Objective:A series of some novel pharmacological active moleculeEthyl-4-(substituted phenyl-5-yl)-6-(6-methoxynapthalen)-2 oxo-cyclohexa-3-ene- 1-ethyl carboxylate derivatives were synthesized and evaluated in vitro for Antibacterial activity against staphylococcus aureus, Escherichia coli, Salmonella Typhi, Bacillus subtilis and antifungal activity against Aspergillusniger, Aspergillusflavus and Penicilliumchrysogenum,Fusariummoneliforme.
Methods: The present research work describes the synthesis of Cyclohexenones by Michael addition. In the present investigation first Chalcones and their derivatives have been synthesized. Chalcones, 3-(6-methoxynaphthalen-1-yl)-1-phenylprop-2-en-1-one(3a-f) were prepared by the Aldol condensation of substituted acetophenone and 6-methoxy-1-napthaldehyde. Base catalyzed condensation of 3-(6-methoxynaphthalen-1-yl)-1-phenyl prop-2-en-1-one (3a-f) with ethyl acetoacetate (4) yields corresponding Ethyl-4-(substituted phenyl-5-yl)-6-(6-methoxynapthalen)-2-oxocyclohexa- 3-ene-1-ethyl carboxylate (5a-f).The newly synthesized compounds were characterized on the basis of elemental analysis, spectroscopic studies viz, FT-IR, 1H NMR and mass.
Results: Literature survey reveals that the synthesized pharmacological active molecule i.e. substituted Ethyl-4-(substituted phenyl-5-yl)-6-(6- methoxynapthalen)-2-oxo-cyclohexa-3-ene-1-ethyl carboxylate (5a-f)was not reported.
Conclusion:All these newly synthesized compounds were evaluated for their in vitro antimicrobial activity. Most of the compounds showed potent activity

B. JADHAV, SATISH

K. AGHAO, ARVIND

K. VIBHUTE, PRASHANT

N. BHARATE, YOGESH

English

Innovare Academic Sciences: E-Journals

National conference on recent Advances in Physical Sciences (RAPS-2020)           Full Proceeding Paper SYNTHESIS AND MICROBIAL EVALUATION OF SOME NOVEL ETHYL-4-(SUBSTITUTED PHENYL-5-YL)-6-(6-METHOXYNAPTHALEN)-2-OXO-CYCLOHEXA-3-ENE-1-ETHYL CARBOXYLATE DERIVATIVES  SATISH B. JADHAV*, PRASHANT K. VIBHUTE, YOGESH N. BHARATE, ARVIND K. AGHAO Department of Chemistry, Balbhim Arts, Science and Commerce College, Beed 431122Maharashtra, India.                                                                     Email: Orgchem.jadhav@gmail.com Received: 25 January 2020, Revised and Accepted: 17 March 2020  ABSTRACT  Objective: A series of some novel pharmacological active moleculeEthyl-4-(substituted phenyl-5-yl)-6-(6-methoxynapthalen)-2-oxo-cyclohexa-3-ene-1-ethyl carboxylate derivatives were synthesized and evaluated in vitro for Antibacterial activity against staphylococcus aureus, Escherichia coli, Salmonella Typhi, Bacillus subtilis and antifungal activity against Aspergillusniger, Aspergillusflavus and Penicilliumchrysogenum,Fusariummoneliforme. Methods: The present research work describes the synthesis of Cyclohexenones by Michael addition. In the present investigation first Chalcones and their derivatives have been synthesized. Chalcones, 3-(6-methoxynaphthalen-1-yl)-1-phenylprop-2-en-1-one(3a-f) were prepared by the Aldol condensation of substituted acetophenone and 6-methoxy-1-napthaldehyde. Base catalyzed condensation of 3-(6-methoxynaphthalen-1-yl)-1-phenyl prop-2-en-1-one (3a-f) with ethyl acetoacetate (4) yields corresponding Ethyl-4-(substituted phenyl-5-yl)-6-(6-methoxynapthalen)-2-oxo-cyclohexa-3-ene-1-ethyl carboxylate (5a-f).The newly synthesized compounds were characterized on the basis of elemental analysis, spectroscopic studies viz, FT-IR, 1H NMR and mass. Results: Literature survey reveals that the synthesized pharmacological active molecule i.e. substituted Ethyl-4-(substituted phenyl-5-yl)-6-(6-methoxynapthalen)-2-oxo-cyclohexa-3-ene-1-ethyl carboxylate (5a-f)was not reported.  Conclusion:All these newly synthesized compounds were evaluated for their in vitro antimicrobial activity. Most of the compounds showed potent activity. Keywords:  Cyclohexenones, Michael addition, ethyl acetoacetate, Chalcones.   INTRODUCTION Heterocyclic and Medicinal chemistry is the science that deals with designing and discovery of new therapeutic chemicals and their development in medicinal chemistry is useful for society. Drug development is perhaps the most elegant approach for discovering compounds exhibiting high specificity and biological activity[1]. Chemist had designed and synthesized a lot of new heterocyclic derivatives related to this moiety and screened those for different pharmacological activities to obtained a molecule which have good pharmacological activity with least adverse effects. The chalcone is not only synthetically important scaffold but also possesses a wide range of promising biological activities Chalcone is a generic term used for the compounds that bears, 1, 3-diphenyl-prop-2-en-1-one framework [2]. Under homogeneous conditions, these compounds are usually prepared by base or acid catalyzed Aldol condensation between aromatic aldehydes and ketones. Chalcones represent an important class of compounds due to their chemical flexibility, as synthons.  Chalcones and the corresponding heterocyclic analogs are valuable intermediatesin organic synthesis [3] and exhibit a multitude of biological activities [4].From a chemical point of view, an important feature of chalcones and their hetero analogs is the ability to act as activated unsaturated systems in conjugated addition reactions of carbanions in the presence of basic catalysts [5,6]. This type of reaction may be exploited with the view of obtaining highly functionalized cyclohexene derivatives [7],but is more commonly used for the preparation of 3,5-diaryl-6-carbethoxycyclohexenones via Michael addition of ethyl acetoacetate. The mentioned Cyclohexenones are efficient synthons in building spiranic compounds [8] or intermediates in the synthesis of fused   heterocycles such as benzoselenadiazoles and benzothiadiazoles [9],benzopyrazoles and benzisoxazoles[10,11]or carbazole derivatives [12].  The Michael reaction of chalcones with active methylenecompounds such as 1,3-dicarbonyls have been the subject of many investigations [13-16]. It is known that a weak base or acid such as Piperidine [17] or phosphorus trichloride [18]often affords open chain adducts, while cyclic products have been obtained in the presence of sodium methoxide [19] or sodium hydroxide [20].Particularly, the products of these cyclic reactions are of interest in terms of their stereochemistry and as starting materials for the synthesis of compounds with possible biological activity [21].These types of reactions may be exploited with the view of obtaining highly functionalized cyclohexene derivatives [22] but are more commonly used for the preparation of 3,5-diaryl-6-carbethoxy-2-cyclohexenones via the Michael addition of ethyl acetoacetate with chalcones. Prompted by all these observations and in continuation of our earlier work on the synthesis and of some chalcones, it was felt worthwhile tosynthesize some 3,5-diaryl-6-carbethoxy-2-cyclohexen-1-ones derivatives. MATERIAL AND METHODS Melting points were determined in open capillaries and are uncorrected. IR spectra were recorded using Perkin –Elmer spectrometer.1H NMR spectra were recorded on Brucker Advance II 400 spectrometer in DMSO by using TMS as internal standard. Thin layer chromatography was performed with E. Merk precoated TLC plates, silica gel 60F254 with thickness of 0.25mm and spots were         Vol 8, Special Issue 1, 2020                                                                                                                                                                                       ISSN-2321-5496   Jadhav et al. Innovare Journal of science, Vol 8, Special Issue 1, 2020,   93 National conference on recent Advances in Physical Sciences (RAPS-2020)  visualized by irradiation with ultraviolet light (254 nm). Physical constants and analytical data of all the compoundsreported in this paper are summarized in Table 1. General procedure for the synthesis of 3-(6-methoxynaphthalen-1-yl)-1-(4-substituted phenyl)prop-2-en-1-one(Chalcone)17 (3a-f). A mixture of 4-substituted acetophenone(2a-f)(0.01mole) and 6-methoxy-1-naphthaldehyde (2)(0.01mole) was stirred in methanol (50 mL) and then a solution of 15 mL potassium hydroxide (0.02mole) was added to it. The mixture was kept overnight at room temperature and then it was poured into crushed ice and acidified with dil. hydrochloric acid.  The chalcones i.e. [3-(6-methoxynaphthalen-1-yl)-1-(4-substituted phenyl)prop-2-en-1-one] (3a-f)precipitate out as solid (Scheme‐I). The obtained solid was filtered, washed with water, dried and purified by recrystallization from acetic acid. General Procedure for Synthesis of 3, 5-diaryl-6-carbethoxy-2-cyclohexen-1-ones 5(a-f) In a clean & dry round bottom flask 3-(4-chlorophenyl)-1-substituted phenylprop-2-en-1-one (Chalcones) (3 mmol) and ethyl acetoacetate (0.39 g, 0.40 mL, 3 mmol) were refluxed for 2 h in 10-15 mL ethanol in the presence of 0.5 mL 10% NaOH. The reaction mixture was then poured with good stirring into 200 mL ice-cold water and kept at room temperature until the reaction product separated as a solid, which was filtered off and recrystallized from ethanol. The physical constant and yields are recorded in table-I. Antimicrobial activity All the newly synthesized compounds 5a-f was tested for their antimicrobial activity. The effects of unknown compounds were compared with the standard drug Penicillin for bacteria and Greseofulvin for fungi. Antibacterial activity was performed against staphylococcus aureus, Escherichia coli, Salmonella Typhi, Bacillus subtilis and antifungal activity against Aspergillusniger, Aspergillusflavus and Penicilliumchrysogenum,Fusariummoneliforme. The antibacterial activity was assayed by cup plate method [23] and antifungal activity was assayed by standard agar disc diffusion method [24].The results are shown in Table II and III respectively. RESULTS AND DISCUSSION Ethyl-4-(substituted phenyl-5-yl)-6-(6-methoxynapthalen)-2-oxo-cyclohexa-3-ene-1-ethyl carboxylate derivatives5a-f, were successfully synthesized as per the scheme-I.The entire synthesized compounds are qualitatively analyzed by running T.L.C. and melting point. Thestructures of the compounds synthesized are confirmed by IR,1HNMR and mass spectral data. Analytical and spectral data (IR, 1H-NMR) of all synthesized compounds were in full agreement with given structure. The IR spectrum of 5a-f exhibited two sharp strong absorption bands above 1700 cm-1and near 1650 cm-1, these absorption bands confirm the presence of the ester function and the carbonyl group conjugated with a carbon–carbon double bond, respectively in Cyclohexenones ring. The characteristic signal in the 1HNMRspectra of compounds 5a-fis the singlet of the vinylic proton in position 3 of the Cyclohexenones ring that occurs at approximately δ 6.55 ppm and confirms that the intramolecular cyclocondensation subsequent to the Michael addition actually took place. The investigation of antibacterial screening data revealed that compounds 5b,d,f shows excellent activity against all bacteria, compound 5a,c shows good activity and compound 5e shows low activity against most of the bacteria. The investigation of antifungal activity data revealed that compound 6b show inhibitory effect against all the fungus, compound 5a,cshow inhibitory effect against Penicilliumchrysogenum and Fusariummoneliforme, compound 5d,f show inhibitory effect against Aspergillusniger, Penicilliumchrysogenum, Aspergillusflavus. Remaining compounds are inactive against all the fungus.    Table 1: Analytical Data and Elemental Analysis of Compounds 5(a-f) Compd. Molecular formula M.P. 0C Yield % Elemental Analysis %C % H Calcd. Found Calcd. Found 5a C26H24O4 116 85 77.98 77.78 6.04 6.00 5b C26H23ClO4 110 90 71.80  71.60  5.33 5.12 5c C26H23BrO4 130 87 65.14 65.05 4.84 4.54 5d C26H23FO4 145 92 74.63  74.43  5.54 5.25 5e C27H26O4 147 90 78.24 78.10 6.32 6.15 5f C26H22Cl2O4 117 80 66.53 66.33 4.72 4.45  Table 2: Antibacterial screening results of the compounds 5a-f  Sr. No.  Compounds E.coli Salmonella typhi Staphylococcus aureus Bacillus subtilis Diameter of growth inhibition zone (mm) 1 5a 13 11 15 16 2 5b 17 19 26 26 3 5c 14 14 21 16 4 5d 17 14 20 20 5 5e 16 12 10 17 6 5f 13 17 22 22 7 Penicillium 22 25 35 38 8 DMSO -ve -ve -ve -ve  -ve  no antibacterial activity  Jadhav et al. Innovare Journal of science, Vol 8, Special Issue 1, 2020,   94 National conference on recent Advances in Physical Sciences (RAPS-2020)  Table 3:  Antifungal screening results of the compounds 5a-f. Sr. No. Compounds Aspergillus niger Aspergillusflavus Penicillumchrysogenum Fusariummoneliforme 1 5a -ve -ve +ve -ve 2 5b -ve -ve -ve -ve 3 5c +ve -ve -ve -ve 4 5d -ve +ve -ve -ve 5 5e +ve RG +ve -ve 6 5f -ve -ve -ve -ve 7 Griseofulvin -ve -ve -ve -ve 8 DMSO +ve +ve +ve +ve                  -ve No growth Antifungal activity present                 +ve            Growth Antifungal activity absent                  RG            Reduced growth  Spectral data of synthesized compounds (5a-f) Ethyl-4-(phenyl-5-yl)-6-(6-methoxynapthalen)-2-oxo-cyclohexa-3-ene-1-ethyl carboxylate (5a):IR (KBr pellets Cm‐1): 1146.82 (C–O str.), 1514.34 (–CH2), 1607.51 (C=C), 1732.15 (C=O of α, β-unsaturated ketone), 1735.15 (C=O of ester), 1162 (-OCH3); 1H NMR (DMSO, 400 MHz) δ 1.06-1.12 (t, 3H, CH3), 2.56-2.70 (m, 2H, -CH-CH-Ar), 3.23-3.41(m, 2H, CH2-CHAr), 3.93 (s, 3H, -OCH3), 4.07- 4.14 (q, 2H, -OCH2), 6.32 (s, 1H, =CH),8.65-7.20 (m, 11H, Ar-H); Mass (m/z): 400.17(M+1). Ethyl-4-(4-chlorophenyl-5-yl)-6-(6-methoxynapthalen)-2-oxo-cyclohexa-3-ene-1-ethyl carboxylate (5b):IR (KBr pellets Cm‐1): 1140.32 (C–O str.), 1510.14 (–CH2), 1600.31 (C=C), 1730.10 (C=O of α, β-unsaturated ketone), 1725.15 (C=O of ester), 1160 (-OCH3); 1H NMR (DMSO, 400 MHz) δ 1.08-1.15 (t, 3H, CH3), 2.46-2.60 (m, 2H, -CH-CH-Ar), 3.21-3.38(m, 2H, CH2-CHAr), 3.90 (s, 3H, -OCH3), 4.06- 4.16 (q, 2H, -OCH2), 6.30 (s, 1H, =CH),8.60-7.10 (m, 10H, Ar-H); Mass (m/z): 434.13 (M+1). Ethyl-4-(4-bromophenyl-5-yl)-6-(6-methoxynapthalen)-2-oxo-cyclohexa-3-ene-1-ethyl carboxylate (5c):IR (KBr pellets Cm‐1): 1145.72 (C–O str.), 1510.14 (–CH2), 1600.81 (C=C), 1730.10 (C=O of α, β-unsaturated ketone), 1732.10 (C=O of ester), 1152 (-OCH3); 1H NMR (DMSO, 400 MHz) δ 1.07-1.12 (t, 3H, CH3), 2.50-2.80 (m, 2H, -CH-CH-Ar), 3.20-3.40(m, 2H, CH2-CHAr), 3.89 (s, 3H, -OCH3), 4.05- 4.12 (q, 2H, -OCH2), 6.28 (s, 1H, =CH),8.62-7.10 (m, 10H, Ar-H); Mass (m/z): 478.08(M+1). Ethyl-4-(4-flourophenyl-5-yl)-6-(6-methoxynapthalen)-2-oxo-cyclohexa-3-ene-1-ethyl carboxylate (5d):IR (KBr pellets Cm‐1): 1136.72 (C–O str.), 1510.14 (–CH2), 1612.31 (C=C), 1712.11 (C=O of α, β-unsaturated ketone), 1725.25 (C=O of ester), 1160 (-OCH3); 1H NMR (DMSO, 400 MHz) δ 1.12-1.20 (t, 3H, CH3), 2.46-2.65 (m, 2H, -CH-CH-Ar), 3.20-3.38(m, 2H, CH2-CHAr), 3.93 (s, 3H, -OCH3), 4.17- 4.27 (q, 2H, -OCH2), 6.31 (s, 1H, =CH),8.70-7.40 (m, 10H, Ar-H); Mass (m/z): 418.46 (M+1). Ethyl-4-(4-methylphenyl-5-yl)-6-(6-methoxynapthalen)-2-oxo-cyclohexa-3-ene-1-ethyl carboxylate (5e):IR (KBr pellets Cm‐1): 1126.12 (C–O str.), 1510.14 (–CH2), 1618.21 (C=C), 1722.05 (C=O of α, β-unsaturated ketone), 1725.10 (C=O of ester), 1152 (-OCH3); 1H NMR (DMSO, 400 MHz) δ 1.10-1.22(t, 3H, CH3),2.14 (s, 3H, CH3), 2.46-2.65 (m, 2H, -CH-CH-Ar), 3.22-3.40(m, 2H, CH2-CHAr), 3.90 (s, 3H, -OCH3), 4.05- 4.16 (q, 2H, -OCH2), 6.22 (s, 1H, =CH),8.65-7.22 (m, 10H, Ar-H); Mass (m/z): 414.18 (M+1). Ethyl-4-(2,4-dichlorophenyl-5-yl)-6-(6-methoxynapthalen)-2-oxo-cyclohexa-3-ene-1-ethyl carboxylate (5f):IR (KBr pellets Cm‐1): 1150.82 (C–O str.), 1512.24 (–CH2), 1627.50 (C=C), 1742.17 (C=O of α, β-unsaturated ketone), 1735.15 (C=O of ester), 1160 (-OCH3); 1H NMR (DMSO, 400 MHz) δ 1.11-1.22 (t, 3H, CH3),2.55-2.68 (m, 2H, -CH-CH-Ar), 3.20-3.41(m, 2H, CH2-CHAr), 3.95 (s, 3H, -OCH3), 4.20- 4.45 (q, 2H, -OCH2), 6.29 (s, 1H, =CH),8.60-7.22 (m, 9H, Ar-H); Mass (m/z): 469.36(M+1). CONCLUSION In conclusion, we have reported some novel Ethyl-4-(substituted phenyl-5-yl)-6-(6-methoxynapthalen)-2-oxo-cyclohexa-3-ene-1-ethyl carboxylate derivatives. From the above studies it can be concluded   that the synthesized compounds exhibit significant antibacterial activityagainst pathogenic bacteria. Further studies are needed to determine the mode of action of the studied compounds. ACKNOWLEDGMENTS                                                                                    The author gratefully acknowledges SAIF and CIL Chandigarh, for IR, NMR spectra .The author thanks to Principal, Balbhim College, Beed for providing research facility. The author also thanks to Head Department of Biotechnology Milind College of Science, Aurangabad for microbial activity.  REFERENCES 1. Graham l Patrick. An Introduction toMedicinal chemistry, 3rd edition, Published in USA by Oxford University Press Inc, New york, 2001;163-180.  2. B ABohm, Human uses of flavonoids, in: B.A. Bohm (Ed.), Introduction to Flavonoids, Harwood Academic Publishers, Amsterdam, 1998, pp.365e393.  3. D NDhar, The chemistry of chalcones and related compounds, The Chemistry of Chalcones and Related Compounds, Wiley-Inter science, New York, 1981. 4. J R Dimmock, D W Elias, M ABeazely, N MKandepu,Bioactivities of chalcones,Curr. Med. Chem. 1999;6: 1125–1150. 5. 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SYNTHESIS AND MICROBIAL EVALUATION OF SOME NOVEL ETHYL-4-(SUBSTITUTED PHENYL-5-YL)-6-(6-METHOXYNAPTHALEN)-2-OXO-CYCLOHEXA-3-ENE-1-ETHYL CARBOXYLATE DERIVATIVES

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SYNTHESIS AND MICROBIAL EVALUATION OF SOME NOVEL ETHYL-4-(SUBSTITUTED PHENYL-5-YL)-6-(6-METHOXYNAPTHALEN)-2-OXO-CYCLOHEXA-3-ENE-1-ETHYL CARBOXYLATE DERIVATIVES

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