Browse
Submit Data
Databases
API
Help

Dataset Information

16 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis of function-oriented 2-phenyl-2H-chromene derivatives using L-pipecolinic acid and substituted guanidine organocatalysts.

ABSTRACT: Organocatalytic domino oxa-Michael/aldol reactions between salicylaldehyde with electron deficient olefins are presented. We screened guanidine, 1,1,3,3-tetramethylguanidine (TMG) and L-pipecolinic acid as organocatalysts for this transformation. 3-Substituted 2-phenyl-2H-chromene derivatives are synthesized with high yields and with poor enantioselectivity (5-17% ee) using L-pipecolinic acid while TMG works well with cinnamaldehyde without using co-catalyst. These 3-substituted-2-phenyl-2H-chromene derivatives are further derivatized to synthesize triazole and biotin-containing chromene derivatives, to facilitate purification of protein targets.

SUBMITTER: Das BC

PROVIDER: S-EPMC3140427 | biostudies-literature | 2010 May

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Synthesis of function-oriented 2-phenyl-2H-chromene derivatives using L-pipecolinic acid and substituted guanidine organocatalysts.

Das Bhaskar C BC Mohapatra Seetaram S Campbell Philip D PD Nayak Sabita S Mahalingam Sakkarapalayam M SM Evans Todd T

Tetrahedron letters 20100501 19

Organocatalytic domino oxa-Michael/aldol reactions between salicylaldehyde with electron deficient olefins are presented. We screened guanidine, 1,1,3,3-tetramethylguanidine (TMG) and L-pipecolinic acid as organocatalysts for this transformation. 3-Substituted 2-phenyl-2H-chromene derivatives are synthesized with high yields and with poor enantioselectivity (5-17% ee) using L-pipecolinic acid while TMG works well with cinnamaldehyde without using co-catalyst. These 3-substituted-2-phenyl-2H-chro ...[more]

PMID: 21785516

Similar Datasets

6,8-Di-bromo-3-nitro-2-phenyl-2H-chromene.

Project description:In the title compound, C15H9Br2NO3, the chromene unit is not quite planar (r.m.s. deviation from planarity = 0.0888?Å). The di-hydro-pyran ring adopts an envelope conformation with the phenyl-substituted C atom fused to the di-hydro-pyran ring as the flap. The dihedral angle between the plane defined by this C atom and the adjacent C and O atoms and the mean plane of the di-hydro-pyran ring excluding the phenyl-substituted C atom is 25.1?(3)°. The dihedral angle between the mean plane of the chromene unit and the phenyl ring is 85.7?(1)°. The crystal structure features C-H?O hydrogen bonds and Br?O contacts [3.289?(3)?Å] involving the nitro O atoms.

| S-EPMC3685035 | biostudies-literature

4-Chloro-phenyl 2-oxo-2H-chromene-3-carboxyl-ate.

Project description:In title compound, C(16)H(9)ClO(4), the coumarin ring system is approximately planar [maximum deviation = 0.056?(1)?Å] and is oriented with respect to the benzene ring at an angle of 22.60?(7)°. Inter-molecular C-H?O hydrogen bonding is present in the crystal.

| S-EPMC3297301 | biostudies-literature

4-(Oct-yloxy)phenyl 2-oxo-2H-chromene-3-carboxyl-ate.

Project description:In the title compound, C(24)H(26)O(5), the 2H-chromene ring system is essentially planar, with a maximum deviation of 0.029?(2)?Å from the best-fit mean plane incorporating both rings. The dihedral angle between the 2H-chromene ring system and the benzene ring is 21.00?(1)°. In the crystal, pairs of C-H?O hydrogen bonds generate an R(2) (2)(8) ring pattern. These contacts are bolstered by weaker bifurcated C-H?O hydrogen bonds.

| S-EPMC3569748 | biostudies-literature

Crystal structure of 2-oxo-N'-phenyl-2H-chromene-3-carbohydrazide.

Project description:In the title compound, C16H12N2O3, the 2H-chromene moiety is essentially planar, with an r.m.s. deviation of the nine constituent atoms from the mean plane of 0.0093 Å, and makes a dihedral angle of 76.84 (3)° with the pendant phenyl ring. An intra-molecular N-H⋯O hydrogen bond helps to determine the conformation of the side chain. In the crystal, N-H⋯O and N-H⋯N hydrogen bonds link the mol-ecules, forming [100] chains.

| S-EPMC4719947 | biostudies-literature

Synthesis, Antiprotozoal Activity, and Cheminformatic Analysis of 2-Phenyl-2H-Indazole Derivatives.

Project description:Indazole is an important scaffold in medicinal chemistry. At present, the progress on synthetic methodologies has allowed the preparation of several new indazole derivatives with interesting pharmacological properties. Particularly, the antiprotozoal activity of indazole derivatives have been recently reported. Herein, a series of 22 indazole derivatives was synthesized and studied as antiprotozoals. The 2-phenyl-2H-indazole scaffold was accessed by a one-pot procedure, which includes a combination of ultrasound synthesis under neat conditions as well as Cadogan's cyclization. Moreover, some compounds were derivatized to have an appropriate set to provide structure-activity relationships (SAR) information. Whereas the antiprotozoal activity of six of these compounds against E. histolytica, G. intestinalis, and T. vaginalis had been previously reported, the activity of the additional 16 compounds was evaluated against these same protozoa. The biological assays revealed structural features that favor the antiprotozoal activity against the three protozoans tested, e.g., electron withdrawing groups at the 2-phenyl ring. It is important to mention that the indazole derivatives possess strong antiprotozoal activity and are also characterized by a continuous SAR.

| S-EPMC8068258 | biostudies-literature

Design, synthesis, and antiprotozoal evaluation of new 2,4-bis[(substituted-aminomethyl)phenyl]quinoline, 1,3-bis[(substituted-aminomethyl)phenyl]isoquinoline and 2,4-bis[(substituted-aminomethyl)phenyl]quinazoline derivatives.

Project description:A series of new 2,4-bis[(substituted-aminomethyl)phenyl]quinoline, 1,3-bis[(substituted-aminomethyl)phenyl]isoquinoline, and 2,4-bis[(substituted-aminomethyl)phenyl]quinazoline derivatives was designed, synthesised, and evaluated in vitro against three protozoan parasites (Plasmodium falciparum, Leishmania donovani, and Trypanosoma brucei brucei). Biological results showed antiprotozoal activity with IC50 values in the µM range. In addition, the in vitro cytotoxicity of these original molecules was assessed with human HepG2 cells. The quinoline 1c was identified as the most potent antimalarial candidate with a ratio of cytotoxic to antiparasitic activities of 97 against the P. falciparum CQ-sensitive strain 3D7. The quinazoline 3h was also identified as the most potent trypanosomal candidate with a selectivity index (SI) of 43 on T. brucei brucei strain. Moreover, as the telomeres of the parasites P. falciparum and Trypanosoma are possible targets of this kind of nitrogen heterocyclic compounds, we have also investigated stabilisation of the Plasmodium and Trypanosoma telomeric G-quadruplexes by our best compounds through FRET melting assays.

| S-EPMC6968685 | biostudies-literature

Synthesis of New C-3 Substituted Kynurenic Acid Derivatives.

Project description:The application of kynurenic acid (KYNA) as an electron-rich aromatic system in the modified Mannich reaction has been examined. The extension possibility of the reaction was tested by using amines occurring in a number of bioactive products, such as morpholine, piperidine, or N-methylpiperazine and aldehydes of markedly different reactivities, like formaldehyde and benzaldehyde. The influence of substituents attached to position 3 on the aminoalkylation was also investigated. Thus, reactions of 3-carbamoyl-substituted precursors with tertiary amine containing side-chains were also tested to afford new KYNA derivatives with two potential cationic centers. By means of NMR spectroscopic measurements, supported by DFT calculations, the dominant tautomer form of KYNA derivatives was also determined.

| S-EPMC7071119 | biostudies-literature

Crystal structure of 4-bromo-phenyl-2-oxo-2H-chromene-3-carboxyl-ate.

Project description:In the title compound, C16H9BrO4, the coumarin ring system is approximately planar, with an r.m.s deviation of the ten fitted non-H atoms of 0.031?Å, and forms a dihedral angle of 25.85?(10)° with the bromo-benzene ring. The carbonyl atoms are syn. In the crystal, mol-ecules are connected along [001] via C-H?O inter-actions, forming C(6) chains. Neighbouring C(6) chains are connected via several ?-? inter-actions [range of centroid-centroid distances = 3.7254?(15)-3.7716?(16)?Å], leading to sheets propagating in the bc plane.

| S-EPMC4420041 | biostudies-literature

4-(Dec-yloxy)phenyl 2-oxo-7-trifluoro-methyl-2H-chromene-3-carboxyl-ate.

Project description:The title compound, C27H29F3O5, is a liquid crystal (LC) and exhibits enanti-otropic SmA phase transitions. In the crystal, the dihedral angle between the 2H-chromene ring system and the benzene ring is 62.97?(2)°. The three F atoms of the -CF3 group are disordered over two sets of sites with occupancy factors 0.71?(4):0.29?(4). In the crystal, pairs of C-H?O hydrogen bonds form inversion dimers and generate R 2 (2)(10) rings. The structure also features C-H?F and C-H?? inter-actions along [100] and [010], respectively.

| S-EPMC3629656 | biostudies-literature

Bronsted Acid/Lewis Acid Cooperatively Catalyzed Addition of Diazoester to 2H-chromene Acetals.

Project description:A novel Brønsted acid/Lewis acid dual catalyst system has been developed to promote an efficient C-C bond formation between a range of oxocarbenium precursors derived from chromene acetals and ethyl diazoacetate. The reaction proceeds under mild conditions and is tolerant of common functionalized 2H-chromene and isochromene acetals. In addition, an asymmetric variant of diazoacetate addition towards 2H-chromene acetal is described. Continued investigations include the further optimization of asymmetric induction towards the formation of diazo ester substituted 2H-chromene.

| S-EPMC4233145 | 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