Browse
Submit Data
Databases
API
Help

Dataset Information

11 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis and characterization of bis(4-amino-2-bromo-6-methoxy)azobenzene derivatives.

ABSTRACT: Aminoazobenzene derivatives with four ortho substituents with respect to the N-N double bond are a relatively unexplored class of azo compounds that show promise for use as photoswitches in biology. Tetra-ortho-methoxy-substituted aminoazobenzene compounds in particular can form azonium ions under physiological conditions and exhibit red-light photoswitching. Here, we report the synthesis and characterization of two bis(4-amino-2-bromo-6-methoxy)azobenzene derivatives. These compounds form red-light-absorbing azonium ions, but only under very acidic conditions (pH < 1). While the low pK _a makes the azonium form unsuitable, the neutral versions of these compounds undergo trans-to-cis photoisomerization with blue-green light and exhibit slow (?_1/2 ? 10 min) thermal reversion and so may find applications under physiological conditions.

SUBMITTER: Martinez-Lopez D

PROVIDER: S-EPMC6964645 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Synthesis and characterization of bis(4-amino-2-bromo-6-methoxy)azobenzene derivatives.

Martínez-López David D Babalhavaeji Amirhossein A Sampedro Diego D Woolley G Andrew GA

Beilstein journal of organic chemistry 20191230

Aminoazobenzene derivatives with four <i>ortho</i> substituents with respect to the N-N double bond are a relatively unexplored class of azo compounds that show promise for use as photoswitches in biology. Tetra-<i>ortho</i>-methoxy-substituted aminoazobenzene compounds in particular can form azonium ions under physiological conditions and exhibit red-light photoswitching. Here, we report the synthesis and characterization of two bis(4-amino-2-bromo-6-methoxy)azobenzene derivatives. These compou ...[more]

PMID: 31976009

Similar Datasets

4-Bromo-N,N'-bis-(4-methoxy-phen-yl)benzamidine.

Project description:The title compound, C(21)H(19)BrN(2)O(2), is an amidine containing electron-donating meth-oxy groups and a bulky Br atom on the benzene rings. The solid-state structure reveals a non-centrosymmetric mol-ecule, with an E configuration around the C=N double bond. The C-N bonds show distinct amine [1.3689?(19)?Å] and imine [1.285?(2)?Å] characteristics. In the crystal, symmetry-related mol-ecules are linked via a very weak N-H?N inter-action, and C-H?O and C-H?? inter-actions.

| S-EPMC2971424 | biostudies-literature

Bis(2-amino-5-bromo-pyridinium) fumarate dihydrate.

Project description:In the title compound, 2C(5)H(6)BrN(2) (+)·C(4)H(2)O(4) (2-)·2H(2)O, the complete fumarate dianion is generated by crystallographic inversion symmetry. The cation is approximately planar, with a maximum deviation of 0.036 (1) Å. In the anion, the carboxyl-ate group is twisted slightly away from the attached plane; the dihedral angle between carboxyl-ate and (E)-but-2-ene planes is 6.11 (14)°. In the crystal, the carboxyl-ate O atoms form bifurcated (N-H⋯O and C-H⋯O) and N-H⋯O hydrogen bonds with the cations. The crystal packing is stabilized by R(2) (2)(8) ring motifs which are generated by pairs of N-H⋯O hydrogen bonds. The crystal structure is further consolidated by water mol-ecules via O(water)-H⋯O and N-H⋯O(water) hydrogen bonds. The components are linked by these inter-actions into three-dimensional network.

| S-EPMC3007988 | biostudies-literature

1-Bromo-acetyl-2,6-bis-(4-methoxy-phen-yl)-3,5-dimethyl-piperidin-4-one.

Project description:In the title compound, C(23)H(26)BrNO(4), the piperidinone ring adopts a boat conformation. The dihedral angle between the two benzene rings is 70.9?(1)°. The two meth-oxy groups are close to coplanar with the attached benzene rings [C-C-O-C torsion angles of 6.3?(5) and 16.4?(4)°]. A weak C-H?Br intra-molecular inter-action is observed. In the crystal structure, mol-ecules are linked into a chain along [101] by inter-molecular C-H?O hydrogen bonds. A short inter-molecular Br?O contact [3.063?(2)?Å] is observed.

| S-EPMC2959452 | biostudies-literature

Synthesis and Photocontrolled Supramolecular Self-Assembly of Azobenzene-Functionalized Perylene Bisimide Derivatives.

Project description:Azobenzene (Azo) units were successfully introduced into perylene bisimide (PBI) structures in order to realize the photocontrolling of the morphology of the supramolecular assembly of PBI by a photoisomerization process. A total of three Azo-functionalized perylene bisimide derivatives (PBI1, PBI2, and PBI3) with different alkyl chain lengths were designed and synthesized by imidization of 3,4,9,10-perylene tetracarboxylic dianhydride with the corresponding amines. The structures of these compounds were characterized by proton nuclear magnetic resonance (1H NMR) and matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF-MS). The photoisomerization behaviors of Azo units in PBIs were investigated using ultraviolet-visible (UV-VIS) absorption spectroscopy, which were obviously effected by solvents and the alkyl chain length. Furthermore, the photoisomerization of Azo units has the obviously regulatory effect on the morphology of supramolecular assembly of PBIs, especially for the medium-length alkyl chain-linked Azo-functionalized PBI derivative (PBI2). This research realized the photocontrolling of the morphology of the supramolecular assembly of PBI derivatives by photoisomerization of Azo units.

| S-EPMC6681406 | biostudies-literature

rac-2-Bromo-3-eth-oxy-1,3-bis-(4-methoxy-phen-yl)propan-1-one.

Project description:In the racemic (S,S/R,R) title compound, C(19)H(21)BrO(4), the two benzene rings are almost coplanar to each other, forming a dihedral angle of 3.58 (10)°. The crystal packing is strengthened by inter-molecular Br-O [2.9800 (16) Å] short contacts, which link the molecules into infinite one-dimensional chains along [001].

| S-EPMC2967939 | biostudies-literature

Synthesis and Characterization of Bis-Triazolyl-Pyridine Derivatives as Noncanonical DNA-Interacting Compounds.

Project description:Besides the well-known double-helical conformation, DNA is capable of folding into various noncanonical arrangements, such as G-quadruplexes (G4s) and i-motifs (iMs), whose occurrence in gene promoters, replication origins, and telomeres highlights the breadth of biological processes that they might regulate. Particularly, previous studies have reported that G4 and iM structures may play different roles in controlling gene transcription. Anyway, molecular tools able to simultaneously stabilize/destabilize those structures are still needed to shed light on what happens at the biological level. Herein, a multicomponent reaction and a click chemistry functionalization were combined to generate a set of 31 bis-triazolyl-pyridine derivatives which were initially screened by circular dichroism for their ability to interact with different G4 and/or iM DNAs and to affect the thermal stability of these structures. All the compounds were then clustered through multivariate data analysis, based on such capability. The most promising compounds were subjected to a further biophysical and biological characterization, leading to the identification of two molecules simultaneously able to stabilize G4s and destabilize iMs, both in vitro and in living cells.

| S-EPMC8584640 | biostudies-literature

4-Bromo-8-methoxy-quinoline.

Project description:The non-H atoms of the title mol-ecule, C(10)H(8)BrNO, are essentially coplanar. In the crystal structure, mol-ecules are linked by weak inter-molecular C-H??(arene) inter-actions, forming one-dimensional chains along the a axis.

| S-EPMC2961403 | biostudies-literature

Synthesis and Site-Specific Incorporation of Red-Shifted Azobenzene Amino Acids into Proteins.

Project description:A series of red-shifted azobenzene amino acids were synthesized in moderate-to-excellent yields via a two-step procedure in which tyrosine derivatives were first oxidized to the corresponding quinonoidal spirolactones followed by ceric ammonium nitrate-catalyzed azo formation with the substituted phenylhydrazines. The resulting azobenzene-alanine derivatives exhibited efficient trans/cis photoswitching upon irradiation with a blue (448 nm) or green (530 nm) LED light. Moreover, nine superfolder green fluorescent protein (sfGFP) mutants carrying the azobenzene-alanine analogues were expressed in E. coli in good yields via amber codon suppression with an orthogonal tRNA/PylRS pair, and one of the mutants showed durable photoswitching with the LED light.

| S-EPMC4685939 | biostudies-literature

Methoxy-Substituted Tyramine Derivatives Synthesis, Computational Studies and Tyrosinase Inhibitory Kinetics.

Project description:Targeting tyrosinase for melanogenesis disorders is an established strategy. Hydroxyl-substituted benzoic and cinnamic acid scaffolds were incorporated into new chemotypes that displayed in vitro inhibitory effects against mushroom and human tyrosinase for the purpose of identifying anti-melanogenic ingredients. The most active compound 2-((4-methoxyphenethyl)amino)-2-oxoethyl (E)-3-(2,4-dihydroxyphenyl) acrylate (Ph9), inhibited mushroom tyrosinase with an IC50 of 0.059 nM, while 2-((4-methoxyphenethyl)amino)-2-oxoethyl cinnamate (Ph6) had an IC50 of 2.1 nM compared to the positive control, kojic acid IC50 16700 nM. Results of human tyrosinase inhibitory activity in A375 human melanoma cells showed that compound (Ph9) and Ph6 exhibited 94.6% and 92.2% inhibitory activity respectively while the positive control kojic acid showed 72.9% inhibition. Enzyme kinetics reflected a mixed type of inhibition for inhibitor Ph9 (Ki 0.093 nM) and non-competitive inhibition for Ph6 (Ki 2.3 nM) revealed from Lineweaver-Burk plots. In silico docking studies with mushroom tyrosinase (PDB ID:2Y9X) predicted possible binding modes in the catalytic site for these active compounds. Ph9 displayed no PAINS (pan-assay interference compounds) alerts. Our results showed that compound Ph9 is a potential candidate for further development of tyrosinase inhibitors.

| S-EPMC8122972 | biostudies-literature

4-amino bis-pyridinium derivatives as novel antileishmanial agents.

Project description:The antileishmanial activity of a series of bis-pyridinium derivatives that are analogues of pentamidine have been investigated, and all compounds assayed were found to display activity against promastigotes and intracellular amastigotes of Leishmania donovani and Leishmania major, with 50% effective concentrations (EC50s) lower than 1 ?M in most cases. The majority of compounds showed similar behavior in both Leishmania species, being slightly more active against L. major amastigotes. However, compound VGP-106 {1,1'-(biphenyl-4,4'-diylmethylene)bis[4-(4-bromo-N-methylanilino)pyridinium] dibromide} exhibited significantly higher activity against L. donovani amastigotes (EC50, 0.86 ± 0.46 ?M) with a lower toxicity in THP-1 cells (EC50, 206.54 ± 9.89 ?M). As such, VGP-106 was chosen as a representative compound to further elucidate the mode of action of this family of inhibitors in promastigote forms of L. donovani. We have determined that uptake of VGP-106 in Leishmania is a temperature-independent process, suggesting that the compound crosses the parasite membrane by diffusion. Transmission electron microscopy analysis showed a severe mitochondrial swelling in parasites treated with compound VGP-106, which induces hyperpolarization of the mitochondrial membrane potential and a significant decrease of intracellular free ATP levels due to the inhibition of ATP synthesis. Additionally, we have confirmed that VGP-106 induces mitochondrial ROS production and an increase in intracellular Ca(2+) levels. All these molecular events can activate the apoptotic process in Leishmania; however, propidium iodide assays gave no indication of DNA fragmentation. These results underline the potency of compound VGP-106, which may represent a new avenue for the development of novel antileishmanial compounds.

| S-EPMC4068582 | 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