Synthesis, characterization and computational studies of 1,3-bis[(E)-furan-2-yl)methylene]urea and 1,3-bis[(E)-furan-2-yl)methylene]thiourea

AbstractUrea and thiourea derivatives: 1,3-bis[(E)-furan-2-yl)methylene]urea (BFMU) and 1,3-bis[(E)-furan-2-yl)methylene]thiourea (BFMT) were synthesized and characterized by spectrometry analyses (UV, IR, 1H NMR and 13C NMR). They were screened for antibacterial (Salmonella typhi, Staphylococcus aureus, Pseudomonas aeruginosa, Xanthomonas axonopodis and Streptococcus bovis) and antifungal (Fusarium oxysporum, Colletotrichum gloeosporioides and Cercospora zeae-maydis) activities. Quantum chemical calculations of frontier molecular orbital energies (EHOMO and ELUMO), and their associated global parameters were carried out by DFT levels of theory, with complete relaxation in the potential energy surface using 6-31G* basis set (DFT/B3LYP/6-31G*). Azomethine functional groups (C=N) appeared at δ 7.6 ppm and δ 7.0 ppm in the proton spectra, the peaks between δ 105 and δ 160 ppm of 13C spectra represent the methylene carbons (C=C). BFMU is a better inhibitor of P. aeruginosa and S. bovis, while BFMT is a better inhibitor of S. typhi, S. aureus and X. axonopodis and the fungi isolates (F. oxysporum, C. gloeosporioides and C. zeae-maydis) used. The global parameters agreed favorably with the experimental results, indicating the higher activity of BFMT.

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Fluorinated s-Triazinyl Piperazines as Antimicrobial Agents

Zeitschrift für Naturforschung C ◽

10.1515/znc-2011-7-805 ◽

2011 ◽

Vol 66 (7-8) ◽

pp. 345-352 ◽

Cited By ~ 1

Author(s):

Rahul V. Patel ◽

Premlata Kumari ◽

Kishor H. Chikhalia

Keyword(s):

Antimicrobial Agents ◽

Inhibitory Concentration ◽

Salmonella Typhi ◽

The Novel ◽

Proteus Vulgaris ◽

Aspergillus Clavatus ◽

H Nmr ◽

Chemical Structures ◽

Triazine Derivatives ◽

C Nmr

A series of 1,3,5-triazine derivatives that contain 4-amino-2-trifl uoromethyl-benzonitrile, 8-hydroxyquinoline, and different piperazines as substituents at the carbon atoms of the triazine ring have been synthesized by a simple and efficient synthetic protocol. The chemical structures of the compounds were elucidated with the aid of IR, 1H NMR and 13C NMR spectroscopy, and elemental analysis. The antimicrobial activity of the compounds was tested against seven bacteria (Staphylococcus aureus MTCC 96, Bacillus cereus MTCC 619, Escherichia coli MTCC 739, Pseudomonas aeruginosa MTCC 741, Klebsiella pneumoniae MTCC 109, Salmonella typhi MTCC 733, Proteus vulgaris MTCC 1771) and four fungi (Aspergillus niger MTCC 282, Aspergillus fumigatus MTCC 343, Aspergillus clavatus MTCC 1323, Candida albicans MTCC 183). The results indicate that some of the novel s-triazines have noteworthy activity in minimum inhibitory concentration as well as agar diffusion tests.

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A Facile and Catalyst-free Synthesis of Hexahydroacridine-1,8(2H,5H )-dione and Octahydroacridin-10(1H )-yl)thiourea Derivatives: Inter- and Intramolecular Aza-Michael addition

Heterocyclic Communications ◽

10.1515/hc-2020-0005 ◽

2020 ◽

Vol 26 (1) ◽

pp. 26-32 ◽

Cited By ~ 1

Author(s):

Nader Noroozi Pesyan ◽

Narmin Akhteh ◽

Hana Batmani ◽

Barış Anıl ◽

Ertan Şahin

Keyword(s):

Hydroxylamine Hydrochloride ◽

X Ray Diffraction ◽

Reaction Conditions ◽

One Pot ◽

Thiourea Derivatives ◽

H Nmr ◽

Nmr Spectrometry ◽

The One ◽

Convenient Technique ◽

C Nmr

AbstractAn easy and convenient technique for the one-pot synthesis of novel compounds of hexahydroacridine-1,8(2H,5H)-dione and octahydroacridin-10(1H)-yl) thiourea derivatives has been developed by the reaction of the octahydro-1H-xanthenes with hydroxylamine hydrochloride and thiosemicarbazide in ethylene glycol, which is a green solvent, under mild reaction conditions. IR, 1H NMR, 13C NMR spectrometry, and X-ray diffraction analysis were used to identify the structures of these compounds.

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Nontemplate synthesis, characterization and theoretical study of tetraazamacrocycles

Analele Universitatii Ovidius Constanta - Seria Chimie ◽

10.2478/v10310-012-0020-7 ◽

2012 ◽

Vol 23 (1) ◽

pp. 121-127

Author(s):

İbrahim Șen ◽

Cem Burak Yildiz ◽

Akın Azizoğlu

Keyword(s):

Density Functional ◽

Basis Sets ◽

Frontier Molecular Orbital ◽

Spectroscopic Techniques ◽

Functional Theory ◽

Hartree Fock ◽

H Nmr ◽

Ft Ir ◽

Molecular Electrostatic Potential Maps ◽

C Nmr

Abstract The syntheses of new tetraaza macrocyclic compounds of variable ring sizes by non-template methods and their characterization with the help of elemental analysis and spectroscopic techniques (FT-IR, 1H-NMR, and 13C-NMR) have been reported in detail. The vibrational frequencies determined experimentally are compared with those obtained theoretically from density functional theory (DFT) and Hartree-Fock (HF) calculations. The comparisons between the experimental and theoretical results indicate that B3LYP level with both the 3-21G(d) and 6-31G+(d,p) basis sets is able to provide satisfactory results for predicting IR properties. The frontier molecular orbital diagrams and molecular electrostatic potential maps of title compounds have been also calculated and visualized at the B3LYP/6-31G+(d,p) level of theory.

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Antibacterial Activity of Germacrone Sesquiterpene from Curcuma Xanthorrhiza Rhizomes

ALCHEMY Jurnal Penelitian Kimia ◽

10.20961/alchemy.v12i2.1726 ◽

2016 ◽

Vol 12 (2) ◽

pp. 103 ◽

Cited By ~ 1

Author(s):

Hartiwi Diastuti ◽

Yana Maolana Syah ◽

Lia Dewi Juliawaty ◽

Marlia Singgih

Keyword(s):

Escherichia Coli ◽

Staphylococcus Aureus ◽

Antibacterial Activity ◽

Enterobacter Aerogenes ◽

Salmonella Typhi ◽

White Crystal ◽

H Nmr ◽

Curcuma Xanthorrhiza ◽

Vacuum Liquid Chromatography ◽

C Nmr

The aim of this research was to isolate and indentify the terpenoid compound from Curcuma xanthorrhiza rhizomes and its antibacterial activity. Isolation was carried out by using vacuum liquid chromatography and centrifugal chromatography. The structure was determined by NMR spectroscopy (1H-NMR, 13C-NMR 1D and 2D), then compare with data from literatures. Antibacterial test was carried out by using microdillution methods and evaluated against eight bacteria. They are Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Enterobacter aerogenes, Pseudomonas aeruginosa, Salmonella typhi, Shigella dysentriae and Vibrio cholerae. The result showed that the isolate was a white crystal which was indetified as germacron-type sesquiterpene. Germacron have highest activity againts P. aeruginosa, MIC 15.6 µg/mL and MBC 31.2 µg/mL.

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Antibacterial Activity of Germacrone Sesquiterpene from Curcuma Xanthorrhiza Rhizomes

ALCHEMY Jurnal Penelitian Kimia ◽

10.20961/alchemy.12.2.1726.103-111 ◽

2016 ◽

Vol 12 (2) ◽

pp. 103

Author(s):

Hartiwi Diastuti ◽

Yana Maolana Syah ◽

Lia Dewi Juliawaty ◽

Marlia Singgih

Keyword(s):

Escherichia Coli ◽

Staphylococcus Aureus ◽

Antibacterial Activity ◽

Enterobacter Aerogenes ◽

Salmonella Typhi ◽

White Crystal ◽

H Nmr ◽

Curcuma Xanthorrhiza ◽

Vacuum Liquid Chromatography ◽

C Nmr

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Conformational behaviour of highly hindered ethanes: meso- and racemic-2,2,2′,2′-tetramethyl-1,1′-biindanyl

Canadian Journal of Chemistry ◽

10.1139/v96-200 ◽

1996 ◽

Vol 74 (10) ◽

pp. 1795-1809 ◽

Cited By ~ 1

Author(s):

T. Bruce Grindley ◽

Paula J. MacLeod ◽

James A. Pincock ◽

T. Stanley Cameron

Keyword(s):

Potential Energy ◽

Potential Energy Surface ◽

Energy Surface ◽

Hindered Rotation ◽

Cell Parameters ◽

Slow Exchange ◽

H Nmr ◽

Line Shape Analysis ◽

Major Species ◽

C Nmr

MM3(94), AM1, and STO-3G calculations on racemic 2,2,2′,2′-tetramethyl-1,1′-biindanyl (1) show that seven minima are present on its conformational potential energy surface. 1 crystallizes in the space group Pbcn (no. 60) with cell parameters a = 11.190(7), b = 11.679(7), c = 13.19(1) Å, V = 1724(3) Å3, Z = 4, R = 0.0357, Rw = 0.0362 in the conformation predicted to be the global minimum by STO-3G and AM1, but not by MM3(94). Application of the Karplus equation and observation of a deshielded proton signal indicate that the same conformation is the major species present in solution, perhaps along with another conformation. The meso isomer 2 shows evidence of slow exchange between conformers in its room temperature NMR spectra. Barriers to exchange were obtained from 13C NMR coalescence experiments and from 1H NMR line shape analysis of the exchanging AB pattern. The potential energy surface for 2 was calculated as for 1 and used to determine the nature of the process observed. The slow exchange was calculated to be between two enantiomeric conformers. The populated conformers for both 1 and 2 had the benzene rings from the two halves of the dimer stacked in an offset manner and the favourable interactions associated with this stacking may be a factor in the relative stabilities of these conformations. Key words: MM3, molecular mechanics, hindered rotation, dialkyldiphenylethanes, X-ray crystal structure.

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Conformational structure of ethylene glycol dibenzoate. Vibrational and NMR spectra

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19811913 ◽

1981 ◽

Vol 46 (8) ◽

pp. 1913-1929 ◽

Cited By ~ 3

Author(s):

Bohdan Schneider ◽

Pavel Sedláček ◽

Jan Štokr ◽

Danica Doskočilová ◽

Jan Lövy

Keyword(s):

Ethylene Glycol ◽

Vibrational Spectra ◽

Nmr Spectra ◽

Coupling Constants ◽

Conformational Structure ◽

Infrared And Raman Spectra ◽

H Nmr ◽

Liquid States ◽

Crystalline Forms ◽

C Nmr

It was found that three crystalline forms of ethylene glycol dibenzoate can be prepared. Infrared and Raman spectra of these three forms, as well as of the glassy and liquid states, were measured. From 3JHH coupling constants obtained by analysis of the 13C satellite band of the -CH2- group in 1H NMR spectra, and from the 3JCH coupling constants of the -CO.O.CH2- fragment obtained by analysis of the carbonyl band in 13C NMR spectra it was found that in the liquid state the -CH2-CH2- group exists predominantly in the gauche conformational structure, and the bonds C-O-C-C assume predominantly a trans orientation. The results of the analysis of NMR and vibrational spectra were used for the structural interpretation of conformationally sensitive bands in vibrational spectra of ethylene glycol dibenzoate.

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Synthesis of 2-amino-5,7-dimethyl-4-oxopyrido[3,4-e]-1,3-thiazines

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19833426 ◽

1983 ◽

Vol 48 (12) ◽

pp. 3426-3432 ◽

Cited By ~ 4

Author(s):

Dušan Koščík ◽

Pavol Kristian ◽

Ondrej Forgáč

Keyword(s):

Spectral Data ◽

Chlorine Atom ◽

Mass Spectra ◽

High Reactivity ◽

Secondary Amines ◽

Dimroth Rearrangement ◽

H Nmr ◽

New Synthesis ◽

C Nmr

New synthesis of pyrido[3,4-e]-1,3-thiazines consisting in reaction of 2,6-dimethyl-4-chloronicotinoyl isothiocyanate with primary or secondary amines, or with benzaldehyde phenylhydrazone, is described. High reactivity of the chlorine atom does not allow isolation of the corresponding thioureas, arising as intermediates, except in the case of the benzylamino derivative. Structure of the products was unequivocally confirmed by their spectral data (IR, UV, 1H NMR, 13C NMR and mass spectra). The synthesized derivatives do not undergo the Dimroth rearrangement.

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Oxynemorensine, an alkaloid from Senecio nemorensis L., var. subdecurrens GRISEB

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19800548 ◽

1980 ◽

Vol 45 (2) ◽

pp. 548-558 ◽

Cited By ~ 7

Author(s):

Antonín Klásek ◽

Petr Sedmera ◽

Jindřich Vokoun ◽

Anna Boeva ◽

Svatava Dvoráčková ◽

...

Keyword(s):

Unsaturated Acid ◽

Mass Spectra ◽

H Nmr ◽

C Nmr

From S. nemorensis L., var. subdecurrens GRISEB. there were isolated the previously obtained alkaloids nemorensine (I), retroisosenine (II), bulgarsenine (III) and, in addition, the alkaloid oxynemorensine which was assigned the structure VIII on the basis of the interpretation of the 1H-NMR, 13C-NMR, mass spectra, and on that of the identification of the products of hydrolysis and reduction. Furthermore, the isolation of the cis-nemorensic acid (V) as well as that of the unsaturated acid IV, and the transformation of bulgarsenine (III) to nemorensine (I) were described.

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21,22-Disubstituted 18α,19βH-Ursane Derivatives with Oxabicyclooctane System in Ring E

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19930173 ◽

1993 ◽

Vol 58 (1) ◽

pp. 173-190 ◽

Cited By ~ 1

Author(s):

Eva Klinotová ◽

Jiří Klinot ◽

Václav Křeček ◽

Miloš Buděšínský ◽

Bohumil Máca

Keyword(s):

Spectral Data ◽

Spin Systems ◽

Coupling Constants ◽

Complete Analysis ◽

Nmr Spectrum ◽

Proton Proton ◽

H Nmr ◽

Proton Coupling ◽

C Nmr

Reaction of 3β-acetoxy-21,22-dioxo-18α,19βH-ursan-28,20β-olide (IIIa) and 20β,28-epoxy-21,22-dioxo-19α,19βH-ursan-3β-yl acetate (IIIb) with diazomethane afforded derivatives XII-XIV with spiroepoxide group in position 21 or 22, which were further converted into hydroxy derivatives XV and XVII. Ethylene ketals VIII-X were also prepared. In connection with the determination of position and configuration of the functional groups at C(21) and C(22), the 1H and 13C NMR spectral data of the prepared compounds are discussed. Complete analysis of two four-spin systems in the 1H NMR spectrum of bisethylenedioxy derivative Xb led to the proton-proton coupling constants from which the structure with two 1,4-dioxane rings condensed with ring E, and their conformation, was derived.

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