Relationship between chemical structure and biological activity of alkali metal o-, m- and p-anisates. FT-IR and microbiological studies

Synthesis of new heterocyclic compounds containing four five-membered rings together was the main goal of this work. The new derivatives of [tetrakis (1,2,4-triazole /1,3,4-thiadiazole /1,3,4-oxadiazole][bis-(benzene-1,3,5-triyl)] dioxymethylene A7-A18 were synthesized by the reaction of [bis-(dimethyl 5-yl-isophthalate)] dioxymethylene compound A1 which was previously prepared from the reaction of 1,2-dibromomethan and dimethyl 5-hydroxyisophthalate, then treated with hydrazine hydrate to yield the corresponding acid hydrazide A2. In the next step, compound A2 was refluxed with 4-substituted isothiocyanate to give substituted thiosemicarbazides A3-A6. The treatment of the latter compounds in basic medium of 2M of NaOH afforded 1,2,4-Triazole derivatives A7-A10. Whereas the reaction of the same compounds with concentrated sulfuric acid gave 1,3,4-thiadiazoles A11-A14. Furthermore, the new derivatives of 1,3,4-oxadiazole A15-A18 were obtained by the reaction of thiosemicarbazides and tosyl chloride in presence of pyridine. (C. H. N.) elemental analysis, FT-IR, and 1HNMR techniques were used to characterize the chemical structure of some of the new synthesized compounds which also exhibited an important biological activity.

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Spectroscopic characteristic (FT-IR, FT-Raman, UV, 1H and 13C NMR), theoretical calculations and biological activity of alkali metal homovanillates

Journal of Molecular Structure ◽

10.1016/j.molstruc.2015.12.062 ◽

2016 ◽

Vol 1109 ◽

pp. 1-12 ◽

Cited By ~ 1

Author(s):

M. Samsonowicz ◽

M. Kowczyk-Sadowy ◽

J. Piekut ◽

E. Regulska ◽

W. Lewandowski

Keyword(s):

Biological Activity ◽

Alkali Metal ◽

13C Nmr ◽

Theoretical Calculations ◽

Spectroscopic Characteristic ◽

1H And 13C Nmr ◽

Ft Ir ◽

Ft Raman

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Faculty Opinions recommendation of Chemical structure and biological activity of the Caenorhabditis elegans dauer-inducing pheromone.

Faculty Opinions – Post-Publication Peer Review of the Biomedical Literature ◽

10.3410/f.1007436.284717 ◽

2005 ◽

Author(s):

Linda Huang

Keyword(s):

Biological Activity ◽

Caenorhabditis Elegans ◽

Chemical Structure

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Preparation and Characterization of Soybean Oil-based Flame Retardant Rigid Polyurethane Foams Containing Phosphaphenanthrene Groups

Letters in Organic Chemistry ◽

10.2174/1570178617666200224104336 ◽

2020 ◽

Vol 17 (10) ◽

pp. 760-771

Author(s):

Qirui Gong ◽

Niangui Wang ◽

Kaibo Zhang ◽

Shizhao Huang ◽

Yuhan Wang

Keyword(s):

Soybean Oil ◽

Flame Retardant ◽

Chemical Structure ◽

Cell Structure ◽

Polyurethane Foams ◽

Limiting Oxygen Index ◽

Rigid Polyurethane Foams ◽

Degradation Activation Energy ◽

Ft Ir

A phosphaphenanthrene groups containing soybean oil based polyol (DSBP) was synthesized by epoxidized soybean oil (ESO) and 9,10-dihydro-oxa-10-phosphaphenanthrene-10-oxide (DOPO). Soybean oil based polyol (HSBP) was synthesized by ESO and H2O. The chemical structure of DSBP and HSBP were characterized with FT-IR and 1H NMR. The corresponding rigid polyurethane foams (RPUFs) were prepared by mixing DSBP with HSBP. The results revealed apparent density and compression strength of RPUFs decreased with increasing the DSBP content. The cell structure of RPUFs was examined by scanning electron microscope (SEM) which displayed the cells as spherical or polyhedral. The thermal degradation and flame retardancy of RPUFs were investigated by thermogravimetric analysis, limiting oxygen index (LOI), and UL 94 vertical burning test. The degradation activation energy (Ea) of first degradation stage reduced from 80.05 kJ/mol to 37.84 kJ/mol with 80 wt% DSBP. The RUPF with 80 wt% DSBP achieved UL94 V-0 rating and LOI 28.3. The results showed that the flame retardant effect was mainly in both gas phase and condensed phase.

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Synthesis of New α-Amino Phosphonates Containing 3-Amino-4(3H) Quinazolinone Moiety as Anticancer and Antimicrobial Agents: DFT, NBO, and Vibrational Studies

Current Organic Synthesis ◽

10.2174/1570179414666170703141629 ◽

2018 ◽

Vol 15 (2) ◽

pp. 286-296 ◽

Cited By ~ 4

Author(s):

Mohamed K. Awad ◽

Mahmoud F. Abdel-Aal ◽

Faten M. Atlam ◽

Hend A. Hekal

Keyword(s):

Biological Activity ◽

Cell Line ◽

Quantum Chemical ◽

Density Functional ◽

Carcinoma Cell ◽

Liver Carcinoma ◽

Anticancer Activities ◽

Functional Theory ◽

Ft Ir ◽

Good Agreement

Aim and Objective: Synthesis of new .-aminophosphonates containing quinazoline moiety through Kabachnik-Fields reaction in the presence of copper triflate catalyst [32], followed by studying their antimicrobial activities and in vitro anticancer activities against liver carcinoma cell line (HepG2) with the hope that new anticancer agents could be developed. Also, the quantum chemical calculations are performed using density functional theory (DFT) to study the effect of the changes of molecular and electronic structures on the biological activity of the investigated compounds. Materials and Method: The structures of the synthesized compounds are confirmed by FT-IR, 1H NMR, 13C NMR, 31P NMR and MS spectral data. The synthesized compounds show significant antimicrobial and also remarkable cytotoxicity anticancer activities against liver carcinoma cell line (HepG2). Density functional theory (DFT) was performed to study the effect of the molecular and electronic structure changes on the biological activity. Results: It was found that the electronic structure of the substituents affects on the reaction yield. The electron withdrawing substituent, NO2 group 3b, on the aromatic aldehydes gave a good yield more than the electron donating substituent, OH group 3c. The electron deficient on the carbon atom of the aldehydic group may increase the interaction of the Lewis acid (Cu(OTf)2) and the Lewis base (imine nitrogen), and accordingly, facilitate the formation of imine easily, which is attacked by the nucleophilic phosphite species to give the α- aminophosphonates. Conclusion: The newly synthesized compounds exhibit a remarkable inhibition of the growth of Grampositive, Gram-negative bacteria and fungi at low concentrations. The cytotoxicity of the synthesized compounds showed a significant cytotoxicity against the liver cancer cell line (HepG 2). Also, it was shown from the quantum chemical calculations that the electron-withdrawing substituent increases the biological activity of the α-aminophosphonates more than the electron donating group which was in a good agreement with the experimental results. Also, a good agreement between the experimental FT-IR and the calculated one was found.

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5-((8-Hydroxyquinolin-5-yl)diazenyl)-3-methyl-1H-pyrazole-4-carboxylic Acid

Molbank ◽

10.3390/m1238 ◽

2021 ◽

Vol 2021 (2) ◽

pp. M1238

Author(s):

Ion Burcă ◽

Valentin Badea ◽

Calin Deleanu ◽

Vasile-Nicolae Bercean

Keyword(s):

Chemical Structure ◽

Functional Group ◽

Coupling Reaction ◽

2D Nmr ◽

Azo Coupling ◽

2D Nmr Spectroscopy ◽

Azo Compound ◽

Ft Ir ◽

New Compounds ◽

Carboxylic Functional Group

A new azo compound was prepared via the azo coupling reaction between 4-(ethoxycarbonyl)-3-methyl-1H-pyrazole-5-diazonium chloride and 8-hydroxyquinoline (oxine). The ester functional group of the obtained compound was hydrolyzed and thus a new chemical structure with a carboxylic functional group resulted. The structures of the new compounds were fully characterized by: UV–Vis, FT-IR, 1D and 2D NMR spectroscopy, and HRMS spectrometry.

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Electrochemically Produced Copolymers of Pyrrole and Its Derivatives: A Plentitude of Material Properties Using “Simple” Heterocyclic Co-Monomers

Materials ◽

10.3390/ma14020281 ◽

2021 ◽

Vol 14 (2) ◽

pp. 281

Author(s):

Tomasz Jarosz ◽

Przemyslaw Ledwon

Keyword(s):

Biological Activity ◽

Material Properties ◽

Building Block ◽

Conjugated Polymer ◽

Chemical Structure ◽

Heterocyclic System ◽

Repeat Unit ◽

Polymeric Materials ◽

Pyrrole Derivatives ◽

Pyrrole Monomer

Polypyrrole is a classical, well-known conjugated polymer that is produced from a simple heterocyclic system. Numerous pyrrole derivatives exhibit biological activity, and the repeat unit is a common building block present in the chemical structure of many polymeric materials, finding wide application, primarily in optoelectronics and sensing. In this work, we focus on the variety of copolymers and their material properties that can be produced electrochemically, even though all these systems are obtained from mixtures of the “simple” pyrrole monomer and its derivatives with different conjugated and non-conjugated species.

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Chemical Structure and Biological Activity of Humic Substances Define Their Role as Plant Growth Promoters

Molecules ◽

10.3390/molecules26082256 ◽

2021 ◽

Vol 26 (8) ◽

pp. 2256

Author(s):

Serenella Nardi ◽

Michela Schiavon ◽

Ornella Francioso

Keyword(s):

Biological Activity ◽

Humic Substances ◽

Chemical Structure ◽

Molecular Size ◽

Growth Promoters ◽

Root Cells ◽

Sustainable Technologies ◽

Intracellular Signals ◽

Key Functional Groups ◽

Regulatory Functions

Humic substances (HS) are dominant components of soil organic matter and are recognized as natural, effective growth promoters to be used in sustainable agriculture. In recent years, many efforts have been made to get insights on the relationship between HS chemical structure and their biological activity in plants using combinatory approaches. Relevant results highlight the existence of key functional groups in HS that might trigger positive local and systemic physiological responses via a complex network of hormone-like signaling pathways. The biological activity of HS finely relies on their dosage, origin, molecular size, degree of hydrophobicity and aromaticity, and spatial distribution of hydrophilic and hydrophobic domains. The molecular size of HS also impacts their mode of action in plants, as low molecular size HS can enter the root cells and directly elicit intracellular signals, while high molecular size HS bind to external cell receptors to induce molecular responses. Main targets of HS in plants are nutrient transporters, plasma membrane H+-ATPases, hormone routes, genes/enzymes involved in nitrogen assimilation, cell division, and development. This review aims to give a detailed survey of the mechanisms associated to the growth regulatory functions of HS in view of their use in sustainable technologies.

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Biological Activity of Humic Substances Is Related to Their Chemical Structure

Soil Science Society of America Journal ◽

10.2136/sssaj2006.0055 ◽

2007 ◽

Vol 71 (1) ◽

pp. 75-85 ◽

Cited By ~ 57

Author(s):

Adele Muscolo ◽

Maria Sidari ◽

Emilio Attinà ◽

Ornella Francioso ◽

Vitaliano Tugnoli ◽

...

Keyword(s):

Biological Activity ◽

Humic Substances ◽

Chemical Structure

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1H-NMR Analysis of Degree of Substitution in N,O-Carboxymethyl Chitosans from Various Chitosan Sources and Types

Advanced Materials Research ◽

10.4028/www.scientific.net/amr.506.158 ◽

2012 ◽

Vol 506 ◽

pp. 158-161 ◽

Cited By ~ 5

Author(s):

A. Jaidee ◽

Pornchai Rachtanapun ◽

S. Luangkamin

Keyword(s):

Chemical Structure ◽

Carboxymethyl Chitosan ◽

Degree Of Substitution ◽

Resonance Spectroscopy ◽

Nmr Analysis ◽

Reaction Conditions ◽

H Nmr ◽

Fourier Transformed Infrared Spectroscopy ◽

Chitosan Oligomer ◽

Ft Ir

N,O-Carboxymethyl chitosans were synthesized by the reaction between shrimp, crab and squid chitosans with monochloroacetic acid under basic conditions at 50°C. The mole ratio of reactants was obtained from various reaction conditions of shrimp chitosan polymer and oligomer types. The mole ratio 1:12:6 of chitosan:sodium hydroxide:monochloroacetic acid was used for preparing carboxymethyl of chitosan polymer types while carboxymethyl of chitosan oligomer types were used the mole ratio 1:6:3 of chitosan:sodium hydroxide:monochloroacetic acid. The chemical structure was analyzed by fourier transformed infrared spectroscopy (FT-IR) and proton nuclear magnatic resonance spectroscopy (1H-NMR). The FT-IR was used for confirm the insertion of carboxymethyl group on chitosan molecules. The 1H-NMR was used for determining the degree of substitution (DS) of carboxymethylation at hydroxyl and amino sites of chitosans. Carboxymethyl chitosan samples had the total DS of carboxymethylation ranging from 1.0-2.2. The highest of DS of carboxymethylation was from shrimp chitosan oligomer type.

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