Bioorganic & Medicinal Chemistry Letters, Nov 1, 2021
A small library of new piperidine-triazole hybrids with 3-aryl isoxazole side chains has been des... more A small library of new piperidine-triazole hybrids with 3-aryl isoxazole side chains has been designed and synthesized. Their cytotoxicity against a panel of seven cancer cell lines has been established. For the most promising compound, an IC50 value of 3.8 μM on PUMA/Bcl-xL interaction in live cancer cells was established through BRET analysis. A rationale was proposed for these results through complete molecular modelling studies.
Aus dem Dienyleisencarbonyl‐ester (1) erhält man den Alkohol (II), der nach Oxidation zum Aldehyd... more Aus dem Dienyleisencarbonyl‐ester (1) erhält man den Alkohol (II), der nach Oxidation zum Aldehyd (III) nach Grignard zum Alkohol (V) führt und den Ether (VI) liefert.
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.
Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2021
Abstract Corrosion protection of carbon steel (CS) is an important challenge in the industry fiel... more Abstract Corrosion protection of carbon steel (CS) is an important challenge in the industry field. The search for an effective protection approach is still a hot research question. In the present work, three hydrazone derivatives (HZ-OH, HZ-Me, and HZ-Cl) were used in 1.0 M HCl solution for API grade CS corrosion mitigation. Their corrosion inhibition performance was evaluated by electrochemical tests while steel surface was analyzed by X-ray photoelectron spectroscopy (XPS), contact angle and scanning electron microscope (SEM). Electrochemical tests showed an inhibition efficiency between 91% and 98% for CS exposed to acidic solution containing 0.05 mol/L of the three hydrazone derivatives. All compounds were classified as mixed type inhibitors, inhibiting both cathodic and anodic corrosion reactions. XPS showed that inhibitor molecules formed a stable layer on steel surface through chemical and physical interactions. The adsorption of molecules onto the steel surface was found to follow Langmuir model. DFT and MD simulations were used to investigate the interaction of hydrazones with Fen (n = 1–4) and Fe2O3(001) surface, respectively. They confirmed that the inhibitor with two hydroxy groups (HZ-OH) had a greater interaction with iron atoms.
The oxidative metabolism of arachidonic acid AA is known to yield a variety of biologically activ... more The oxidative metabolism of arachidonic acid AA is known to yield a variety of biologically active substances. Among them, both enantiomers of 12-hydroxyeicosatetraenoic acid (12-HETE) have been the subjeet, of much interest. In order te extend their biological evaluation, we developed a new enantiospecific synthesis allowing radioactive labelling with tritium. Dimethyl L-malate was converted to the key known ri,3-unsaturated aldehyde 4 in 18% overall yield. Further elaboration of 4 to 12(S)-IIETE and to its tritium labelled form [5,6-31-12]-12(S)-HETE as its methyl ester 38 was ac-complished using two phosphonium salts 3 and 5 similarly prepared via the common intermediate alkynol 22. Tritium was introduced lately since 38 was furnished when needed by tritiation of methyl 5,6-didehydro-12(S)-HETE. As 12(R)-HETE was equally prepared starting form dimethyl D-malate, this synthesis can give access to 12-HETE in both enantiomeric form and the lithium labelled material allowed us te stu...
ABSTRACT β-Keto phosphonates ω-functionalized by an ester group 1a - f, by a hydroxyl 5, and with... more ABSTRACT β-Keto phosphonates ω-functionalized by an ester group 1a - f, by a hydroxyl 5, and with a triple bond conjugated to the carbonyl group 2a - c were prepared by reacting dimethyl (lithiomethyl)-phosphonate (3) with adequate electrophiles. Cyclic anhydrides such as succinic and glutaric anhydrides were employed for the synthesis of the two first homologs 1a and 1b. To obtain the other longer homologs 1c - f, 3-acylthiazolidine-2-thiones 7a - d easily prepared using cheap 2-mercaptothiazoline proved to be the electrophiles of choice. On the other hand, the synthesis of keto phosphonates 2a - c required the use of N-methoxy-N-methylamides.
A new flavone glucoside, apigenin 4&a... more A new flavone glucoside, apigenin 4'-(6″-methylglucuronide) (1), together with six known compounds, cirsilineol, jaceosidin, melitensin, apigenin, apigenin 7-(6″-methylglucuronide) and prunasin, were isolated from the ethanolic extract of the aerial parts of Centaurea nicaeensis All. var. walliana M. (Asteraceae) collected from Souk-Ahras, eastern Algeria. The structures were established by spectral analysis, mainly HRESI-MS, UV and 2D-NMR experiments (COSY, HSQC and HMBC).
The reaction of enamines with allyl bromide and metallic indium in THF to afford homoallylamines ... more The reaction of enamines with allyl bromide and metallic indium in THF to afford homoallylamines was greatly accelerated by the addition of one equivalent of a suitable carboxylic acid, such as acetic acid. It was established that the likely mechanism consists of a nucleophilic addition of an indium sesquihalide to the iminium salt formed by protonation of the enamine. Substituted allyl bromides also reacted with complete allylic transposition (γ‐addition). In contrast to indium‐mediated allylation of carbonyl compounds in which only two of the three allyl groups of the sesquihalide are involved, all three allyl groups are involved in the reaction with enamines. As a result only 2/3 equiv of indium are required. This allylation was also performed with zinc, tin, bismuth, and aluminum in the presence of a catalytic amount of InCl3 instead of indium. However, these reactions invariably gave lower yields. The analogous reaction of methyl bromoacetate instead of allyl bromide was also s...
Quinoline derivatives R 0410 Synthesis of New Carbo-and Heterocyclic Analogues of 8-HETE and Eval... more Quinoline derivatives R 0410 Synthesis of New Carbo-and Heterocyclic Analogues of 8-HETE and Evaluation of Their Activity Towards the PPARs.-In the present study, the most active compound is (VIIIb), which is similar or better than most of the reference substances. It belongs to a new class of dual agonists with a higher potency on subtype α and a partial agonist activity on PPARα.
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.
Bioorganic & Medicinal Chemistry Letters, Nov 1, 2021
A small library of new piperidine-triazole hybrids with 3-aryl isoxazole side chains has been des... more A small library of new piperidine-triazole hybrids with 3-aryl isoxazole side chains has been designed and synthesized. Their cytotoxicity against a panel of seven cancer cell lines has been established. For the most promising compound, an IC50 value of 3.8 μM on PUMA/Bcl-xL interaction in live cancer cells was established through BRET analysis. A rationale was proposed for these results through complete molecular modelling studies.
Aus dem Dienyleisencarbonyl‐ester (1) erhält man den Alkohol (II), der nach Oxidation zum Aldehyd... more Aus dem Dienyleisencarbonyl‐ester (1) erhält man den Alkohol (II), der nach Oxidation zum Aldehyd (III) nach Grignard zum Alkohol (V) führt und den Ether (VI) liefert.
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.
Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2021
Abstract Corrosion protection of carbon steel (CS) is an important challenge in the industry fiel... more Abstract Corrosion protection of carbon steel (CS) is an important challenge in the industry field. The search for an effective protection approach is still a hot research question. In the present work, three hydrazone derivatives (HZ-OH, HZ-Me, and HZ-Cl) were used in 1.0 M HCl solution for API grade CS corrosion mitigation. Their corrosion inhibition performance was evaluated by electrochemical tests while steel surface was analyzed by X-ray photoelectron spectroscopy (XPS), contact angle and scanning electron microscope (SEM). Electrochemical tests showed an inhibition efficiency between 91% and 98% for CS exposed to acidic solution containing 0.05 mol/L of the three hydrazone derivatives. All compounds were classified as mixed type inhibitors, inhibiting both cathodic and anodic corrosion reactions. XPS showed that inhibitor molecules formed a stable layer on steel surface through chemical and physical interactions. The adsorption of molecules onto the steel surface was found to follow Langmuir model. DFT and MD simulations were used to investigate the interaction of hydrazones with Fen (n = 1–4) and Fe2O3(001) surface, respectively. They confirmed that the inhibitor with two hydroxy groups (HZ-OH) had a greater interaction with iron atoms.
The oxidative metabolism of arachidonic acid AA is known to yield a variety of biologically activ... more The oxidative metabolism of arachidonic acid AA is known to yield a variety of biologically active substances. Among them, both enantiomers of 12-hydroxyeicosatetraenoic acid (12-HETE) have been the subjeet, of much interest. In order te extend their biological evaluation, we developed a new enantiospecific synthesis allowing radioactive labelling with tritium. Dimethyl L-malate was converted to the key known ri,3-unsaturated aldehyde 4 in 18% overall yield. Further elaboration of 4 to 12(S)-IIETE and to its tritium labelled form [5,6-31-12]-12(S)-HETE as its methyl ester 38 was ac-complished using two phosphonium salts 3 and 5 similarly prepared via the common intermediate alkynol 22. Tritium was introduced lately since 38 was furnished when needed by tritiation of methyl 5,6-didehydro-12(S)-HETE. As 12(R)-HETE was equally prepared starting form dimethyl D-malate, this synthesis can give access to 12-HETE in both enantiomeric form and the lithium labelled material allowed us te stu...
ABSTRACT β-Keto phosphonates ω-functionalized by an ester group 1a - f, by a hydroxyl 5, and with... more ABSTRACT β-Keto phosphonates ω-functionalized by an ester group 1a - f, by a hydroxyl 5, and with a triple bond conjugated to the carbonyl group 2a - c were prepared by reacting dimethyl (lithiomethyl)-phosphonate (3) with adequate electrophiles. Cyclic anhydrides such as succinic and glutaric anhydrides were employed for the synthesis of the two first homologs 1a and 1b. To obtain the other longer homologs 1c - f, 3-acylthiazolidine-2-thiones 7a - d easily prepared using cheap 2-mercaptothiazoline proved to be the electrophiles of choice. On the other hand, the synthesis of keto phosphonates 2a - c required the use of N-methoxy-N-methylamides.
A new flavone glucoside, apigenin 4&a... more A new flavone glucoside, apigenin 4'-(6″-methylglucuronide) (1), together with six known compounds, cirsilineol, jaceosidin, melitensin, apigenin, apigenin 7-(6″-methylglucuronide) and prunasin, were isolated from the ethanolic extract of the aerial parts of Centaurea nicaeensis All. var. walliana M. (Asteraceae) collected from Souk-Ahras, eastern Algeria. The structures were established by spectral analysis, mainly HRESI-MS, UV and 2D-NMR experiments (COSY, HSQC and HMBC).
The reaction of enamines with allyl bromide and metallic indium in THF to afford homoallylamines ... more The reaction of enamines with allyl bromide and metallic indium in THF to afford homoallylamines was greatly accelerated by the addition of one equivalent of a suitable carboxylic acid, such as acetic acid. It was established that the likely mechanism consists of a nucleophilic addition of an indium sesquihalide to the iminium salt formed by protonation of the enamine. Substituted allyl bromides also reacted with complete allylic transposition (γ‐addition). In contrast to indium‐mediated allylation of carbonyl compounds in which only two of the three allyl groups of the sesquihalide are involved, all three allyl groups are involved in the reaction with enamines. As a result only 2/3 equiv of indium are required. This allylation was also performed with zinc, tin, bismuth, and aluminum in the presence of a catalytic amount of InCl3 instead of indium. However, these reactions invariably gave lower yields. The analogous reaction of methyl bromoacetate instead of allyl bromide was also s...
Quinoline derivatives R 0410 Synthesis of New Carbo-and Heterocyclic Analogues of 8-HETE and Eval... more Quinoline derivatives R 0410 Synthesis of New Carbo-and Heterocyclic Analogues of 8-HETE and Evaluation of Their Activity Towards the PPARs.-In the present study, the most active compound is (VIIIb), which is similar or better than most of the reference substances. It belongs to a new class of dual agonists with a higher potency on subtype α and a partial agonist activity on PPARα.
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.
Uploads
Papers by Paul Mosset