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An expeditious synthetic approach towards the synthesis of Bis-Schiff bases (aldazines) using ultrasound

Khan KM, Jamil W, Ambreen N, Taha M, Perveen S, Morales GA

Ultrason Sonochem, 2014 May;21(3):1200-5.
PMID: 24398059 DOI: 10.1016/j.ultsonch.2013.12.011

Aldazines (Bis-Schiff bases) 1-24 were synthesized using aromatic aldehydes (heterocyclic and benzaldehydes) and hydrazine hydrate under reflux using conventional heating and/or via ultrasound irradiation using BiCl3 as catalyst. Ultrasonication conditions with cat. BiCl3 proved to be an effective, environmentally friendly synthetic procedure. This methodology is robust in the presence of electron donating and electron withdrawing groups affording desired products with high yields (>95%) in just a couple of minutes vs. hours using conventional heating.

Matched MeSH terms: Chemistry Techniques, Synthetic/methods*
Fulltext Synthesis and characterization of the inclusion complex of dicationic ionic liquid and β-cyclodextrin

Subramaniam P, Mohamad S, Alias Y

Int J Mol Sci, 2010 Sep 28;11(10):3675-85.
PMID: 21152293 DOI: 10.3390/ijms11103675

The supramolecular structure of the inclusion complex of β-cyclodextrin (β-CD) with 1,1',2,2'-tetramethyl-3,3'-(p-phenylenedimethylene) diimidazolium dibromide (TetraPhimBr), a dicationic ionic liquid, has been investigated. The inclusion complex with 1:1 molar ratio was prepared by a kneading method. Fourier transform infrared spectroscopy (FTIR), powder X-ray diffraction (XRD) analysis, (1)H NMR and thermogravimetric analysis (TGA) confirmed the formation of the inclusion complex. The results showed that the host-guest system is a fine crystalline powder. The decomposition temperature of the inclusion complex is lower than that of its parent molecules, TetraPhimBr and β-CD individually.

Matched MeSH terms: Chemistry Techniques, Synthetic/methods
Fulltext Characterization of modified tapioca starch solutions and their sprays for high temperature coating applications

Naz MY, Sulaiman SA, Ariwahjoedi B, Shaari KZ

ScientificWorldJournal, 2014;2014:375206.
PMID: 24592165 DOI: 10.1155/2014/375206

The objective of the research was to understand and improve the unusual physical and atomization properties of the complexes/adhesives derived from the tapioca starch by addition of borate and urea. The characterization of physical properties of the synthesized adhesives was carried out by determining the effect of temperature, shear rate, and mass concentration of thickener/stabilizer on the complex viscosity, density, and surface tension. In later stage, phenomenological analyses of spray jet breakup of heated complexes were performed in still air. Using a high speed digital camera, the jet breakup dynamics were visualized as a function of the system input parameters. The further analysis of the grabbed images confirmed the strong influence of the input processing parameters on full cone spray patternation. It was also predicted that the heated starch adhesive solutions generate a dispersed spray pattern by utilizing the partial evaporation of the spraying medium. Below 40°C of heating temperature, the radial spray cone width and angle did not vary significantly with increasing Reynolds and Weber numbers at early injection phases leading to increased macroscopic spray propagation. The discharge coefficient, mean flow rate, and mean flow velocity were significantly influenced by the load pressure but less affected by the temperature.

Matched MeSH terms: Chemistry Techniques, Synthetic/instrumentation
Comparative study of the oxidative and physical stability of liposomal and nanoliposomal polyunsaturated fatty acids prepared with conventional and Mozafari methods

Rasti B, Jinap S, Mozafari MR, Yazid AM

Food Chem, 2012 Dec 15;135(4):2761-70.
PMID: 22980870 DOI: 10.1016/j.foodchem.2012.07.016

The relative oxidative stability of freshly prepared and stored liposomal and nanoliposomal systems of docosahexaenoic acid (DHA, 22:6 n-3) and eicosapentaenoic acid (EPA, 20:5 n-3) were investigated. The effects of organic solvents on the oxidative stability of liposomal polyunsaturated fatty acids (PUFAs) produced by two methods, the Bangham thin-film hydration (conventional rotary evaporation method and using organic solvents) and Mozafari (direct hydration and without using organic solvents) methods, were compared. The highest physicochemical stability was observed in PUFA liposomes prepared by the Mozafari method, followed by conventional liposomes and bulk PUFAs. There was no significant change in physicochemical stability during 10 months of cold storage (4°C) in the dark. Moreover, the comparison between liposomes (>200 nm) and nanoliposomes (50-200 nm) revealed that the surface charge, physical stability and oxidative stability of liposomal PUFAs increased as the size of the liposomes decreased. The differences in the oxidative stability of PUFAs may be due to the protective effects of aqueous systems, which indicate the advantage of using non-organic solvent (water and CO(2)) techniques in liposome manufacturing.

Matched MeSH terms: Chemistry Techniques, Synthetic/methods*
Synthesis and applications of graphene-based TiO(2) photocatalysts

Tan LL, Chai SP, Mohamed AR

ChemSusChem, 2012 Oct;5(10):1868-82.
PMID: 22987439 DOI: 10.1002/cssc.201200480

Graphene is one of the most promising materials in the field of nanotechnology and has attracted a tremendous amount of research interest in recent years. Due to its large specific surface area, high thermal conductivity, and superior electron mobility, graphene is regarded as an extremely attractive component for the preparation of composite materials. At the same time, the use of photocatalysts, particularly TiO(2), has also been widely studied for their potential in addressing various energy and environmental-related issues. However, bare TiO(2) suffers from low efficiency and a narrow light-response range. Therefore, the combination of graphene and TiO(2) is currently one of the most active interdisciplinary research areas and demonstrations of photocatalytic enhancement are abundant. This Review presents and discusses the current development of graphene-based TiO(2) photocatalysts. The theoretical framework of the composite, the synthetic strategies for the preparation and modification of graphene-based TiO(2) photocatalysts, and applications of the composite are reviewed, with particular attention on the photodegradation of pollutants and photocatalytic water splitting for hydrogen generation.

Matched MeSH terms: Chemistry Techniques, Synthetic/methods*
Synthesis and biological evaluation of chalcone derivatives (mini review)

Bukhari SN, Jasamai M, Jantan I

Mini Rev Med Chem, 2012 Nov;12(13):1394-403.
PMID: 22876958

Chalcones are the principal precursors for the biosynthesis of flavonoids and isoflavonoids. A three carbon α, β-unsaturated carbonyl system constitutes chalcones. Chalcones are the condensation products of aromatic aldehyde with acetophenones in attendance of catalyst. They go through an assortment of chemical reactions and are found advantageous in synthesis of pyrazoline, isoxazole and a variety of heterocyclic compounds. In synthesizing a range of therapeutic compounds, chalcones impart key role. They have showed worth mentioning therapeutic efficacy for the treatment of various diseases. Chalcone based derivatives have gained heed since they own simple structures, and diverse pharmacological actions. A lot of methods and schemes have been reported for the synthesis of these compounds. Amongst all, Aldol condensation and Claisen-Schmidt condensation still grasp high up position. Other distinguished techniques include Suzuki reaction, Witting reaction, Friedel-Crafts acylation with cinnamoyl chloride, Photo-Fries rearrangement of phenyl cinnamates etc. These inventive techniques utilize various catalysts and reagents including SOCl(2) natural phosphate, lithium nitrate, amino grafted zeolites, zinc oxide, water, Na(2)CO(3), PEG400, silicasulfuric acid, ZrCl(4) and ionic liquid etc. The development of better techniques for the synthesis of α, β- unsaturated carbonyl compounds is still in high demand. In brief, we have explained the methods and catalysts used in the synthesis of chalcones along with their biological activities in a review form to provide information for the development of new-fangled processes targeting better yield, less reaction time and least side effects with utmost pharmacological properties.

Matched MeSH terms: Chemistry Techniques, Synthetic/methods*
ZnAlMCM-41: a very ecofriendly and reusable solid acid catalyst for the highly selective synthesis of 1,3-dioxanes by the Prins cyclization of olefins

Selvaraj M, Assiri MA, Singh H, Appaturi JN, Subrahmanyam C, Ha CS

Dalton Trans, 2021 Jan 21.
PMID: 33475664 DOI: 10.1039/d0dt04158k

The Prins cyclization of styrene (SE) with paraformaldehyde (PFCHO) was conducted with mesoporous ZnAlMCM-41 catalysts for the synthesis of 4-phenyl-1,3-dioxane (4-PDO) using a liquid phase heterogeneous catalytic method. For a comparison study, the Prins cyclization reaction was also conducted over different nanoporous catalysts, e.g. mesoporous solid acid catalysts, AlMCM-41(21) and ZnMCM-41(21), and microporous catalysts, USY, Hβ, HZSM-5, and H-mordenite. The recyclable mesoporous ZnAlMCM-41 catalysts were reused in this reaction to evaluate their catalytic stabilities. Since ZnAlMCM-41(75) has higher catalytic activity than other solid acid catalysts, washed ZnAlMCM-41(75)/W-ZnAlMCM-41(75) was prepared using an efficient chemical treatment method and used with various reaction parameters to find an optimal parameter for the highly selective synthesis of 4-PDO. W-ZnAlMCM-41(75) was also used in the Prins cyclization of olefins with PFCHO and formalin (FN, 37% aqueous solution of formaldehyde (FCHO)) under different reaction conditions to obtain 1,3-dioxanes, which are widely used as solvents or intermediates in organic synthesis. Based on the nature of catalysts used under different reaction conditions, a reasonable plausible reaction mechanism for the Prins cyclization of SE with PFCHO is proposed. Notably, it can be seen from the catalytic results of all catalysts that the W-ZnAlMCM-41(75) catalyst has higher 4-PDO selectivity with exceptional catalytic activity than other microporous and mesoporous catalysts.

Matched MeSH terms: Chemistry Techniques, Synthetic
Optimising the Azeotropic Drying of 18F-Fluorine Wayto Improve the 18F-Fluorocholine Radiochemical Yield

Hassan H, Bakar SA, Halim KN, Idris J, Saad FF, Nordin AJ

Curr Radiopharm, 2016;9(2):121-7.
PMID: 26239237

BACKGROUND AND OBJECTIVE: 18F-Fluorocholine has been suggested as one of the reputable imaging tracers for diagnosis of prostate tumour in Positron Emission Tomography / Computed Tomography (PET/CT) modality. Nevertheless, it has never been synthesised in Malaysia. We acknowledged that the major problem with 18F-Fluorocholine is due to its relatively low radiochemical yield at the end of synthesis (EOS). Therefore, this article presents improved 18FFluorocholine radiochemical yields after carrying out optimisation on azeotropic drying of 18F-Fluorine.
METHODS: In the previous study, the azeotropic drying of non-carrier-added (n.c.a) 18F-Fluorine in the reactor was conducted at atmospheric pressure (0 atm) and shorter duration time. In this study, however, the azeotropic drying of non-carried-added (n.c.a) 18FFluorine was made at a high vacuum pressure (- 0.65 to - 0.85 bar) with an additional time of 30 seconds. At the end of the synthesis, the mean radiochemical yield was statistically compared between the two azeotropic drying conditions so as to observe whether the improvement made was significant to the radiochemical yield.
RESULTS: From the paired sample t-test analysis, the improvement done to the azeotropic drying of non-carrier-added (n.c.a) 18F-Fluorine was statistically significant (p < 0.05). With the improvement made, the 18F-Fluorcholine radiochemical yield was found to have increase by one fold.
CONCLUSION: Improved 18F-Fluorocholine radiochemical yields were obtained after the improvement had been done to the azeotropic drying of non-carrier-added (n.c.a) 18F-Fluorine. It was also observed that improvement made to the azeotropic drying of non-carrier-added (n.c.a) 18F-Fluorine did not affect the 18F-Fluorocholine quality control analysis.

Matched MeSH terms: Chemistry Techniques, Synthetic/methods
Fulltext Microwave-Assisted Synthesis of Mono- and Disubstituted 4-Hydroxyacetophenone Derivatives via Mannich Reaction: Synthesis, XRD and HS-Analysis

Aljohani G, Said MA, Lentz D, Basar N, Albar A, Alraqa SY, et al.

Molecules, 2019 Feb 07;24(3).
PMID: 30736403 DOI: 10.3390/molecules24030590

An efficient microwave-assisted one-step synthetic route toward Mannich bases is developed from 4-hydroxyacetophenone and different secondary amines in quantitative yields, via a regioselective substitution reaction. The reaction takes a short time and is non-catalyzed and reproducible on a gram scale. The environmentally benign methodology provides a novel alternative, to the conventional methodologies, for the synthesis of mono- and disubstituted Mannich bases of 4-hydroxyacetophenone. All compounds were well-characterized by FT-IR, ¹H NMR, 13C NMR, and mass spectrometry. The structures of 1-{4-hydroxy-3-[(morpholin-4-yl)methyl]phenyl}ethan-1-one (2a) and 1-{4-hydroxy-3-[(pyrrolidin-1-yl)methyl]phenyl}ethan-1-one (3a) were determined by single crystal X-ray crystallography. Compound 2a and 3a crystallize in monoclinic, P2₁/n, and orthorhombic, Pbca, respectively. The most characteristic features of the molecular structure of 2a is that the morpholine fragment adopts a chair conformation with strong intramolecular hydrogen bonding. Compound 3a exhibits intermolecular hydrogen bonding, too. Furthermore, the computed Hirshfeld surface analysis confirms H-bonds and π⁻π stack interactions obtained by XRD packing analyses.

Matched MeSH terms: Chemistry Techniques, Synthetic*
Synthesis and evaluation on pH- and temperature-responsive chitosan-p(MAA-co-NIPAM) hydrogels

Rasib SZM, Ahmad Z, Khan A, Akil HM, Othman MBH, Hamid ZAA, et al.

Int J Biol Macromol, 2018 Mar;108:367-375.
PMID: 29222015 DOI: 10.1016/j.ijbiomac.2017.12.021

In this study, chitosan-poly(methacrylic acid-co-N-isopropylacrylamide) [chitosan-p(MAA-co-NIPAM)] hydrogels were synthesized by emulsion polymerization. In order to be used as a carrier for drug delivery systems, the hydrogels had to be biocompatible, biodegradable and multi-responsive. The polymerization was performed by copolymerize MAA and NIPAM with chitosan polymer to produce a chitosan-based hydrogel. Due to instability during synthesis and complexity of components to produce the hydrogel, further study at different times of reaction is important to observe the synthesis process, the effect of end product on swelling behaviour and the most important is to find the best way to control the hydrogel synthesis in order to have an optimal swelling behaviour for drug release application. Studied by using Fourier transform infra-red (FTIR) spectroscopy found that, the synthesized was successfully produced stable chitosan-based hydrogel with PNIPAM continuously covered the outer surface of hydrogel which influenced much on the stability during synthesis. The chitosan and PMAA increased the zeta potential of the hydrogel and the chitosan capable to control shrinkage above human body temperature. The chitosan-p(MAA-co-NIPAM) hydrogels also responses to pH and temperature thus improved the ability to performance as a drug carrier.

Matched MeSH terms: Chemistry Techniques, Synthetic*
Fulltext Introduction to Photonics: Principles and the Most Recent Applications of Microstructures

Amiri IS, Azzuhri SRB, Jalil MA, Hairi HM, Ali J, Bunruangses M, et al.

Micromachines (Basel), 2018 Sep 11;9(9).
PMID: 30424385 DOI: 10.3390/mi9090452

Light has found applications in data transmission, such as optical fibers and waveguides and in optoelectronics. It consists of a series of electromagnetic waves, with particle behavior. Photonics involves the proper use of light as a tool for the benefit of humans. It is derived from the root word "photon", which connotes the tiniest entity of light analogous to an electron in electricity. Photonics have a broad range of scientific and technological applications that are practically limitless and include medical diagnostics, organic synthesis, communications, as well as fusion energy. This will enhance the quality of life in many areas such as communications and information technology, advanced manufacturing, defense, health, medicine, and energy. The signal transmission methods used in wireless photonic systems are digital baseband and RoF (Radio-over-Fiber) optical communication. Microwave photonics is considered to be one of the emerging research fields. The mid infrared (mid-IR) spectroscopy offers a principal means for biological structure analysis as well as nonintrusive measurements. There is a lower loss in the propagations involving waveguides. Waveguides have simple structures and are cost-efficient in comparison with optical fibers. These are important components due to their compactness, low profile, and many advantages over conventional metallic waveguides. Among the waveguides, optofluidic waveguides have been found to provide a very powerful foundation for building optofluidic sensors. These can be used to fabricate the biosensors based on fluorescence. In an optical fiber, the evanescent field excitation is employed to sense the environmental refractive index changes. Optical fibers as waveguides can be used as sensors to measure strain, temperature, pressure, displacements, vibrations, and other quantities by modifying a fiber. For some application areas, however, fiber-optic sensors are increasingly recognized as a technology with very interesting possibilities. In this review, we present the most common and recent applications of the optical fiber-based sensors. These kinds of sensors can be fabricated by a modification of the waveguide structures to enhance the evanescent field; therefore, direct interactions of the measurand with electromagnetic waves can be performed. In this research, the most recent applications of photonics components are studied and discussed.

Matched MeSH terms: Chemistry Techniques, Synthetic
A Green Alternative for Aryl Iodide Preparation from Aromatic Amines

Shahnavaz Z, Zaharani L, Johan MR, Khaligh NG

Curr Org Synth, 2020;17(2):131-135.
PMID: 32013833 DOI: 10.2174/1570179417666200203121437

BACKGROUND: In continuation of our previous work and the applications of saccharin, we encouraged to investigate the one-pot synthesis of the aryl iodides by the diazotization of the arene diazonium saccharin salts.
OBJECTIVE: Arene diazonium salts play an important role in organic synthesis as intermediate and a wide variety of aromatic compounds have been prepared using them. A serious drawback of arene diazonium salts is their instability in a dry state; therefore, they must be stored and handled carefully to avoid spontaneous explosion and other hazard events.
METHODS: The arene diazonium saccharin salts were prepared as active intermediates in situ through the reaction of various aryl amines with tert-butyl nitrite (TBN) in the presence of saccharin (Sac-H). Then, in situ obtained intermediates were used into the diazotization step without separation and purification in the current protocol.
RESULTS: A variety of aryl iodides were synthesized at a greener and low-cost method in the presence of TBN, Sac-H, glacial acetic acid, and TEAI.
CONCLUSION: In summary, a telescopic reaction is developed for the synthesis of aryl iodides. The current methodology is safe, cost-effective, broad substrate scope, and metal-free. All used reagents are commercially available and inert to moisture and air. Also, the saccharine and tetraethylammonium cation could be partially recovered from the reaction residue, which reduces waste generation, energy consumption, raw material, and waste disposal costs.

Matched MeSH terms: Chemistry Techniques, Synthetic
Fulltext Molecular Differentiated Initiator Reactivity in the Synthesis of Poly(caprolactone)-Based Hydrophobic Homopolymer and Amphiphilic Core Corona Star Polymers

Deng E, Nguyen NT, Hild F, Hamilton IE, Dimitrakis G, Kingman SW, et al.

Molecules, 2015 Nov 09;20(11):20131-45.
PMID: 26569198 DOI: 10.3390/molecules201119681

Macromolecules that possess three-dimensional, branched molecular structures are of great interest because they exhibit significantly differentiated application performance compared to conventional linear (straight chain) polymers. This paper reports the synthesis of 3- and 4-arm star branched polymers via ring opening polymerisation (ROP) utilising multi-functional hydroxyl initiators and Sn(Oct)2 as precatalyst. The structures produced include mono-functional hydrophobic and multi-functional amphiphilic core corona stars. The characteristics of the synthetic process were shown to be principally dependent upon the physical/dielectric properties of the initiators used. ROP's using initiators that were more available to become directly involved with the Sn(Oct)₂ in the "in-situ" formation of the true catalytic species were observed to require shorter reaction times. Use of microwave heating (MWH) in homopolymer star synthesis reduced reaction times compared to conventional heating (CH) equivalents, this was attributed to an increased rate of "in-situ" catalyst formation. However, in amphiphilic core corona star formation, the MWH polymerisations exhibited slower propagation rates than CH equivalents. This was attributed to macro-structuring within the reaction medium, which reduced the potential for reaction. It was concluded that CH experiments were less affected by this macro-structuring because it was disrupted by the thermal currents/gradients caused by the conductive/convective heating mechanisms. These gradients are much reduced/absent with MWH because it selectively heats specific species simultaneously throughout the entire volume of the reaction medium. These partitioning problems were overcome by introducing additional quantities of the species that had been determined to selectively heat.

Matched MeSH terms: Chemistry Techniques, Synthetic
Fulltext A convenient method for the synthesis of (prop-2-ynyloxy)benzene derivatives via reaction with propargyl bromide, their optimization, scope and biological evaluation

Batool T, Rasool N, Gull Y, Noreen M, Nasim FU, Yaqoob A, et al.

PLoS One, 2014;9(12):e115457.
PMID: 25545159 DOI: 10.1371/journal.pone.0115457

A highly convenient method has been developed for the synthesis of (prop-2-ynyloxy) benzene and its derivatives. Differently substituted phenol and aniline derivatives were allowed to react with propargyl bromide in the presence of K2CO3 base and acetone as solvent. The compounds were synthesized in good yields (53-85%). Low cost, high yields and easy availability of compounds helped in the synthesis. Electron withdrawing groups favor the formation of stable phenoxide ion thus in turn favors the formation of product while electron donating groups do not favor the reaction. Phenol derivatives gave good yields as compared to that of aniline. As aprotic polar solvents favor SN2 type reactions so acetone provided best solvation for the reactions. K2CO3 was proved to be good for the synthesis. Antibacterial, Antiurease and NO scavenging activity of synthesized compounds were also examined. 4-bromo-2-chloro-1-(prop-2-ynyloxy)benzene 2a was found most active compound against urease enzyme with a percentage inhibition of 82.00±0.09 at 100 µg/mL with IC50 value of 60.2. 2-bromo-4-methyl-1-(prop-2-ynyloxy)benzene 2d was found potent antibacterial against Bacillus subtillus showing excellent inhibitory action with percentage inhibition of 55.67±0.26 at 100 µg/ml wih IC50 value of 79.9. Based on results, it can be concluded that some of the synthesized compounds may have potential antiurease and antibacterial effects against several harmful substances.

Matched MeSH terms: Chemistry Techniques, Synthetic/methods
Fulltext Development of drug delivery systems based on layered hydroxides for nanomedicine

Barahuie F, Hussein MZ, Fakurazi S, Zainal Z

Int J Mol Sci, 2014;15(5):7750-86.
PMID: 24802876 DOI: 10.3390/ijms15057750

Layered hydroxides (LHs) have recently fascinated researchers due to their wide application in various fields. These inorganic nanoparticles, with excellent features as nanocarriers in drug delivery systems, have the potential to play an important role in healthcare. Owing to their outstanding ion-exchange capacity, many organic pharmaceutical drugs have been intercalated into the interlayer galleries of LHs and, consequently, novel nanodrugs or smart drugs may revolutionize in the treatment of diseases. Layered hydroxides, as green nanoreservoirs with sustained drug release and cell targeting properties hold great promise of improving health and prolonging life.

Matched MeSH terms: Chemistry Techniques, Synthetic/methods
Fulltext Conventional study on novel dicationic ionic liquid inclusion with β-cyclodextrin

Mohamad S, Surikumaran H, Raoov M, Marimuthu T, Chandrasekaram K, Subramaniam P

Int J Mol Sci, 2011;12(9):6329-45.
PMID: 22016662 DOI: 10.3390/ijms12096329

This study focuses on the synthesis and characterization of the inclusion complex of β-Cyclodextrin (β-CD) with dicationic ionic liquid, 3,3'-(1,4-Phenylenebis [methylene]) bis(1-methyl-1H-imidazol-3-ium) di(bromide) (PhenmimBr). The inclusion complex was prepared at room temperature utilizing conventional kneading technique. Proton ((1)H) NMR and 2D ((1)H-(1)H) COSY NMR were the primary characterization tools employed to verify the formation of the inclusion complex. COSY spectra showed strong correlations between protons of imidazolium and protons of β-CD which indicates that the imidazolium ring of PhenmimBr has entered the cavity of β-CD. UV absorption indicated that β-CD reacts with PhenmimBr to form a 2:1 β-CD-PhenmimBr complex with an apparent formation constant of 2.61 × 10(5) mol&(-2) L(2). Other characterization studies such as UV, FT-IR, XRD, TGA, DSC and SEM studies were also used to further support the formation of the β-CD-PhenmimBr inclusion complex.

Matched MeSH terms: Chemistry Techniques, Synthetic/methods
A novel five-step synthetic route to 1,3,4-oxadiazole derivatives with potent α-glucosidase inhibitory potential and their in silico studies

Iftikhar M, Shahnawaz, Saleem M, Riaz N, Aziz-Ur-Rehman, Ahmed I, et al.

Arch Pharm (Weinheim), 2019 Dec;352(12):e1900095.
PMID: 31544284 DOI: 10.1002/ardp.201900095

A series of new N-aryl/aralkyl derivatives of 2-methyl-2-{5-(4-chlorophenyl)-1,3,4-oxadiazole-2ylthiol}acetamide were synthesized by successive conversions of 4-chlorobenzoic acid (a) into ethyl 4-chlorobenzoate (1), 4-chlorobenzoylhydrazide (2) and 5-(4-chlorophenyl)-1,3,4-oxadiazole-2-thiol (3), respectively. The required array of compounds (6a-n) was obtained by the reaction of 1,3,4-oxadiazole (3) with various electrophiles (5a-n) in the presence of DMF (N,N-dimethylformamide) and sodium hydroxide at room temperature. The structural determination of these compounds was done by infrared, 1 H-NMR (nuclear magnetic resonance), 13 C-NMR, electron ionization mass spectrometry, and high-resolution electron ionization mass spectrometry analyses. All compounds were evaluated for their α-glucosidase inhibitory potential. Compounds 6a, 6c-e, 6g, and 6i were found to be promising inhibitors of α-glucosidase with IC50 values of 81.72 ± 1.18, 52.73 ± 1.16, 62.62 ± 1.15, 56.34 ± 1.17, 86.35 ± 1.17, 52.63 ± 1.16 µM, respectively. Molecular modeling and ADME (absorption, distribution, metabolism, excretion) predictions supported the findings. The current synthesized library of compounds was achieved by utilizing very common raw materials in such a way that the synthesized compounds may prove to be promising drug leads.

Matched MeSH terms: Chemistry Techniques, Synthetic/methods*
Fulltext Synthesis, characterization, quantum chemical calculations and anticancer activity of a Schiff base NNOO chelate ligand and Pd(II) complex

Ahmad N, Anouar EH, Tajuddin AM, Ramasamy K, Yamin BM, Bahron H

PLoS One, 2020;15(4):e0231147.
PMID: 32287324 DOI: 10.1371/journal.pone.0231147

This paper reports the synthesis, characterization, anticancer screening and quantum chemical calculation of a tetradentate Schiff base 2,2'-((1E,1'E)-((2,2-dimethylpropane-1,3-diyl)bis- (azanylylidene))bis(methanylylidene))bis(4-fluorophenol) (L2F) and its Pd (II) complex (PdL2F). The compounds were characterized via UV-Visible, NMR, IR spectroscopy and single crystal x-ray diffraction. Density Functional Theory (DFT) and time-dependent DFT calculations in gas and solvent phases were carried out using B3LYP, B3P86, CAM-B3LYP and PBE0 hybrid functionals combined with LanL2DZ basis set. Complexation of L2F to form PdL2F was observed to cause a bathochromic shift of the maximum absorption bands of n-π* from 327 to 410 nm; an upfield shift for δ (HC = N) from 8.30 to 7.96 ppm and a decreased wavenumber for ν(C = N) from 1637 to 1616 cm-1. Overall, the UV-Vis, NMR and IR spectral data are relatively well reproduced through DFT and TD-DFT methods. L2F and PdL2F showed IC50 of 90.00 and 4.10 μg/mL, respectively, against human colorectal carcinoma (HCT116) cell lines, signifying increased anticancer activity upon complexation with Pd (II).

Matched MeSH terms: Chemistry Techniques, Synthetic/methods
Fulltext Efficient Synthesis of Novel Pyridine-Based Derivatives via Suzuki Cross-Coupling Reaction of Commercially Available 5-Bromo-2-methylpyridin-3-amine: Quantum Mechanical Investigations and Biological Activities

Ahmad G, Rasool N, Ikram HM, Gul Khan S, Mahmood T, Ayub K, et al.

Molecules, 2017 Jan 27;22(2).
PMID: 28134790 DOI: 10.3390/molecules22020190

The present study describes palladium-catalyzed one pot Suzuki cross-coupling reaction to synthesize a series of novel pyridine derivatives 2a-2i, 4a-4i. In brief, Suzuki cross-coupling reaction of 5-bromo-2-methylpyridin-3-amine (1) directly or via N-[5-bromo-2-methylpyridine-3-yl]acetamide (3) with several arylboronic acids produced these novel pyridine derivatives in moderate to good yield. Density functional theory (DFT) studies were carried out for the pyridine derivatives 2a-2i and 4a-4i by using B3LYP/6-31G(d,p) basis with the help of GAUSSIAN 09 suite programme. The frontier molecular orbitals analysis, reactivity indices, molecular electrostatic potential and dipole measurements with the help of DFT methods, described the possible reaction pathways and potential candidates as chiral dopants for liquid crystals. The anti-thrombolytic, biofilm inhibition and haemolytic activities of pyridine derivatives were also investigated. In particular, the compound 4b exhibited the highest percentage lysis value (41.32%) against clot formation in human blood among all newly synthesized compounds. In addition, the compound 4f was found to be the most potent against Escherichia coli with an inhibition value of 91.95%. The rest of the pyridine derivatives displayed moderate biological activities.

Matched MeSH terms: Chemistry Techniques, Synthetic*
Fulltext Facile, regio- and diastereoselective synthesis of spiro-pyrrolidine and pyrrolizine derivatives and evaluation of their antiproliferative activities

Almansour AI, Kumar RS, Beevi F, Shirazi AN, Osman H, Ismail R, et al.

Molecules, 2014 Jul 10;19(7):10033-55.
PMID: 25014532 DOI: 10.3390/molecules190710033

A number of novel spiro-pyrrolidines/pyrrolizines derivatives were synthesized through [3+2]-cycloaddition of azomethine ylides with 3,5-bis[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones 2a-n. Azomethine ylides were generated in situ from the reaction of 1H-indole-2,3-dione (isatin, 3) with N-methylglycine (sarcosine), phenylglycine, or proline. All compounds (50 μM) were evaluated for their antiproliferative activity against human breast carcinoma (MDA-MB-231), leukemia lymphoblastic (CCRF-CEM), and ovarian carcinoma (SK-OV-3) cells. N-α-Phenyl substituted spiro-pyrrolidine derivatives (5a-n) showed higher antiproliferative activity in MDA-MB-231 than other cancer cell lines. Among spiro-pyrrolizines 6a-n, a number of derivatives including 6a-c and 6i-m showed a comparable activity with doxorubicin in all three cell lines. Among all compounds in three classes, 6a, 6b, and 6m, were found to be the most potent derivatives showing 64%, 87%, and 74% antiproliferative activity in MDA-MB-231, SK-OV-3, and CCRF-CEM cells, respectively. Compound 6b showed an IC50 value of 3.6 mM in CCRF-CEM cells. These data suggest the potential antiproliferative activity of spiro-pyrrolidines/pyrrolizines.

Matched MeSH terms: Chemistry Techniques, Synthetic

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