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Most Common Benzoxazole Derivatives As Antimicrobial Agent (1990-2018)

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Most Common Benzoxazole Derivatives As Antimicrobial Agent (1990-2018) Sarah Sattar Jabbar*et al. /International Journal of Pharmacy & Technology ISSN: 0975-766X CODEN: IJPTFI Available Online through Review Article www.ijptonline.com MOST COMMON BENZOXAZOLE DERIVATIVES AS ANTIMICROBIAL AGENT (1990-2018) Sarah Sattar Jabbar* Department of Pharmaceutical Chemistry, Collage of Pharmacy, University of Baghdad, Baghdad, Iraq. Email: [email protected] Received on: 20-10-2018 Accepted on 29-11-2018 Abstract: In this review, it was aimed to identify antimicrobial activity of newly synthesized benzoxazole derivatives which were synthesized and assayed for antibacterial and antifungal activity in previous study and showed a better antimicrobial effect that could be more effective against resistant pathogens. Benzoxazole derivatives have been extensively studied in the past few decades. The benzoxazole have shown significant antimicrobial activity against a wide variety of microorganisms like fungi, Gram +ve and Gram –ve bacteria. The review focuses out various important synthetic derivatives of benzoxazole which may in turn helpful to the information seekers to develop some novel derivatives of medicinal interest possessing benzoxazole moiety that could be better agents in term of efficacy and safety. Key word: benzoxazole , benzoxazole derivatives , Antimicrobial Agent Introduction Bacterial infection is a major category of human disease, for which many antibacterial compounds were developed. The dramatically rising prevalence of multidrug-resistant microbial infection in the past few decades has become a serious health care problem. Under these circumstances, the development of novel class of antimicrobial agent is going on. Benzoxazole plays an important role in medicinal chemistry and exhibit wide range of biological activities. The main objective of the medicinal chemistry is to synthesize the compounds that show promising activity as therapeutic agents with lower toxicity. Benzoxazole Benzoxazole is an aromatic organic compound having benzene fused oxazole ring structure as shown in Fig.1(1). IJPT| Dec-2018| Vol. 10 | Issue No.4 | 6695-6712 Page 6695 Sarah Sattar Jabbar*et al. /International Journal of Pharmacy & Technology Fig.1: General Structure of Benzoxazole. Benzoxazole finds use in research as a starting material for the synthesis of larger bioactive structures. Biologically active benzoxazole derivatives have been known for long time, they are the isosteres of cyclic nucleotides and easily interact with the biopolymers of the organisms(2) . History Oxazole is considered to be derived from furan by the replacement of –CH= (methane group) from the position -3 by the azomethine nitrogen (-N=). Oxazole ring system is numbered as follows. The chemistry of oxazoles began in 1876 with the synthesis of 2-methyloxazole, although parent oxazole 5 was synthesized in 1947and 1962. The interest in the chemistry of oxazole was developed during the world war when the penicillin was consider to contains the oxazole ring system. But discovery of oxazoles as dienes in Diels-Alder reaction and in 1,3-dipolarcycloaddition reaction of mesotonic heterocycles gave impetus to the development of oxazoles chemistry. The fusion of benzene ring to the 4,5-positions of the oxazole ring results in benzoxazole and numbering as shown in Fig.1 (3). The heterocyclic ring comprises of very core of the active moiety or the pharmacophore. Several Benz-fused hetero, bicyclic ring systems as indole, benzoxazole, have been studied and found to be possessing interesting pharmacological activities (4). A number of methods have been reported for the preparation of these heterocycles including the condensation of carboxylic acids, orthoesters, acid chlorides, nitriles amides, aldehydes and esters with o- substituted amino aromatics derivatives from orthoesters (3). IJPT| Dec-2018| Vol. 10 | Issue No.4 | 6695-6712 Page 6696 Sarah Sattar Jabbar*et al. /International Journal of Pharmacy & Technology Reactions of benzoxazole 1. Nitration The nitration of benzoxazole proceeds readily. In most cases nitration appears to take place preferentially in the 5 or 6 places. However the nitro group may also enter 4 or 7-position, especially if 5 or 6 positions are blocked as shown in Fig.2 (3). Fig.2: Nitration Reaction of benzoxazole. 2. Chloroacetylation 2-mercapto benzoxazole on chloroacetylation gave 2-chloroacetyl mercaptobenzoxazole Fig.3. (3). Fig.3: Chloroacetylation Reaction of Benzoxazole. 3-Alkylation The reaction of sub. benzoxazole with butylcyclohexanol gave (2-butylcyclohexyloxy) benzoxazole fig 4.(3). Fig.4: Alkylation Reaction of Benzoxazole. Use of Benzoxazole Recent observations suggest that substituted benzoxazoles and related heterocycles, possess potential activity with lower toxicities in the chemotherapeutic approach in man. Benzoxazole is used primarily in industry and research, and has no household use. Benzoxazole finds use in research as a starting material for the synthesis of larger, usually bioactive structures. Benzoxazoles can be considered as structural isosteres of IJPT| Dec-2018| Vol. 10 | Issue No.4 | 6695-6712 Page 6697 Sarah Sattar Jabbar*et al. /International Journal of Pharmacy & Technology the naturally occurring nucleic bases adenine and guanine, which allow them to interact easily with polymers of living systems (5). Benzoxazoles have been reported to show a broad spectrum of biological activities such as, antihistaminic (6), antifungal (7), Cyclooygenase inhibiting (8), antitumor (9), antiulcer (10), anti-convulsant (11), hypoglycemic (12), anti-inflammatory(13), cytotoxic activity(14), antimicrobial (15), DNA Topoisomerase Inhibitor (16), antibacterial (17), Herbicidal Activity (18), antiviral, analgesic (19), antitubercular (20), antioxidant (21) and anthelmintic activities (22), antiparasitics ,elastase inhibitors, protein kinase inhibitors, steroid sulfatase inhibitors. Chemistry of Benzoxazole Benzoxazole is an aromatic organic compound with a molecular formula C7H5NO, a benzene -fused oxazole ring structure, and an odor similar to pyridine (1). General Properties Table1: chemical characteristics of Benzoxazole Structure Activity Relationship (SAR) Decisive for the Presence of halogen permit biological activity penetration through the and substitution lipophilic cell wall with CH2 was significant for the improved antifungal activity R=electron with drawing group improve antibacterial activity Fig.5: Structure Activity Relationship of Benzoxazole. IJPT| Dec-2018| Vol. 10 | Issue No.4 | 6695-6712 Page 6698 Sarah Sattar Jabbar*et al. /International Journal of Pharmacy & Technology SAR of benzoxazole been studied and found that position 2(X) decisive for the biological activity and position 5 (Y) prevailing the intensity of activity. The substitution at position X with the CH2 group was significant for the improved antifungal activity and hydrophobic properties of the substituents at position X are indicative for the antifungal activity (4).Presence of halogen at position 5 (Y) of benzoxazole ring will permit these compounds penetrate through the lipophilic cell wall (23). The Substitution of R at position 2 at benzoxazole ring with electron withdrawing group favourable for the antibacterial activity (24). Hydrophobicity which is important for the penetration and distribution of benzoxazole derivatives (25). 2,5-disubstituted benzoxazoles have potent antimicrobial activities against some Gram-positive, Gram- negative bacteria and the yeast. Candida albicans, providing a wide variety of in-vitro antimicrobial effects, especially indicating significant activity against the enterobacter Pseudomonas aeruginosa. These examples highlight the level of interest in new synthetic approaches to benzoxazole derivatives and have prompted researches around the globe to synthesize and explore the wide applicability of this important pharmacophoric scaffold (26). Benzoxazole Derivatives The design of new compounds to deal with resistant bacteria and fungi has become one of the most important areas of antibacterial and antifungal research today. The benzoxazoles are a large chemical family used as antimicrobial agents against a wide spectrum of microorganisms. The high therapeutic activity of the related drugs have encouraged the medicinal chemists to synthesize a large number of novel chemotherapeutic agents. The incorporation of the benzoxazole nucleus is an important synthetic strategy in drug discovery. This class of molecules have broaden the scope in remedying various dispositions in clinical medicine. This heterocyclic system has different activities as it can act as bacteriostatic or bactericid, as well as fungicide (27). In the pharmaceutical field, new drugs are continuously discovered by molecular modification of compound. Molecular modification can possibly result in augmenting the activity. Molecular modification involves combination of separate group having similar activity in one compound by eliminating, substituting or adding new moiety to compound. Molecular modification is a productive source of new drug; therefore IJPT| Dec-2018| Vol. 10 | Issue No.4 | 6695-6712 Page 6699 Sarah Sattar Jabbar*et al. /International Journal of Pharmacy & Technology the need to synthesize new molecules as potential medicinal agents is more relevant today. Among medicinal agents, there is growing interest in the development of newer, effective antifungal and antimicrobial agents. Among the variety of compounds studied, benzoxazole derivatives form an important class (3). Turker L.et al,1990;(28) have been
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