Browse
Submit Data
Databases
API
Help

Dataset Information

12 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

10-Methoxy-benzo[g]imidazo[1,2-a][1,8]naphthyridine-4-carbonitrile.

ABSTRACT: In the title compound, C(16)H(10)N(4)O, both the meth-oxy and nitrile substituents lie in the plane defined by the benzo[g]imidazo[1,2-a]-1,8-naphthyridine ring system, resulting in a nearly planar geometry for the entire mol-ecule (r.m.s. deviation of the non-H atoms from the mean plane is 0.044?Å). In the solid-state, the mol-ecules form a three-dimensional polymer through inter-molecular C-H?N and C-H?O hydrogen bonds. In addition, the packing mode results in stabilizing ?-? stacking inter-actions between the asymmetric units.

SUBMITTER: Tarasov AV

PROVIDER: S-EPMC2970372 | biostudies-literature | 2009 Sep

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

10-Methoxy-benzo[g]imidazo[1,2-a][1,8]naphthyridine-4-carbonitrile.

Tarasov Andrii V AV Volovnenko Tatyana A TA Lugan Noël N Volovenko Yulian M YM

Acta crystallographica. Section E, Structure reports online 20090926 Pt 10

In the title compound, C(16)H(10)N(4)O, both the meth-oxy and nitrile substituents lie in the plane defined by the benzo[g]imidazo[1,2-a]-1,8-naphthyridine ring system, resulting in a nearly planar geometry for the entire mol-ecule (r.m.s. deviation of the non-H atoms from the mean plane is 0.044 Å). In the solid-state, the mol-ecules form a three-dimensional polymer through inter-molecular C-H⋯N and C-H⋯O hydrogen bonds. In addition, the packing mode results in stabilizing π-π stacking inter-ac ...[more]

PMID: 21577970

Similar Datasets

14-(2,3-Dichloro-phen-yl)-9,10-dimethyl-benzimidazo[1,2-a]benzo[f][1,8]naphthyridine-6-carbonitrile.

Project description:In the title compound, C(27)H(16)Cl(2)N(4), the benzimidazo[1,2-a]benzo[f][1,8]naphthyridine system is nearly planar (r.m.s. deviation for all non-H atoms = 0.033?Å). The dichloro-phenyl substituent is rotated by -67.5?(2)° from this plane. In the crystal structure, mol-ecules form stacks along the crystallographic (100) direction due to ?-? stacking inter-actions with a centroid-centroid distance of 3.4283?(9)?Å.

| S-EPMC2969033 | biostudies-literature

Discovery of Imidazo[1,2-α][1,8]naphthyridine Derivatives as Potential HCV Entry Inhibitor.

Project description:RO8191 represents a newly discovered small-molecule IFN-like agent that displays potent anti-HCV activity. With it as lead, a series of compounds bearing an imidazo[1,2-α][1,8]naphthyridine core and an amide bond-linked side chain were designed and synthesized. These compounds were evaluated on HCV cell culture system (HCVcc-hRluc-JFH1), and some of them exhibited remarkable anti-HCV activity (EC50 = 0.017-0.159 μM) and low toxicity (CC50 > 25 μM). Moreover, it was revealed that these newly identified anti-HCV agents exert their antiviral effect through a distinct mechanism of action from that of RO8191 by targeting the viral entry process. Thus, our study provides a starting point for the development of potential HCV entry inhibitor.

| S-EPMC4569878 | biostudies-literature

2,7-Dimethyl-1,8-naphthyridine.

Project description:The asymmetric unit of the title compound, C(10)H(10)N(2), contains one half-mol-ecule with the two shared C atoms lying on a twofold rotation axis. The 1,8-naphthyridine is almost planar with a dihedral angle of 0.42?(3)° between the fused pyridine rings. In the crystal, mol-ecules are linked into infinite chains along the c axis by inter-molecular C-H?N hydrogen bonds, generating R(2) (2)(8) ring motifs. In addition, the crystal structure is further stabilized by C-H?? inter-actions.

| S-EPMC2977386 | biostudies-literature

2,7-Bis-(trichloro-meth-yl)-1,8-naphthyridine.

Project description:The complete mol-ecule of the title compound, C(10)H(4)Cl(6)N(2), is generated by crystallographic twofold symmetry, with two C atoms lying on the rotation axis; the 1,8-naphthyridine ring is almost planar with an r.m.s. deviation of 0.0002?Å. In the crystal structure, the mol-ecules are stacked in an anti-parallel manner along [001]. Short Cl?Cl [3.3502?(4)] and Cl?N [3.2004?(11)-3.2220?(10)?Å] contacts are observed in the crystal structure.

| S-EPMC2983609 | biostudies-literature

2-Methyl-6-(trifluoro-meth-yl)imidazo[1,2-a]pyridine-3-carbonitrile.

Project description:In the title compound, C(10)H(6)F(3)N(3), the imidazo[1,2-a]pyridine group is essentially planar with a maximum deviation of 0.021?(1)?Å. The F atoms in the trifluoro-methyl group and the methyl H atoms are each disordered over two sets of sites with refined site occupancies of 0.68?(1):0.32?(1). In the crystal, mol-ecules are linked into infinite chains through two C-H?N inter-actions forming R(2) (2)(12) and R(2) (2)(8) hydrogen-bond ring motifs. These chains are stacked along the a axis.

| S-EPMC3052008 | biostudies-other

2-Tri-fluoro-methyl-10H-benzo[4,5]imidazo[1,2-a]pyrimidin-4-one.

Project description:In the mol-ecule of the title compound, C11H6F3N3O, the three fused rings of the benzo[4,5]imidazo[1,2-a]pyrimidine unit are essentially coplanar, the maximum deviation from the mean plane being 0.096?(2)?Å. In the crystal, N-H?O hydrogen bonds link the mol-ecules into chains running along the b-axis direction.

| S-EPMC3790404 | biostudies-literature

Bis(7-amino-2,4-dimethyl-1,8-naphthyridine)dinitratocadmium(II).

Project description:In the title compound, [Cd(NO(3))(2)(C(10)H(11)N(3))(2)], two naph-thyridine ring systems are coordinated to the Cd ion through the two N atoms in a bidentate chelating mode, whereas the remaining coordination sites are occupied by two O atoms from two different nitrate groups to complete the octahedral geometry. Inter-moleular N-H?O hydrogen bonds link the mol-ecules to form a one-dimensionnal sheet parallel to the ac plane. Weak slipped ?-? stacking involving the naphthyridine ring systems stabilizes the structure.

| S-EPMC2914938 | biostudies-literature

7-Acetyl-amino-2,4-dimethyl-1,8-naphthyridine.

Project description:The air-stable title compound, C(12)H(13)N(3)O, which is of inter-est due to its anti-bacterial properties, is an almost planar mol-ecule in which the ten atoms forming the 1,8-naphthyridine ring have an r.m.s. deviation of 0.03?Å from the least-squares plane calculated using the ten atoms. The plane of the acetyl-amino group is slightly inclined [11.7?(2)°] to the plane of the 1,8-naphthyridine ring.

| S-EPMC2915183 | biostudies-other

1-Methyl-3-(4-chloro-benzo-yl)imidazo[1,2-a]pyridin-1-ium-2-olate.

Project description:In the mol-ecule of the title compound, C(15)H(11)ClN(2)O(2), the nine-membered heterobicycle is approximately planar [largest deviation from least-squares plane = 0.012?(2)?Å] and forms a dihedral angle of 51.14?(8)° with the plane of the 4-chloro-phenyl group. There is a non-classical intra-molecular hydrogen bond between the pyridine ?-H atom and the O atom of the benzoyl group. The crystal structure is stabilized by weak C-H?O and C-H?Cl inter-actions involving the 'olate' O atom and the Cl atom attached to the benzoyl group as acceptors.

| S-EPMC3201236 | biostudies-literature

Synthesis, Characterization, and Antifungal Activity of Novel Benzo[4,5]imidazo[1,2-d][1,2,4]triazine Derivatives.

Project description:A series of novel fused heterocyclic compounds bearing benzo[4,5]imidazo[1,2-d][1,2,4]triazine 4a-4w were designed and conveniently synthesized via the intermediates 2-(halogenated alkyl)-1H-benzo[d]imidazoles 2a, 2b, and 2-((1-(substituted phenyl)hydrazinyl)alkyl)-1H-benzo[d]imidazoles 3a-3g. The structures of all target compounds were characterized by FT-IR, ¹H NMR, 13C NMR, and EI-MS, of which, the structure of compound 4n was further determined by the single crystal X-ray diffraction. The crystal structure of 4n was crystallized in the triclinic crystal system, space group P 1 ¯ with a = 9.033 (6) Å, b = 10.136 (7) Å, c = 10.396 (7) Å, ? = 118.323 (7)°, ? = 91.750 (8)°, ? = 104.198 (7)°, Z = 2, V = 800.2 (9) Å³; total R indices: R? = 0.0475, wR? = 0.1284. The antifungal activity of title compounds 4a-4w in vitro against the phytopathogenic fungi Botrytis cinerea (B. cinerea), Rhizoctonia solani (R. solani) and Colletotrichum capsici (C. capsici) were evaluated, the bioassay results demonstrated that most of the title compounds exhibited obvious fungicidal activities at 50 ?g/mL. This work indicated that benzo[4,5]imidazo[1,2-d][1,2,4]triazine derivatives could be considered as a new leading structure in searching for novel agricultural fungicides.

| S-EPMC6017302 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

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