Patrick Rollin - Academia.edu (original) (raw)

Papers by Patrick Rollin

BMC complementary medicine and therapies, Mar 7, 2023

ChemInform, Jun 18, 2010

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Tetrahedron Letters, 2002

A general selective synthesis of b-, gand d-hydroxyethenyl ethers, a class of compounds containin... more A general selective synthesis of b-, gand d-hydroxyethenyl ethers, a class of compounds containing two mutually reactive functionalities positioned at an interacting distance, is based on the reaction of diols with 1,2-bis-(phenylsulfonyl)ethylene (BPSE) followed by reductive elimination of the resulting b-phenylsulfonyl acetals with sodium amalgam.

ChemInform, Aug 12, 2010

Synthesis of Deoxy Derivatives of the Glucosinolates Glucotropaeolin and Glucobrassicin. -Several... more Synthesis of Deoxy Derivatives of the Glucosinolates Glucotropaeolin and Glucobrassicin. -Several protected sugars, e.g. (I), are converted into the corresponding glucosinolates, e.g. (VI), by preparation of the thiol ( III), coupling with hydroximoyl chlorides, sulfation and deprotection reactions.

ChemInform, Aug 19, 2010

Synthetic Studies on Indole and Related Compounds. Part 42. Total Synthesis of Optically Active C... more Synthetic Studies on Indole and Related Compounds. Part 42. Total Synthesis of Optically Active Chanoclavine-I. -Total synthesis of the title compound (VII) is achieved via intramolecular Heck reaction of (III) as a key step. -(YOKOYAMA, Y.;

Carbohydrate Research, Feb 1, 1997

SN2-Displacement of the anomeric bromine atom in 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-d-glucopyr... more SN2-Displacement of the anomeric bromine atom in 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-d-glucopyranosyl bromide with the tetrabutylammonium salt of triphenylmethanethiol afforded the corresponding trityl 1-thio-β-d-glucoside which led to the fully protected S-acetyl-2-fluoro-1-thio-β-d-glucose derivative, and then to the free thiol 5 by selective S-deacetylation at low temperature. 2-Fluoro-glucotropaeolin (1) was obtained by a conventional procedure from 5.

HAL (Le Centre pour la Communication Scientifique Directe), 1998

Glucosinolates hydrolysis products are attracting increasing attention since many studies have su... more Glucosinolates hydrolysis products are attracting increasing attention since many studies have suggested that they may be involved in the anticarcinogenic property of cruciferous vegetables. In this study, we show that diindolylmethane (DIM) and sulforaphane, produced during the hydrolysis of glucobrassicin and glucoraphanin, respectively, exert a dose-dependent cytotoxicity on human colon adenocarcinoma HT29 cells. Moreover, these products are able to inhibit quiescent cells to re-enter the cell cycle. Interestingly, our results clearly show that low doses of DIM and sulforaphane, although very effective on undifferentiated intestinal HT29 cells, do not affect the viability of the differentiated CaCo2 cells. The reversibility of their effects has also been tested and is discussed.

Carbohydrate chemistry, 2021

Dietary R-sulforaphane is a highly potent inducer of the Keap1/Nrf2/ARE pathway. Furthermore, sul... more Dietary R-sulforaphane is a highly potent inducer of the Keap1/Nrf2/ARE pathway. Furthermore, sulforaphane is currently being used in clinical trials to assess its effects against different tumour processes. This study reports an efficient preparation of enantiopure R-sulforaphane based on the enzymatic hydrolysis of its natural precursor glucoraphanin. As an alternative to broccoli seeds, we have exploited Tuscan black kale seeds as a suitable source for gram-scale production of glucoraphanin. The defatted seed meal contained 5.1% (w/w) of glucoraphanin that was first isolated through an anion exchange chromatographic process, and then purified by gel filtration. The availability of glucoraphanin (purity ≈ 95%, weight basis) has allowed us to develop a novel simple hydrolytic process involving myrosinase (EC 3.2.1.147) in a biphasic system to directly produce R-sulforaphane. In a typical experiment, 1.09 g of enantiopure R-sulforaphane was obtained from 150 g of defatted Tuscan black kale seed meal.

Journal of Enzyme Inhibition and Medicinal Chemistry, 2018

Finding a new type of cholinesterase inhibitor that would overcome the brain availability and pha... more Finding a new type of cholinesterase inhibitor that would overcome the brain availability and pharmacokinetic parameters or hepatotoxic liability has been a focus of investigations dealing with the treatment of Alzheimer's disease. Isothiocyanates have not been previously investigated as potential cholinesterase inhibitors. These compounds can be naturally produced from their glucosinolate precursors, secondary metabolites widely distributed in our daily Brassica vegetables. Among 11 tested compounds, phenyl isothiocyanate and its derivatives showed the most promising inhibitory activity. 2-Methoxyphenyl ITC showed best inhibition on acetylcholinesterase with IC 50 of 0.57 mM, while 3-methoxyphenyl ITC showed the best inhibition on butyrylcholinesterase having 49.2% at 1.14 mM. Assessment of the antioxidant efficacy using different methods led to a similar conclusion. The anti-inflammatory activity was also tested using human COX-2 enzyme, ranking phenyl isothiocyanate, and 3-methoxyphenyl isothiocyanate as most active, with $99% inhibition at 50 lM.

Journal of Food Composition and Analysis, 2020

Chemischer Informationsdienst, May 3, 1977

Tetrahedron Letters, Aug 1, 1992

The reardon of a number of organomagnesium halides with a 4-(2-Wn'dyl)thiomPrhy61,3-dioxolone 1 m... more The reardon of a number of organomagnesium halides with a 4-(2-Wn'dyl)thiomPrhy61,3-dioxolone 1 mainly @or&d C-branched pyridylthiopropan0.k 2. i'kse wrsnn'le synthons restdted@om an atypical combined a.?~-~hia-asivted C-4 olkylorion of the cyclic ketalsystem.

European journal of medicinal chemistry, Aug 1, 2021

A total of forty-three compounds were synthesized, including thirty-two new ones. Among those com... more A total of forty-three compounds were synthesized, including thirty-two new ones. Among those compounds, seventeen were selected and tested on human tumor cell lines: PC-3 (prostate adenocarcinoma), HCT-116 (colorectal tumor), NCIH-460 (lung carcinoma), SKMEL-103 (melanoma) and AGP-01 (gastric tumor). Alkynylated 1,2,4-oxadiazoles 2m, 3g and 3k exhibited antiproliferative activities against NCIH-460 in culture. Alkynylated N-cyclohexyl-1,2,4-oxadiazoles 3a-m and bis-heterocycle glucoglycero-1,2,3-triazole-N-cyclohexyl-1,2,4-oxadiazole derivatives 5a-k and 6-11 were evaluated for their in vitro efficacy towards Mycobacterium tuberculosis (Mtb) H37Ra and H37Rv strains. In general, glycerosugars conjugated to 1,2,4-oxadiazole via a 1,2,3-triazole linkage (5a, 5e, 5j, 5k, and 7) showed in vitro inhibitory activity against Mtb (H37Rv). The largest molecules bis-triazoles 10 and 11, proved inactive against TB. Probably, the absence of the N-cyclohexyl group in compound 8 and 1,2,4-oxadiazole nucleus in compound 9 were responsible for its low activity. Glucoglycero-triazole-oxadiazole derivatives 5e (10 μM) and 7 (23.9 μM) were the most promising antitubercular compounds, showing a better selective index than when tested against RAW 264.7 and HepG2 cells. Vero cell were used to investigate cytotoxicity of compounds 5a, 5h, 5j, 5k, and these compounds showed good cell viability. Further, in silico studies were performed for most active compounds (5e and 7) with potential drug targets, DprE1 and InhA of Mtb to understand possible interactions aided with molecular dynamic simulation (100ns).

An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.