alexa Synthesis, Characterization of Substituted (4-Oxo-3-Phenyl-3,4-Dihydro Quinazolin-2-yl)Methyl Nitrite Derivatives and Evaluation of their Antimicrobial Activity
ISSN: 2150-3494
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Synthesis, Characterization of Substituted (4-Oxo-3-Phenyl-3,4-Dihydro Quinazolin-2-yl)Methyl Nitrite Derivatives and Evaluation of their Antimicrobial Activity

Chaitanya P1, Guguloth R2*, Damodhar S1 and Ravinder AN1

1University College of Technology, Osmania University, Hyderabad, Telangana, India

2Department of Chemistry, University College of Science, Osmania University, Hyderabad, Telangana, India

*Corresponding Author:
Guguloth R
Department of Chemistry
University College of Science
Osmania University, Hyderabad, Telangana, India
Tel: 9486745607
E-mail: [email protected]

Received date: May 02, 2017; Accepted date: May 23, 2017; Published date: June 09, 2017

Citation: Chaitanya P, Guguloth R, Damodhar S, Ravinder AN (2017) Synthesis, Characterization of Substituted (4-Oxo-3-Phenyl-3,4-Dihydro Quinazolin-2-yl) Methyl Nitrite Derivatives and Evaluation of their Antimicrobial Activity. Chem Sci J 8:157. doi: 10.4172/2150-3494.1000157

Copyright: © 2017 Chaitanya P, et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

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Abstract

Synthesis of substituted (4-oxo-3-phenyl-3,4-dihydro quinazolin-2-yl)methyl nitrite derivatives[5(a-j)] have been prepared oxidation reaction of 6-chloro-2-(chloromethyl)-3-[phenyl] quinazolin-4(3H)-one(4) with AgNO3. Compound (5) prepared from starting meterial are 5-chloro-2-[(chloroacetyl)amino]benzoic acid (1) is undergoes to cyclization with acetic anhydride to form 5-chloro-2-[(chloroacetyl)amino]benzoic acid (2) in yield 72%. 5-chloro-2-[(chloroacetyl) amino]benzoic acid(2) undergoes ro cyclisation with acetic anhydride under reflux conidition to form 6-chloro- 2-(chloromethyl)-4H-3,1-benzoxazin-4-one (3) now this compound have been reacted with glycial acetic acid in presence of aniline to form 6-chloro-2-(chloromethyl)-3-[phenyl] quinazolin-4(3H)-one(4). Chareterization done by 1H-NMR, 13C-NMR, IR, MASS spectral analysis. Evaluation of antibacterial activity by Gram-positive bacteria viz. Bacillus subtilis, Bacillus sphaericus and Staphylococcus aureus and three Gram-negative bacteria viz. Pseudomonas aeruginosa, Klebsiella aerogenes and Chromobacterium violaceum and antifungal activity against Candida albicans, Aspergillus fumigates, Trichophyton rubrum and Trichophyton mentagrophytes. Most of the compounds are exihibits more potential activity.

Keywords

(4-Oxo-3-phenyl-3,4-dihydro quinazolin-2-yl)methyl nitrite derivatives; 6-Chloro-2-(chloromethyl)-3-[phenyl] quinazolin- 4(3H)-one; Anti-microbial activity

Introduction

Quinazoline is a bicycle compound consisting of a pyrimidine system fused at 2, 3 positions with benzene ring. It is considered as an important chemical synthesis of various physiological significance and pharmacological utility. These rings are exhibits like non-typeable. Haemophilus influenza [1]. It is a multiscale response to stress required for repair and regeneration after injury [2]. Many pathophysiological pathways like cytokines, interlukin, NF-kB, protein kinases (Adenosine Monophosphate-activated protein Kinase- AMPK), tyrosine kinases and various immunological responses regulate and mediate the process of inflammation [3-6]. During inflammation, NF-kB has a proapoptotic role in neutrophils which may represent an important anti-inflammatory mechanism during acute inflammation [7-9]. In the process of inflammation, prostaglandin synthesis is a vital step where cyclooxygenase 2 (COX-2) enzymes is one of the two key enzymes. In the second step, COX reduces PGG2 to PGH2 [10,11]. COX is majorly involved in the process of inflammation and is the targeted protein for most of the NSAIDs (non-steroidal anti-inflammatory drugs). It is also found to be key protein in various physiological processes like gastric secretions [12], gastro intestinal motility and in other pathological conditions like inflammation, arthritis and colon cancer [13]. Quinazolinone derivatives were previously reported as inhibitors of various enzymes involved in process of inflammation (COX, prostaglandin E2) [14,15], allergic reactions (Histamine H3 receptor inhibition) [16], and also in tumor suppressing process through interacting with DNA, tubulin and thus acting as anticancer agents [17,18]. Some series of quinazolinone derivatives were also shown to have remarkable antimicrobial and antifungal properties [19-23]. In addition molecules with quinazolinone scaffold acts as regulators of calcium and sodium at cellular membranes by inhibiting sodium/ calcium exchange process [24]. The preparation of heteroatom bearing multi-structure in a molecule has received much attention in recent years [25]. However, literature survey revealed that heterocycles containing quinazoline have seldom been reported. Based on the wide spectrum of biological profile of quinazoline and their increasing importance in pharmaceutical, and biological field, and in continuation of our ongoing research on biologically active heterocycles, it was thought of interest to accommodate quinazoline moieties in a single molecular frame work to synthesize some new heterocyclic compounds with potential biological activity. The present investigation deals with the synthesis of some new Substituted (4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)methyl nitrite [5(a-h)] in good yields, from mono halo anthranilic acid (1). The antibacterial and antifungal activities of the compounds [5(a-h)] have also been evaluated [26,27].

Materials and Methods

In this experiment all reagents are used analytical reagent grade obtained from Sigma-Aldrich, Merck, SD fine and avira chemicals. With using standard procedures we purified Water, methanol, acetone, ether etc. (4-oxo-3-phenyl-3,4-dihydro quinazolin-2-yl)methyl nitrite derivatives 1H NMR and 13C NMR spectra were recorded on Bruker 400 MHz NMR instrument using tetra methyl silane (TMS) as internal standard compound and coupling constants (J) are reported in Hz units. VG AUTOSPEC mass spectrometer. Electronic spectra of all compounds were recorded on Schimadzu UV-V is 1601 spectrophotometer. ESI mass spectra were Melting points of the ligands and metal complexes decomposition temperature were determined on Polmon instrument (Model No. MP-102). IR spectra of the compounds were recorded using KBr pellets in the range 40-60°C on Perkin-Elmer Infrared model 337. The percentage composition of C, H, N of the compounds were determined by using micro analytical techniques on Perkin Elmer 240 C (USA) elemental analyzer. All reactions were monitored by thin-layer chromatography (TLC) on pre-coated silica gel F254 plates from Merck, and compounds visualized either by exposure to UV light. Chromatographic columns 60-120 mesh silica gel for separations were used. Elemental analyses (C, H, N) determined by means of a Perkin-Elmer 240 C, H, N and O elemental analyzer, were within ± 0.4% of Perkin-Elmer theory (Table 1).

S.No X R Mol.For Mol.Wt Yield(%) M.Pt°C
5a         H imge C15H11N3O4 297.5 72 168
5b H imge C15H10ClN3O4 331.71 78 178
5c H imge C16H14N3O5 327.29 65 174
5d H imge C16H13N3O4 311.29 71 187
5e Cl imge C15H10ClN3O4 329.72 80 201
5f Cl imge C15H9Cl2N3O4 363.24 68 198
5g Cl imge C16H12ClN3O5 360.74 76 187
5h Cl imge C16H12ClN3O4 344.74 72 176

Table 1: Elemental analyses (C, H, N) determined by means of a Perkin–Elmer 240 C, H, N and O elemental analyzer, were within ± 0.4% of Perkin–Elmer theory.

Experimental

Synthesis of 5-chloro-2-[(chloroacetyl)amino]benzoic acid (2)

Chloroanthranilic acid (6.85 gm), chloroacetyl chloride (15 ml) and pyridine (4 ml) were stirred at room temperature in 30 ml of dry toluene for 6 hours. The solvent was removed under reduced pressure and the obtained residue was poured on to crushed ice. The product obtained was filtered, washed with water, dried at room temperature and recrystallized from a mixture of chloroform and ethyl acetate. Yield: 75%; mp: 191°C.

Synthesis of 6-chloro-2-(chloromethyl)-4H-3,1-benzoxazin- 4-one (3)

5-chloro-2-[(chloroacetyl)amino]benzoic acid (2.3 gm) was taken in a flask and acetic anhydride (10 ml) was added. The reaction mixture was refluxed for one hour under anhydrous condition. Excess of acetic anhydride was distilled off to the possible extent and on cooling the reaction mixture gets solidified. The resultant product was dried. It was purified by recrystallization from ethanol.

IR (cm-1) νmax: 3240, 2922, 2198, 1703, 1603, 1534, 1443, 1231, 1158, 1069, 993, 751, 685, 628, cm-1, 1H NMR (DMSO-d6) δ: 6.13-7.57 (m,3H, aromatic-H), 3.88 (s, 2H, CH2-Cl); 13C NMR (DMSO-d6) δ: 172.9, 151.3, 149.4, 143.1, 138.2, 132.4, 131.2, 129.3, 31.4; MS m/z (%): 195.4 (100, M+), 147.2 (42), 133.5 (25), 119 (20). Yield: 72%; mp: 187°C.

Synthesis of 6-chloro-2-(chloromethyl)-3-[phenyl] quinazolin- 4(3H)-one (4)

6-chloro-2-(chloromethyl)-4H-3,1-benzoxazin-4-one (3 gms) was taken into a dry round bottom flask along with glacial acetic acid (15 ml) and appropriate aniline was added slowly to the reaction mixture. The reaction mixture was refluxed for 2-3 h. The reaction mixture was poured onto crushed ice and the resultant product was filtered, dried and purified by recrystallization from ethanol.

IR (cm-1) νmax: 3240, 3158, 2936, 2168, 1760, 1608, 1528, 1445, 1239, 1162, 1069, 993, 751, 695, 622 cm-1, 1H NMR (DMSO-d6) δ: 6.02-7.84 (m, 8H, aromatic-H), 3.90 (s, 2H, CH2-Cl),13C NMR (DMSO-d6) δ: 171.2, 152.1, 137.2, 136.0, 135.5, 134.6, 133.8, 131.7, 130.8, 128.3, 129.4, 125.2, 122.6, 120.8, 33.2. MS m/z (%): 271.8 (56, M+H+), 222.7 (75), 146.5 (100), 133.5 (25). Yield: 76%; mp: 193°C.

Synthesis of substituted (4-oxo-3-phenyl-3,4-dihydroquinazolin- 2-yl)methyl nitrite IV-5(a-h)

A solution of the appropriate chloro alkyl derivative (III a-h) in dry acetonitrile (5 ml) was treated with a solution of AgNO3 (2 mmol) in dry acetonitrile (5 ml) and the whole mixture was stirred at room temperature for 3 h. The mixture was then filtered, evaporated to dryness and the residue was crystallized from absolute ethanol.

Synthesis of phenyl substituted (4-oxo-3-phenyl-3,4- dihydroquinazolin-2-yl)methyl nitrite (5a): IR (cm-1) νmax: 3265, 3187, 2987, 2901, 2103, 1756, 1610, 1546, 1440, 751, 685, 628 cm-1, 1H NMR (DMSO-d6) δ: 6.15-7.78 (m, 8H, aromatic-H), 3.67 (s, 2H, CH2-ONO2), 1.81 (s, 3H, CH3);13C NMR (DMSO-d6) δ: 169.1, 149.3, 136.1, 135.2, 134.1, 132.5, 131.4, 130.4, 126.1, 125.4, 124.5, 122.4, 122.3, 120.2, 35.3, 24.4; MS m/z (%): 297.5 (M+H+). Yield: 72%; mp:168°C. Analytically calculated for C15H11N3O4: C, 47.44; H, 5.06; N, 36.87. Found: C, 47.29; H, 5.00; N, 36.80.

Synthesis of 4-chloro phenyl substituted (4-oxo-3-phenyl-3,4- dihydroquinazolin-2-yl)methyl nitrite (5b): IR (cm-1) νmax: 3225, 3168, 2982, 2905, 1758, 1605, 1541, 1421, 756, 667, 643 cm-1, 1H NMR (DMSO-d6) δ: 6.50-7.80 (m, 8H, aromatic-H), 3.75 (s, 2H, CH2-ONO2), 1.91 (s, 3H, CH3),13C NMR (DMSO-d6) δ: 167.1, 149.3, 138.1, 135.2, 134.1, 133.5, 131.4, 130.4, 126.1, 125.4, 124.5, 122.4, 122.3, 120.2, 38.3, 25.4;MS m/z (%):331.7 (M+H+). Yield: 78%; mp: 178°C. Analytically calculated for C15H10N3O4Cl: C, 51.44; H, 6.06; N, 34.87. Found: C, 50.29; H, 6.00; N, 33.80.

Synthesis of 4-methoxy phenyl substituted (4-oxo-3-phenyl- 3,4-dihydroquinazolin-2-yl)methyl nitrite (5c): IR (cm-1) νmax: 3222, 3192, 2992, 2900, 1767, 1610, 1555, 1435, 786, 682, 637 cm-1, 1H NMR (DMSO-d6) δ: 6.70-7.92 (m, 8H, aromatic-H), 3.91 (s, 2H, CH2-ONO2), 1.85 (s, 3H, CH3);13C NMR (DMSO-d6) δ: 172.1, 152.3, 138.1, 135.2, 134.1, 133.5, 131.4, 130.4, 126.1, 125.4, 124.5, 122.4, 122.3, 120.2, 38.3, 28.4;MS m/z (%):327.29 (M+H+). Yield: 65%; mp: 174°C. Analytically calculated for C16H14N3O5: C, 50.44; H, 6.79; N, 33.34. Found: C, 50.15; H, 6.05; N, 33.82.

Synthesis of 4-methyl phenyl substituted (4-oxo-3-phenyl-3,4- dihydroquinazolin-2-yl)methyl nitrite (5d): IR (cm-1) νmax: 3296, 3162, 2922, 2905, 2198, 1703, 1603, 1553, 1443, 1231, 1158, 993, 751, 685, 628 cm-1; 1H NMR (DMSO-d6) δ: 6.14-7.76 (m, 8H, aromatic-H), 3.98 (s, 2H, CH2-ONO2), 1.89 (s, 3H, CH3);13C NMR (DMSO-d6) δ: 170.6, 150.3, 138.1, 137.5, 136.2, 134.5, 133.4, 131.4, 129.1, 127.4, 125.5, 124.4, 122.3, 121.2, 31.3, 21.4;MS m/z (%): 311.29 (40, M+H+), 299.3, (75) 222.4 (50), 146.3 (100), 133.4 (20). Yield: 71%; mp: 187°C. Analytically calculated for C16H13N3O4: C, 49.44; H, 6.14; N, 33.34. Found: C, 48.15; H, 6.05; N, 33.82.

Synthesis of phenyl substituted (4-oxo-3-phenyl-3,4- dihydroquinazolin-2-yl)methyl nitrite (5e): IR (cm-1) νmax: 3296, 3162, 2922, 2198, 1703, 1603, 1553, 1443, 1231, 1158, 993, 751, 685, 628 cm-1; 1H NMR (DMSO-d6) δ: 6.11-7.88 (m, 8H, aromatic-H), 4.12 (s, 2H, CH2-ONO2);13C NMR (DMSO-d6) δ: 170.1, 151.2, 138.0, 136.1, 135.2, 134.2, 133.2, 131.1, 130.1, 129.3, 127.4, 126.2, 122.2, 121.3, 34.7; MS m/z (%): 329.72. Yield: 80%; mp: 201°C, analytically calculated for C15H10N3O4Cl: C, 50.44; H, 6.79; N, 33.34. Found: C, 50.15; H, 6.05; N, 33.82.

Synthesis of 4-chloro phenyl substituted (4-oxo-3-phenyl-3,4- dihydroquinazolin-2-yl)methyl nitrite (5f): IR (cm-1) νmax: 3278, 3193, 2965, 2161, 1732, 1627, 1553, 1443, 1231, 1158, 993, 751, 685, 618 cm-1, 1H NMR (DMSO-d6) δ: 6.5-7.80 (m, 8H, aromatic-H), 4.10 (s, 2H, CH2-ONO2),13C NMR (DMSO-d6) δ: 172.1, 152.2, 139.0, 136.1, 135.2, 134.2, 133.2, 131.1, 130.1, 129.3, 127.4, 126.2, 122.2, 121.3, 36.7; MS m/z (%): 363.24. Yield: 68%; mp: 198°C, analytically calculated for C15H9N3O4Cl2: C, 58.41; H, 4.79; N, 34.14. Found: C, 54.15; H, 6.45; N, 34.82.

Synthesis of 4-methoxy phenyl substituted (4-oxo-3-phenyl- 3,4-dihydroquinazolin-2-yl)methyl nitrite (5g): IR (cm-1) νmax: 3272, 3195, 2978, 2162, 1783, 1627,1553, 1443, 1231, 1158, 993, 751, 685,618 cm-1; 1H NMR (DMSO-d6) δ: 6.4-7.90 (m, 8H, aromatic-H), 4.15 (s, 2H, CH2-ONO2),13C NMR (DMSO-d6) δ: 175.1, 154.2, 140.0, 138.1, 135.2, 134.2, 133.2, 131.1, 130.1, 129.3, 127.4, 126.2, 122.2, 124.3, 38.7; MS m/z (%): 360.74. Yield: 76%; mp: 187°C, analytically calculated for C16H12N3O5Cl: C, 55.41; H, 5.79; N, 35.14. Found: C, 54.12; H, 5.45; N, 34.82.

Synthesis of 4-methyl phenyl substituted (4-oxo-3-phenyl-3,4- dihydroquinazolin-2-yl)methyl nitrite (5h): IR (cm-1) νmax: 3292, 3156, 2968, 2101,1732, 1627, 1553, 1443, 1231, 1158, 993, 751, 685, 618 cm-1; 1H NMR (DMSO-d6) δ: 6.3-7.70 (m, 8H, aromatic-H), 3.90 (s, 2H, CH2-ONO2); 13C NMR (DMSO-d6) δ: 172.1, 152.2, 139.0, 136.1, 135.2, 134.2, 133.2, 131.1, 130.1, 129.3, 127.4, 126.2, 122.2, 121.3, 36.7; MS m/z (%): 344.74. Yield: 72%; mp: 176°C, analytically calculated for C16H12N3O4Cl: C, 67.41; H, 5.23; N, 36.15 Found: C, 64.15; H, 5.45; N, 34.82.

Antibacterial Activity

The in vitro antibacterial activity (4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)methyl nitrite 5(a-h) derivatives was assessed against three representative Gram-positive bacteria viz. Bacillus subtilis, Bacillus sphaericus and Staphylo coccus aureus, and three Gram-negative bacteria viz. Pseudomonas aeruginosa, Klebsiella aerogenes and Chromobacterium violaceum by the broth dilution method recommended by National Committee for Clinical Laboratory Standards [27]. Bacteria were grown overnight in Luria Bertani (LB) broth at 37°C, harvested by centrifugation and then washed twice with sterile distilled water. Stock solutions of the series of compounds were prepared in DMSO. Each stock solution was diluted with standard method broth (Difco) to prepare serial two-fold dilutions in the range of 50 to 0.8 μg/mL. Ten microliters of the broth containing about 105 colony-forming units (cfu)/mL of test bacteria were added to each well of a 96-well micro titer plate (Table 2). Culture plates were incubated for 24 h at 37°C, and the growth of bacteria was monitored by visually and spectrophotometrically. Penicillin and Streptomycin were also screened under identical conditions for comparison. The obtained data of compounds 5(a-h) are presented in Table 3 as the minimal inhibitory concentration (MIC, μg/mL). It has been observed that the compounds exhibit interesting biological activity, however, with a degree of variation (Figure 1). In the series of 5(a-h), the compounds 5b, 5d, 5f and 5g are found to be the most active against Gram-positive bacteria and the Gram-negative bacteria. The remaining compounds showed moderate to good activity against all the Gram-positive bacteria and the Gram-negative bacteria.

chemical-sciences-journal-Graphical-Anti-Bacterial-Screening

Figure 1: Graphical form of Anti-Bacterial Screening.

Compound Minimum Inhibitory Concentration (MIC) in µg/mL
B. subtilis B. sphaericus S. aureus P. aeruginosa K. aerogenes C. violaceum
5a 21 22 24 28 21 23
5b 32 31 29 36 32 31
5c 22 21 18 23 24 22
5d 33 32 29 34 33 22
5e 20 22 25 30 29 30
5f 34 32 29 34 32 31
5g 32 32 29 35 32 32
5h 22 26 22 17 18 25
SM 33 31 29 35 33 31

Table 2: Antibacterial activity of compounds 5(a-h).SM=Streptomycin.

Antifungal activity

The compounds 36(a-h) were also screened for their antifungal activity against Candida albicans (C. albicans) (ATCC 10231), Aspergillus fumigates (A. fumigatus) (HIC 6094), Trichophyton rubrum (T. rubrum) (IFO 9185), and Trichophyton mentagrophytes (T. mentagrophytes) (IFO 40996) in dimethyl sulfoxide (DMSO) by disc diffusion method. Amphotericin B was used as a standard drug and the mean inhibition zone (MZI) data were measured and compared with controls, the MZI values of the compounds screened are given in Table 3.The antifungal screening data showed appreciable activity of the test compounds. Among the screened compounds, compound 5b, 5d, 5f and 5g (Figure 2).

chemical-sciences-journal-Graphical-Anti-Fungal-Screening

Figure 2: Graphical form of Anti-Fungal Screening.

Compound Mean Zone Inhibition (MZI)a in 10 µg/mL
C. albicans A. fumigatus T. rubrum T. mentagropytes
5a 21 18 17 21
5b 32 32 29 26
5c 21 22 25 18
5d 33 32 29 25
5e 18 21 23 20
5f 32 30 26 27
5g 31 32 29 25
5h 20 22 26 27
Amphotericin B 32 31 29 26

Table 3:Antifungal activity of compounds 5(a-h). A Values are mean (n=3).

Conclusions

In conclusion, a series of quinazoline 5(a-h) was prepared. The antibacterial activity of these compounds was evaluated against various bacteria. The compounds showed variable degree of antimicrobial activity. Among the screened compounds 5b, 5d, 5f and 5g were found to be the most active against all the microorganisms employed both for antibacterial and antifungal activity. With this set of analogues, we are now in a position to investigate the multiple biological activities of these compounds.

Acknowledgements

The author and co-author are grateful thanking to the Head, Department of Pharmacy and Biotechnology, for providing necessary laboratory facilities, We also thankful to Head, Department of Chemistry, Osmania University, We also grateful thanks to Director, Indian Institute of Chemical Technology, Hyderabad, India, for providing NMR, CMR, IR and Mass spectral data. Finally we thankful to Head, Department of Biotechnology, Osmania University, India, for Biological evaluation studies.

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