization in substituted compounds, 1-5, is lower than in 6 from, firstly, of the less favorable interactions: π(X=C) ? π^*(C=C) and π(X=C) ? π^*(C=X), despite of the larger π(C=C) ? π^*(C=X) conjugation, with X = N and/or O, of 1-5 than π(C=C) ? π^*(C=C) of 6. But, most importantly, the weight of the interaction: n_π(O) ? σ^*(C-C), was determined from NBO and NRT methods as proportional to the π-π^* conjugation and thus demonstrating be decisive to establish the level of π electronic delocalization.     

Reaction of amides of 2,3-dibromopropionic and 2-bromoacrylic acids with pyridine and triphenylphosphine

By refluxing pyridine with 2,3-dibromopropionic acid amide in acetonitrile, amide of 3-bromo-2-pyridiniumbromidopropionic acid I was synthesized. The latter is inert toward the second molecule of pyridine under the used conditions. Compound I was found to react with triphenylphosphine to form a mixture of 3-triphenylphosphoniumbromidopropionitrile II and 1-triphenylphosphoniumbromido-2-pyridiniumbromidoethane III. Schemes of reactions were suggested involving attack of phosphine on the carbonyl group as the first stage. The reaction of α-bromoacrylic acid amide with triphenylphosphine was shown to yield also compound II. Evidently, this reaction proceeds through intermediate formation of enolphosphonium salt.     

X-ray diffraction investigation of perfluoro-4-methylenecyclohexa-2,5-dienones

Perfluorinated 8-phenyl-7,8-diethylbicyclo[4.2.0]octa-1,4,6-trien-3-one (3), 2-(4-oxocyclohexa-2,5-dienylidene)-1,1-diethylbenzocyclobutene (4) and 2-(4-oxocyclohexa-2,5-dienylidene)-5-(2-phenyl-cis-1,2-diethylbenzocyclobuten-1-yloxy)-1,1-diethylbenzocyclobutene (5), including the 4-methylencyclohexa-2,5-dienone fragment, were prepared by the reaction of perfluoro-1,1-(1) and-1,2-diethylbenzocyclobutene (2) with pentafluorobenzene in SbF₅. Single crystal X-ray diffraction study of compounds 3–5 revealed that the oxygen atom of the C=O group participated in the formation of supramolecular architectures in all three compounds, and C=O…π bonding may be considered as the corresponding synthon (with increased separation in the case of compound 5). C-F…π bonding acts as a second synthon. F…F interactions in crystals 3–5 were classified as stabilizing or enforced.     

Synthesis of hydrazone derivatives of benzofuran and their antibacterial and antifungal activity

A series of benzofuran hydrazones 6a–6n were synthesized from benzofuran aldehyde and substituted aromatic hydrazides 5a–5n. Structures of all compounds were confimed by IR, ¹H and ¹³C NMR, and Mass spectral data. These compounds were evaluated for their antibacterial activity against gram-negative bacteria (Escherichia coli, –ve), gram-positive bacteria (Bacillus Subtillis, +ve), and antifungal activity against Candida albicans. All compounds demonstrated considerable activity against bacteria and fungi.     

Synthesis of New Potential Hydrophobic Agents Composed of Three-Module Type Molecules

A new synthetic route was developed to three-module type potential hydrophobic agents, with the molecule consisting of an N-[3-(triethoxysilyl)propyl]amide anchor part (I), a connecting unit formed upon 1,3-propansultone ring cleavage (II), and a polyfluoroheptyloxy functional hydrophobic spacer (III). Proceeding from commercially available polyfluorinated heptanols 1a and 1b and 1,3-propanesultone 3, potassium sulfonates 4a and 4b were prepared. The reaction of 4a and 4b with phosphorus oxychloride resulted in the first synthesis of fluorine-containing sulfonyl chlorides 5a and 5b, which were reacted with 3-aminopropyltriethoxysilane 6 to give the target N-[3-(triethoxysilyl)propyl]-3-(polyfluoroheptyloxy)propane-1-sulfonamides 7a and 7b. The structures of the compounds were proved by NMR spectroscopy, mass spectrometry, and elemental analysis. The studies of their hydrophobizing properties are in progress.