Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Monoclinic polymorph of 3,7-dimethyl-1-(5-oxohex-yl)-3,7-dihydro-1H-purine-2,6-dione.

ABSTRACT: The structure of the title compound, pentoxifylline, C(13)H(18)N(4)O(3), has been previously characterized as a triclinic polymorph [Pavel?ík et al. (1989 ?). Acta Cryst. C45, 836-837]. We have discovered the monoclinic form. There are no strong hydrogen bonds in the crystal structure, rather, moderate C-H?O hydrogen bonds are present, which serve to stabilize the three-dimensional architecture.

SUBMITTER: Stepanovs D

PROVIDER: S-EPMC3247589 | biostudies-literature | 2011 Nov

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Monoclinic polymorph of 3,7-dimethyl-1-(5-oxohex-yl)-3,7-dihydro-1H-purine-2,6-dione.

Stepanovs Dmitrijs D Mishnev Anatoly A

Acta crystallographica. Section E, Structure reports online 20111005 Pt 11

The structure of the title compound, pentoxifylline, C(13)H(18)N(4)O(3), has been previously characterized as a triclinic polymorph [Pavelčík et al. (1989 ▶). Acta Cryst. C45, 836-837]. We have discovered the monoclinic form. There are no strong hydrogen bonds in the crystal structure, rather, moderate C-H⋯O hydrogen bonds are present, which serve to stabilize the three-dimensional architecture. ...[more]

PMID: 22219894

Similar Datasets

8-(2-Hy-droxy-phen-yl)-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione.

Project description:The title compound, C(13)H(12)N(4)O(3), is an imidazole derivative featuring an annealed purine ring system. The benzimidazole-inspired moiety is essentially planar (r.m.s. of all fitted non-H atoms = 0.0205 Å). An intra-molecular O-H⋯N hydrogen bond occurs. In the crystal, inter-molecular N-H⋯O and C-H⋯O hydrogen bonds are observed, which connect the mol-ecules into chains along [110]. The shortest centroid-centroid distance between two aromatic systems is 3.7771 (11) Å.

| S-EPMC3200978 | biostudies-literature

A second monoclinic polymorph of 2-(diformyl-methyl-idene)-3,3-dimethyl-2,3-dihydro-1H-indole.

Project description:The crystal structure of the title compound, C(13)H(13)NO(2), is a polymorph of the structure first reported by Helliwell et al. [Acta Cryst. (2006), E62, o737-o738]. It is also monoclinic (space group P2(1)/c), but with completely different cell constants. The mol-ecular conformations of these polymorphs differ by a 180° rotation of one formyl group. The present mol-ecule is planar [maximum deviation 0.089?(2)?Å] with the exception of the two methyl groups which lie on either side of the plane. There are strong intra- and inter-molecular N-H?O hydrogen bonds. The latter link pairs of mol-ecules across crystallographic centers of symmetry. Two aldehyde O atoms are brought close together [2.896?(4)?Å in this arrangement but are not hydrogen bonded. In the earlier polymorph, one formyl group is rotated by 180° to yield inter-molecular hydrogen bonding and an infinite polymeric chain. The other formyl group is involved in the same intra-molecular hydrogen bonding as has been found here.

| S-EPMC2970324 | biostudies-literature

A second monoclinic polymorph of 6-amino-1,3-dimethyl-5-[(E)-2-(methyl-sulfan-yl)benzyl-idene-amino]-pyrimidine-2,4(1H,3H)-dione.

Project description:A new monoclinic form of the title compound, C(14)H(16)N(4)O(2)S, has been identified unexpectedly during an attempt to synthesize a coordination compound. The heterocyclic ring is essentially planar (r.m.s. deviation = 0.005?Å) and makes a dihedral angle of 8.77?(5)° with the benzene ring. This is in contrast to 12.24?(7)° reported for the first monoclinic polymorph [Booysen et al. (2011 ?). Acta Cryst. E67, o1592]. An intra-molecular N-H?S hydrogen bond is observed. In the crystal, inter-molecular N-H?O hydrogen bonds link the mol-ecules into zigzag chains along the b axis. The closest distance between the centroids of symmetry-related heterocyclic rings is 3.5161?(6)?Å.

| S-EPMC3213476 | biostudies-literature

Bis(1,3-dimethyl-1H-imidazolium) hexa-fluoro-silicate: the second monoclinic polymorph.

Project description:The title compound, 2C5H9N2 (+)·SiF6 (2-), (I), crystallized as a new polymorph, different from the previously reported one (Ia) [Light et al. (2007 ▶) private communication (refcode: NIQFAV). CCDC, Cambridge, England]. The symmetry [space groups P21/n for (I) and C2/c for(Ia)] and crystal packing patterns are markedly different for this pair of polymorphs. In (I), all imidazolium cations in the lattice are nearly parallel to each other, whereas a herringbone arrangement can be found in (Ia). In (I), each SiF6 (2-) dianion forms four short C-H⋯F contacts with adjacent C5H9N2 (+) cations, resulting in the formation of layers parallel to the ac plane. In (Ia), the C-H⋯F contacts are generally longer and result in the formation of layers along the bc plane.

| S-EPMC3793725 | biostudies-literature

A monoclinic polymorph of N,N'-bis-(2,6-diisopropyl-phen-yl)formamidine.

Project description:A new polymorph of N,N'-bis-(2,6-diisopropyl-phen-yl)formamidine, C(25)H(36)N(2), is reported, which is different from the previously reported ortho-rhom-bic structure. The mol-ecule crystallizes in the E-anti configuration, with tautomeric disorder of the N-bonded H atoms and no clear distinction between imine and amine functionalities. The mol-ecules form hydrogen-bonded dimers with inter-molecular N⋯N distances shorter than those in the ortho-rhom-bic polymorph.

| S-EPMC2962078 | biostudies-literature

Monoclinic polymorph of 4-[(1H-benz-imidazol-1-yl)meth-yl]benzoic acid.

Project description:Three polymorphs of the title compound, C(15)H(12)N(2)O(2), were obtained accidentally as single crystals in the hydro-thermal reaction of the title compound with manganese bromide in the presence of N,N'-dimethyl-formamide at 373?K. Here we report the structure of the first polymorph. The benzimidazole ring is almost planar, the maximum deviation from the mean plane being 0.016?(1)?Å. The benzimidazole and benzene rings are approximately perpendicular, making a dihedral angle 85.56?(7)°, which is a reflection of the axial rotation of the flexible benzimidazolyl arm. In the crystal, adjacent mol-ecules are connected through O-H?N hydrogen bonds into a chain along [100], and neighboring chains are further linked by via weak C-H?O hydrogen-bonding inter-actions, forming a two-dimensional network.

| S-EPMC3201311 | biostudies-literature

Second monoclinic polymorph of 4-[(1H-benzimidazol-1-yl)meth-yl]benzoic acid.

Project description:Recently, we reported the first monoclinic [Kuai & Cheng (2011). Acta Cryst., E67, o2787] and the ortho-rhom-bic polymorph [Kuai & Cheng (2011). Acta Cryst., E67, o3014] of the title compound, C(15)H(12)N(2)O(2). Another monoclinic polymorph was obtained accidentally by the hydro-thermal reaction of the title compound with manganese chloride in the presence of potassium hydroxide at 413 K. The asymmetric unit consists of four independent mol-ecules. In the crystal, O-H⋯N hydrogen bonds link the independent mol-ecules into four separate chains parallel to the b axis.

| S-EPMC3238873 | biostudies-literature

3,5-Bis[1-acetyl-5-(4-chloro-phen-yl)-4,5-dihydro-1H-pyrazol-3-yl]-2,6-dimethyl-pyridine.

Project description:The title compound, C(29)H(27)Cl(2)N(5)O(2), contains a central pyridine ring and two functionalized pyrazoline rings. The pyridine ring and the two attached pyrazoline rings are nearly coplanar, whereas the terminal chloro-phenyl rings are nearly perpendicular to the attached pyrazoline rings [dihedral angles = 86.78?(1) and 77.70?(1)°]. Mol-ecules are linked by weak inter-molecular C-H?O hydrogen bonding.

| S-EPMC2960675 | biostudies-literature

Design, Synthesis, and Biological Evaluation of 8-Mercapto-3,7-Dihydro-1H-Purine-2,6-Diones as Potent Inhibitors of SIRT1, SIRT2, SIRT3, and SIRT5.

Project description:Sirtuins (SIRT1-7) are a family of NAD+-dependent deacetylases. They regulate many physiological processes and play important roles in inflammation, diabetes, cancers, and neurodegeneration diseases. Sirtuin inhibitors have potential applications in the treatment of neurodegenerative diseases and various cancers. Herein, we identified new sirtuin inhibitors based on the scaffold of 8-mercapto-3,7-dihydro-1H-purine-2,6-dione. To elucidate the inhibitory mechanism, the binding modes of the inhibitors in SIRT3 were established by molecular docking, showing that the inhibitors occupy the acetyl lysine binding site and interact with SIRT3, mainly through hydrophobic interactions. The interactions were validated by site-directed mutagenesis of SIRT3 and structure-activity relationship analysis of the inhibitors. Consistently, enzyme kinetic assays and microscale thermophoresis showed that these compounds are competitive inhibitors to the acetyl substrate, and mix-type inhibitors to NAD+. Furthermore, we demonstrated that the compounds are potent SIRT1/2/3/5 pan-inhibitors. This study provides novel hits for developing more potent sirtuin inhibitors.

| S-EPMC7356367 | biostudies-literature

7-(1,3-Dioxolan-2-ylmeth-yl)-1,3-di-methyl-purine-2,6(1H,3H)-dione trichloro-acetic acid solvate.

Project description:In the title compound, C(11)H(14)N(4)O(4)·C(2)HCl(3)O(2), the dioxolane ring adopts an envelope conformation. Doxophylline [7-(1,3-dioxolan-2-yl-meth-yl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione] and trichloro-acetic acid mol-ecules are linked by O-H⋯N and C-H⋯O hydrogen bonds.

| S-EPMC2915388 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data