Self-complementarity is a useful concept in supramolecular chemistry, molecular biology and polym... more Self-complementarity is a useful concept in supramolecular chemistry, molecular biology and polymeric systems. Two resorcinarene tetrabenzoxazines decorated with four oxalamide groups were synthesized and characterized. The oxalamide groups possessed self-complementary hydrogen bonding sites between the carbonyls and amide groups. The self-complementary nature of the oxalamide groups resulted in self-included dimeric assemblies. The hydrogen bonding interactions within the tetrabenzoxazines gave rise to the formation of dimers, which were confirmed by single-crystal X-ray diffractions analysis and supported by NMR spectroscopy and mass spectrometry. The self-included dimers were connected by numerous and strong intermolecular N-H⋅⋅⋅O and C-H⋅⋅⋅O hydrogen bonds supplemented with C-H⋅⋅⋅π interactions, forming one-dimensional polymers, which were then further linked into three-dimensional networks.
A new synthetic strategy involving the Pinner reaction offers various amidino-functionalized 2-su... more A new synthetic strategy involving the Pinner reaction offers various amidino-functionalized 2-substituted benzoxazoles via amidino-substituted 2-aminophenols with sub-micromolar antiproliferative activities.
Bis-urea derivatives 1–3, featuring a biphenyl spacer, were synthesized, characterized and invest... more Bis-urea derivatives 1–3, featuring a biphenyl spacer, were synthesized, characterized and investigated about their anion binding properties in DMSO solution and in the solid state.
European journal of medicinal chemistry, Jan 5, 2017
Regioselective 1,4-disubstituted 1,2,3-triazole tethered pyrimidine-2,4-dione derivatives (5-23) ... more Regioselective 1,4-disubstituted 1,2,3-triazole tethered pyrimidine-2,4-dione derivatives (5-23) were successfully prepared by the copper(I)-catalyzed click chemistry. While known palladium/copper-cocatalyzed method based on Sonogashira cross-coupling followed by the intramolecular 5-endo-dig ring closure generated novel 6-alkylfuro[2,3-d]pyrimidine-2-one-1,2,3-triazole hybrids (24b-37b), a small library of their 5-alkylethynyl analogs (24a-37a) was synthesized and described for the first time by tandem terminal alkyne dimerization and subsequent 5-endo-trig cyclization, which was additionally corroborated with computational and X-ray crystal structure analyses. The nature of substituents on alkynes and thereof homocoupled 1,3-diynes predominantly influenced the ratio of the formed products in both pathways. In vitro antiproliferative activity of prepared compounds evaluated on five human cancer cell lines revealed that N,N-1,3-bis-(1,2,3-triazole)-5-bromouracil (5-7) and 5,6-disubs...
Acta Crystallographica Section C Crystal Structure Communications, Sep 1, 2003
In the title compound, [Fe(C(5)H(5))(C(14)H(13)O)], the plane of the heterocyclic ring is almost ... more In the title compound, [Fe(C(5)H(5))(C(14)H(13)O)], the plane of the heterocyclic ring is almost perpendicular to the plane of the substituted cyclopentadienyl ring, and the heterocyclic ring adopts a half-chair conformation. The conformation of the nearly parallel cyclopentadienyl (Cp) rings [the dihedral angle between their planes is 2.7 (1) degrees ] is almost halfway between eclipsed and staggered, and the rings are mutually twisted by about 19.4 (2) degrees (mean value). The mean lengths of the C-C bonds in the substituted and unsubstituted cyclopentadienyl ring are 1.420 (2) and 1.406 (3) A, respectively, and the Fe-C distances range from 2.029 (2) to 2.051 (2) A. The phenyl and unsubstituted cyclopentadienyl rings are involved in C-H.pi interactions, with intermolecular H.centroid distances of 2.85 and 3.14 A for C-H.pi(Ph), and 2.88 A for C-H.pi(Cp). In two of these interactions, the C-H bond points towards one of the ring bonds rather than towards the ring centroid. In the crystal structure, the C-H.pi interactions connect the molecules into a three-dimensional framework.
Acta Crystallographica Section C Crystal Structure Communications, Apr 1, 2003
Crystal structure analysis of the title compound, C(13)H(12)ClNO, reveals three crystallographica... more Crystal structure analysis of the title compound, C(13)H(12)ClNO, reveals three crystallographically independent molecules in the asymmetric unit. The main conformational difference between these molecules is the orientation of the phenyl rings with respect to the pyrrole rings. The coplanar arrangement of the aldehyde groups attached to the pyrrole rings influences the pyrrole-ring geometry. The C2-C3 and N1-C5 bonds are noticeably longer than the C4-C5 and N1-C2 bonds. Two independent molecules of the title compound form dimers via intermolecular C-H.O hydrogen bonds [D.A = 3.400 (3) A and D-H.A = 157 degrees ]. The perpendicular orientation of the phenyl and pyrrole rings of one independent molecule and its symmetry-related molecule allows C-H.pi interactions, with an H.centroid distance of 2.85 A and a C-H.pi angle of 155 degrees. The distances between the H atom and the pyrrole-ring atoms indicate that the C-H bond points towards one of the bonds in the pyrrole ring.
... Jennifer K. Angelosante Lauren M. Schopp Breia J. Lewis Amber D. Vitalo Dustin T. Tit... more ... Jennifer K. Angelosante Lauren M. Schopp Breia J. Lewis Amber D. Vitalo Dustin T. Titus Rebecca A. Swanson April N. Stanley Brendan P. Abolins Michelle J. Frome Lisa E. Cooper David L. Tierney Curtis Moore Arnold L. Rheingold Christopher JA Daley ...
In the title compound, [Fe(C(5)H(5))(C(14)H(13)O)], the plane of the heterocyclic ring is almost ... more In the title compound, [Fe(C(5)H(5))(C(14)H(13)O)], the plane of the heterocyclic ring is almost perpendicular to the plane of the substituted cyclopentadienyl ring, and the heterocyclic ring adopts a half-chair conformation. The conformation of the nearly parallel cyclopentadienyl (Cp) rings [the dihedral angle between their planes is 2.7 (1) degrees ] is almost halfway between eclipsed and staggered, and the rings are mutually twisted by about 19.4 (2) degrees (mean value). The mean lengths of the C-C bonds in the substituted and unsubstituted cyclopentadienyl ring are 1.420 (2) and 1.406 (3) A, respectively, and the Fe-C distances range from 2.029 (2) to 2.051 (2) A. The phenyl and unsubstituted cyclopentadienyl rings are involved in C-H.pi interactions, with intermolecular H.centroid distances of 2.85 and 3.14 A for C-H.pi(Ph), and 2.88 A for C-H.pi(Cp). In two of these interactions, the C-H bond points towards one of the ring bonds rather than towards the ring centroid. In the ...
Self-complementarity is a useful concept in supramolecular chemistry, molecular biology and polym... more Self-complementarity is a useful concept in supramolecular chemistry, molecular biology and polymeric systems. Two resorcinarene tetrabenzoxazines decorated with four oxalamide groups were synthesized and characterized. The oxalamide groups possessed self-complementary hydrogen bonding sites between the carbonyls and amide groups. The self-complementary nature of the oxalamide groups resulted in self-included dimeric assemblies. The hydrogen bonding interactions within the tetrabenzoxazines gave rise to the formation of dimers, which were confirmed by single-crystal X-ray diffractions analysis and supported by NMR spectroscopy and mass spectrometry. The self-included dimers were connected by numerous and strong intermolecular N-H⋅⋅⋅O and C-H⋅⋅⋅O hydrogen bonds supplemented with C-H⋅⋅⋅π interactions, forming one-dimensional polymers, which were then further linked into three-dimensional networks.
A new synthetic strategy involving the Pinner reaction offers various amidino-functionalized 2-su... more A new synthetic strategy involving the Pinner reaction offers various amidino-functionalized 2-substituted benzoxazoles via amidino-substituted 2-aminophenols with sub-micromolar antiproliferative activities.
Bis-urea derivatives 1–3, featuring a biphenyl spacer, were synthesized, characterized and invest... more Bis-urea derivatives 1–3, featuring a biphenyl spacer, were synthesized, characterized and investigated about their anion binding properties in DMSO solution and in the solid state.
European journal of medicinal chemistry, Jan 5, 2017
Regioselective 1,4-disubstituted 1,2,3-triazole tethered pyrimidine-2,4-dione derivatives (5-23) ... more Regioselective 1,4-disubstituted 1,2,3-triazole tethered pyrimidine-2,4-dione derivatives (5-23) were successfully prepared by the copper(I)-catalyzed click chemistry. While known palladium/copper-cocatalyzed method based on Sonogashira cross-coupling followed by the intramolecular 5-endo-dig ring closure generated novel 6-alkylfuro[2,3-d]pyrimidine-2-one-1,2,3-triazole hybrids (24b-37b), a small library of their 5-alkylethynyl analogs (24a-37a) was synthesized and described for the first time by tandem terminal alkyne dimerization and subsequent 5-endo-trig cyclization, which was additionally corroborated with computational and X-ray crystal structure analyses. The nature of substituents on alkynes and thereof homocoupled 1,3-diynes predominantly influenced the ratio of the formed products in both pathways. In vitro antiproliferative activity of prepared compounds evaluated on five human cancer cell lines revealed that N,N-1,3-bis-(1,2,3-triazole)-5-bromouracil (5-7) and 5,6-disubs...
Acta Crystallographica Section C Crystal Structure Communications, Sep 1, 2003
In the title compound, [Fe(C(5)H(5))(C(14)H(13)O)], the plane of the heterocyclic ring is almost ... more In the title compound, [Fe(C(5)H(5))(C(14)H(13)O)], the plane of the heterocyclic ring is almost perpendicular to the plane of the substituted cyclopentadienyl ring, and the heterocyclic ring adopts a half-chair conformation. The conformation of the nearly parallel cyclopentadienyl (Cp) rings [the dihedral angle between their planes is 2.7 (1) degrees ] is almost halfway between eclipsed and staggered, and the rings are mutually twisted by about 19.4 (2) degrees (mean value). The mean lengths of the C-C bonds in the substituted and unsubstituted cyclopentadienyl ring are 1.420 (2) and 1.406 (3) A, respectively, and the Fe-C distances range from 2.029 (2) to 2.051 (2) A. The phenyl and unsubstituted cyclopentadienyl rings are involved in C-H.pi interactions, with intermolecular H.centroid distances of 2.85 and 3.14 A for C-H.pi(Ph), and 2.88 A for C-H.pi(Cp). In two of these interactions, the C-H bond points towards one of the ring bonds rather than towards the ring centroid. In the crystal structure, the C-H.pi interactions connect the molecules into a three-dimensional framework.
Acta Crystallographica Section C Crystal Structure Communications, Apr 1, 2003
Crystal structure analysis of the title compound, C(13)H(12)ClNO, reveals three crystallographica... more Crystal structure analysis of the title compound, C(13)H(12)ClNO, reveals three crystallographically independent molecules in the asymmetric unit. The main conformational difference between these molecules is the orientation of the phenyl rings with respect to the pyrrole rings. The coplanar arrangement of the aldehyde groups attached to the pyrrole rings influences the pyrrole-ring geometry. The C2-C3 and N1-C5 bonds are noticeably longer than the C4-C5 and N1-C2 bonds. Two independent molecules of the title compound form dimers via intermolecular C-H.O hydrogen bonds [D.A = 3.400 (3) A and D-H.A = 157 degrees ]. The perpendicular orientation of the phenyl and pyrrole rings of one independent molecule and its symmetry-related molecule allows C-H.pi interactions, with an H.centroid distance of 2.85 A and a C-H.pi angle of 155 degrees. The distances between the H atom and the pyrrole-ring atoms indicate that the C-H bond points towards one of the bonds in the pyrrole ring.
... Jennifer K. Angelosante Lauren M. Schopp Breia J. Lewis Amber D. Vitalo Dustin T. Tit... more ... Jennifer K. Angelosante Lauren M. Schopp Breia J. Lewis Amber D. Vitalo Dustin T. Titus Rebecca A. Swanson April N. Stanley Brendan P. Abolins Michelle J. Frome Lisa E. Cooper David L. Tierney Curtis Moore Arnold L. Rheingold Christopher JA Daley ...
In the title compound, [Fe(C(5)H(5))(C(14)H(13)O)], the plane of the heterocyclic ring is almost ... more In the title compound, [Fe(C(5)H(5))(C(14)H(13)O)], the plane of the heterocyclic ring is almost perpendicular to the plane of the substituted cyclopentadienyl ring, and the heterocyclic ring adopts a half-chair conformation. The conformation of the nearly parallel cyclopentadienyl (Cp) rings [the dihedral angle between their planes is 2.7 (1) degrees ] is almost halfway between eclipsed and staggered, and the rings are mutually twisted by about 19.4 (2) degrees (mean value). The mean lengths of the C-C bonds in the substituted and unsubstituted cyclopentadienyl ring are 1.420 (2) and 1.406 (3) A, respectively, and the Fe-C distances range from 2.029 (2) to 2.051 (2) A. The phenyl and unsubstituted cyclopentadienyl rings are involved in C-H.pi interactions, with intermolecular H.centroid distances of 2.85 and 3.14 A for C-H.pi(Ph), and 2.88 A for C-H.pi(Cp). In two of these interactions, the C-H bond points towards one of the ring bonds rather than towards the ring centroid. In the ...
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