Alain Maggiani

N-Aryltriazole ribonucleosides with potent antiproliferative activity against drug-resistant pancreatic cancer

Novel N-aryltriazole nucleosides were synthesized via Cu-mediated C-N cross-coupling reaction starting with 3-aminotriazole ribonucleoside and various boronic acids. Two of them exhibited potent apoptosis-related antiproliferative activity against the drug-resistant pancreatic cancer cell line MiaPaCa-2, with an increased potency compared to gemcitabine, the reference treatment for pancreatic cancer. A preliminary SAR study suggests that the appended N-aryl moiety and the substituent at its para-position, as well as the ribose sugar component, contribute considerably to the observed antiproliferative activity.

S-Aryltriazole acyclonucleosides: Synthesis and biological evaluation against hepatitis C virus

Novel S-aryltriazole acyclonucleosides were designed as structural analogs based on the previously identified antiviral aryltriazole acyclonucleosides in our laboratories. These S-aryltriazole nucleosides were synthesized in excellent yields via S(N)Ar-mediated S-arylation, followed by subsequent ammonolysis. X-ray structural analysis revealed special structural feature brought by the S-linkage, which may represent an unfavorable factor contributing to the lack of anti-HCV activity for this family of triazole nucleosides.

Bitriazolyl acyclonucleosides synthesized via Huisgen reaction using internal alkynes show antiviral activity against tobacco mosaic virus.

A family of novel bitriazolyl acyclonucleosides were synthesized using a simple and convenient one-step synthetic procedure via the Huisgen reaction by addition of NaN(3) onto triazole nucleosides bearing internal alkynyl groups introduced at the 5-position of the triazole ring. Some of the compounds exhibited interesting antiviral activity against tobacco mosaic virus, demonstrating the importance of the bitriazolyl motif for the observed antiviral activity.

Influence of the nature of the Lewis acid on the rearrangement of 1-phenyl-7-oxanorbornadiene derivatives

Abstract 1-phenyl-7-oxanorbornadiene derivatives are rearranged into 6-hydroxyfulvenes or 4-phenylphenols derivatives when they are reacted with Lewis acids. The course of the reaction, which is highly selective, depends exclusively on the nature of the Lewis acid used.

Synthesis and Spectrokinetic Studies of a New Family of Photochromic 2H‐Chromenes (=2H‐1‐Benzopyrans): Dimethyl 6‐Aryl‐2,2‐dimethyl‐2H‐chromene‐7,8‐dicarboxylates

A series of dimethyl 6-aryl-2,2-dimethyl-2H-chromene-7,8-dicarboxylates were synthesized, and the photochromic properties of this new family of dimethyl-2H-chromenes were studied under continuous irradiation. The presence of the methoxycarbonyl groups was shown to stabilize the colored forms. This stabilization depended on the solvent, and in two cases the formation of long-lived opened forms was observed. Under irradiation with a mercury lamp, this family of 2H-chromenes showed a strong resistance to photodegradation.

Synthesis and Spectrokinetic Studies of a New Family of Dimethyl [2H]-Chromenes: Dimethyl 6-Aryl-2,2Dimethyl-[2H]-Chromene-7,8-Dicarboxylates

Abstract The synthesis of a series of dimethyl 6-aryl-2,2-dimethyl-[2H]-chromene-7,8-dicarboxylates is described. The photochromic properties of this new family of dimethyl-[2H]-chromenes have been studied in solution, under continuous irradiation. The presence of the methoxycarbonyl groups was shown to stabilise the coloured forms. The fading rates are generally low in comparison with the standard “naked” chromenes in the same experimental conditions. This stabilisation depends on the solvent used. We could observe the presence of one permanent opened form. Moreover, it seems that the synthesised molecules have a strong resistance toward photodegradation.

7-Oxabicyclo[2.2.1]heptadiene derivatives: reactivity towards Brønsted acids

7-Oxabicyclo[2.2.1]heptadiene derivatives can be converted to phenols, fulvenes and/or the products from a retro-Diels–Alder-like reaction by treatment with Bronsted acids; the outcome of the reaction depends on the experimental conditions and the nature of the Bronsted acid used.