University of North Florida

Kenneth K Laali

Novel CUR&#x2014; and CUR&#x2014;BFcompounds as well as novel bis and mono-NSAID/CUR&#x2014;BFand NSAID/CUR hybrids exhibiting anti-tumor properties are presented. CUR compounds bearing fluorinated moieties with selective fluorine introduction into the &#x3b1;-carbonyl moiety as well as CUR&#x2014;BFadducts and CURs with diverse substitution patterns in the phenyl rings including fluorinated substituents (SCF, OCF, and F) and/or bulky activating groups (OMe, OAc, and OBz) are presented. Fluorinated aryl-pyrazoles and isoxazoles as well as novel CUR and CUR&#x2014;BFcompounds with monocyclic aromatic and bicyclic-heteroaromatic lateral rings, bearing fluorine(s), OCF, CF, and SCFgroups, and their alpha-carbonyl-fluorinated analogs, as well as their pyrazole and isoxazole derivatives are presented. The CUR-pyrazoles embody analogs that are fluorinated at the phenyl-pyrazole moiety. The hybrids, compounds, and their derivatives exhibited exceptional cytotoxic and anti-proliferative activity against several cancer cell-lines. The hybrid NSAID/CUR compounds also exhibited exceptional anti-inflammatory activity over NSAID or curcumin alone.

Curcuminoid-inspired synthetic compounds as anti-tumor agents

Novel CUR&#x2014; and CUR&#x2014;BFcompounds exhibiting anti-tumor properties are presented. CUR compounds bearing fluorinated moieties with selective fluorine introduction into the &#x3b1;-carbonyl moiety as well as CUR&#x2014;BFadducts and CURs with diverse substitution patterns in the phenyl rings including fluorinated substituents (SCF, OCF, and F) and/or bulky activating groups (OMe, OAc, and OBz) are presented. Fluorinated aryl-pyrazoles and isoxazoles as well as novel CUR and CUR&#x2014;BFcompounds with monocyclic aromatic and bicyclic-heteroaromatic lateral rings, bearing fluorine(s), OCF3, CF3, and SCF3 groups, and their alpha-carbonyl-fluorinated analogs, as well as their pyrazole and isoxazole derivatives are presented. The CUR-pyrazoles embody analogs that are fluorinated at the phenyl-pyrazole moiety. The compounds and their derivatives exhibited exceptional cytotoxic and anti-proliferative activity against several cancer cell-lines. Deuterated CUR&#x2014;BF2 and CUR compounds were also synthesized.

4-(pentafluorosulfanyl)benzenediazonium tetrafluoroborate salt was synthesized and isolated. The pentafluorosulfanyl salt was examined in a wide assortment of reactions to form novel SF-bearing alkenes, alkynes, and biaryl derivatives using Heck-Matsuda, Sonogashira, and Suzuki coupling protocols. Dediazoniation of the salt furnished the corresponding p-SF&#x2014;CHX, CHOS(O)(CF)&#x2550;NSOCF, and p-SF&#x2014;CH&#x2014;NTfderivatives. The azide derivative p-SF&#x2014;CHNentered into click chemistry with phenylacetylenes to furnish the corresponding triazoles. Various SF-bearing alkenes were synthesized by coupling reactions using a metal catalyst. Fluorodediazoniation selectively furnished the fluoro derivative p-SF&#x2014;CHF. Homolytic dediazoniation gave the unsymmetrical biaryls, thus demonstrating the broad utility of pentafluorosulfanyl diazonium salts as building blocks of SF5-aromatics that are in high demand in many branches of chemistry including biomedicine and materials chemistry.

Synthesis of 4-(pentafluorosulfanyl)benzenediazonium tetrafluoroborate and analogs

4-(pentafluorosulfanyl)benzenediazonium tetrafluoroborate salt was synthesized and isolated. The pentafluorosulfanyl salt was examined in a wide assortment of reactions to form novel SF-bearing alkenes, alkynes, and biaryl derivatives using Heck-Matsuda, Sonogashira, and Suzuki coupling protocols. Dediazoniation of the salt furnished the corresponding p-SF&#x2014;CHX,CHOS(O)(CF)&#x2550;NSOCF, and p-SF&#x2014;CH-NTfderivatives. The azide derivative p-SF&#x2014;CHNentered into click chemistry with phenylacetylenes to furnish the corresponding triazoles. Various SF-bearing alkenes were synthesized by coupling reactions using a metal catalyst. Fluorodediazoniation selectively furnished the fluoro derivative p-SF&#x2014;CHF. Homolytic dediazoniation gave the unsymmetrical biaryls, thus demonstrating the broad utility of pentafluorosulfanyl diazonium salts as building blocks of SF5-aromatics that are in high demand in many branches of chemistry including biomedicine and materials chemistry.

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Jacksonville, FL, United States of America

Kenneth K Laali