In the present study, 2-bromo-4-chlorophenyl-2-bromobutanoate (3) was synthesized via the reaction of 2-bromo-4-chlorophenol with 2-bromobutanoyl bromide in the presence of pyridine. A variety of 2-bromo-4-chlorophenyl-2-bromobutanoate derivatives (5a-f) were synthesized with moderate to good yields via a Pd-catalyzed Suzuki cross-coupling reaction. To find out the reactivity and electronic properties of the compounds, Frontier molecular orbital analysis, non-linear optical properties, and molecular electrostatic potential studies were performed.
Halogenated polycyclic aromatic hydrocarbons (HPAHs, H = F, Cl, Br) are a new class of PAHs derivatives that mainly originate from the incomplete combustion of halogen-laden materials and via metallurgical operations. These compounds circulate extensively in various environmental matrices. This survey provides a comprehensive review on governing synthesis routes of HPAHs, their environmental occurrence, and their health and ecological effects. The review comprehensively enlists and presents emission sources of these emerging organic pollutants into the air that serves as their main reservoir. The formation of HPAHs ensues through successive addition reactions of related precursors accompanied by ring cyclization steps; in addition to direct unimolecular fragmentation of parents halogenated. Halogenation of parent PAHs rapidly occurs in saline ecosystems, thus multiplying the availability of these notorious compounds in the environment. Certain HPAHs appear to be more carcinogenic than dioxins. Transmission routes of HPAHs from their emission sources to water bodies, soil, aquatic life, plants, terrestrial animals, and humans are well-documented. Later, the direct and indirect diffusion of HPAHs from air to the biotic (plants, animals, humans) and abiotic components (soil, water, sediments) are described in detail. The study concludes that HPAHs are permeable to the carbon matrices resulting in the alleviation of the source-to-sink interface. As a potential future perspective, understanding the transmission interfaces lays a foundation to intervene in the introduction of these toxicants into the food chain.
Two halogenated C15 acetogenins, named lembyne-A and lembyne-B, have been isolated from an unrecorded Laurencia species collected off the Malaysian waters. Their structures were deduced on the basis of spectroscopic evidence. Previously known elatol and iso-obtusol showed potent antibacterial activity against some marine bacteria.
The variety of halogenated substances and their derivatives widely used as pesticides, herbicides and other industrial products is of great concern due to the hazardous nature of these compounds owing to their toxicity, and persistent environmental pollution. Therefore, from the viewpoint of environmental technology, the need for environmentally relevant enzymes involved in biodegradation of these pollutants has received a great boost. One result of this great deal of attention has been the identification of environmentally relevant bacteria that produce hydrolytic dehalogenases—key enzymes which are considered cost-effective and eco-friendly in the removal and detoxification of these pollutants. These group of enzymes catalyzing the cleavage of the carbon-halogen bond of organohalogen compounds have potential applications in the chemical industry and bioremediation. The dehalogenases make use of fundamentally different strategies with a common mechanism to cleave carbon-halogen bonds whereby, an active-site carboxylate group attacks the substrate C atom bound to the halogen atom to form an ester intermediate and a halide ion with subsequent hydrolysis of the intermediate. Structurally, these dehalogenases have been characterized and shown to use substitution mechanisms that proceed via a covalent aspartyl intermediate. More so, the widest dehalogenation spectrum of electron acceptors tested with bacterial strains which could dehalogenate recalcitrant organohalides has further proven the versatility of bacterial dehalogenators to be considered when determining the fate of halogenated organics at contaminated sites. In this review, the general features of most widely studied bacterial dehalogenases, their structural properties, basis of the degradation of organohalides and their derivatives and how they have been improved for various applications is discussed.
Red algae genus Laurencia (Rhodomelaceae, Ceramiales) are known to produce a wide range of chemically interesting secondary halogenated metabolites. This investigation delves upon extraction, isolation, structural elucidation and antibacterial activity of inherently available secondary metabolites of Laurencia majuscula Harvey collected from two locations in waters of Sabah, Malaysia. Two major halogenated compounds, identified as elatol (1) and iso-obtusol (2) were isolated. Structures of these compounds were determined from their spectroscopic data such as IR, 1H-NMR, 13C-NMR and optical rotation. Antibacterial bioassay against human pathogenic bacteria was conducted using disc diffusion (Kirby-Bauer) method. Elatol (1) inhibited six species of bacteria, with significant antibacterial activities against Staphylococcus epidermis, Klebsiella pneumonia and Salmonella sp. while iso-obtusol (2) exhibited antibacterial activity against four bacterial species with significant activity against K. pneumonia and Salmonella sp. Elatol (1) showed equal and better antibacterial activity compared with tested commercial antibiotics while iso-obtusol (2) only equaled the potency of commercial antibiotics against K. pneumonia and Salmonella sp. Further tests conducted using dilution method showed both compounds as having bacteriostatic mode of action against the tested bacteria.