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Synthesis of Aryl (5-Substituted Benzofuran-2-Yl) Carbamate Derivatives As Antimicrobial Agents

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Synthesis of Aryl (5-Substituted Benzofuran-2-Yl) Carbamate Derivatives As Antimicrobial Agents Online - 2455-3891 Vol 10, Issue 3, 2017 Print - 0974-2441 Research Article SYNTHESIS OF ARYL (5-SUBSTITUTED BENZOFURAN-2-YL) CARBAMATE DERIVATIVES AS ANTIMICROBIAL AGENTS SHANKAR BUDHWANI1*, SHAILENDRA SHARMA2, NAVANATH KALYANE3 1Department of Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Jodhpur National University, Jodhpur, Rajasthan, India. 2Department of Pharmacy, Jodhpur Institute of Pharmacy, Jodhpur National University, Jodhpur, Rajasthan, India. 3Department of Pharmaceutical Chemistry, B.L.D.E.A’S College of Pharmacy, Bijapur, Karnataka, India. Email: [email protected] Received: 25 November 2016, Revised and Accepted: 20 December 2016 ABSTRACT Objectives: Benzofurans are very interesting heterocycles, which are available in nature and show a wide range of pharmacological activities, viz., antifungal, antibacterial, antitumor, antimalarial and antioxidant activity. Methods: A convenient method for the preparation of aryl (5-substituted benzofuran-2-yl) carbamate derivatives 6a-6j has been developed. The target compounds 1-(5-nitrobenzofuran-2-yl)-3-arylurea (6a-6e) and 1-(5-bromobenzofuran-2-yl)-3arylurea (6f-6j) have been prepared by reacting 5-nitrobenzofuran-2-carbonyl azide 5a or 5-bromobenzofuran-2-carbonyl azide 5b with substituted phenols in reasonable overall yields. All the synthesized compounds were characterized using Fourier transform infrared (FTIR), 1H NMR and mass spectrometry and were subjected to antimicrobial screening against two Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis), two Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa), and two fungi (Candida albicans and Aspergillus niger) using two-fold dilution method. Results and Discussion: All the values of FTIR, 1H NMR and mass spectra were found to be prominent. The results indicate that synthesized compound 6i showed potent antimicrobial activity comparable to standard. Conclusion: The detailed synthesis, spectroscopic data, and antimicrobial activities of synthesized compounds were reported. Keywords: Benzofuran, Antibacterial activity, Antifungal activity. © 2017 The Authors. Published by Innovare Academic Sciences Pvt Ltd. This is an open access article under the CC BY license (http://creativecommons. org/licenses/by/4. 0/) DOI: http://dx.doi.org/10.22159/ajpcr.2017.v10i3.16332 INTRODUCTION Hence, this paper highlights the simple convenient method of synthesis of benzofuran derivatives and antimicrobial evaluation. All the Benzofuran is one of the most important classes of fused ring synthesized compounds were characterized using Fourier transform heterocyclic compounds. The benzofuran derivatives are naturally infrared (FTIR), 1H NMR and mass spectrometry and were subjected occurring and possess many biological applications [1-3]. Angelicin, to minimum inhibitory concentration (MIC) antimicrobial screening psoralen, and bergapten are the examples of naturally occurring against two Gram-positive bacteria (Staphylococcus aureus and Bacillus benzofuran derivatives with biological applications [4-6]. The isolation subtilis), two Gram-negative bacteria (Escherichia coli and Pseudomonas of benzofuran derivatives from natural sources is laborious and time- aeruginosa), and two fungi (Candida albicans and Aspergillus niger) consuming. Hence, the synthetic chemists are interested in synthesizing using two-fold dilution method. the benzofuran derivatives. Numerous synthesized benzofuran derivatives were found to be biologically active [7-9]. Nowadays, MATERIALS AND METHODS many synthetic benzofurans are used as good inhibitor [10,11], antimicrobial [12-14], anti-inflammatory [15,16], antiviral [17], Materials antioxidant [18-21], antitumor [22], antiproliferative [23,24], and All chemicals were purchased from Sigma-Aldrich, SD Fine, antialzheimer [25]. Spectrochem, Merck, and Himedia. Yields refer to purified products and are not optimized. Melting points were determined on a VEEGO- Fight against the microbes is never ending battle. The harmful microbe’s VMP I melting point apparatus and are uncorrected. IR spectra were poses biggest problem in the society as far as health and hygiene is recorded on a JASCO-FTIR 4100 spectrophotometer. 1H NMR was concerned. Antimicrobial chemotherapy has been a leading cause recorded on a MERCURY VARIAN 400 MHz instrument and chemical for the dramatic rise of average life expectancy in the 20th Century. However, disease-causing microbes that have become resistant to the solvent. Trimethylsilane was used as the internal standard for NMR. antibiotic drug therapy are an increasing public health problem. One Massshifts spectroscopy(δ) were reported (MS) inanalyses parts per were million done with on an dimethyl Applied sulfoxide Biosystem as part of the problems is that bacteria and other microbes that cause API 2000. Thin layer chromatography was performed on precoated infections are remarkably resilient and have developed several ways aluminum plates with silica gel. to resist antibiotics and other antimicrobial drugs. Another part of the problem is due to increasing use, and misuse, of existing antibiotics in Methods human and veterinary medicine and in agriculture. As the resistance General method for synthesis of 5-substituted benzofuran-2-carbonyl to antimicrobial agents increasing day by day, it is very necessary to azide (5a-5b): 5-substituted benzofuran-2-carbohydrazide 4a-4b synthesize new compounds which will show less bacterial resistance (0.02 mole) was dissolved in a mixture of 30 ml of acetic acid and and good inhibitory activity [26]. 30 ml of 1,4-dioxane and cooled to 0°C using ice salt bath. An ice cold Table 1: Characterization and Physical Properties of Synthesised 5‑substituted benzofuran derivatives by IR, 1H‑NMR and Mass Spectroscopy Name of compound IR in cm−1 1H NMR DMSO‑d6:d ppm ESI‑MS (m/z) M.P. Yield [M+H]+ % in % Phenyl (5-nitrobenzofuran-2-yl) -NH stretch at 3364 cm 7.39-7.82 (m, 9H, ArH), 10.50 (s, 1H, NH) 299.3 148-150°C 52 carbamate (6a) -CH stretch at 2930 cm −1 -C=O stretch at1716 cm−1 -C=C-Ar stretch at 1526 −1cm -CH bending- at 1434 cm −1 C-N stretch at 1334 cm −1 4-methoxyphenyl (5-nitrobenzofuran-2-yl) -NH stretch at 3344 cm−1 4.10(s, 3H, OCH3) 6.97-8.57 (m, 8H, ArH), 329.3 145-147°C 56 carbamate (6b) -CH stretch at 2920 cm −1 9.57 (s, 1H, NH) -C=O stretch at1726 cm−1 -C=C-Ar stretch at 1516 −1cm -CH bending- at 1424 cm −1 C-N stretch at 1335 cm −1 2-chlorophenyl (5-nitrobenzofuran-2-yl) -NH stretch at 3361 cm−1 7.38-7.83 (m, 8H, ArH), 9.96 (s, 1H, NH) 333.7 198-200°C 69 carbamate (6c) -CH stretch at 2910 cm −1 -C=O stretch at1715 cm−1 -C=C-Ar stretch at 1525 −1cm -CH bending- at 1430 cm −1 C-N stretch at 1335 cm −1 4-chlorophenyl (5-nitrobenzofuran-2-yl) -NH stretch at 3364 cm−1 7.38-7.82 (m, 8H, ArH), 9.97 (s, 1H, NH) 333.6 196-198°C 45 etal. Budhwani carbamate (6d) -CH stretch at 2930 cm −1 -C=O stretch at1717 cm−1 -C=C-Ar stretch at 1526 −1cm -CH bending- at 1434 cm −1 C-N stretch at 1334 cm −1 ethyl (5-nitrobenzofuran-2-yl) -NH stretch at 3344 cm−1 1.28-1.319 (t, 3H, CH3) 3.47-3.51 (m, 2H, CH2) 251.2 78-80°C 65 carbamate (6e) -CH stretch at 2920 cm −1 7.15-8.67 (m, 4H, ArH), 9.92 (s, 1H, NH) -C=O stretch at1726 cm−1 -C=C-Ar stretch at 1516 −1cm 10,Issue3,2017,377-381 Vol Asian JPharmClinRes, -CH bending- at 1434 cm −1 C-N stretch at 1335 cm −1 phenyl (5-bromobenzofuran-2-yl) -NH stretch at 3344 cm−1 7.39-7.82 (m, 9H, ArH), 10.51 (s, 1H, NH) 333.2 140-142°C 65 carbamate (6f) -CH stretch at 2920 cm −1 -C=O stretch at1726 cm−1 -C=C-Ar stretch at 1516 −1cm -CH bending- at 1424 cm −1 C-N stretch at 1335 cm −1 4-methoxyphenyl (5-bromobenzofuran-2-yl) -NH stretch at 3361 cm−1 4.20 (s, 3H, OCH3) 6.97-8.57 (m, 8H, ArH), 363.2 138-140°C 69 carbamate (6g) -CH stretch at 2910 cm −1 9.61 (s, 1H, NH) -C=O stretch at1715 cm−1 -C=O axial deformation −1at 1640 cm -C=C-Ar stretch at 1525 cm −1 -CH bending- at 1430 cm −1 −1 (Contd...) 378 Table 1: (Continued) Name of compound IR in cm−1 1H NMR DMSO‑d6:d ppm ESI‑MS (m/z) M.P. Yield [M+H]+ % in % 2-chlorophenyl (5-bromobenzofuran-2-yl) -NH stretch at 3364 cm 7.38-7.83 (m, 8H, ArH), 9.99 (s, 1H, NH) 367.6 169-171°C 54 carbamate (6h) -CH stretch at 2930 cm −1 -C=O stretch at1717 cm−1 -C=O axial deformation −1at 1630 cm -C=C-Ar stretch at 1526 cm −1 -CH bending- at 1434 cm −1 4-chlorophenyl (5-bromobenzofuran-2-yl) -NH stretch at 3344 cm −1 7.38-7.82 (m, 8H, ArH), 9.98 (s, 1H, NH) 367.5 146-150°C 39 carbamate (6i) -CH stretch at 2920 cm −1 -C=O stretch at1726 cm−1 -C=O axial deformation −1at 1630 cm -C=C-Ar stretch at 1516 cm −1 -CH bending- at 1434 cm −1 ethyl (5-bromobenzofuran-2-yl) -NH stretch at 3344 cm −1 1.28-1.32(t, 3H, CH3) 3.47-3.52 (m, 2H, CH2) 285.1 71-73°C 55 carbamate (6j) -CH stretch at 2910 cm −1 7.17-8.65(m, 4H, ArH), 9.90 -C=O stretch at1715 cm−1 (s, 1H, NH) -C=O axial deformation −1at 1670 cm -C=C-Ar stretch at 1526 cm −1 -CH bending- at 1432 cm −1 −1 etal. Budhwani the test tubes 0.1 the test all ofmedia.To property thegrowth ensure to control as the positive with nutrient media served but only compoundand no vehicle no test tube with One test control.
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