Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Sterically shielded pyramidal amino groups in two 4,4'-(arylmethylene)bis(6-allyl-3-chloro-2-methylaniline) derivatives.

ABSTRACT: 4,4'-(Phenylmethylene)bis(6-allyl-3-chloro-2-methylaniline), C(27)H(28)Cl(2)N(2), (I), and 4,4'-(2-thienylmethylene)bis(6-allyl-3-chloro-2-methylaniline), C(25)H(26)Cl(2)N(2)S, (II), adopt similar molecular conformations, although the thienyl group in (II) exhibits orientational disorder over two sets of sites with occupancies of 0.614 (3) and 0.386 (3). The amino groups in both compounds are pyramidal. A single N-H...N hydrogen bond links the molecules of (I) into cyclic centrosymmetric dimers. Molecules of (II) are linked by an ordered C-H...pi(arene) hydrogen bond to form cyclic centrosymmetric dimers, and these dimers are linked into statistically interrupted chains by a second C-H...pi(arene) hydrogen bond involving a donor in the minor component of the disordered thienyl unit.

SUBMITTER: Blanco MC

PROVIDER: S-EPMC2737426 | biostudies-literature | 2009 Sep

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Sterically shielded pyramidal amino groups in two 4,4'-(arylmethylene)bis(6-allyl-3-chloro-2-methylaniline) derivatives.

Blanco Maria C MC Palma Alirio A Bahsas Ali A Hursthouse Michael B MB Cobo Justo J Glidewell Christopher C

Acta crystallographica. Section C, Crystal structure communications 20090826 Pt 9

4,4'-(Phenylmethylene)bis(6-allyl-3-chloro-2-methylaniline), C(27)H(28)Cl(2)N(2), (I), and 4,4'-(2-thienylmethylene)bis(6-allyl-3-chloro-2-methylaniline), C(25)H(26)Cl(2)N(2)S, (II), adopt similar molecular conformations, although the thienyl group in (II) exhibits orientational disorder over two sets of sites with occupancies of 0.614 (3) and 0.386 (3). The amino groups in both compounds are pyramidal. A single N-H...N hydrogen bond links the molecules of (I) into cyclic centrosymmetric dimers. ...[more]

PMID: 19726866

Similar Datasets

Sterically Shielded Hydrophilic Analogs of Indocyanine Green.

Project description:A modular synthetic process enables two or four shielding arms to be appended strategically over the fluorochromes of near-infrared cyanine heptamethine dyes to create hydrophilic analogs of clinically approved indocyanine green. A key synthetic step is the facile substitution of a heptamethine 4'-Cl atom by a phenol bearing two triethylene glycol chains. The lead compound is a heptamethine dye with four shielding arms, and a series of comparative spectroscopy studies showed that the shielding arms (a) increased dye photostability and chemical stability and (b) inhibited dye self-aggregation and association with albumin protein. In mice, the dye cleared from the blood primarily through the renal pathway rather than the biliary pathway for ICG. This change in biodistribution reflects the much smaller hydrodynamic diameter of the shielded hydrophilic ICG analog compared to the 67 kDa size of the ICG/albumin complex. An attractive feature of versatile synthetic chemistry is the capability to systematically alter the dye's hydrodynamic diameter. The sterically shielded hydrophilic ICG dye platform is well-suited for immediate incorporation into dynamic contrast-enhanced (DCE) spectroscopy or imaging protocols using the same cameras and detectors that have been optimized for ICG.

| S-EPMC9894567 | biostudies-literature

Synthesis and reduction kinetics of sterically shielded pyrrolidine nitroxides.

Project description:A series of sterically shielded pyrrolidine nitroxides were synthesized, and their reduction by ascorbate (vitamin C) indicate that nitroxide 3, a tetraethyl derivative of 3-carboxy-PROXYL, is reduced at the slowest rate among known nitroxides, i.e., at a 60-fold slower rate than that for 3-carboxy-PROXYL.

| S-EPMC3486517 | biostudies-literature

?-4,4'-Bipyridine-?N:N'-bis-[bis-(2-chloro-benzoato-?O,O')lead(II)].

Project description:In the title dinuclear complex, [Pb(2)(C(7)H(4)ClO(2))(4)(C(10)H(8)N(2))], the Pb(II) atom is five-coordinated by four carboxyl-ate O atoms from two 2-chloro-benzoate ligands and one N atom from a bridging 4,4'-bipyridine (4,4'-bpy) ligand, displaying a hemi-directed coordination. The 4,4'-bpy ligand has an inversion center at the mid-point of the central C-C bond. The empty side of the metal ion is capped by two carboxyl-ate O atoms from a neighboring mol-ecule, with weak Pb?O contacts [Pb?O = 3.069?(2) and 3.071?(3)?Å]. The crystal structure is stabilized by C-H?O hydrogen bonds and ?-? stacking inter-actions between the benzene and pyridine rings [centroid-centroid distance = 3.749?(3)?Å].

| S-EPMC3152032 | biostudies-literature

3,3'-Bis(chloro-meth-yl)-4,4'-dieth-oxy-1,1'-biphen-yl.

Project description:The asymmetric unit of the title compound, C18H20Cl2O2, consists of a half-mol-ecule, the other half being generated by an inversion center, located at the mid-point of the benzene-benzene bond. Except for the two Cl atoms, all other atoms of the compound are nearly coplanar, with the atomic displacements from the mol-ecular mean plane ranging from 0.0037 (19) to 0.071 (2) Å. The two Cl atoms are in trans positions and are displaced with respect to the mean plane by 1.687 (2) and -1.693 (3) Å. The crystal packing is governed by van der Waals inter-actions.

| S-EPMC3998594 | biostudies-literature

Synthesis of unnatural amino acids functionalized with sterically shielded pyrroline nitroxides.

Project description:A series of unnatural amino acids functionalized with sterically shielded pyrroline nitroxides were synthesized. Their reduction by ascorbate/glutathione indicates that L-cysteine functionalized with gem-diethylpyrroline nitroxide is reduced at the slowest rate and is comparable to that measured for the most resistant to reduction pyrroline and pyrrolidine nitroxides.

| S-EPMC4201325 | biostudies-literature

Synthesis of 4,4'-(arylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ols) and evaluation of their antioxidant and anticancer activities.

Project description:BackgroundPyrazoles have attracted particular attention due to the diverse biological activities associated with this heterocyclic system, and some have been shown to be cytotoxic to several human cell lines. Several drugs currently on the market have this heterocycle as the key structural motif, and some have been approved for the treatment of different types of cancer.Results4,4'-(Arylmethylene)bis(1H-pyrazol-5-ols) derivatives 3a-q were synthetized by a three components reaction of 3-methyl-1-phenyl-5-pyrazolone (1) with various benzaldehydes 2 catalyzed by sodium acetate at room temperature. The structures of all synthesized compounds were characterized by physicochemical properties and spectral means (IR and NMR) and were evaluated for their radical scavenging activity by DPPH assay and tested in vitro on colorectal RKO carcinoma cells in order to determine their cytotoxic properties. All 4,4'-(arylmethylene)bis(1H-pyrazol-5-ols) derivatives 3a-q were synthetized in high to excellent yield, and pure products were isolated by simple filtration. All compounds have good radical scavenging activity, and half of them are more active than ascorbic acid used as standard.ConclusionSeveral derivatives proved to be cytotoxic in the RKO cell line. In particular, compound 3i proved to be a very potent scavenger with an IC50 of 6.2 ± 0.6 µM and exhibited an IC50 of 9.9 ± 1.1 μM against RKO cell. Autophagy proteins were activated as a survival mechanism, whereas the predominant pathway of death was p53-mediated apoptosis.

| S-EPMC8176600 | biostudies-literature

4,4'-Dianilino-3,3'-(4-chloro-benzyl-idene)bis-[furan-2(5H)-one].

Project description:In the mol-ecule of the title compound, C(27)H(21)ClN(2)O(4), the dihedral angle between the furan rings is 67.00?(3)°. The chloro-phenyl ring is oriented at dihedral angles of 76.61?(3) and 69.36?(3)° with respect to the furan rings. An intra-molecular N-H?O inter-action results in the formation of an eight-membered ring with a twisted conformation. In the crystal structure, inter-molecular N-H?O and C-H?O inter-actions link the mol-ecules into a three-dimensional network, forming R(2) (2)(16) ring motifs. Three weak C-H?? inter-actions are also found.

| S-EPMC2969224 | biostudies-literature

Poly(aniline-co-melamine)@MnFe2O4 nanocatalyst for the synthesis of 4,4′-(arylmethylene) bis (1H-pyrazole-5-ol) derivatives, and 1,4- dihydropyrano[2,3-c]pyrazoles and evaluation of their antioxidant, and anticancer activities

Project description:In this work, magnetic poly(aniline-co-melamine) nanocomposite as an efficient heterogeneous polymer-based nanocatalyst was fabricated in two steps. First, poly(aniline-co-melamine) was synthesized through the chemical oxidation by ammonium persulfate, then the magnetic nanocatalyst was successfully prepared from the in-situ coprecipitation method in the presence of poly(aniline-co-melamine). The resulting poly(aniline-co-melamine)@MnFe2O4 was characterized by FTIR, FESEM, XRD, VSM, EDX, TGA, and UV-vis analyses. The catalytic activity of poly(aniline-co-melamine)@MnFe2O4 was investigated in the synthesis of 4,4′-(arylmethylene)bis(1H-pyrazole-5-ol) derivatives, and new alkylene bridging bis 4,4′-(arylmethylene)bis(1H-pyrazole-5-ol) derivatives in excellent yields. The yield of 1,4-dihydropyrano[2,3-c]pyrazoles, 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol), yields, and new alkylene bridging bis 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol) derivatives were obtained 89%–96%, 90%–96%, and 92%–96%, respectively. The poly(aniline-co-melamine)@MnFe2O4 nanocatalyst can be recycled without pre-activation and reloaded up to five consecutive runs without a significant decrease in its efficiency. In addition, the antioxidant activity of some derivatives was evaluated by DPPH assay. Results showed that the maximum antioxidant activity of 4,4′-(arylmethylene)bis(1H-pyrazole-5-ol) derivatives and 1,4-dihydropyrano[2,3-c]pyrazoles were 75% and 90%, respectively. Furthermore, 4,4′-(arylmethylene)bis(1H-pyrazole-5-ol) derivatives and 1,4-dihydropyrano[2,3-c]pyrazoles showed good potential for destroying colon cancer cell lines. Consequently, the poly(aniline-co-melamine)@MnFe2O4 nanocomposite is an excellent catalyst for green chemical processes owing to its high catalytic activity, stability, and reusability.

| S-EPMC9649443 | biostudies-literature

N,N'-Bis(4-chloro-benzyl-idene)-3,3'-dimeth-oxy-biphenyl-4,4'-diamine.

Project description:The title compound, C(28)H(22)Cl(2)N(2)O(2), crystallized with two independent mol-ecules (A and B) in the asymmetric unit. The two mol-ecules differ essentially in the orientation of the outer aromatic rings. These dihedral angles are 56.07?(13) and 27.62?(15)?Å for mol-ecules A and B, respectively. In the crystal, A mol-ecules are related as centrosymmetric pairs through a weak ?-? inter-action [centroid-centroid distance = 3.6959?(15)?Å]. There are also a number of inter-molecular C-H?O, C-H?N and C-H?? inter-actions present.

| S-EPMC3120541 | biostudies-literature

Bis[?-4,4',6,6'-tetra-chloro-2,2'-(piperazine-1,4-diyldimethyl-ene)diphenolato]dicopper(II).

Project description:In the centrosymmetric dinuclear Cu(II) title complex, [Cu(2)(C(18)H(16)Cl(4)N(2)O(2))(2)], the Cu(II) atom adopts a square-pyramidal geometry with a tetra-dentate ligand in the basal plane. The apical site is occupied by a phenolate O atom from an adjacent ligand, forming a dimer. The mol-ecular structure is stabilized by intra-molecular C-H?O and C-H?Cl hydrogen bonds.

| S-EPMC2971750 | 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