No full-text available
To read the full-text of this research,
you can request a copy directly from the author.
Synthesis, Antibacterial and Antifungal Properties of Cyclohexane Tosyloxyimine Derivative
Abstract
Abstract
Due to increasing antimicrobial resistance, functionally substituted cyclohexane derivatives are being explored as
potential antimicrobial agents. Reaction of diethyl 4-hydroxy-6-(hyd-roxyimino)-4-methyl-2-phenylcyclohexane-1,3-
dicarboxylate with 4-toluenesulfonyl chloride in boiling acetone in the presence of equimolar triethylamine resulted in
formation of diethyl - 4-hydroxy-4-methyl-2-phenyl-6-((tosyloxy)imino) cyclohexane-1,3-dicarboxylate. The structure of
novel compound was characterized by 1H and 13C NMR spectra and elemental analysis was performed. Agar well diffusion
assay was used to screen novel compound against Gram-positive bacteria, Gram-negative bacteria and fungi. Test
compound showed better antimicrobial properties against Gram-negative bacteria as compared to Gram-positive
bacteria and fungi. Acinetobacter baumannii BDU-32 was found to be most sensitive bacteria while Candida
pseudotropicalis BDU MA88 was found to be most sensitive yeast.
Keywords: Acinetobacter baumannii; Agar well diffusion; Antimicrobial resistance; Cyclohexane; Tosyloxyimine
derivatives
... Test compound was screened for antibacterial and antifungal activities by using standard agar well diffusion assay [11]. Mueller-Hinton agar was used to determine antibacterial activity while Sabouraud Dextrose Agar (SDA) was used to determine antifungal activity. ...
... 1H-indene, 1-hexadecyl-2, 3-dihydro exhibited antiangiogenic and anticancer activity (Xu et al., 2023). Cyclohexane is an alicyclic hydrocarbon which possesses many biological activities anti-inflammatory, antioxidant, antimicrobial and cytotoxic effects (Shoaib, 2019). The SEM images (Fig. 2) revealed a flake like morphology in the powered extract. ...
The medicinal herb Anisomeles heyneana Benth is endemic to peninsular India. In current study the phytoconstituents in the leaves of Anisomeles heyneana were investigated. The plant material was collected from the Western Ghats in India. The phytochemicals were extracted from the leaves by preparing a methanol extract and analyzed using GC-MS and SEM-EDX. The GC-MS analysis of extract revealed the presence of 22 compounds in it. These compounds included phenolics, flavonoids, coumarins, glycosides, fatty acids, terpene and steroids. The predominant compounds in the leaves were 13, 27-cycloursan-3-one (100%), γ-sitosterol (82.04%) and n-hexadecanoic acid (34.08%). An energy-dispersive X-ray spectrometer (EDS) was employed to analyse the mass percentage of trace elements. Scanning electron microscopy showed the presence of carbon, oxygen, sodium, magnesium, aluminium, silicon, phosphorus, chlorine, calcium, magnesium, and iron. The carbon was the highest component (48.76 %) as compared with other minerals.
... Test compound was screened for antibacterial and antifungal activities by using standard agar well diffusion assay [11]. Mueller-Hinton agar was used to determine antibacterial activity while Sabouraud Dextrose Agar (SDA) was used to determine antifungal activity. ...
Due to increasing antimicrobial resistance, functionally substituted cyclohexane derivatives are being explored as antimicrobial agents. Agar well diffusion method was used to evaluate antibacterial and antifungal properties of diethyl-4-hydroxy-4-methyl-2-(3-nitrophenyl)-6-oxocyclohexane-1,3-dicarboxylate against Gram-positive bacteria, Gram-negative bacteria and fungi. Test compound exhibited moderate antibacterial properties against Gram-negative bacteria, while Gram-positive bacteria were found to be resistant. Candida tropicalis was found to be most sensitive yeast. Our findings reveal that tested compound can act as potential antimicrobial agent in the future.
The synthesized organic compound ((2-chloro-4-cyano-5-ethoxy-3,5-dioxopentan-2-yl) phosphonic acid)) was evaluated against pathogenic microorganisms using agar well diffusion method. The results obtained reveled that, the diameters of inhibition zones were ranging between 24.0-36.3 mm for gram-negative bacteria, from 28.3 mm to 34.5 mm for gram-positive bacteria and between 18.2-20.3 mm for genus Candida. The MIC value 62.5 µg/mL showed that among gram-negative bacteria, Escherichia coli and Pseudomonas aeruginosa were the most sensitive to the compound compared to Acinetobacter baumannii and Klebsiella pneumoniae. Gram-positive bacteria (Staphylococcus aureus, Bacillus mesentericus and Bacillus subtilis) had the same sensitivity to the compound with 125 µg/mL as MIC value. Among fungal strains, Candida tropicalis with MIC value 62.5 µg/mL was the most sensitive to the compound compared to Candida albicans (250 µg/mL) and Candida guilliermondii (125 µg/mL).
Streptomyces is recognized as a crucial generator of bioactive molecules that benefit humanity, such as antibiotics and other medications. The Streptomyces strain obtained from the gut of Apis mellifera yemintica was utilized in this investigation to screen for antibacterial and antiproliferative activities using secondary metabolites. On the basis of morphological and molecular identification, the isolated strain ess_amH1 was confirmed as Streptomyces sp., and phylogenetic tree construction revealed 96% sequence similarity with Streptomyces griseus. The ethyl acetate solvent extract generated from the strain ess_amH1 demonstrated high antibacterial activity against ATCC bacterial pathogens, as well as pathogenic yeast, according to the disc diffusion assay. The ethyl acetate solvent extract also induced dose-dependent cytotoxicity in breast cancer and hepatocarcinoma cell lines, with IC50 concentrations at 50 and 75 µg/mL, respectively. The findings confirm that the Streptomyces sp. strain ess_amH1 isolated from a competitive symbiotic habitat, i.e., the gut of A. mellifera yemintica, produces promising bioactive chemicals.
Development of resistance to antimicrobial drugs is a global health concern not only for humans but also for animals. Rate of microbial resistance to antibiotics has alarmingly increased in last two decades. Factors responsible for this ever increasing antibiotic resistance are attributed to microorganisms as well as excessive and unwise use of antimicrobial drugs. Drug efflux pumps and biofilm formation are examples of microbial factors which contribute to antimicrobial resistance. It is dire need of hour to develop new antimicrobial drugs to ameliorate this condition. New antimicrobial agents with unique mode of action should be explored. In this regard, synthetic organic compounds are target of worldwide drug development studies which are being conducted for investigating new antimicrobial drugs. Cyclohexane and its functionally substituted derivatives are important compounds with diverse biological properties. These compounds can serve as probable alternatives to antibiotics with potential antimicrobial properties. This review summarizes the experimental evidences and studies exploring antimicrobial activities of cyclohexane and its functionally substituted derivatives as probable antimicrobial agents of future.
Abstract
The development of resistance to antimicrobial agents is a global health problem for humans as well as animals. Over the
past decade, the rate of microbial resistance to antibiotics has alarmingly increased. Factors contributing to this ever
increasing antibiotic resistance pertain to microorganism as well as excessive and unwise use of the antibiotics. Biofilm
formation and use of efflux pumps are the examples of microbial factors responsible for emergence of antimicrobial
resistance. To ameliorate this condition, it is dire need of time to develop new antimicrobial agents. In this regard,
chemical organic compounds are best available substances with potential antimicrobial properties. This review
summarizes the antimicrobial activities of some important organic compounds as well as potential of functionally
substituted chemical organic compounds as probable antimicrobial agents of future. These important organic compounds
include functionally substituted derivatives of cyclohexane, quaternary ammonium compounds, hydrazones, pyrazolone,
triazole, thiones, isatin, indole, chalcones, quinoxaline, anthraquinones, coumarins, thiophenes, piperidine,
benzoxazolinone, phthalazinone, sulfones, thiazole and volatile organic compounds.
Keywords: Antimicrobial Resistance; Cyclohexane; Functionally Substituted Derivatives; Biofilm; Organic Compounds
The reaction of 2,4-diacetyl-5-hydroxy-5-methyl-3-phenylcyclohexanone-1 with phenylhydrazine is
conducted, and the crystal structures of its products, 1-(6-hydroxy-3,6-dimethyl)-2,4-diphenyl-4,5,6,7-
tetrahydro-2H-indazol-5-yl)ethane-1-one and 1-(2-hydroxy-2-methyl-6-phenyl-4-(2-phenylhydrazono)-5-
(1-(2-henylhydrazono)ethyl)cyclohexyl)ethane-1-one, are determined by single crystal XRD.
Purpose: To investigate the effect of 2-[(4-hydroxy-phenylamino)-methylene]-5,5-dimethyl-cyclohex (HPDH) on mammary carcinogenesis induced by 7,12-dimethylbenz(a)anthracene in female Sprague Dawley rats. Methods: Among three groups of rats (50 each) used in the study, the control group was fed standard diet alone, ibuprofen group received standard diet containing 1200 mg/kg ibuprofen while HPDH group was administered standard diet containing 1200 mg/kg HPDH. The treatment was for 10 days for all the groups. All the animals received 20 mg of DMBA intragastrically by gavage. Clinical parameters for the rats were recorded weekly. Micrometer caliper was used to measure the diameter of all the tumors at the end of the experiment and tumor volume calculated. Histological evaluation was performed using hematoxylin and eosin (H&E) staining. High performance liquid chromatography (HPLC) was used to determine the level of HPDH and ibuprofen in the serum of the animals. Results: The data revealed a significant decrease in the number of rats with mammary tumor, number of tumors/rat and tumor volume by 54, 72 and 75 %, respectively, in HPDH group compared to control group. The ibuprofen-treated rats also showed significant decrease in the number of rats with tumor, number of tumors/rat and tumor volume by 43, 55, and 59 %, respectively. Treatment of rats with HPDH increased the latency period of tumor induction significantly (p < 0.005). Median detection period (50 % of tumors) was 92, 83 and 56 days, respectively, in HPDH, ibuprofen and control groups, respectively, after DMBA induction. Conclusion: These results demonstrate that HPDH possesses strong chemopreventive activity against mammary carcinogenesis. © Pharmacotherapy Group, Faculty of Pharmacy, University of Benin, Benin City, 300001 Nigeria. All rights reserved.
Multicomponent condensation of 3-aryl(hetaryl)-2,4-diacetyl-5-hydroxy-5-methylcyclohexanones with 2-cyanoethanethioamide and alkylating agents in the presence of morpholine afforded 3-(alkylsulfanyl)-8-aryl(hetaryl)-7-acetyl-6-hydroxy-1,6-dimethyl-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles, 1-[1-amino-6-aryl(hetaryl)-8-hydroxy-6,7,8,9-tetrahydrothieno[2,3-c]isoquinolin-7-yl]ethanones, and 3,3′-[ethane-1,2-diylbis(sulfanediyl)]bis[7-acetyl-6-hydroxy-1,6-dimethyl-8-(furan-2-yl)-5,6,7,8-tetrahydroisoquinolin-4-carbonitrile].
Functionalized alkyl-substituted cyclohexanones, pyridines, and 2,3,5,6,7,8-hexahydroisoquinolines were synthesized by condensation of aliphatic aldehydes with CH acids.
New derivatives of partially hydrogenated isoquinolines were obtained by condensation of 2,4-diacetyl-3-aryl(hetaryl)-5-hydroxy-5-methylcyclohexanones with malononitrile and its dimer, 2-amino-1,1,3-tricyano-1-propene, and alkylation reactions of the obtained compounds were studied.
The reaction of diethyl-4-hydroxy-4-methyl-2-phenyl-6-oxocyclohexane-1,3-dicarboxylate with Nisobutylethylenediamine is performed and the crystal structure of this reaction product (diethyl-1-isobutyl-9-hydroxy-9-methyl-7-phenyl-1,4-diazaspiro[4,5]decane-6,8-dicarboxylate) is determined by X-ray crystallography.
In the present study, 1-(4,5-dihydro-3,6-dimethyl-4-(1,3-diphenyl-1H-pyrazol-4-yl)-3aH-indazol-5-yl)methanone derivatives (9–12) and isoxazoleyl (13–16) have been synthesized by the condensation of 1,3-diphenyl-1H-pyrazole-4-carbaldehyde (1–4) with acetyl acetone via Knoevenagel/Michael/aldol reactions in a sequential manner to yield intermediate cyclohexanone (5–8). The intermediates (5–8) treated with NH2NH2 · H2O/NH2OH · HCl afforded 4-indazolyl-1,3,4-trisubstituted pyrazole and isoxazoleyl derivatives. All of these compounds are reported for the first time, and the structures of these compounds were confirmed by means of infrared, 1H NMR, 13C NMR, and mass spectroscopy.
A series of novel spiro(cyclohexane-1,2′-thiazolidine) derivatives 1–5 and spiro(cyclohexane1,2′-thiazolo-pyridine) derivatives 6–14 were synthesized. Arylidene thiazolidine derivative 2b was reacted with hydroxylamine hydrochloride, hydrogen peroxide or ethyl cyanoacetate to give spiro(cyclohexane-1,2′-thiazolidine), and spiro(cyclohexane-1,2′-thiazole) derivatives 15–17. Moreover, some of the newly prepared products were screened for their antibacterial, antioxidant, and anticancer activities, and some of them showed moderate to good biological activities. The results showed that the compounds 9, 7a, and 8 have the highest antioxidant activity (92.52, 85.00, and 84.61 %, respectively at 100 μg/mL) when compared with butylated hydroxyl toluene as a standard (93.6 %). Also, the compound 9 showed the highest anticancer activity against two cell lines (MCF-7 and HepG2).
The condensation of diethyl 4-hydroxy-4-methyl-6-oxo-2-(4-substitutedphenyl)-cyclohexane-1,3-dicarboxylates and N′-(2-chloropropyl)ethane-1,2-diamine leads to diethyl 1-(2-chloropropyl)-9-hydroxy-9-methyl-7-phenyl-1,4-diazaspiro[4.5]decane-6,8-dicarboxylate (2) and its para-substituted methyl (1), chloro (3), bromo (4), and nitro (5) derivatives with a new stereogenic center, which were fully characterized by elemental analysis, ESI-MS, IR, 1H and 13C NMR spectroscopies and X-ray single-crystal analysis (for 2). The condensation reaction is regioselective, only cyclohexanone carbonyl moiety undergoes the transformation, leaving the β-keto ester carbonyls unreacted. Withing the compounds 1–5, the increase in the Hammett’s σp, related normal σpn, inductive σI, negative σp- and positive σp+ polar conjugation and Taft’s σpo substituent constants generally leads to the corresponding drift of δOH and δNH NMR chemical shifts to lower field.
Base-catalyzed reactions of isopropyl acetoacetate with aromatic and heterocyclic aldehydes afforded the corresponding diisopropyl 6-hydroxy-6-methyl-4-oxocyclohexane-1,3-dicarboxylates which were brought into reactions with mono- and difunctional nitrogen-containing nucleophiles. According to the X-ray diffraction data, diisopropyl 4-oxocyclohexane-1,3-dicarboxylates in crystal exist in the ketone form.
- A I Ismiev
- A M Magerramov
- V A Sukach
- M V Vovk
Ismiev AI, Magerramov AM, Sukach VA, Vovk MV
(2016) Zh Org Farm Khim 14(4): 16.
Regioselective Ethanolamination and Ketalization of
- A P Krivenko
- E A Kozlova
Krivenko AP, Kozlova EA,Grigorèv (2003)
Regioselective Ethanolamination and Ketalization of
Methods for in vitro evaluating antimicrobial activity: A
- M Balouiri
- M Sadiki
- S K Ibnsouda
Balouiri M, Sadiki M, Ibnsouda SK (2016) Methods for
in vitro evaluating antimicrobial activity: A Review.
Journal of Pharmaceutical Analysis 6(2): 71-79.