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A series of new compounds containing monoterpenoid fragments, sulfide and carboxy groups was synthesized. The reaction of monoterpene thiols with bromoacetic acid and ethyl 2-bromo-2,2-difluoroacetate afforded new thiomonoterpene carboxylic acids in 80–96% and 56–80% yields, respectively. The synthesized compounds were studied for antimicrobial activity. Some structure–property interrelations were revealed, which depended on the monoterpene fragment structure and the presence of fluorine atoms in the carboxymethyl group. [ABSTRACT FROM AUTHOR]

In recent years, hydrofluorocarbon compounds such as chlorofluorocarbons, hydrochlorofluorocarbons, and 2‐bromo‐2‐chloro‐1,1,1‐trifluoroethane (halothane) have been used as fluorine‐containing building blocks to construct functional fluorine‐containing compounds, e. g., polymers, liquid crystals, and medicines. Hydrofluorocarbons promote the formation of reactive fluoroalkyl or fluoroalkenyl species via anionic or radical processes, and these species can act as nucleophiles or electrophiles depending on the reaction conditions. Progress in fluorine chemistry using hydrofluorocarbons in the last 30 years is described in this review and diverse reactions are discussed, including the fluoroalkyl/alkenyl products and proposed mechanisms involved. [ABSTRACT FROM AUTHOR]

The strategic fluorination of oxidatively vulnerable sites in bioactive compounds is a relatively recent, widely used approach allowing us to modulate the stability, bio-absorption, and overall efficiency of pharmaceutical drugs. On the other hand, natural and tailor-made amino acids are traditionally used as basic scaffolds for the development of bioactive molecules. The main goal of this review article is to emphasize these general trends featured in recently approved pharmaceutical drugs. [ABSTRACT FROM AUTHOR]

The strategic fluorination of oxidatively vulnerable sites in bioactive compounds is a relatively recent, widely used approach allowing us to modulate the stability, bio-absorption, and overall efficiency of pharmaceutical drugs. On the other hand, natural and tailor-made amino acids are traditionally used as basic scaffolds for the development of bioactive molecules. The main goal of this review article is to emphasize these general trends featured in recently approved pharmaceutical drugs.

Keywords: Freons; halothane; fluoroalkyl/vinyl source; nucleophilic/electrophilic reaction; fluorine-containing compounds EN Freons halothane fluoroalkyl/vinyl source nucleophilic/electrophilic reaction fluorine-containing compounds 1 1 1 09/12/23 20230901 NES 230901 The cover picture shows the use of freons and halothane as building blocks for constructing fluorinated materials as well as pharmaceuticals. Freons, halothane, fluoroalkyl/vinyl source, nucleophilic/electrophilic reaction, fluorine-containing compounds. [Extracted from the article]

3-Cyano-6-(2-thienyl)-4-trifluoromethylpyridine-2(1H)-one (1) and its thiono analog 2 were prepared by the reaction of (2-thenoyl)-ω,ω,ω-trifluoroacetone with cyanoacetamide or cyanothioacetamide, respectively. Interaction of compound 1 with ethyl chloroacetate or chloroacetamide led to the regioselective formation of O-alkylated pyridines 3 and 10. The latter compounds underwent some successive reactions to furnish the promising furopyridines (4 and 7–9) and pyrazolopyridines (12–15). The reaction of 2 with chloroacetamides or chloroacetonitrile furnished 2-functionalized 3-amino-6-(2-thienyl)-4-trifluoromethyl-thieno[2,3-b]pyridines (16a, b) which were used as key intermediates in the synthesis of the title thienopyridines. Structures of the newly synthesized compounds were established on the basis of their elemental and spectral (IR, 1H NMR and mass) analyses.

Using normal boiling point, melting point, refractive index, and relative density as examples, it has been demonstrated that physical properties of perfluorinated organic homologs can be approximated with sufficient accuracy by recurrent equations of the A( n+ k) = aA( n) + b type with k =1 or 2 (the latter being valid for melting point). [ABSTRACT FROM AUTHOR]

3-Cyano-6-(2-thienyl)-4-trifluoromethylpyridine-2(1 H )-one ( 1 ) and its thiono analog 2 were prepared by the reaction of (2-thenoyl)- ω , ω , ω -trifluoroacetone with cyanoacetamide or cyanothioacetamide, respectively. Interaction of compound 1 with ethyl chloroacetate or chloroacetamide led to the regioselective formation of O -alkylated pyridines 3 and 10 . The latter compounds underwent some successive reactions to furnish the promising furopyridines ( 4 and 7 – 9 ) and pyrazolopyridines ( 12 – 15) . The reaction of 2 with chloroacetamides or chloroacetonitrile furnished 2-functionalized 3-amino-6-(2-thienyl)-4-trifluoromethyl-thieno[2,3- b ]pyridines ( 16a , b ) which were used as key intermediates in the synthesis of the title thienopyridines. Structures of the newly synthesized compounds were established on the basis of their elemental and spectral (IR, 1 H NMR and mass) analyses. [ABSTRACT FROM AUTHOR]

Asymmetric synthesis of fluorine-containing compounds using organocatalysts has been extensively investigated and several important strategies have been developed in the last decade. This review focuses on the recent advances in the introduction of the fluorine atom into organic molecules by: i) electrophilic fluorination reactions; ii) the use of easily available fluorine-containing building blocks, both of interest in our research laboratory.

Abstract: The Rh2(OAc)4 catalyzed [3+2] cycloaddition of 4-diazo-1-phenyl-3-(trifluoromethyl)-1H-pyrazol-5(4H)-one with aromatic alkynes was studied, and this protocol can be efficiently applied to the synthesis of the novel CF3-substituted ring-fused furo[2,3-c]pyrazoles. [Copyright &y& Elsevier]

Abstract: An efficient 1,3-dipolar cycloaddition method was performed for the synthesis of a series of monofluoro- and trifluoromethane-3,5-disubstituted 1,2,4-triazoles. This efficient cycloaddition method was to react hydrazonoyl hydrochlorides with a series of aldehydes in the presence of NEt3 as catalytic basic agent to provide the corresponding product in 28–94%. Their growth inhibitory results against cancer cells indicated that some of the fluorine- and trifluoromethane-containing compounds could effectively inhibit the growth of NCI-H226 and T-cell leukemia (Jurkat) cells. Among the compounds, trifluoromethane-containing 1,2,4-triazoles possessed the five-membered ring groups on the C-5 position of the triazolic ring, including cyclopentyl, 3-furyl, 3-thienyl, and 2-pyrrolyl, possessed the significant inhibitory activity for NCI-H226 cancer cells. [Copyright &y& Elsevier]

Abstract: Treatment of fluoroalkylated electron-deficient olefins with various boronic acids in the presence of a catalytic amount of Rh(I) coordinated with (S)-BINAP in toluene/H2O at the reflux temperature for 3h gave the corresponding conjugate addition products with high enantioselectivity in high yields. [Copyright &y& Elsevier]

The reaction between 1,1,1,5,5,5-hexafluoro-2,4-pentanedione and 2-(aminomethyl)pyridine, or its salts with carboxylic acids, was found to produce a mixture of diastereomeric 2-(2′-pyridyl)-3-hydroxy-3,5-bis-trifluoromethyl-1-pyrrolines with high (up to 85% de) of kinetic (3R*,5S*)-diastereoselectivity. The thermodynamic (3R*,5R*) diastereomer was prepared as a major product (90% de) by epimerization of the kinetic (3R*,5S*) diastereomer with triethylamine. [Copyright &y& Elsevier]

one-pot method for the synthesis of trifluoromethyl-containing heterocyclic pyracetam derivatives has been suggested by the reaction of pyracetam, hexafluoroacetone, and 1,3-binucleophiles, viz., 3-aminocrotononitrile, 6-aminouracyls, 6-aminothiouracyl, N-benzyl-3-aminocyclohexenone, and 2-aminothiazoline. [ABSTRACT FROM AUTHOR]

• 13 new fluorine-containing proguanil derivatives were designed and synthesized. • Derivatives with trifluoromethyl phenyl or n -heptane substitutions exert a strongest antiproliferative activities. • Derivative 7a blocks the tumor cell growth by influencing AMPK-mTOR signal pathway. Proguanil, a member of biguanide family, has excellent anti-proliferative activities. Fluorine-containing compounds have been demonstrated to have super biological activities including enhanced binding interactions, metabolic stability, and reduced toxicity. In this study, based on the intermediate derivatization methods, we synthesized 13 new fluorine-containing proguanil derivatives, and found that 7a , 7d and 8e had much lower IC 50 than proguanil in 5 human cancerous cell lines. The results of clonogenic and scratch wound healing assays revealed that the inhibitory effects of derivatives 7a , 7d and 8e on proliferation and migration of human cancer cell lines were much better than proguanil as well. Mechanistic study based on representative derivative 7a indicated that this compound up-regulates AMPK signal pathway and downregulates mTOR/4EBP1/p70S6K. In conclusion, these new fluorine-containing derivatives show potential for the development of cancer chemotherapeutic drugs. [ABSTRACT FROM AUTHOR]