- Newly synthesized oxadiazole based mannich base derivatives of fatty acid: In silico study and in vivo anti-hyperglycaemic estimation
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A receptor peroxisome proliferator activated receptor-gamma was targeted by series of new fatty acid chemical entities (M1-M22) which was designed, synthesized and characterized by spectral analysis. Metabolites molecular properties were calculated using Lipinski’s rule of five using molinspiration online software. Docking studies were done on co-crystallized protein structure of PPAR γ, PDB-1FM9 showing M15, M17 and M8 to be best located in the active sites with scores -10.43, -10.21 and -10.00 respectively. The free binding energy estimation was done using model of Maestro 9.0 (Schrodinger) and lies between -80.15 to -61.26 kcal/mol which is significant as compared to that of standard (-48.58 Kcal/mol). Nine best docked derivatives were evaluated in-vivo for oral glucose tolerance and antihyperglycemic activity by streptozotocin induced diabetes model and M15 exhibited most promising antidiabetic activity more than the standard glibenclamide. The promising results encourage future investigation on fatty acids for development of active compounds.
- Kapoor, Garima,Pathak, Dharam Pal,Bhutani, Rubina,Husain, Asif,Jain, Sandeep,Kant, Ravi,Iqbal, Md. Azhar
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- Synthesis of various nitrogen heterocycles as antimicrobial surface agents
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A number of novel, thiazole 5, oxadiazole 6, thiadiazole 7, triazole 8, 9, and fused triazole derivatives 10, 11, 12 were obtained from a valuable and inexpensive fatty acids (stearic acid). Propoxylation of these compounds using 5 moles of propylene oxide produced nonionic surface active agents (13, 14,15 16, 17,18,19,20). The surface properties and the biodegradability of the latter compounds were evaluated. Some of the synthesized compounds were investigated for their antimicrobial activities.
- El-Sayed, Refat,Asghar, Basim H.
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- Synthesis of 5-heptadecyl- and 5-heptadec-8-enyl substituted 4-amino-1,2,4-triazole-3-thiol and 1,3,4-oxadiazole-2-thione from (Z)-octadec-9-enoic acid: preparation of Palladium(II) complexes and evaluation of their antimicrobial activity
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Abstract: Two 4-amino-1,2,4-triazoles and two 1,3,4-oxadiazoles are obtained in a common synthetic route including hydrogenation-hydrazidation of (Z)-methyl octadec-9-enoate to octadecanoic hydrazide under atmospheric air. Preservation of olefinic bond in heptadec-8-enyl group is achieved by carrying out hydrazidation reaction under the presence of an argon atmosphere. The disappearance of the olefinic bond is detected by physical data, IR, 1H, and13C NMR spectroscopy. New palladium complexes derived from 4-amino-5-heptadecyl-1,2,4-triazole-3-thiol and 5-heptadecyl-1,3,4-oxadiazole-2(3H)-thione are obtained and characterized by elemental analysis (solid state), IR, 1H, 13C NMR spectroscopy, XRD, and XPS. These resulting metallic entities are also identified in solution based in mass spectrometry (MS-ESI) experiments. Most compounds and their palladium(II) complexes are tested in vitro against Gram-positive, Gram-negative bacteria, and fungi, some of them showed variable activity. Graphic abstract: [Figure not available: see fulltext.].
- Chehrouri, Manel,Gholinejad, Mohammad,Moreno-Cabrerizo, Cristina,Othman, Adil A.,Sansano, José M.
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- Synthesis, ADME, docking studies and in vivo anti-hyperglycaemic potential estimation of novel Schiff base derivatives from octadec-9-enoic acid
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A new series of octadec-9-enoic acid schiff base entities (S1-S30) were designed and synthesized targeting peroxisome proliferator activated receptor-gamma for agonist action. Molinspiration software (online) was used to estimate drug like molecular properties of the metabolites. Docking disquisition on co-crystallized protein of PPAR-γ (PDB ID 1FM9) was carried out which showed S21, S10 and S7 as best situated in the vital sites of receptor having docking scores ?9.19, ?8.68 and ?8.64 respectively. Free binding energy measured using model of Maestro 9.0 and was in range of from ?40.01 and ?80.54 kcal/mol, significant when compared with pioglitazone (?51.58 Kcal/mol). Seven best docked derivatives were assessed for in-vivo oral glucose tolerance on normal rats and anti-hyperglycaemic activity by streptozotocin induced diabetes model. S21 unveiled to be the best measured analogue among all the synthesized entities. Encouraging outcomes motivates fatty acids for further development of more effective and safer compounds.
- Kapoor, Garima,Pathak, Dharam Pal,Bhutani, Rubina,Husain, Asif,Jain, Sandeep,Iqbal, Md. Azhar
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p. 478 - 492
(2019/01/04)
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- A new class of human fatty acid synthase inhibitors: Synthesis and their anticancer evaluation
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A series of 3-pentadecyl/heptadecyl-6-subsituted phenyl[l,2,4]triazolo[3,4-&][l,3,4]thiadiazoles have been designed, synthesized and screened for their in vitro antitumour activity against breast cancer cell Jines. Three compounds namely, 3- pentadecyl-6-phenyl[l,2,4]triazolo[3,4-b][l,3,4]thiadiazole (6e), 3-heptadecyl-6-phenyl[l,2,4]triazolo[3,4-i][l,3,4]thiadiazole (6j) and 3-heptadecyl-6(3-nitrophenyl)[l,2,4]triazolo[3,4b][l,3,4]-thiadiazole (6g) have displayed comparable activities towards human breast cancer lines. Molecular docking studies have been carried out on the crystal structure of human fatty acid synthase thioesterase domain (2PX6) by using GLIDE integrated Maestro 9.3 version. The designed compounds have shown good binding interactions with the active site residues present in the enzyme and have given very good G-scores when compared to the known inhibitor orlistat.
- Jubie,Bincy,Jameera Begam,Ashish,Kalirajan,Afzal Azam
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p. 671 - 678
(2019/05/22)
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- Cyclocondensation between fatty acid hydrazides and 1,1,1-trifluoro-4-alkoxy-3-alken-2-ones: Introducing a trifluoromethylated head onto fatty acid moieties
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This paper reports the regioselective synthesis of new trifluoromethylated lipid derivatives, namely, 1-(5-hydroxy-5-trifluoromethyl-3-alkyl-4,5-dihydro-1H-pyrazol-1-yl)alkan-1-ones, through cyclocondensation reactions between a series of fatty hydrazides (palmitoyl, stearoyl, and oleoyl hydrazides) obtained from fatty acids from renewable resources (1,1,1-trifluoro-4-alkoxy-3-alken-2-ones [F3CC(O)CH?C(R1)OR, where R1 = H and R?Et; R1 = –(CH2)6CH3, –(CH2)6CH3, –(CH2)8CH3, –(CH2)9CH3, –(CH2)10CH3, –(CH2)12CH3, –(CH2)2Ph], and R?Me). Experimental observations showed that the lipophilic characteristic of 5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-pyrazoles (5–7) prevent the acid catalyzed dehydration to aromatization of 1H-pyrazole ring, although in some cyclocondensations a proportion of the aromatic derivative 1-(5-trifluoromethyl-3-alkyl-1H-pyrazol-1-yl)alkan-1-one was obtained. All products were characterized using multinuclear (1H, 13C, 19F) NMR spectroscopy.
- Teixeira, Wystan K. O.,Gon?alves, Helena A.,de Mello, Débora L.,Moura, Sidnei,Flores, Darlene C.,Flores, Alex F. C.
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p. 2078 - 2086
(2017/10/13)
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- Synthesis and antimicrobial studies of 5-n-alkyl-1,3,4-oxadiazole-2-thiol derivatives from fatty acids
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The novel 5-N-alkyl-1,3,4-oxadiazole-2-thiol derivatives have been synthesized by esterification of fatty acid followed by reaction the ester with hydrazine hydrate. The acid hydrazide was converted to 1,3,4-oxadiazole by ring closure mechanism. The synthesized compounds have been characterized by physical (melting point and TLC) and spectral (IR, 1H NMR and mass) data. All the compounds were screened for their antimicrobial activity. The compounds 3F1 & 3F4 showed good inhibition activity against all four types of bacteria; while compound 3F2 & 3F3 shown moderate activity.
- Naga Sudha,Yella Subbaiah,Srikanth,Venkata Ramana Reddy,Sneha Latha,Vijaya Lakshmi
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p. 2369 - 2371
(2017/10/31)
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- Novel fatty acid analogues as human fatty acid synthase thioesterase domain inhibitors: Synthesis and their cytotoxicity screening
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A new class of 1, 3, 4-oxadiazoles substituted stearic/palmitic acid analogues were prepared. In-silico docking studies have been done into the crystal structure of thioesterase domain of human fatty acid synthase (2PX6) that gave some important structural information on the ligand binding interactions. The residues His 2481, Tyr 2462 & Ala 2448 formed hydrogen bonds with 1, 3, 4-oxadiazole ring. All the target compounds exhibited good binding interactions with the active site residues. Cytotoxicity has been done for some selected compounds against human lung carcinoma cell lines (A-549) by SRB method. The compounds showed strong cytotoxicity.
- Jubie, Selvaraj,Yadhav, Pawan Kumar,Chandrasekar, Moola Joghee Nanjan,Priya, Jeyapal Gomathi,Mvnl, Chaitanya,Dhanabal, Palanisamy
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p. 495 - 499
(2015/06/22)
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- Improved protocol toward 1,3,4-oxadiazole-2(3H)-thiones and scale-up synthesis in the presence of SDS as a micelle promoted catalyst
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Convenient procedure for in situ cyclization of hydrazinecarbodithioate potassium salts to 1,3,4-oxadiazole-2(3H)-thiones under normal phase micellar media catalysis promoted by sodium dodecyl sulfate (SDS) as an anionic surfactant is reported. The main advantage of this procedure is to provide shorter reaction time for the completion of cyclization; scale-up synthesis is possible and the oxadiazoles were obtained in high to excellent yields (87-100%), making the protocol an attractive alternative to the available methods.
- Yildirim, Ayhan
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p. 473 - 478
(2015/06/30)
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- Synthesis and Surface Characterization Studies of Polyether-Linked Symmetric Higher Sulfanyl-1,3,4-Oxadiazoles
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The synthesis and the characterization of a series of novel symmetric double length alkyl-chained sulfanyl-1,3,4-oxadiazoles functionalized with a polyether head group are reported. In addition, surface characterization studies were conducted on the metal surface of these synthesized compounds. The metal surfaces were characterized by contact angle measurements via the sessile-drop method, and 3D images of the metal surface were obtained using an optical profilometer. The surface studies showed that the inhibitor molecule increases the hydrophobic character and decreases the wettability of the metal surface.
- Yildirim,?ztürk
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p. 1535 - 1550
(2015/09/01)
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- A METHOD TO PRODUCE HYDRAZIDE
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A method to produce hydrazide from triacylglycerol, the method includes steps of mixing vegetable oil with an organic solvent in a reactor forming a mixture, adding hydrazinemonohydrate into the mixture, stirring the mixture, adding catalyst, stirring the mixture to form hydrazide and separating the hydrazide from the mixture. Most illustrative drawing:
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Page/Page column 4; 5
(2013/05/23)
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- Antimicrobial evaluation of 4-methylsulfanyl benzylidene/3-hydroxy benzylidene hydrazides and QSAR studies
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A series of 4-methylsulfanyl benzylidene/3-hydroxy benzylidene hydrazides (1-20) was synthesized and tested for in vitro antimicrobial activity against S. aureus, B. subtilis, E. coli, C. albicans and A. niger. The results of antimicrobial studies indicated that 3-phenylacrylic acid-(3-hydroxybenzylidene) -hydrazide, 16, was the most effective as it showed both bactericidal and fungicidal properties and other compounds possessed bacteriostatic/fungistatic activity. The multi-target QSAR model demonstrated that the topological parameter, Balaban topological index (J) is effective in describing the antimicrobial activity of synthesized substituted hydrazides. Springer Science+Business Media, LLC 2010.
- Kumar, Davinder,Narang, Rakesh,Judge, Vikramjeet,Kumar, Devinder,Narasimhan, Balasubramanian
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p. 382 - 394
(2012/08/27)
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- Regiospecific synthesis of new fatty N-acyl trihalomethylated pyrazoline derivatives from fatty acid methyl esters (FAMEs)
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A series of new fatty N-acyl trihalomethylated pyrazoline derivatives from fatty acid methyl esters was synthesized by the cyclocondensation of respective fatty hydrazides with 4-alkoxy-1,1,1-trialomethyl-3-alquen-2-ones. Efficient and regiospecific cyclizations catalyzed by BF3·MeOH gave the desired products in good to excellent yields and at high purity.
- Beck, Paulo,Dos Santos, Juliane M.,Kuhn, Bruna L.,Moreira, Dayse N.,Flores, Alex F. C.,Martins, Marcos A. P.,D'Oca, Marcelo G. M.,Piovesan, Luciana A.
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p. 2122 - 2127
(2013/04/10)
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- Synthesis, antimicrobial evaluation and QSAR studies of 3-ethoxy-4-hydroxybenzylidene/4-nitrobenzylidene hydrazides
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A series of 3-ethoxy-4-hydroxybenzylidene/4-nitrobenzylidene hydrazides (1-20) was synthesized and tested for in vitro antimicrobial activity. The results of antimicrobial studies indicated that the compounds having dinitro, methoxy, hydroxy and nitro substituents on phenyl ring of the aromatic acids were most active ones. The QSAR investigation indicated the importance of the topological parameter, third order molecular connectivity index ( 3χ) in describing the antimicrobial activity of synthesized hydrazides.
- Kumar, Davinder,Kapoor, Archana,Thangadurai, Ananda,Kumar, Pradeep,Narasimhan, Balasubramanian
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p. 1293 - 1296
(2012/01/07)
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- Benzylidene/2-chlorobenzylidene hydrazides: Synthesis, antimicrobial activity, QSAR studies and antiviral evaluation
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A series of benzylidene hydrazides (1-20) was synthesized and tested, in vitro, for antibacterial, antifungal and antiviral activities. The microbial screening results indicated that compounds having chloro and nitro substituents were the most active ones. The antiviral evaluation depicted that compounds 9 and 19 were active against Vesicular stomatitis virus (VSV) in HeLa cell cultures. QSAR investigations indicated that the multi-target QSAR model was effective in describing the antimicrobial (antibacterial and antifungal) activity over the one-target QSAR models. Further the mt-QSAR model indicated that the topological parameters, second order molecular connectivity index (2χ) and third order Kier's alpha shape index (κα3) are effective in describing the antimicrobial activity of synthesized hydrazides.
- Kumar, Davinder,Judge, Vikramjeet,Narang, Rakesh,Sangwan, Sonia,De Clercq, Erik,Balzarini, Jan,Narasimhan, Balasubramanian
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experimental part
p. 2806 - 2816
(2010/08/20)
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- Preparation of saturated and unsaturated fatty acid hydrazides and long chain C-glycoside ketohydrazones
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A method is described to prepare both saturated and unsaturated fatty acid acyl hydrazides using a lipase as a catalyst. Hydrazides were generated from fatty acid methyl esters as well as directly from vegetable oils, and an organic co-solvent was not needed to maintain the integrity of the unsaturated fatty acids. Both C. antarctica lipase immobilized on acrylic resin and immobilized M. miehei lipase were used to catalyze the reaction, and they provided the desired acyl hydrazides with similar yields of 82.8% and 84.6%, respectively. Analysis of the products by MALDI-TOF-MS and GC-MS fragmentation pathways shows pure products free of starting methyl esters or triacylglycerols. These hydrazide molecules have been used, in conjunction with carbohydrate C-glycoside ketones, to prepare long chain C-glycoside ketohydrazones. This preparation does not require protecting groups or anomeric activation, and various C-glycoside ketohydrazones that retain the closed ring conformation of the parent sugars are described. These compounds have potential as renewable, sugar-based detergents in which the sugar moiety serves as the polar head group while the hydrazide alkyl chain is the non-polar component. The Royal Society of Chemistry 2010.
- Carpenter, Chrissie A.,Kenar, James A.,Price, Neil P. J.
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experimental part
p. 2012 - 2018
(2011/02/23)
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- Dynamic combinatorial libraries constructed on polymer scaffolds
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(Figure Presented) Functionalized polymers were prepared by grafting acylhydrazides onto a polyvinylbenzaldehyde scaffold through reversible hydrazone linkages. The dynamic nature of these linkages allows the functionalized polymers to exchange and reshuffle their appendages, and the resultant mixture of polymers can be considered as a dynamic combinatorial library constructed upon a polymer scaffold. The dynamic nature of these functionalized polymers was demonstrated.
- Fulton, David A.
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supporting information; experimental part
p. 3291 - 3294
(2009/05/11)
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- Synthesis of corrosion preventive long-chain N-alkyl-2-(phenylthio)- acetohydrazides and 2-oxo-2-phenylethyl-2-alkanoylhydrazinecarbodithioates
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Long-chain N-alkyl-2-(phenylthio)acetohydrazides were synthesized via the reactions of 2-(phenylthio)acetohydrazide with long-straight-chain aldehydes and then reduction with sodium borohydride. The reactions of long-straight-chain hydrazides with carbon disulfide in alkaline media give the corresponding carbodithioate salts. Heating of potassium 2-alkanoylhydrazinecarbodithioates with phenacyl bromide do not yield cyclization and failed to give the corresponding long-chain thiazolidine-2-thiones, but gave the corresponding 2-oxo-2-phenylethyl-2-alkanoylhydrazinecarbodithioates via nucleophilic substitution reaction. In addition, the synthesized compounds were tested for their corrosion prevention capabilities in acidic or in mineral oil media.
- Yildirim, Ayhan,Cetin, Mehmet
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body text
p. 1279 - 1283
(2009/12/05)
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- An efficient microwave-assisted one-pot conversion of carboxylic acids into hydrazides
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A microwave-assisted protocol was developed to prepare hydrazides from corresponding carboxylic acids in good yields through transacylation with acethydrazide.
- Peng, Yanqing,Song, Gonghua
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p. 768 - 769
(2007/10/03)
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- Synthesis of 1-Nonanoyl/octadecanoyl-4-substituted Thiosemicarbazides and substituted 1,2,4-Trizoles as biological active compounds
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4-Alkyl/aryl-5-nonanoyl/octadecanoyl-2,4-dihydro-3H-1,2, 4-triazoline-3-thiones were synthesized as potential antimicrobial agents. The course of synthesis included the reaction of nonanoyl/octadecanoyl hydrazines with selected alkyl/aryl isothiocyanates. The prepared thiosemicarbazides gave by cyclization the required 1,2,4-triazoles. A number of synthesized compounds were subjected to in vitro testing against two gram-positive, two gram-negative bacteria and two fungi.
- Colanceska-Ragenovic, Katica,Dimova, Vesna,Kakurinov, Vlado,Gabor, Dora Molnar
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p. 905 - 908
(2007/10/03)
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- Synthesis, analgesic and anti-inflammatory activities of some 1-acyl/aracyl-5-aminopyrazole derivatives
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A series of 1-acyl/aracyl-3,4-disubstituted-5-aminopyrazoles (IV) were synthesized by the reaction of 1-acyl/aracylhydrazines (I) with an appropriately substituted ketenedithioacetal (II/III). Compounds IV were tested for their analgesic activity by rat caudal immersion test and anti-inflammatory activity by carrageenin induced edema in rat paw test. 1-Benzoyl-3-mercapto-4-carboxamido-5-aminopyrazole (IVk) proved to be the most active compound of the series in both tests.
- Gadad, Andanappa K.,Kittur, Bharatesh S.,Kapsi, Shivakumar G.,Mahajanshetti, Chanbasappa S.,Rajur, Sharanabasava B.
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p. 1082 - 1085
(2007/10/03)
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