Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

1-Isobutyl-N,N-dimethyl-1H-imidazo[4,5-c]quinolin-4-amine.

ABSTRACT: In the title compound, C(16)H(20)N(4), the 1H-imidazo[4,5-c]quinoline ring system is approximately planar, with a maximum deviation of 0.0719?(15)?Å. An intra-molecular C-H?N hydrogen bond contributes to the stabilization of the mol-ecule, forming an S(6) ring motif. In the crystal, the mol-ecules are stacked along the b axis through weak aromatic ?-? inter-actions between benzene and imidazole and benzene and pyridine rings [centroid-centroid distances = 3.6055?(10) and 3.5342?(10)?Å, respectively].

SUBMITTER: Loh WS

PROVIDER: S-EPMC3051498 | biostudies-literature | 2011 Jan

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

1-Isobutyl-N,N-dimethyl-1H-imidazo[4,5-c]quinolin-4-amine.

Loh Wan-Sin WS Fun Hoong-Kun HK Kayarmar Reshma R Viveka S S Nagaraja G K GK

Acta crystallographica. Section E, Structure reports online 20110115 Pt 2

In the title compound, C(16)H(20)N(4), the 1H-imidazo[4,5-c]quinoline ring system is approximately planar, with a maximum deviation of 0.0719 (15) Å. An intra-molecular C-H⋯N hydrogen bond contributes to the stabilization of the mol-ecule, forming an S(6) ring motif. In the crystal, the mol-ecules are stacked along the b axis through weak aromatic π-π inter-actions between benzene and imidazole and benzene and pyridine rings [centroid-centroid distances = 3.6055 (10) and 3.5342 (10) Å, respectiv ...[more]

PMID: 21523077

Similar Datasets

3-[(1-Isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)amino]-benzoic acid.

Project description:In the title compound, C(21)H(20)N(4)O(2), the statistically planar 1H-limidazole ring [maximum deviation = 0.003?(1)?Å] makes dihedral angles of 1.33?(9) and 8.23?(7)°, respectively, with the essentially planar fused pyridine ring [maximum devation = 0.018?(1)?Å] and the pendant benzene ring, which is attached to the pyridine ring by an -NH- group. An intra-molecular C-H?N inter-action, which generates an S(6) ring, helps to estalish the mol-ecular conformation. In the crystal, the mol-ecules are linked by N-H?O, C-H?O and O-H-N hydrogen bonds, which generate bifurcated R(1) (2)(6) and R(2) (2)(9) ring motifs, resulting in supra-molecular [001] chains. The crystal structure also features weak ?-? stacking [centroid-centroid distance = 3.5943?(9)?Å] and C-H?? inter-actions.

| S-EPMC3213588 | biostudies-literature

4-Chloro-benzaldehyde (1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)hydrazone monohydrate.

Project description:In the title compound, C(21)H(20)ClN(5)·H(2)O, the 1H-imidazo[4,5-c]quinoline ring is approximately planar, with a maximum deviation of 0.0795 (7) Å, and it forms a dihedral angle of 7.65 (3)° with the chloro-phenyl ring. In the crystal, the components are linked into chains along the a axis via inter-molecular N-H⋯O, O-H⋯N and C-H⋯O hydrogen bonds. One of the H atoms of the water mol-ecule is disordered over two positions with a site-occupancy ratio of 0.80 (4):0.20 (4).

| S-EPMC3051724 | biostudies-literature

4-Hydrazinyl-1-isobutyl-1H-imidazo[4,5-c]quinoline.

Project description:In the title compound, C(14)H(17)N(5), the 1H-imidazo[4,5-c]quinoline ring system is essentially planar, with a maximum deviation of 0.0325 (7) Å. In the crystal, a pair of inter-molecular N-H⋯N hydrogen bonds link neighbouring mol-ecules, forming an inversion dimer and generate an R(2) (2)(10) ring motif. These dimers are further connected into a chain along the b axis via inter-molecular C-H⋯N hydrogen bonds, resulting in an R(2) (2)(14) ring motif.

| S-EPMC3051739 | biostudies-literature

1-Isobutyl-4-meth-oxy-1H-imidazo[4,5-c]quinoline.

Project description:In the title compound, C(15)H(17)N(3)O, the 1H-imidazo[4,5-c]quinoline ring system is approximately planar, with a maximum deviation of 0.036?(1)?Å. The C-N-C-C torsion angles formed between this ring system and the isobutyl unit are -99.77?(16) and 79.71?(17)°. In the crystal, inter-molecular C-H?O hydrogen bonds link the mol-ecules into chains along the c axis.

| S-EPMC3200859 | biostudies-other

Structure-activity relationships of new 1H-imidazo[4,5-c]quinolin-4-amine derivatives as allosteric enhancers of the A3 adenosine receptor.

Project description:1H-Imidazo[4,5-c]quinolin-4-amine derivatives have been synthesized as allosteric modulators of the human A3 adenosine receptor (AR). Structural modifications were made at the 4-amino and 2 positions. The compounds were tested in both binding and functional assays, and many were found to be allosteric enhancers of the action of A3AR agonists by several different criteria. First, a potentiation of the maximum efficacy of the agonist Cl-IB-MECA was observed for numerous derivatives. Also, a number of these compounds decreased the rate of dissociation of the agonist [125I]I-AB-MECA from the A3AR. Most prominently, compound 43 (LUF6000) was found to enhance agonist efficacy in a functional assay by 45% and decrease dissociation rate similarly without influencing agonist potency. The structural requirements for allosteric enhancement at the A3AR were distinct from the requirements to inhibit equilibrium binding. Thus, we have prepared allosteric enhancers of the human A3AR that have an improved allosteric effect in comparison to the inhibition of equilibrium binding at the orthosteric site.

| S-EPMC2547348 | biostudies-literature

Novel 2- and 4-substituted 1H-imidazo[4,5-c]quinolin-4-amine derivatives as allosteric modulators of the A3 adenosine receptor.

Project description:4-Arylamino and 2- cycloalkyl (including amino substitution) modifications were made in a series of 1H-imidazo[4,5-c]quinolin-4-amine derivatives as allosteric modulators of the human A(3) adenosine receptor (AR). In addition to allosteric modulation of the maximum functional efficacy (in [(35)S]GTPgammaS G protein binding assay) of the A(3)AR agonist Cl-IB-MECA (15), some analogues also weakly inhibited equilibrium radioligand binding at ARs. 4-(3,5-Dichlorophenylamino) (6) or 2-(1-adamantyl) (20) substitution produced allosteric enhancement (twice the maximal agonist efficacy), with minimal inhibition of orthosteric AR binding. 2-(4-Tetrahydropyranyl) substitution abolished allosteric enhancement but preserved inhibition of orthosteric binding. Introduction of nitrogen in the six-membered ring at the 2 position, to improve aqueous solubility and provide a derivatization site, greatly reduced the allosteric enhancement. 2-(4-(Benzoylamino)cyclohexyl) analogues 23 and 24 were weak negative A(3)AR modulators. Thus, consistent with previous findings, the allosteric and orthosteric inhibitory A(3)AR effects in imidazoquinolines are structurally separable, suggesting the possible design of additional derivatives with enhanced positive or negative allosteric A(3)AR activity and improved selectivity in comparison to inhibition of orthosteric binding.

| S-EPMC2765805 | biostudies-literature

6-Bromo-1,3-dimethyl-1H-imidazo[4,5-b]pyridin-2(3H)-one.

Project description:The non-H atoms of the two independent mol-ecules in the asymmetric unit of the title compound, C(8)H(8)BrN(3)O, are planar (r.m.s. deviations = 0.015 and 0.019?Å). In the crystal, the mol-ecules are linked into a zigzag chain along the c axis by C-H?O hydrogen bonds.

| S-EPMC3007224 | biostudies-literature

1,3-Dimethyl-1H-indazol-6-amine.

Project description:The mol-ecular skeleton of the title compound, C(9)H(11)N(3), is almost planar, with a maximum deviation of 0.0325?(19)?Å for the amino N atom. In the crystal, N-H?N hydrogen bonds establish the packing.

| S-EPMC3344439 | biostudies-literature

4,5-Dimethyl-1,2-diphenyl-1H-imidazole monohydrate.

Project description:In the title compound, C(17)H(16)N(2)·H(2)O, the imidazole ring is essentially planar [maximum deviation = 0.0037 (7) Å]. The imidazole ring makes dihedral angles of 80.74 (7) and 41.62 (7)° with the phenyl rings attached to the N and C atoms, respectively. The dihedral angle between the two phenyl rings is 75.83 (8)°. Inter-molecular O-H⋯N and O-H⋯O hydrogen bonds are found in the crystal structure.

| S-EPMC3007850 | biostudies-literature

1H-Imidazo[4,5-f][1,10]phenanthrolin-7-ium perchlorate monohydrate.

Project description:In the title crystal structure, C(13)H(9)N(4) (+)·ClO(4) (-)·H(2)O, cations, anions and water mol-ecules are linked through inter-molecular N-H?O, O-H?N and O-H?O hydrogen bonds, forming layers parallel to (001). In addition, there are weak ?-? stacking inter-actions between the layers, involving the cations and with centroid-centroid distances in the range 3.584?(2)-3.662?(2)?Å, forming a three-dimensional network.

| S-EPMC2970354 | 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