Recent advances in the synthetic chemistry of 1,5-benzothiazepines: A minireview

Benzothiazepine, a prominent “drug prejudice core”, is a heterocyclic moiety of immense importance due to its presence in a wide range of bioactive compounds. They act as a primary “biolinker” in diverse synthetic routes to obtain bioactive molecules and serve as important templates in synthetic and medicinal chemistry. They are known to possess a plethora of pharmacological activities, which include Ca²⁺ channel blockers, CNS acting agents, anti-HIV, ACE inhibitors, antimicrobial, antifungal, anticancer. Their promising behaviour as drug molecules led the scientific community to develop novel, mild, green, and highly efficient synthetic routes for their synthesis. The conventional synthesis generally involved the condensation of chalcones with 2-aminothiophenol in the presence of acid/base with high-temperature heating, mostly resulting in poor yields or mixtures. However, recent trends are replacing these conditions with mild and green conditions through organocatalysis or other methodologies. In this review, an attempt has been made by authors to summarize (a) Recent developments in the synthetic strategies of 1,5-benzoathiazepines and its derivatives (b) Conventional methods for the synthesis of 1,5-benzothiazepines including progress in the green chemistry routes (c) Applications of various metals and organocatalysts to achieve the enantioselective synthesis of title compounds.     

Synthesis and Characterization of Silver–PVA Nanocomposite for Sensor and Antibacterial Applications

Silver–polyvinyl alcohol (PVA) nanocomposite is synthesized by a simple chemical reduction method in aqueous media and characterized by various techniques such as UV–Visible spectroscopy, transmission electron microscopy, X-ray diffraction and infrared spectroscopy. The morphology of the obtained silver nanoparticles is spherical in shape with an average diameter of 24 nm. The prepared silver–PVA nanocomposite is demonstrated to detect the concentration of heavy metal contaminant cadmium in water based on linear change in surface plasmon resonance absorption strength. The antibacterial tests show the inhibiting action of this nanocomposite against pathogenic bacteria Escherichia coli and Pseudomonas aeruginosa (gram negative), Bacillus cereus and Staphylococcus aureus (gram positive), which are found commonly in water. These observed optical and antibacterial properties, suggest the possible utilization of prepared silver–PVA nanocomposite in the water purification application.     

Dehydration of 1,4-dioxane through blend membranes of poly(vinyl alcohol) and chitosan by pervaporation

Blend membranes prepared from poly(vinyl alcohol) (PVA) and chitosan (CS) were crosslinked with glutaraldehyde and used in the pervaporation dehydration of 1,4-dioxane. Membranes were characterized by Fourier transform infrared spectroscopy (FTIR), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC) and X-ray diffraction (X-RD) to assess, respectively, the intermolecular interactions, thermal stability and crystallinity. Equilibrium sorption studies were carried out in pure liquids and binary mixtures of different compositions of water + 1,4-dioxane mixtures to assess the polymer–liquid interactions. The crosslinked membrane showed a good potential in breaking the azeotrope of 82 wt.% aqueous 1,4-dioxane giving a selectivity of 117 with a reasonable water flux of 0.37 kg/m² h. The effect of operating parameters such as feed composition, membrane thickness and permeate pressure was evaluated.     

Synthesis and antimicrobial activity of novel 2‐(aryl)‐3‐[5‐(2‐oxo‐2H‐3‐chromenyl)‐1,3‐oxazol‐2‐yl]‐1,3‐thiazolan‐4‐ones

A series of novel 2‐(aryl)‐3‐[5‐(2‐oxo‐2H‐3‐chromenyl)‐1,3‐oxazol‐2‐yl]‐1,3‐thiazolan‐4‐ones 4a , 4b , 4c , 4e , 4f , 4g , 4h , 4i , 4j have been synthesized and assayed for their antibacterial activity against Gram‐positive bacteria viz. Bacillus subtilis (ATCC 6633), Staphylococcus aureus (ATCC 6538p), Micrococcus luteus (IFC 12708), and Gram‐negative bacteria viz. Proteus vulgaris (ATCC 3851), Salmonella typhimurium (ATCC 14028), Escherichia coli (ATCC 25922), and also antifungal activity against Candida albicans (ATCC 10231), Aspergillus fumigatus (HIC 6094), Trichophyton rubrum (IFO 9185), and Trichophyton mentagrophytes (IFO 40996). Among the screened compounds, 4d , 4e , 4f , 4g , and 4j exhibited potent inhibitory activity compared with the standard drug at the tested concentrations. The results reveal that, the presence of difluorophenyl in 4f and pipernyl ring in 4j at 2‐position of thiazolidine‐4‐one ring show significant inhibitory activity. The other compounds also showed appreciable activity against the test bacteria and fungi and emerged as potential molecules for further development. J. Heterocyclic Chem., 2011.     

Nonsteroidal Anti‐inflammatory Drug‐based N‐Allylidene Benzohydrazides and 1‐Acyl‐2‐pyrazolines: Their Synthesis as Potential Cytotoxic Agents In Vitro

A series of 1‐acyl‐2‐pyrazoline derivatives derived from nonsteroidal anti‐inflammatory drugs was designed as potential anticancer agents. Synthesis of these compounds was carried out via the condensation reaction of chalcones and acid hydrazides under heating. The methodology did not require the use of any costly reagents or catalysts, and the acid hydrazide reactants were readily prepared from mefenamic acid or ibuprofen. A variety of 1‐acyl‐2‐pyrazolines was prepared in good to excellent yields. An N‐allylidene benzohydrazide intermediate was isolated during the reaction optimization study, the structure of which was confirmed unambiguously by X‐ray single crystal data. A range of N‐allylidene benzohydrazides were also prepared in good yields. Some of the compounds synthesized showed promising cytotoxic activities when tested against HCT‐15 human colon cancer cell line in vitro.     

Assessment of inhalation exposure potential of broken uranium ore piles in low-grade uranium mine

This paper presents the assessment of inhalation exposure potential of broken uranium ore piles in different stopes of Jaduguda uranium mines of India. ²²²Rn emanation coefficient of broken uranium ore was measured in laboratory by collecting air sample from airtight glass jar containing ore sample. An attempt was also made to correlate the emanation coefficient with ²²⁶Ra content of the ore. The ²²²Rn progeny doses estimated based on radon activity concentration of broken ore, occupancy period and equilibrium ratio in different stopes were well below the prescribed limit of International Commission on Radiological Protection. The maximum ²²²Rn progeny dose contribution from broken ore piles was worked out to be 0.22 mSv year^?1. This suggests that the broken ore piles are not the significant contributor of inhalation exposure under the existing ventilation condition of Jaduguda uranium mine.     

A simultaneous TG-DTG-DSC-quadrupole mass spectrometric study

Mechanistic aspects of the thermal decomposition of benzyl-triethyl-ammonium tetrafluoroborate (BTEATFB) employing simultaneous TG-DSC coupled with a quadrupole mass spectrometer are considered in this work. The experiments were conducted in an inert atmosphere of helium. The decomposition of BTEATFB proceeds through several competing mechanisms. While nucleophilic substitution reaction occurs through the formation of a tertiary amine and plays an important role in the initial stages of the decomposition, and the probability of Hoffman elimination also exists.     

Ugi three-component coupling reaction for the synthesis of 2-(6-oxo-11-phenyl-7,8-dihydrobenzo[b]pyrrolo[1,2-d][1,4]diazocin-5(6H)-yl)-2-phenylacetamide derivatives

A three-component, four center Ugi reaction of 3-(1-(2-aminophenyl)-5-phenyl-1H-pyrrol-2-yl)propanoic acid with aromatic aldehyde and t-butyl isocyanide has been achieved to produce a novel class of N-tert-butyl-2-(6-oxo-11-phenyl-7,8-dihydrobenzo[b]pyrrolo[1,2-d][1,4]diazacine-5(6H)-yl)-2-phenylacetamides in moderate to good yields.     

Ring opening of epoxides with alcohols using Fe(Cp)2BF4 as catalyst

Fe(Cp)₂BF₄ is an efficient catalyst for the alcoholysis of aromatic, aliphatic, and cyclic epoxides giving excellent yields of the corresponding β-alkoxy alcohols under ambient conditions. The methanolysis of styrene oxide using Fe(Cp)₂BF₄ as a catalyst (5 mol %) gave excellent yield of 2-methoxy-2-phenylethanol with complete regio-selectivity. The ring opening of cyclic epoxides gave 77–97% yields of trans-β-methoxy alcohols, in 0.5–6 h. The use of 1,2-epoxyhexane and 1,2-epoxydodecane as substrates gave both regioisomers in excellent yields. The first order rate of reaction with respect to catalyst was observed for the kinetics of ring opening of 1,2-epoxyhexane with methanol.