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Facile Green Synthesis and Potent Antimicrobial Efficacy of Β-Aminoheteronapthol Via Tailored Betti’S Protocol and Their Bis-Aryl Hydrazone Click Products

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Facile Green Synthesis and Potent Antimicrobial Efficacy of Β-Aminoheteronapthol Via Tailored Betti’S Protocol and Their Bis-Aryl Hydrazone Click Products J. Chem. Sci. Vol. 125, No. 6, November 2013, pp. 1573–1594. c Indian Academy of Sciences. Facile green synthesis and potent antimicrobial efficacy of β-aminoheteronapthol via tailored Betti’s protocol and their bis-aryl hydrazone click products K M KHANDARKARa,b,∗, M D SHANTIa, M AHMEDc and J S MESHRAMa aDepartment of Chemistry, Rashtrasant Tukadoji Maharaj Nagpur University, Nagpur 440 033, India bApplied Chemistry Department, G H Raisoni Academy of Engineering and Technology, Nagpur 440 016, India cDepartment of Chemistry, Government Polytechnic Sakoli, Bhandara 441 802, India e-mail: [email protected] MS received 27 March 2013; revised 23 June 2013; accepted 4 July 2013 Abstract. A series of novel Mannich base and their hydrazone derivatives were synthesized by highly resourceful, chic, simple and green technique with exceptionally facile reaction conditions of one-pot, three component reaction with an array of biologically and pharmaceutically active novel heterocycles. The proto- col offers a valuable alternative to known methods and will find applications in the field of green synthesis and antimicrobial study against pathogenic microbes, supporting the development of bioinformatical database of novel and derelict heterocycles. These data indicate their potential to become antifungal agents. The novel products were established by elemental, IR, mass spectroscopic and NMR analysis. The environmental advan- tages of the method include short reaction time, excellent yield, easy work-up, absence of extraction and chromatographic purification steps. Keywords. Green synthesis; zeolite catalyst; click reaction; antimicrobial efficacy. 1. Introduction scientific community. Hence the usage of most of the existing antimicrobials have limited capacity in over- The incidence of microbial infections in the immune coming the threat of resistance and it is limited not compromised population has significantly increased only by the rapidly developing drug resistance, but also over the past several years. In particular, Candida species, the unsatisfactory status of present treatments of bacte- especially Candida albicans, are often significant rial and fungal infections and drug side effects. 2 Thus pathogens in patients infected with human immunode- it would be advantageous to provide a pharmacophore ficiency virus (HIV). Another pathogen, Pneumocysist species with useful properties that can be used commer- carinii, causes a form of pneumonia (PCP) that is cially against pathogenic and resistant microbes. believed to be one of the leading causes of death in Mannich bases had abundant commercial appli- patients suffering from AIDS. Furthermore, the treat- cations and it was estimated that at least 35% of ment of infectious diseases is more complicated in Mannich bases related articles are published in phar- immuno-suppressed patients, such as those infected maceutical journals. The first synthesis of racemic with the HIV, undergoing anticancer treatment and Mannich-bases of 2-naphthol was achieved by Betti at organ transplants. Therefore, there is a vital need for the turn of the twentieth century. 3 Thereafter numer- the development of new antimicrobial agents having ous modifications of this reaction surfaced. 4 Since these potent activity against the resistant microorganisms. 1 compounds have multiple centres for chelation with The rapid development of resistance to existing metal ions, they are likely to be potent inhibitors of antibacterial and antifungal drugs posses a major threat metallo-enzymes. 5 Also, these compounds have the to public health which creates a serious challenge to the potential to be used as scavengers in cases of heavy metal poisoning. 6 They have a broad range of biologi- cal activities including diuretic, anticonvulsant, antipsy- chotic, antimalarial, antiviral, centrally acting muscle relaxant, and anticancer. Also, Mannich-bases of ∗For correspondence various bioactive compounds have been prepared as 1573 1574 K M Khandarkar et al. prodrugs as means of overcoming some of their limi- click reactions are well-known, and their applications tations. 7 So keeping importance of Mannich-base moi- have revolutionized numerous fields including bio- ety in mind, we had synthesized a series of substituted conjugate chemistry, material chemistry and polymer coumarin derivatives via classical Betti’s condensa- sciences. 22–25 The non-aldol addition reaction between tion reaction with their pharmacophores modelling and a carbonyl and a nucleophilic nitrogen as a click in vitro microbial activity. 8 Despite the importance of reaction has key benefits of availability of amines for the compounds, the serious downsides of their com- bioconjugation, rapid incorporation into molecular mercial syntheses include some or all of the following: frameworks, and a simple resultant click product that refluxing for extensive reaction time, large quantities of minimally impacts the nature of the biomolecules. 26 mineral or Lewis/Bronsted acids as activators, which Against this background, and also in the context of on work-up are hydrolysed with generation of large our interest in the synthesis of biologically significant quantities of corrosive and toxic waste by-products; the heterocycles via multi-component and click reactions, use of stoichiometric quantities of reagents that produce we report here the green preparation of a library of phar- metal salts as waste; poor yields; or production of mix- macologically relevant click fused bisarylhydrazones, tures of regioisomers with low selectivity. The enan- containing a Betti’s base fabricated by a process that tioselective transformations and industrial applications combines the use of zeolite with the synthetic effi- are the foremost impediment in the microwave-assisted ciency associated with MCRs, providing a convergence synthesis of these compounds. of reaction and environmental economies. 27 The aforementioned problems of greener synthetic In this paper, green synthesis of potent Betti’s prod- approach of Betti’s reaction product are overcome in uct and hydrazone derivatives are exemplified with present work by one-pot multicomponent zeolite cata- their antimicrobial efficacy. Here, in order to reduce lysed condensation bioactive Betti’s reaction products. the time period of Betti’s reaction product, enantio- Inspired by the above facts and in continuation of our selective transformations and to achieve green chemi- ongoing research programme in the field of synthe- cal synthesis, the reaction was carried out in catalytic sis and antimicrobial activity of medicinally impor- medium of zeolites which enhance reaction rate, sup- tant compounds, 9 we report here the click synthesis of port reagents, regioselectivity, entrain by-products and novel hydrazide-hydrazone/bisaryl hydrazone deriva- enhance product selectivity. 28–30 tives of bioactive Betti’s product and evaluated them for Furthermore, we have found a novel series of Betti’s antimicrobial activity. products and hydrazone derivatives that are effec- Hydrazones are the most important pharmacophoric tive against resistant microbes, and provide significant cores of several antimicrobial, anticonvulsant, anal- activity advantage over the art. It has been found that the gesic, antiinflammatory, antinociceptive, antiplatelet, compounds of this innovation and composition contain- antitubercular, and antitumoural drugs. 10 Hydrazides ing these compounds are effective antimicrobial agents and hydrazones are present in many of the bioac- against a broad range of pathogenic microorganisms tive heterocyclic compounds that are of wide interest with advantages in low susceptibility to microbial resis- because of their diverse biological and clinical applica- tance, reduced toxicity, and improved pharmacology. tions. This created interest in researchers who have syn- thesized variety of hydrazide derivatives and screened them for their various biological activities. 11 Hydra- 2. Experimental zones have been explored for the reversible conjuga- tion 12 and labelling 13 of biomolecules. However, their The solvents and reagents used in the synthetic work application has been limited, as most hydrazones are were of analytical grade obtained from Qualigens India prone to hydrolysis and premature cleavage, whereas and were purified by distillation where necessary. Melt- hydrazones (and oximes) that are fully stable under ing points were determined in open capillaries and biological and mildly acidic conditions undergo slower uncorrected. Infrared spectra were recorded on Bruker hydrolysis and are difficult to exchange or cleave. Alfa-T with direct sampling for analysis. 1HNMR The formation kinetics of the bis-aryl hydrazone spectra were recorded on a Cryo-magnet NMR Spec- bond are 20 to 900 times higher than those of conven- trometer 400 MHz (Bruker) instrument using tetra- tional hydrazone/oxime bonds between alkyl aldehydes/ methylsilane (TMS) as an internal standard with CDCl3 ketones and alkyl hydrazide or aminoxy probes. 14 and DMSO as a solvent. Chemical shifts are given The hydrazide hydrazones have been demonstrated to in parts per million (δ scale) and the coupling con- possess antibacterial, 15–17 anticonvulsant 18–20 and anti- stants are given in Hz. Mass spectra were recorded tubercular 21 activities. Furthermore, the benefits of on a Waters Micromass Q-T of Micro spectrometer. Tailored Betti’s product and their click hydrazones 1575 The reactions were monitored and the purity of pro- lization) or 96% (3.978 g, filtration), m. p. 192– ducts were
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