Bernadette Norberg - Academia.edu (original) (raw)
Papers by Bernadette Norberg
Canadian Journal of Chemistry, 1987
The synthesis of the title compounds has been described recently. It was anticipated that the pro... more The synthesis of the title compounds has been described recently. It was anticipated that the product would be a diastereomeric mixture. Surprisingly, only one isomer was obtained. The present work is an attempt to find the conformationnal properties accounting for those observations. X-ray structure determination of 3R-[p-hydroxybenzyl]-6-carbethoxy-2-oxopiperazine shows that the molecule adopts a folded conformation and that the absolute configuration at C6 is [R]. Investigation in solution using 1H nuclear magnetic resonance shows the existence of three conformers and discusses the relative populations. Those findings are also relevant in terms of the activity of such compounds at the opiate receptor level.
Acta Crystallographica Section C Crystal Structure Communications, 2000
... Frédéric Ooms, a * Bernadette Norberg, a Emre M. Isin, b Neal Castagnoli, b Cornelis J. Van d... more ... Frédéric Ooms, a * Bernadette Norberg, a Emre M. Isin, b Neal Castagnoli, b Cornelis J. Van der Schyf b + and Johan Wouters a. ... against MPTP neurotoxicity (Di Monte et al., 1997 [Di Monte, DA, Royland, JE, Anderson, A., Castagnoli, K., Castagnoli, N. Jr & Langston, JW (1997). ...
Acta crystallographica. Section C, Crystal structure communications, 2002
The crystal structures of 4-methyl-2-[N-(3,4-methylenedioxybenzylidene)hydrazino]thiazole, C(12)H... more The crystal structures of 4-methyl-2-[N-(3,4-methylenedioxybenzylidene)hydrazino]thiazole, C(12)H(11)N(3)O(2)S, and its reduction product 4-methyl-2-[N-(3,4-methylenedioxybenzylidene)hydrazono]-4,5-dihydrothiazole, C(12)H(13)N(3)O(2)S, have been determined and compared. In the reduction product, the tautomer observed bears an H atom on the exocyclic N atom. Both compounds form hydrogen-bonded dimers over centers of inversion.
CrystEngComm
Mesoporous carbon/iron carbide hybrid materials with surface areas reaching 800 m 2 g 21 were syn... more Mesoporous carbon/iron carbide hybrid materials with surface areas reaching 800 m 2 g 21 were synthesized via an exotemplating route using monolithic mesoporous silica as template and the ionic liquid 1-butyl-3-methylimidazolium tetrachloridoferrate(III) [Bmim][FeCl 4 ] as carbon and iron source. After heat treatment (750 uC under argon) of the [Bmim][FeCl 4 ] precursor confined within the silica matrix, the silica exotemplate was removed with HF leaving the mesoporous C/Fe 3 C hybrid behind. The surface areas and the pore sizes depend on the exotemplate and the surface areas a significantly larger than any other surface area reported for C/Fe 3 C hybrid materials so far. The approach is thus a prototype for the synthesis of high-surface area iron carbide-based hybrid materials with potential application in catalysis.
![Research paper thumbnail of {4(S)-(Piperidin-1-ylcarbonyl)-4-[3-(trifluoromethyl)phenylsulfonamido]butyl}guanidinium chloride: a model of a graftable thrombin inhibitor](https://attachments.academia-assets.com/46635033/thumbnails/1.jpg)
](Acta crystallographica. Section C, Crystal structure communications, 2006
In the title compound, C18H27F3N5O3S+.Cl-, the guanidine group forms N-H...Cl hydrogen bonds, wit... more In the title compound, C18H27F3N5O3S+.Cl-, the guanidine group forms N-H...Cl hydrogen bonds, with four N...Cl distances in the range 3.164 (3)-3.337 (4) A. In the crystal packing, the cations are further linked by N-H...O and C-H...O interactions. The structure is compared with that of argatroban complexed with thrombin and is the subject of docking studies in the active site of thrombin.
ChemInform, 2003
The title compound (BM531), C(17)H(26)N(4)O(5)S, has been designed for use as both a thromboxane ... more The title compound (BM531), C(17)H(26)N(4)O(5)S, has been designed for use as both a thromboxane synthase inhibitor (TXSI) and a thromboxane receptor antagonist (TXRA). We report here the X-ray crystal structure determination of the compound.
Acta Crystallographica Section C Crystal Structure Communications, 2001
The crystal structures of three angiotensin-II receptor antagonists involving different spacer gr... more The crystal structures of three angiotensin-II receptor antagonists involving different spacer groups (CO, CONH and NHCO) between the aryl rings are presented, namely 2-[4-[(3-butyl-1,4-dioxo-2,3-diazaspiro[4.4]non-2-yl)methyl]benzoyl]benzoic acid, C(26)H(28)N(2)O(5), (I), 2-[4-[(3-butyl-1,4-dioxo-2,3-diazaspiro[4.4]non-2-yl)methyl]benzamido]benzoic acid, C(26)H(29)N(3)O(5), (II), and 2-[4-[(3-butyl-1,4-dioxo-2,3-diazaspiro[4.4]non-2-yl)methyl]anilinocarbonyl]benzoic acid monohydrate, C(26)H(29)N(3)O(5) x H(2)O, (III). The aryl rings of (II) are almost coplanar, in contrast with compounds (I) and (III). The conformation of (II) is induced by an intramolecular N-H.O hydrogen bond between the amide and carboxylic acid groups.
Crystals, 2012
The absolute configuration and structure of aegelinol, a pyranocoumarin isolated from Ferulago as... more The absolute configuration and structure of aegelinol, a pyranocoumarin isolated from Ferulago asparagifolia Boiss (Apiaceae), has been determined by crystallography. Crystal structure of the inclusion complex of aegelinol in β-cyclodextrin was determined (a = 15.404(1) Å, b = 15.281(1) Å, c = 17.890(1) Å, α = 99.662(1), β = 113.4230(1), γ = 102.481(1)°, P1; R 1 = 6.71%) and allowed unambiguous determination of the absolute configuration of the stereogenic center of aegelinol. The pyranocoumarin guest is included within the cylindrical cavity formed by dimeric β-cyclodextrin molecules with a head-to-head arrangement. Crystal structure of aegelinol alone was also determined (a = 6.8921(3) Å, b = 11.4302(9) Å, c = 44.964(3) Å, P2 1 2 1 2 1 ; R 1 = 4.44%) and allowed precise determination of its geometry. Aegelinol crystallizes with three molecules in the asymmetric unit held together by H-bonds and π-stacking interactions.
Acta Crystallographica Section C-crystal Structure Communications, 1998
Tetrahedron Letters, 1997
Regioselective catalytic hydrogemtion ofN-acyl 3-phenylindole-2-carboxylates isthekeystep forthep... more Regioselective catalytic hydrogemtion ofN-acyl 3-phenylindole-2-carboxylates isthekeystep forthepreparation ofcirandtramindoline-2-cerboxamides which canbeconsidered asphenylakmine semi-rigid derivatives. 631997 Publisbed byElsevier Science Ltd.
Supramolecular Chemistry, 2012
Crystal structure of the cyclomaltohexaose (α-cyclodextrin, α-CD) inclusion complex with p-aminob... more Crystal structure of the cyclomaltohexaose (α-cyclodextrin, α-CD) inclusion complex with p-aminobenzoic acid (pABA) has been determined by X-ray diffraction. The host:guest stoichiometry is 1:1. The pABA molecule is included in the cavity with its axis coincident with the axis of α-CD; the benzoic group is inserted in the cavity, while the amino group sticks out from the cavity. Four water
Organic Letters, 2003
A new access to benzhydryl-phenylureas is described. These new interesting urea derivatives were ... more A new access to benzhydryl-phenylureas is described. These new interesting urea derivatives were obtained by reaction of substituted benzils with substituted phenylureas under microwave irradiation. Phenylthiourea, when reacted with benzil, gave 3-phenyl-thiohydantoin. Moreover, benzylurea, as phenethylurea, gave the corresponding 3-substituted hydantoin derivatives, demonstrating that only phenylurea derivatives can result in benzhydryl-phenylureas under the applied conditions. This new reaction proved to be an easy access to substituted 1-benzhydryl-3-phenyl-ureas.
Organic & Biomolecular Chemistry, 2006
A concise and efficient asymmetric synthesis of ACNO analogues of morphine is reported.
European Journal of Medicinal Chemistry, 2014
Salification of new drug substances in order to improve physico-chemical or solid-state propertie... more Salification of new drug substances in order to improve physico-chemical or solid-state properties (e.g. dissolution rate or solubility, appropriate workup process, storage for further industrial and marketing development) is a well-accepted procedure. Amino acids, like aspartic acid, lysine or arginine take a great part in this process and are implicated in several different formulations of therapeutic agent families, including antibiotics (amoxicillin from beta lactam class or cephalexin from cephalosporin class), NSAIDs (ketoprofen, ibuprofen and naproxen from profen family, acetylsalicylic acid) or antiarrhythmic agents (e.g. ajmaline). Even if more than a half of known pharmaceutical molecules possess a salifiable moiety, what can be done for new potential drug entity that cannot be improved by transformation into a salt? In this context, after a brief review of pharmaceutical salts on the market and the implication of amino acids in these formulations, we focus on the advantage of using amino acids even when the target compound is not salifiable by exploiting their zwitterionic potentialities for cocrystal edification. We summarize here a series of new examples coming from literature to support the advantages of broadening the application of amino acids in formulation for new drug substances improvement research for nonsalifiable molecules.
European Journal of Medicinal Chemistry, 2010
Bis-tetrahydroisoquinoline derivatives: Structure analysis of the three stereoisomers of 1,1 0 -(... more Bis-tetrahydroisoquinoline derivatives: Structure analysis of the three stereoisomers of 1,1 0 -(propane-1,3-diyl)-bis-(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline) a b s t r a c t Crystal structure of the three stereoisomers of 1,1 0 -(propane-1,3-diyl)-bis-(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline) hydrochloride after resolution by semi-preparative chiral HPLC establishes the absolute configuration and conformation.
European Journal of Medicinal Chemistry, 2010
Multicomponent molecular complex Crystal structure a b s t r a c t Cocrystallization (formation o... more Multicomponent molecular complex Crystal structure a b s t r a c t Cocrystallization (formation of a "cocrystal") is an emerging method to optimize physico-chemical properties of pharmaceutically active compounds. One elegant technique used to obtain such cocrystals is grinding the components together, either alone or in the presence of a small amount of solvent (so called solvent-drop grinding). Dry grinding has been used here to obtain cocrystals (actually a hydrated salt) of L-Proline and MnCl 2 . In that context, a new crystalline structure of a multicomponent molecular complex composed of L-Proline and MnCl 2 is here reported. The complex was characterized by powder and single-crystal X-ray diffraction and differential scanning calorimetry. This study underlines the interest of grinding as a method to synthesize original solid-state complexes. It also emphasizes the advantage of combining calorimetric and X-ray diffraction to characterize the newly formed solids. Finally, our work provides structural basis for the role that L-Proline can play within multicomponent solid-state molecular complexes, in particular as a potential cocrystal former acting by both ionic and H-bond interactions when combined to molecules of pharmaceutical interest.
![Research paper thumbnail of (3 R ,5 S ,6 R ,8 S ,9 S )-1-Azonia-9-ethyl-3-hydroxy-5-(6-methoxyquinolin-4-yl)-3-methyl-4-oxatricyclo[6.2.2.0]dodecane trifluoromethanesulfonate: insight into the sterochemistry of the cyclization mechanism](https://attachments.academia-assets.com/46635031/thumbnails/1.jpg)
](Acta Crystallographica Section E Structure Reports Online, 2006
Canadian Journal of Chemistry, 1987
The synthesis of the title compounds has been described recently. It was anticipated that the pro... more The synthesis of the title compounds has been described recently. It was anticipated that the product would be a diastereomeric mixture. Surprisingly, only one isomer was obtained. The present work is an attempt to find the conformationnal properties accounting for those observations. X-ray structure determination of 3R-[p-hydroxybenzyl]-6-carbethoxy-2-oxopiperazine shows that the molecule adopts a folded conformation and that the absolute configuration at C6 is [R]. Investigation in solution using 1H nuclear magnetic resonance shows the existence of three conformers and discusses the relative populations. Those findings are also relevant in terms of the activity of such compounds at the opiate receptor level.
Acta Crystallographica Section C Crystal Structure Communications, 2000
... Frédéric Ooms, a * Bernadette Norberg, a Emre M. Isin, b Neal Castagnoli, b Cornelis J. Van d... more ... Frédéric Ooms, a * Bernadette Norberg, a Emre M. Isin, b Neal Castagnoli, b Cornelis J. Van der Schyf b + and Johan Wouters a. ... against MPTP neurotoxicity (Di Monte et al., 1997 [Di Monte, DA, Royland, JE, Anderson, A., Castagnoli, K., Castagnoli, N. Jr & Langston, JW (1997). ...
Acta crystallographica. Section C, Crystal structure communications, 2002
The crystal structures of 4-methyl-2-[N-(3,4-methylenedioxybenzylidene)hydrazino]thiazole, C(12)H... more The crystal structures of 4-methyl-2-[N-(3,4-methylenedioxybenzylidene)hydrazino]thiazole, C(12)H(11)N(3)O(2)S, and its reduction product 4-methyl-2-[N-(3,4-methylenedioxybenzylidene)hydrazono]-4,5-dihydrothiazole, C(12)H(13)N(3)O(2)S, have been determined and compared. In the reduction product, the tautomer observed bears an H atom on the exocyclic N atom. Both compounds form hydrogen-bonded dimers over centers of inversion.
CrystEngComm
Mesoporous carbon/iron carbide hybrid materials with surface areas reaching 800 m 2 g 21 were syn... more Mesoporous carbon/iron carbide hybrid materials with surface areas reaching 800 m 2 g 21 were synthesized via an exotemplating route using monolithic mesoporous silica as template and the ionic liquid 1-butyl-3-methylimidazolium tetrachloridoferrate(III) [Bmim][FeCl 4 ] as carbon and iron source. After heat treatment (750 uC under argon) of the [Bmim][FeCl 4 ] precursor confined within the silica matrix, the silica exotemplate was removed with HF leaving the mesoporous C/Fe 3 C hybrid behind. The surface areas and the pore sizes depend on the exotemplate and the surface areas a significantly larger than any other surface area reported for C/Fe 3 C hybrid materials so far. The approach is thus a prototype for the synthesis of high-surface area iron carbide-based hybrid materials with potential application in catalysis.
Acta crystallographica. Section C, Crystal structure communications, 2006
In the title compound, C18H27F3N5O3S+.Cl-, the guanidine group forms N-H...Cl hydrogen bonds, wit... more In the title compound, C18H27F3N5O3S+.Cl-, the guanidine group forms N-H...Cl hydrogen bonds, with four N...Cl distances in the range 3.164 (3)-3.337 (4) A. In the crystal packing, the cations are further linked by N-H...O and C-H...O interactions. The structure is compared with that of argatroban complexed with thrombin and is the subject of docking studies in the active site of thrombin.
ChemInform, 2003
The title compound (BM531), C(17)H(26)N(4)O(5)S, has been designed for use as both a thromboxane ... more The title compound (BM531), C(17)H(26)N(4)O(5)S, has been designed for use as both a thromboxane synthase inhibitor (TXSI) and a thromboxane receptor antagonist (TXRA). We report here the X-ray crystal structure determination of the compound.
Acta Crystallographica Section C Crystal Structure Communications, 2001
The crystal structures of three angiotensin-II receptor antagonists involving different spacer gr... more The crystal structures of three angiotensin-II receptor antagonists involving different spacer groups (CO, CONH and NHCO) between the aryl rings are presented, namely 2-[4-[(3-butyl-1,4-dioxo-2,3-diazaspiro[4.4]non-2-yl)methyl]benzoyl]benzoic acid, C(26)H(28)N(2)O(5), (I), 2-[4-[(3-butyl-1,4-dioxo-2,3-diazaspiro[4.4]non-2-yl)methyl]benzamido]benzoic acid, C(26)H(29)N(3)O(5), (II), and 2-[4-[(3-butyl-1,4-dioxo-2,3-diazaspiro[4.4]non-2-yl)methyl]anilinocarbonyl]benzoic acid monohydrate, C(26)H(29)N(3)O(5) x H(2)O, (III). The aryl rings of (II) are almost coplanar, in contrast with compounds (I) and (III). The conformation of (II) is induced by an intramolecular N-H.O hydrogen bond between the amide and carboxylic acid groups.
Crystals, 2012
The absolute configuration and structure of aegelinol, a pyranocoumarin isolated from Ferulago as... more The absolute configuration and structure of aegelinol, a pyranocoumarin isolated from Ferulago asparagifolia Boiss (Apiaceae), has been determined by crystallography. Crystal structure of the inclusion complex of aegelinol in β-cyclodextrin was determined (a = 15.404(1) Å, b = 15.281(1) Å, c = 17.890(1) Å, α = 99.662(1), β = 113.4230(1), γ = 102.481(1)°, P1; R 1 = 6.71%) and allowed unambiguous determination of the absolute configuration of the stereogenic center of aegelinol. The pyranocoumarin guest is included within the cylindrical cavity formed by dimeric β-cyclodextrin molecules with a head-to-head arrangement. Crystal structure of aegelinol alone was also determined (a = 6.8921(3) Å, b = 11.4302(9) Å, c = 44.964(3) Å, P2 1 2 1 2 1 ; R 1 = 4.44%) and allowed precise determination of its geometry. Aegelinol crystallizes with three molecules in the asymmetric unit held together by H-bonds and π-stacking interactions.
Acta Crystallographica Section C-crystal Structure Communications, 1998
Tetrahedron Letters, 1997
Regioselective catalytic hydrogemtion ofN-acyl 3-phenylindole-2-carboxylates isthekeystep forthep... more Regioselective catalytic hydrogemtion ofN-acyl 3-phenylindole-2-carboxylates isthekeystep forthepreparation ofcirandtramindoline-2-cerboxamides which canbeconsidered asphenylakmine semi-rigid derivatives. 631997 Publisbed byElsevier Science Ltd.
Supramolecular Chemistry, 2012
Crystal structure of the cyclomaltohexaose (α-cyclodextrin, α-CD) inclusion complex with p-aminob... more Crystal structure of the cyclomaltohexaose (α-cyclodextrin, α-CD) inclusion complex with p-aminobenzoic acid (pABA) has been determined by X-ray diffraction. The host:guest stoichiometry is 1:1. The pABA molecule is included in the cavity with its axis coincident with the axis of α-CD; the benzoic group is inserted in the cavity, while the amino group sticks out from the cavity. Four water
Organic Letters, 2003
A new access to benzhydryl-phenylureas is described. These new interesting urea derivatives were ... more A new access to benzhydryl-phenylureas is described. These new interesting urea derivatives were obtained by reaction of substituted benzils with substituted phenylureas under microwave irradiation. Phenylthiourea, when reacted with benzil, gave 3-phenyl-thiohydantoin. Moreover, benzylurea, as phenethylurea, gave the corresponding 3-substituted hydantoin derivatives, demonstrating that only phenylurea derivatives can result in benzhydryl-phenylureas under the applied conditions. This new reaction proved to be an easy access to substituted 1-benzhydryl-3-phenyl-ureas.
Organic & Biomolecular Chemistry, 2006
A concise and efficient asymmetric synthesis of ACNO analogues of morphine is reported.
European Journal of Medicinal Chemistry, 2014
Salification of new drug substances in order to improve physico-chemical or solid-state propertie... more Salification of new drug substances in order to improve physico-chemical or solid-state properties (e.g. dissolution rate or solubility, appropriate workup process, storage for further industrial and marketing development) is a well-accepted procedure. Amino acids, like aspartic acid, lysine or arginine take a great part in this process and are implicated in several different formulations of therapeutic agent families, including antibiotics (amoxicillin from beta lactam class or cephalexin from cephalosporin class), NSAIDs (ketoprofen, ibuprofen and naproxen from profen family, acetylsalicylic acid) or antiarrhythmic agents (e.g. ajmaline). Even if more than a half of known pharmaceutical molecules possess a salifiable moiety, what can be done for new potential drug entity that cannot be improved by transformation into a salt? In this context, after a brief review of pharmaceutical salts on the market and the implication of amino acids in these formulations, we focus on the advantage of using amino acids even when the target compound is not salifiable by exploiting their zwitterionic potentialities for cocrystal edification. We summarize here a series of new examples coming from literature to support the advantages of broadening the application of amino acids in formulation for new drug substances improvement research for nonsalifiable molecules.
European Journal of Medicinal Chemistry, 2010
Bis-tetrahydroisoquinoline derivatives: Structure analysis of the three stereoisomers of 1,1 0 -(... more Bis-tetrahydroisoquinoline derivatives: Structure analysis of the three stereoisomers of 1,1 0 -(propane-1,3-diyl)-bis-(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline) a b s t r a c t Crystal structure of the three stereoisomers of 1,1 0 -(propane-1,3-diyl)-bis-(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline) hydrochloride after resolution by semi-preparative chiral HPLC establishes the absolute configuration and conformation.
European Journal of Medicinal Chemistry, 2010
Multicomponent molecular complex Crystal structure a b s t r a c t Cocrystallization (formation o... more Multicomponent molecular complex Crystal structure a b s t r a c t Cocrystallization (formation of a "cocrystal") is an emerging method to optimize physico-chemical properties of pharmaceutically active compounds. One elegant technique used to obtain such cocrystals is grinding the components together, either alone or in the presence of a small amount of solvent (so called solvent-drop grinding). Dry grinding has been used here to obtain cocrystals (actually a hydrated salt) of L-Proline and MnCl 2 . In that context, a new crystalline structure of a multicomponent molecular complex composed of L-Proline and MnCl 2 is here reported. The complex was characterized by powder and single-crystal X-ray diffraction and differential scanning calorimetry. This study underlines the interest of grinding as a method to synthesize original solid-state complexes. It also emphasizes the advantage of combining calorimetric and X-ray diffraction to characterize the newly formed solids. Finally, our work provides structural basis for the role that L-Proline can play within multicomponent solid-state molecular complexes, in particular as a potential cocrystal former acting by both ionic and H-bond interactions when combined to molecules of pharmaceutical interest.
Acta Crystallographica Section E Structure Reports Online, 2006