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6-Hy-droxy-1,2-dihydro-4H-pyrrolo-[3,2,1-ij]quinolin-4-one.

ABSTRACT: The mol-ecule of the title compound, C11H9NO2, is essentially planar [r.m.s. deviation of the non-H atoms = 0.056?(1)?Å]. In the crystal, strong O-H?O hydrogen bonds form zigzag chains along the b axis. The mol-ecules form stacks along the a axis due to ?-? inter-actions, the shortest distance between the centroids of the benzene and pyridinone rings being 3.6146?(7)?Å.

SUBMITTER: Rybakov VB

PROVIDER: S-EPMC3588512 | biostudies-literature | 2013 Mar

REPOSITORIES: biostudies-literature

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Novel 2,3-Dihydro-1H-pyrrolo[3,2,1-ij]quinazolin-1-ones: Synthesis and Biological Evaluation.

Project description:Herein we describe the synthesis and evaluation of a series of novel 2,3-dihydro-1H-pyrrolo[3,2,1-ij]quinazolin-1-ones for in vitro cytotoxicity against three human cancer cell lines as well as for potential antimalarial activity against the chloroquine-sensitive strain 3D7 of Plasmodium falciparum. The title compounds were prepared via PdCl₂-mediated endo-dig cyclization of 2-aryl-8-(arylethynyl)-6-bromo-2,3-dihydroquinazolin-4(1H)-ones. The latter were prepared, in turn, via initial Sonogashira cross-coupling of 2-amino-5-bromo-3-iodobenzamide with aryl acetylenes followed by boric acid-mediated cyclocondensation of the intermediate 2-amino-3-(arylethynyl)-5-bromobenzamides with benzaldehyde derivatives. The 2,3-dihydro-1H-pyrrolo[3,2,1-ij]quinazolin-1-ones 4a-k were evaluated for potential in vitro cytotoxicity against the breast (MCF-7), melanoma (B16) and endothelioma (sEnd.2) cell lines. All of the compounds except 4h and 4i were found to be inactive against the three cancer cell lines. Compound 4h substituted with a 4-methoxyphenyl and 4-fluorophenyl groups at the 3- and 5-positions was found to exhibit significant cytotoxicity against the three cancer cell lines. The presence of phenyl and 3-chlorophenyl groups at the 3- and 5-posiitons of the pyrroloquinazolinone 4i, on the other hand, resulted in significant cytotoxicity against vascular tumour endothelial cells (sEnd.2), but reduced activity against the melanoma (B16) and breast cancer (MCF-7) cells except at higher concentrations. The 2,3-dihydro-1H-pyrrolo[3,2,1-ij]quinazolin-1-ones 4a-l were found to be inactive against the chloroquine sensitive 3D7 strain of Plasmodium falciparum.

| S-EPMC6155753 | biostudies-literature

Methyl 4-methyl-2-oxo-1,2,5,6-tetra-hydro-4H-pyrrolo[3,2,1-ij]quinoline-6-carboxyl-ate.

Project description:In the title mol-ecule, C(14)H(15)NO(3), the six-membered heterocyclic ring exhibits an envelope conformation. In the crystal, C-H?? inter-actions link the mol-ecules into centrosymmetric dimers, and weak inter-molecular C-H?O hydrogen bonds link these dimers into columns propagated along [100].

| S-EPMC2977288 | biostudies-literature

2-(2-Hy-droxy-phen-yl)-3,4-dihydro-iso-quinolin-1(2H)-one.

Project description:There are two independent mol-ecules in the asymmetric unit of the title compound, C(15)H(13)NO(2), in both the six-membered dihydro-pyridine rings adopt a half-chair conformation. The two benzene rings make dihedral angles of 43.66 (10) and 62.22 (10)° in the two mol-ecules. In the crystal, the two independent mol-ecules are linked alternately by inter-molecular O-H⋯O hydrogen bonds, forming a zigzag chain along the c axis. Furthermore, inter-molecular C-H⋯π inter-actions link the chains into a three-dimensional network.

| S-EPMC3201540 | biostudies-literature

Methyl 2-(4-hy-droxy-1-methyl-2-oxo-1,2-dihydro-quinolin-3-yl)acetate.

Project description:In the title compound, C(13)H(13)NO(4), the bicyclic quinolone fragment and the ester group are approximately orthogonal, making a dihedral angle of 83.3?(2)° and an intramolecular C-H?O interaction occurs. In the crystal, inter-molecular O-H?O hydrogen bonding generates a zigzag chain along the c axis.

| S-EPMC3011763 | biostudies-literature

3-Hy-droxy-2-(4-hy-droxy-phen-yl)-4H-chromen-4-one.

Project description:In the title compound, C(15)H(10)O(4), the benzene ring is twisted at an angle of 20.7 (1)° relative to the 4H-chromene skeleton. In the crystal, adjacent mol-ecules are linked via a network of O-H⋯O and C-H⋯O hydrogen bonds. The mean planes of adjacent 4H-chromene moieties are parallel or oriented at an angle of 20.9 (1)° in the crystal structure.

| S-EPMC3051623 | biostudies-literature

Crystal structure and DFT study of 8-hy-droxy-1,2,3,5,6,7-hexa-hydro-pyrido[3,2,1-ij]quinoline-9-carbaldehyde.

Project description:In the title compound, C13H15NO2, the fused non-aromatic rings of the julolidine moiety adopt envelope conformations. The hy-droxy group forms an intra-molecular hydrogen bond to the aldehyde O atom, generating an S(6) ring motif. Weak inter-molecular C-H⋯O hydrogen bonds help to stabilize the crystal structure. Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state.

| S-EPMC5418808 | biostudies-literature

6-Eth-oxy-carbonyl-5,7-dihy-droxy-2,3-dihydro-1H-pyrido[3,2,1-ij]quinolinium tribromide.

Project description:In the title salt, C15H16NO4(+.)Br3(-), classical intra-molecular O-H?O hydrogen bonds are found, which results in the co-planarity of the ester substituents with the quinolinium residue [C-C-C-O torsion angle = 1.0?(10)°]. The bromine anions are placed on both sides of heterocyclic cation and form Br?N contacts of 3.674?(9) and 3.860?(9)?Å, which confirms the location of positive charge on the N atom. Non-classical inter-molecular C-H?Br inter-actions stabilize the three-dimensional crystal structure. Moreover, anion?? inter-actions are noted [Br?ring centroid range = 3.367?(9)-3.697?(9)?Å]. The partly saturated heterocycle is disordered over two sofa conformations with occupancies in the ratio 0.56?(2):0.44?(2).

| S-EPMC3588293 | biostudies-other

Synthesis, Docking, and In Vitro Anticoagulant Activity Assay of Hybrid Derivatives of Pyrrolo[3,2,1-ij]Quinolin-2(1H)-one as New Inhibitors of Factor Xa and Factor XIa.

Project description:Coagulation factor Xa and factor XIa are proven to be convenient and crucial protein targets for treatment for thrombotic disorders and thereby their inhibitors can serve as effective anticoagulant drugs. In the present work, we focused on the structure-activity relationships of derivatives of pyrrolo[3,2,1-ij]quinolin-2(1H)-one and an evaluation of their activity against factor Xa and factor XIa. For this, docking-guided synthesis of nine compounds based on pyrrolo[3,2,1-ij]quinolin-2(1H)-one was carried out. For the synthesis of new hybrid hydropyrrolo[3,2,1-ij]quinolin-2(1H)-one derivatives, we used convenient structural modification of both the tetrahydro- and dihydroquinoline moiety by varying the substituents at the C6,8,9 positions. In vitro testing revealed that four derivatives were able to inhibit both coagulation factors and three compounds were selective factor XIa inhibitors. An IC50 value of 3.68 μM for was found for the best factor Xa inhibitor and 2 μM for the best factor XIa inhibitor.

| S-EPMC7222003 | biostudies-literature

7-Amino-4-hy-droxy-4-trifluoro-methyl-3,4-dihydro-quinolin-2(1H)-one.

Project description:The title compound, C(10)H(9)F(3)N(2)O(2), was prepared by the reaction of m-phenyl-enediamine and ethyl 4,4,4-trifluoro-acetoacetate. In the crystal, inter-molecular C-H? F, N-H?F, O-H?N and N-H?O inter-actions contribute to the crystal packing.

| S-EPMC3201506 | biostudies-other

5-Hy-droxy-7-phenyl-5-(prop-2-yn-1-yl)-5,6-dihydro-1-benzofuran-2(4H)-one monohydrate.

Project description:In the title compound, C(17)H(14)O(3)·H(2)O, the six-membered ring, which adopts a half-chair conformation, makes a dihedral angle of 24.3?(2)° with the phenyl ring. In the crystal, the components are linked by O-H?O hydrogen bonds involving the water mol-ecule, and the hy-droxy and carbonyl groups of the organic compound. These inter-actions form a square-like supra-molecular synthon unit which propagates as chains parallel to the crystallographic b axis. A C-H?O interaction also occurs.

| S-EPMC3009225 | biostudies-literature

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