Abdellah Hannioui - Academia.edu (original) (raw)
Papers by Abdellah Hannioui
OALib, 2021
The aim of this work is to study the influence of the nature and position of substitution at ally... more The aim of this work is to study the influence of the nature and position of substitution at allyl benzene on the regioselectivity of the hydrosilylation reaction. We studied hydrosilylation of the various allyl derivatives with cyclic siloxane, H 4 D , and linears hydrosilylating agents, 1,1,3,3-tetramethyldisiloxane and MD H M, in the presence of platinum-based catalysts (Karstedt catalyst, platinum black). We also show the effects of the amount of catalyst on the conversion. Moreover, the influence on the temperature on catalytic activity and selectivity of the hydrosilylation reaction was explained. All new compounds were characterized by 1 H, 13 C, 29 Si NMR and HRMS as well.
A series of cyclic phospha-crown ethers was synthesised through a cyclisation reaction. These com... more A series of cyclic phospha-crown ethers was synthesised through a cyclisation reaction. These compounds were shown to extract alkali metals, ammonium, strontium and calcium ions from the aqueous phase to the organic one. The selectivity in partitioning varied with the relative fit of the ionic radius of the metal ion with the hole size of the macrocycle. For a typical phospa crown-metal ion combination, the formation of a 1:1 complex was suggested by UV spectroscopy investigation.
Ageing impacts on decision making behaviour across a wide range of cognitive tasks and scenarios.... more Ageing impacts on decision making behaviour across a wide range of cognitive tasks and scenarios. Computational modeling has proven highly valuable in providing mechanistic interpretations of these age-related differences; however, the extent to which model parameter differences accurately reflect changes to the underlying neural computations has yet to be tested. Here, we measured neural signatures of decision formation as younger and older participants performed motion discrimination and contrast-change detection tasks, and compared the dynamics of these signals to key parameter estimates from fits of a prominent accumulation-to-bound model (drift diffusion) to behavioural data. Our results indicate marked discrepancies between the age-related effects observed in the model output and the neural data. Most notably, while the model predicted a higher decision boundary in older age for both tasks, the neural data indicated no such differences. To reconcile the model and neural findings, we used our neurophysiological observations as a guide to constrain and adapt the model parameters. In addition to providing better fits to behaviour on both tasks, the resultant neurally-informed models furnished novel predictions regarding other features of the neural data which were empirically validated. These included a slower mean rate of evidence accumulation amongst older adults during motion discrimination and a beneficial reduction in between-trial variability in accumulation rates on the contrast-change detection task, which was linked to more consistent attentional engagement. Our findings serve to highlight how combining human brain signal measurements with computational modelling can yield unique insights into group differences in neural mechanisms for decision making.
![Research paper thumbnail of Ethyl 10α-hydroxy-4,9-dimethyl-14-oxo-3,8,15-trioxatetracyclo[10.3.0.02,4.07,9]pentadecane-13-spiro-5′-pyrazole-3′-carboxylate](https://attachments.academia-assets.com/87970806/thumbnails/1.jpg)
](IUCrData, 2020
The ten-membered ring in the title molecule, C25H29ClN2O7, adopts an approximate chair–chair conf... more The ten-membered ring in the title molecule, C25H29ClN2O7, adopts an approximate chair–chair conformation, whereas the five-membered furan and pyrazole rings display envelope conformations. The mean plane of the furan ring is almost perpendicular to that of the pyrazole ring, as indicated by the dihedral angle between them of 86.45 (9)°. The pyrazole ring is slightly inclined to the plane of the attached phenyl ring, subtending a dihedral angle of 16.88 (8)°. The conformation of the molecule is stabilized by six intramolecular hydrogen bonds and crystal cohesion is ensured by five C—H...O hydrogen bonds, in addition to C—H...π interactions.
Tetrahedron Letters, 2020
Abstract A series of novel spiropyrazoles and spiroisoxazolines was efficiently synthesized. Stru... more Abstract A series of novel spiropyrazoles and spiroisoxazolines was efficiently synthesized. Structural modifications were performed at the C-9 and C-13 positions of 9α- and 9β-hydroxyparthenolide, which were isolated from the aerial parts of Anvillea radiata. The structures and stereochemistry of the cycloadducts were fully established by spectroscopic methods including X-ray diffraction data.
![Research paper thumbnail of 9α-Hydroxy-4,8-dimethyl-3′-phenyl-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one-12-spiro-5′-isoxazole monohydrate](https://attachments.academia-assets.com/87970793/thumbnails/1.jpg)
](IUCrData, 2019
In the title compound, C22H25NO5·H2O, the ten-membered ring displays an approximate chair–chair c... more In the title compound, C22H25NO5·H2O, the ten-membered ring displays an approximate chair–chair conformation, whereas the five-membered furan ring has an envelope conformation, with the C atom of the methine group adjacent to the spiro C atom as the flap. The isoxazole ring is almost planar and its plane is slightly inclined to the plane of the attached phenyl ring. The mean plane of the furan ring is nearly perpendicular to that of the isoxazole ring, as indicated by the dihedral angle between them of 89.39 (12)°. In the crystal, the organic molecules are linked into [010] chains by O—H...O hydrogen bonds. The water molecule forms O—H...O and O—H...N hydrogen bonds and a weak C—H...O interaction is also observed. Together, these lead to a three-dimensional network.
Archiv der Pharmazie, 2014
Journal of Sulfur Chemistry, 2014
ABSTRACT The treatment of alkylated nitro derivatives of indazole with stannous chloride in alkan... more ABSTRACT The treatment of alkylated nitro derivatives of indazole with stannous chloride in alkanethiol gave after coupling of the obtained amines with 4-methoxybenzenesulfonyl chloride in pyridine the new N-(4-alkylsulfanylindazol-7-yl)-4-methoxybenzene sulfonamides via the nucleophilic substitution of hydrogen in position 4 of indazole, together with the expected 4-methoxy-N-(indazol-7-yl)-benzenesulfonamides. All the newly synthesized compounds have been characterized by elemental analysis and spectroscopic data.
Tetrahedron, 2012
ABSTRACT 2-Vinyl-5,10,15,20-tetraphenylporphyrinatozinc(II) reacts with nitrile imines, generated... more ABSTRACT 2-Vinyl-5,10,15,20-tetraphenylporphyrinatozinc(II) reacts with nitrile imines, generated in situ from ethyl hydrazono-α-bromoglyoxylates, affording the corresponding pyrazolines in good to excellent yields. Treatment of pyrazoline derivatives with DDQ affords the corresponding pyrazole derivatives with moderate to excellent yields. When the hydrolysis of ester group in the pyrazoline derivatives was considered, it was observed the concomitant oxidation of the heterocyclic unit, which allowed directly obtaining porphyrin-pyrazole derivatives with a carboxylic group, in very good yields.The photophysical properties of the pyrazoline and pyrazole porphyrin derivatives show that the influence of the heterocyclic substituents is limited by the tendency of these molecules to aggregate. All other properties and especially the triplet kinetics remain unaffected. The adducts with low tendency to aggregate showed very high singlet oxygen yield, which makes these compounds interesting for their use as photosensitizers for PDT.
Acta crystallographica. Section E, Structure reports online, 2014
The indazole ring system of the title compound, C17H18ClN3O4S, is almost planar (r.m.s. deviation... more The indazole ring system of the title compound, C17H18ClN3O4S, is almost planar (r.m.s. deviation = 0.0113 Å) and forms dihedral angles of 32.22 (8) and 57.5 (3)° with the benzene ring and the mean plane through the 4-eth-oxy group, respectively. In the crystal, mol-ecules are connected by pairs of N-H⋯O hydrogen bonds into inversion dimers, which are further linked by π-π inter-actions between the diazole rings [inter-centroid distance = 3.4946 (11) Å], forming chains parallel to [101].
Acta crystallographica. Section E, Structure reports online, 2014
The mol-ecule of the title compound, C11H8N2, is approximately planar (r.m.s.deviation for all no... more The mol-ecule of the title compound, C11H8N2, is approximately planar (r.m.s.deviation for all non-H atoms = 0.023 Å). The malono-nitrile C-C-C angle is 113.54 (13)°. In the crystal, mol-ecules stack head-to-tail along [010]. There are no significant inter-molecular inter-actions present.
Synthetic Communications, 2008
New N-(1H-7-indazolyl)-pyridinones have been prepared by the condensation of 2-pyrone derivatives... more New N-(1H-7-indazolyl)-pyridinones have been prepared by the condensation of 2-pyrone derivatives with 7-aminoindazole in the presence of acid medium. They have been characterized by means of H and C NMR, IR, and mass spectroscopy. The structure of the compounds and the mechanism of their formation are reported.
Synthetic Communications, 2011
The synthesis of new 7-alkoxy-4-amino-protected indazole and 4-amino-protected indazole derivativ... more The synthesis of new 7-alkoxy-4-amino-protected indazole and 4-amino-protected indazole derivatives by the reduction of the nitro group of 4-nitroindazoles using anhydrous stannous chloride in different alcohols is described.
HETEROCYCLES, 2011
The position of the nitro group in indazoles and their structure have influence on their reaction... more The position of the nitro group in indazoles and their structure have influence on their reaction behavior.
![Research paper thumbnail of Synthesis and 1,3-Dipolar Cycloaddition Reactions of New Pyrazolo[1,5,4-ef]-[1,5]bezodiazepines](https://attachments.academia-assets.com/87970749/thumbnails/1.jpg)
](HETEROCYCLES, 2004
Arylnitroso compounds 1-3 easily reacted with dimethyl bromomalonate to give the corresponding Na... more Arylnitroso compounds 1-3 easily reacted with dimethyl bromomalonate to give the corresponding Naryl-C,C-dimethoxycarbonylnitrones (4-6). Treatment of C,C-dimethoxycarbonyl-N-(1-naphthyl)nitrone (4) with acetylene compounds (dimethyl acetylenedicarboxylate, methyl 2-butynoate or ethyl phenylpropiolate) caused 1,3-dipolar cycloaddition to furnish the corresponding 1H-benz[g]indolines (7a-c). In a similar manner, the reactions of nitrones 5 and 6 with acetylene compounds afforded the corresponding indolines 9a-c and 11a-c together with 4-oxazolines 13a-c and 14a-c.
European Journal of Medicinal Chemistry, 2012
Recently, it has been reported that compounds bearing a sulfonamide moiety possess many types of ... more Recently, it has been reported that compounds bearing a sulfonamide moiety possess many types of biological activities, including anticancer activity. The present work reports the synthesis and antiproliferative evaluation of some N-(6(4)-indazolyl)benzenesulfonamides and 7-ethoxy-N-(6(4)-indazolyl)benzenesulfonamides. All compounds were evaluated for their in vitro antiproliferative activity against three tumor cell lines: A2780 (human ovarian carcinoma) A549 (human lung adenocarcinoma) and P388 (murine leukemia). The results indicated that sulfonamides 2c, 3c, 6d, 8, 13, 3b and 16 were endowed with a pharmacologically interesting antiproliferative activity with compounds 2c and 3c showing the lower IC(50) (from 0.50 ± 0.09 to 1.83 ± 0.52 μM and from 0.58 ± 0.17 to 5.83 ± 1.83 μM, respectively). Moreover, these indazoles were able to trigger apoptosis through the upregulation of the typical apoptosis markers p53 and bax. As regard to the hypothetic targets of these compounds, a preliminary docking analysis showed that all compounds seemed to interact with β-tubulin, in particular compound 3b that showed the lower Ki. The cytofluorimetric analysis of the cell cycle phases indicates that all compounds, when administered at their IC(75), caused a block in the G2/M phase of the cell cycle with the generation of subpopulations of cells with a number of chromosome >4n. When the IC(50)s were applied we observed a prevalent block in the G0/G1 phase except for compounds 16 and 8 where a partial G2/M block was present with a concomitant decrease of cells in the G0/G1 and S phases of the cell cycle. Altogether these results suggest a possible, but not exclusive, interaction with microtubules.
Arkivoc, 2009
N-Aryl-C-ethoxycarbonylnitrile imines react with meso-tetrakis(pentafluorophenyl)porphyrin in 1,3... more N-Aryl-C-ethoxycarbonylnitrile imines react with meso-tetrakis(pentafluorophenyl)porphyrin in 1,3-dipolar cycloadditions to yield novel pyrazolochlorins in moderate yields. The nitrile imines were generated in situ by base-induced dehydrobromination of ethyl hydrazono-αbromoglyoxylates. A number of different experimental conditions were considered for these cycloadditions, namely different bases, solvents and temperature; the best results were obtained using potassium carbonate in refluxing toluene. The photophysical properties of the new chlorins were investigated and the results suggest that two of them have potential for use in photodynamic therapy.
![Research paper thumbnail of Ethyl 3-[6-(4-methoxybenzenesulfonamido)-2 H -indazol-2-yl]propanoate monohydrate](https://attachments.academia-assets.com/87970765/thumbnails/1.jpg)
](Acta Crystallographica Section E Structure Reports Online, 2013
In the title compound, C19H21N3O5S·H2O, the central indazole system is essentially planar (r.m.s.... more In the title compound, C19H21N3O5S·H2O, the central indazole system is essentially planar (r.m.s. deviation = 0.012 Å), while both the benzene ring and the mean plane defined by the non-H atoms of the ethyl propionic ester unit (r.m.s. deviation = 0.087 Å) are nearly perpendicular to the indazole plane, as indicated by the dihedral angles of 82.45 (8) and 75.62 (8)°, respectively. Consequently, the molecule adopts a U-shaped geometry. In the crystal, the water molecule, which is linked to the indazole system by a strong O—H...N hydrogen bond, is also involved in two additional N—H...O and O—H...O interactions, which link the organic molecules into chains along theb-axis direction.
OALib, 2021
The aim of this work is to study the influence of the nature and position of substitution at ally... more The aim of this work is to study the influence of the nature and position of substitution at allyl benzene on the regioselectivity of the hydrosilylation reaction. We studied hydrosilylation of the various allyl derivatives with cyclic siloxane, H 4 D , and linears hydrosilylating agents, 1,1,3,3-tetramethyldisiloxane and MD H M, in the presence of platinum-based catalysts (Karstedt catalyst, platinum black). We also show the effects of the amount of catalyst on the conversion. Moreover, the influence on the temperature on catalytic activity and selectivity of the hydrosilylation reaction was explained. All new compounds were characterized by 1 H, 13 C, 29 Si NMR and HRMS as well.
A series of cyclic phospha-crown ethers was synthesised through a cyclisation reaction. These com... more A series of cyclic phospha-crown ethers was synthesised through a cyclisation reaction. These compounds were shown to extract alkali metals, ammonium, strontium and calcium ions from the aqueous phase to the organic one. The selectivity in partitioning varied with the relative fit of the ionic radius of the metal ion with the hole size of the macrocycle. For a typical phospa crown-metal ion combination, the formation of a 1:1 complex was suggested by UV spectroscopy investigation.
Ageing impacts on decision making behaviour across a wide range of cognitive tasks and scenarios.... more Ageing impacts on decision making behaviour across a wide range of cognitive tasks and scenarios. Computational modeling has proven highly valuable in providing mechanistic interpretations of these age-related differences; however, the extent to which model parameter differences accurately reflect changes to the underlying neural computations has yet to be tested. Here, we measured neural signatures of decision formation as younger and older participants performed motion discrimination and contrast-change detection tasks, and compared the dynamics of these signals to key parameter estimates from fits of a prominent accumulation-to-bound model (drift diffusion) to behavioural data. Our results indicate marked discrepancies between the age-related effects observed in the model output and the neural data. Most notably, while the model predicted a higher decision boundary in older age for both tasks, the neural data indicated no such differences. To reconcile the model and neural findings, we used our neurophysiological observations as a guide to constrain and adapt the model parameters. In addition to providing better fits to behaviour on both tasks, the resultant neurally-informed models furnished novel predictions regarding other features of the neural data which were empirically validated. These included a slower mean rate of evidence accumulation amongst older adults during motion discrimination and a beneficial reduction in between-trial variability in accumulation rates on the contrast-change detection task, which was linked to more consistent attentional engagement. Our findings serve to highlight how combining human brain signal measurements with computational modelling can yield unique insights into group differences in neural mechanisms for decision making.
IUCrData, 2020
The ten-membered ring in the title molecule, C25H29ClN2O7, adopts an approximate chair–chair conf... more The ten-membered ring in the title molecule, C25H29ClN2O7, adopts an approximate chair–chair conformation, whereas the five-membered furan and pyrazole rings display envelope conformations. The mean plane of the furan ring is almost perpendicular to that of the pyrazole ring, as indicated by the dihedral angle between them of 86.45 (9)°. The pyrazole ring is slightly inclined to the plane of the attached phenyl ring, subtending a dihedral angle of 16.88 (8)°. The conformation of the molecule is stabilized by six intramolecular hydrogen bonds and crystal cohesion is ensured by five C—H...O hydrogen bonds, in addition to C—H...π interactions.
Tetrahedron Letters, 2020
Abstract A series of novel spiropyrazoles and spiroisoxazolines was efficiently synthesized. Stru... more Abstract A series of novel spiropyrazoles and spiroisoxazolines was efficiently synthesized. Structural modifications were performed at the C-9 and C-13 positions of 9α- and 9β-hydroxyparthenolide, which were isolated from the aerial parts of Anvillea radiata. The structures and stereochemistry of the cycloadducts were fully established by spectroscopic methods including X-ray diffraction data.
IUCrData, 2019
In the title compound, C22H25NO5·H2O, the ten-membered ring displays an approximate chair–chair c... more In the title compound, C22H25NO5·H2O, the ten-membered ring displays an approximate chair–chair conformation, whereas the five-membered furan ring has an envelope conformation, with the C atom of the methine group adjacent to the spiro C atom as the flap. The isoxazole ring is almost planar and its plane is slightly inclined to the plane of the attached phenyl ring. The mean plane of the furan ring is nearly perpendicular to that of the isoxazole ring, as indicated by the dihedral angle between them of 89.39 (12)°. In the crystal, the organic molecules are linked into [010] chains by O—H...O hydrogen bonds. The water molecule forms O—H...O and O—H...N hydrogen bonds and a weak C—H...O interaction is also observed. Together, these lead to a three-dimensional network.
Archiv der Pharmazie, 2014
Journal of Sulfur Chemistry, 2014
ABSTRACT The treatment of alkylated nitro derivatives of indazole with stannous chloride in alkan... more ABSTRACT The treatment of alkylated nitro derivatives of indazole with stannous chloride in alkanethiol gave after coupling of the obtained amines with 4-methoxybenzenesulfonyl chloride in pyridine the new N-(4-alkylsulfanylindazol-7-yl)-4-methoxybenzene sulfonamides via the nucleophilic substitution of hydrogen in position 4 of indazole, together with the expected 4-methoxy-N-(indazol-7-yl)-benzenesulfonamides. All the newly synthesized compounds have been characterized by elemental analysis and spectroscopic data.
Tetrahedron, 2012
ABSTRACT 2-Vinyl-5,10,15,20-tetraphenylporphyrinatozinc(II) reacts with nitrile imines, generated... more ABSTRACT 2-Vinyl-5,10,15,20-tetraphenylporphyrinatozinc(II) reacts with nitrile imines, generated in situ from ethyl hydrazono-α-bromoglyoxylates, affording the corresponding pyrazolines in good to excellent yields. Treatment of pyrazoline derivatives with DDQ affords the corresponding pyrazole derivatives with moderate to excellent yields. When the hydrolysis of ester group in the pyrazoline derivatives was considered, it was observed the concomitant oxidation of the heterocyclic unit, which allowed directly obtaining porphyrin-pyrazole derivatives with a carboxylic group, in very good yields.The photophysical properties of the pyrazoline and pyrazole porphyrin derivatives show that the influence of the heterocyclic substituents is limited by the tendency of these molecules to aggregate. All other properties and especially the triplet kinetics remain unaffected. The adducts with low tendency to aggregate showed very high singlet oxygen yield, which makes these compounds interesting for their use as photosensitizers for PDT.
Acta crystallographica. Section E, Structure reports online, 2014
The indazole ring system of the title compound, C17H18ClN3O4S, is almost planar (r.m.s. deviation... more The indazole ring system of the title compound, C17H18ClN3O4S, is almost planar (r.m.s. deviation = 0.0113 Å) and forms dihedral angles of 32.22 (8) and 57.5 (3)° with the benzene ring and the mean plane through the 4-eth-oxy group, respectively. In the crystal, mol-ecules are connected by pairs of N-H⋯O hydrogen bonds into inversion dimers, which are further linked by π-π inter-actions between the diazole rings [inter-centroid distance = 3.4946 (11) Å], forming chains parallel to [101].
Acta crystallographica. Section E, Structure reports online, 2014
The mol-ecule of the title compound, C11H8N2, is approximately planar (r.m.s.deviation for all no... more The mol-ecule of the title compound, C11H8N2, is approximately planar (r.m.s.deviation for all non-H atoms = 0.023 Å). The malono-nitrile C-C-C angle is 113.54 (13)°. In the crystal, mol-ecules stack head-to-tail along [010]. There are no significant inter-molecular inter-actions present.
Synthetic Communications, 2008
New N-(1H-7-indazolyl)-pyridinones have been prepared by the condensation of 2-pyrone derivatives... more New N-(1H-7-indazolyl)-pyridinones have been prepared by the condensation of 2-pyrone derivatives with 7-aminoindazole in the presence of acid medium. They have been characterized by means of H and C NMR, IR, and mass spectroscopy. The structure of the compounds and the mechanism of their formation are reported.
Synthetic Communications, 2011
The synthesis of new 7-alkoxy-4-amino-protected indazole and 4-amino-protected indazole derivativ... more The synthesis of new 7-alkoxy-4-amino-protected indazole and 4-amino-protected indazole derivatives by the reduction of the nitro group of 4-nitroindazoles using anhydrous stannous chloride in different alcohols is described.
HETEROCYCLES, 2011
The position of the nitro group in indazoles and their structure have influence on their reaction... more The position of the nitro group in indazoles and their structure have influence on their reaction behavior.
HETEROCYCLES, 2004
Arylnitroso compounds 1-3 easily reacted with dimethyl bromomalonate to give the corresponding Na... more Arylnitroso compounds 1-3 easily reacted with dimethyl bromomalonate to give the corresponding Naryl-C,C-dimethoxycarbonylnitrones (4-6). Treatment of C,C-dimethoxycarbonyl-N-(1-naphthyl)nitrone (4) with acetylene compounds (dimethyl acetylenedicarboxylate, methyl 2-butynoate or ethyl phenylpropiolate) caused 1,3-dipolar cycloaddition to furnish the corresponding 1H-benz[g]indolines (7a-c). In a similar manner, the reactions of nitrones 5 and 6 with acetylene compounds afforded the corresponding indolines 9a-c and 11a-c together with 4-oxazolines 13a-c and 14a-c.
European Journal of Medicinal Chemistry, 2012
Recently, it has been reported that compounds bearing a sulfonamide moiety possess many types of ... more Recently, it has been reported that compounds bearing a sulfonamide moiety possess many types of biological activities, including anticancer activity. The present work reports the synthesis and antiproliferative evaluation of some N-(6(4)-indazolyl)benzenesulfonamides and 7-ethoxy-N-(6(4)-indazolyl)benzenesulfonamides. All compounds were evaluated for their in vitro antiproliferative activity against three tumor cell lines: A2780 (human ovarian carcinoma) A549 (human lung adenocarcinoma) and P388 (murine leukemia). The results indicated that sulfonamides 2c, 3c, 6d, 8, 13, 3b and 16 were endowed with a pharmacologically interesting antiproliferative activity with compounds 2c and 3c showing the lower IC(50) (from 0.50 ± 0.09 to 1.83 ± 0.52 μM and from 0.58 ± 0.17 to 5.83 ± 1.83 μM, respectively). Moreover, these indazoles were able to trigger apoptosis through the upregulation of the typical apoptosis markers p53 and bax. As regard to the hypothetic targets of these compounds, a preliminary docking analysis showed that all compounds seemed to interact with β-tubulin, in particular compound 3b that showed the lower Ki. The cytofluorimetric analysis of the cell cycle phases indicates that all compounds, when administered at their IC(75), caused a block in the G2/M phase of the cell cycle with the generation of subpopulations of cells with a number of chromosome >4n. When the IC(50)s were applied we observed a prevalent block in the G0/G1 phase except for compounds 16 and 8 where a partial G2/M block was present with a concomitant decrease of cells in the G0/G1 and S phases of the cell cycle. Altogether these results suggest a possible, but not exclusive, interaction with microtubules.
Arkivoc, 2009
N-Aryl-C-ethoxycarbonylnitrile imines react with meso-tetrakis(pentafluorophenyl)porphyrin in 1,3... more N-Aryl-C-ethoxycarbonylnitrile imines react with meso-tetrakis(pentafluorophenyl)porphyrin in 1,3-dipolar cycloadditions to yield novel pyrazolochlorins in moderate yields. The nitrile imines were generated in situ by base-induced dehydrobromination of ethyl hydrazono-αbromoglyoxylates. A number of different experimental conditions were considered for these cycloadditions, namely different bases, solvents and temperature; the best results were obtained using potassium carbonate in refluxing toluene. The photophysical properties of the new chlorins were investigated and the results suggest that two of them have potential for use in photodynamic therapy.
Acta Crystallographica Section E Structure Reports Online, 2013
In the title compound, C19H21N3O5S·H2O, the central indazole system is essentially planar (r.m.s.... more In the title compound, C19H21N3O5S·H2O, the central indazole system is essentially planar (r.m.s. deviation = 0.012 Å), while both the benzene ring and the mean plane defined by the non-H atoms of the ethyl propionic ester unit (r.m.s. deviation = 0.087 Å) are nearly perpendicular to the indazole plane, as indicated by the dihedral angles of 82.45 (8) and 75.62 (8)°, respectively. Consequently, the molecule adopts a U-shaped geometry. In the crystal, the water molecule, which is linked to the indazole system by a strong O—H...N hydrogen bond, is also involved in two additional N—H...O and O—H...O interactions, which link the organic molecules into chains along theb-axis direction.