Browse
Submit Data
Databases
API
Help

Dataset Information

15 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis, liquid crystalline behaviour and structure-property relationships of 1,3-bis(5-substituted-1,3,4-oxadiazol-2-yl)benzenes.

ABSTRACT: Two series containing 1,3-bis(1,3,4-oxadiazol-2-yl)benzene as a rigid core (RC) and alkyl or perfluoroalkyl as terminal chains were synthesized and characterized. Liquid crystal properties of the synthesized compounds have been investigated by polarizing optical microscopy, differential scanning calorimetry and X-ray diffraction techniques. Conformation effects of the synthesized products on the dipole moments were also investigated.

SUBMITTER: Mabrouki A

PROVIDER: S-EPMC7006484 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Synthesis, liquid crystalline behaviour and structure-property relationships of 1,3-bis(5-substituted-1,3,4-oxadiazol-2-yl)benzenes.

Mabrouki Afef A Fouzai Malek M Soldera Armand A Kriaa Abdelkader A Hedhli Ahmed A

Beilstein journal of organic chemistry 20200131

Two series containing 1,3-bis(1,3,4-oxadiazol-2-yl)benzene as a rigid core (RC) and alkyl or perfluoroalkyl as terminal chains were synthesized and characterized. Liquid crystal properties of the synthesized compounds have been investigated by polarizing optical microscopy, differential scanning calorimetry and X-ray diffraction techniques. Conformation effects of the synthesized products on the dipole moments were also investigated. ...[more]

PMID: 32082434

Similar Datasets

Design, synthesis, and analysis of antagonists of GPR55: Piperidine-substituted 1,3,4-oxadiazol-2-ones.

Project description:A series of 1,3,4-oxadiazol-2-ones was synthesized and tested for activity as antagonists at GPR55 in cellular beta-arrestin redistribution assays. The synthesis was designed to be modular in nature so that a sufficient number of analogues could be rapidly accessed to explore initial structure-activity relationships. The design of analogues was guided by the docking of potential compounds into a model of the inactive form of GPR55. The results of the assays were used to learn more about the binding pocket of GPR55. With this oxadiazolone scaffold, it was determined that modification of the aryl group adjacent to the oxadiazolone ring was often detrimental and that the distal cyclopropane was beneficial for activity. These results will guide further exploration of this receptor.

| S-EPMC4836065 | biostudies-literature

1,3-Bis{[5-(pyridin-2-yl)-1,3,4-oxadiazol-2-yl]sulfan-yl}propan-2-one.

Project description:In the distorted W-shaped mol-ecule of the title compound, C(17)H(12)N(6)O(3)S(2), a twofold axis passes through the carbonyl group. The mol-ecules stack in the crystal through ?-? inter-actions [centroid-centroid distance = 3.883?Å] and weak C-H?N hydrogen-bonding inter-actions, forming a three-dimensional architecture.

| S-EPMC3051430 | biostudies-literature

5-Phenyl-1,3,4-oxadiazol-2-amine.

Project description:In the title complex, C(8)H(7)N(3)O, the C-O [1.369?(2) and 1.364?(3)?Å] and C=N [1.285?(3) and 1.289?(3)?Å] bond lengths in the oxadiazole ring are each almost identical within systematic errors, although different substituents are attached to the ring. The phenyl ring is inclined to the planar oxadiazole ring [r.m.s. deviation 0.002?Å] by 13.42?(18)°. In the crystal, molecules are linked via N-H?N hydrogen bonds, forming double-stranded chains propagating along [010].

| S-EPMC3470405 | biostudies-literature

Synthesis and anticancer activity of N-aryl-5-substituted-1,3,4-oxadiazol-2-amine analogues.

Project description:In continuance of our search for anticancer agents, we report herein the synthesis and anticancer activity of some novel oxadiazole analogues. The compounds were screened for anticancer activity as per National Cancer Institute (NCI US) protocol on leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancers cell lines. N-(2,4-Dimethylphenyl)-5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-amine (4s) showed maximum activity with mean growth percent (GP) of 62.61 and was found to be the most sensitive on MDA-MB-435 (melanoma), K-562 (leukemia), T-47D (breast cancer), and HCT-15 (colon cancer) cell lines with GP of 15.43, 18.22, 34.27, and 39.77, respectively. Maximum GP was observed on MDA-MB-435 (melanoma) cell line (GP = 6.82) by compound N-(2,4-dimethylphenyl)-5-(4-hydroxyphenyl)-1,3,4-oxadiazol-2-amine (4u).

| S-EPMC4058187 | biostudies-other

2,6-Dimethyl-4-(1,3,4-oxadiazol-2-yl)quinoline.

Project description:The title compound, C(13)H(11)N(3)O, a potential chemotherapeutic agent, contains a essential planar [maximum deviation = 0.0144?(14)?Å] quinoline moiety. The quinoline ring system and the five-membered heterocycle form a dihedral angle of 7.81?(6)°. In the crystal, inter-molecular non-classical C-H?N hydrogen bonding is present.

| S-EPMC3011631 | biostudies-literature

Cytotoxic effect, enzyme inhibition, and in silico studies of some novel N-substituted sulfonyl amides incorporating 1,3,4-oxadiazol structural motif.

Project description:The acetylcholinesterase and carbonic anhydrase inhibitors (AChEIs and hCAIs) remain key therapeutic agents for many bioactivities such as anti-Alzheimer and antiobesity antiepileptic, anticancer, antiinfective, antiglaucoma, and diuretic effects. Here, it has been attempted to discover novel multi-target AChEIs and hCAIs that are highly potent, orally bioavailable, may be brain penetrant, and have higher effectiveness at lower doses than tacrine and acetazolamide. After detailed investigations both in vitro and in silico, novel N-substituted sulfonyl amide derivatives (6a-j) were determined to be highly potent inhibitors for AChE and hCAs (KIs are in the range of 23.11-52.49 nM, 18.66-59.62 nM, and 9.33-120.80 nM for AChE, hCA I, and hCA II, respectively). Moreover, according to the cytotoxic effect studies, such as the ADME-Tox, cortex neuron cells, and neuroblastoma SH-SY5Y cell line, compounds 6a, 6d, and 6h, which are the most potent representative versus the target enzymes, were identified as orally bioavailable, highly selective, and brain preferentially distributed AChEIs and hCAIs. The docking studies revealed precise binding modes between 6a, 6d, and 6h and hCA II, hCA I, and AChE, respectively. The results presented here might provide a solid basis for further investigation into more potent AChEIs and hCAIs.

| S-EPMC8994094 | biostudies-literature

5-(4-Methyl-phen-yl)-1,3,4-oxadiazol-2-amine.

Project description:In the crystal structure of the title compound, C(9)H(9)N(3)O, adjacent mol-ecules are linked through N-H?N hydrogen bonds into a three-dimensional network.

| S-EPMC3379265 | biostudies-literature

Ethyl 2-(5-phenyl-1,3,4-oxadiazol-2-ylsulfan-yl)acetate.

Project description:The title mol-ecule, C(12)H(12)N(2)O(3)S, is composed of two individually planar units, viz. 5-phenyl-1,3,4-oxadiazol-2-yl-sulfanyl and ethyl acetate, which are oriented at almost right angles [80.07?(8)°] with respect to each other. The structure is stabilized by weak inter-molecular C-H?O and C-H?N hydrogen bonds. The phenyl and oxadiazole rings show ?-? stacking inter-actions [centroid-centroid distance = 3.846?(2)?Å] and there is also a short ?-inter-action between the carbonyl O atom and the oxadiazole ring [the distance from this O atom to the centroid of the oxadiazole ring is 3.156?(2)?Å].

| S-EPMC2961061 | biostudies-literature

Accurate Analysis of Anisotropic Carrier Mobility and Structure-property Relationships in Organic BOXD Crystalline Materials.

Project description:Charge mobility is an essential factor of organic crystalline materials. Although many investigators have made important progress, the exact relationship between the crystal structure and carrier mobility remains to be clarified. Fortunately, a series of bis-1,3,4-oxadiazole derivatives have been successfully prepared and reported. They have similar main molecular fragments but different crystal packing modes, which provide an ideal research objective for studying the effect of molecular packing on charge mobility in organic photoelectric conversion systems. In this work, the charge mobilities of these molecules are systematically evaluated from the perspective of first-principles calculation, and the effect of a molecular overlap on orbital overlap integral and final charge carrier mobility is fully discussed. It can be seen that the small intermolecular distance (less than 6 Å) is the decisive factor to achieve high electron mobility in π stacking, and better mobility can be obtained by increasing the hole migration distance appropriately. A larger dihedral angle of anisotropy is an important point limiting the charge mobility in the herringbone arrangement. It is hoped that the correlation results between the crystal structure and mobility can assist the experimental study and provide an effective way to improve the photoelectric conversion efficiency of the organic semiconductor devices and multiple basis for multiscale material system characterization and material information.

| S-EPMC8631907 | biostudies-literature

4-[5-(Pyridin-4-yl)-1,3,4-oxadiazol-2-yl]pyridinium benzoate.

Project description:In the title compound, C(12)H(9)N(4)O(+)·C(7)H(5)O(2) (-), ?-? stacking inter-actions [centroid-centroid distance = 3.6275?(14) ?Å] stabilize the crystal structure. The dihedral angles between the central ring and the terminal rings are 3.27?(12) and 10.30?(13)°.

| S-EPMC3051668 | 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