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Synthetic Approaches to Inhibitors of Isoprenoid Biosynthesis
Published in Peter Grunwald, Pharmaceutical Biocatalysis, 2019
Pedro Merino, Loredana Maiuolo, Ignacio Delso, Vincenzo Algieri, Antonio De Nino, Tomas Tejero
The preparation of bisphosphonates with heterocyclic rings (Risedronate (9), Zoledronate (10)) or aminoalkyl groups on the lateral chain (e.g., Pamidronate (5), Alendronate (6), Neridronate (7)) were carried out by reacting carboxylic acids (21), phosphorous trichloride and phosphorous acid in sulfolane as a solvent under microwave irradiation (Scheme 2.6) (Mustafa et al., 2011). Sulfolane was preferably employed as solvent in the first step of reaction because of its polarity that enhanced the effectiveness of microwave heating. Reagents and conditions: (i) H3PO3, PCl3 (mole ratio 3:4), sulfolane, 200–400 W, 65°C, 3–7 min, (ii) H2O, 450–500 W, 150°C, 10 min.
Immunotoxicity studies of sulfolane following developmental exposure in Hsd:Sprague Dawley SD rats and adult exposure in B6C3F1/N mice
Published in Journal of Immunotoxicology, 2021
AtLee T. D. Watson, Victor J. Johnson, Michael I. Luster, Gary R. Burleson, Dawn M. Fallacara, Barney R. Sparrow, Mark F. Cesta, Michelle C. Cora, Keith R. Shockley, Matt D. Stout, Chad R. Blystone, Dori R. Germolec
Sulfolane (2,3,5-tetrahydrothiophene-1,1-dioxide; tetramethylene sulfone) is a high production volume chemical used in liquid-liquid and liquid-vapor extraction of chemicals from petroleum, in fractionalization of wood tars, and as a desulfurization agent in the purification of natural gas. Release of sulfolane into the environment can result in contamination of groundwater and well water in neighboring communities, as evidenced in the city of North Pole, AK where sulfolane has been detected at levels up to 500 parts per billion (ppb) in drinking water (ADEC (Alaska Department of Environmental Conservation) 2012). Therefore, in addition to potential occupational exposure through inhalation and/or dermal routes, residents may potentially receive exposure to sulfolane through ingestion of drinking water and certain foods in these affected communities.
Disposition and metabolism of sulfolane in Harlan Sprague Dawley rats and B6C3F1/N mice and in vitro in hepatocytes from rats, mice, and humans
Published in Xenobiotica, 2020
Suramya Waidyanatha, Sherry R. Black, Chad R. Blystone, Purvi R. Patel, Scott L. Watson, Rodney W. Snyder, Timothy R. Fennell
Sulfolane (tetrahydrothiophene 1,1-dioxide) is a high production volume chemical in the United States with an annual production between 10 and 50 million pounds (ATSDR, 2010; U.S. EPA, 2012). Sulfolane has a low vapor pressure, no odor, and is water miscible (Brown et al., 1966). It is a polar, organosulfur compound used as a solvent in a variety of industrial applications. For example, it is used in liquid–liquid and liquid–vapor extraction processes during extraction of aromatic hydrocarbons from petroleum (Andersen et al., 1976; Brown et al., 1966; HSDB, 2006). Sulfolane has been detected in groundwater near refining sites. For example, in North Pole, Alaska, ground water was contaminated from a nearby petroleum refinery. Sulfolane has been detected in nearly 300 drinking water wells in the area since 2009, with levels ranging between 4 and 7 parts per billion (North Pole, AK Drinking Water Quality Report, 2015). In addition to North Pole, AK, sulfolane has also been detected at sites in Canada and the United States near areas of natural gas or petroleum refining. Therefore, human exposure to sulfolane can occur via inhalation, dermal (e.g. occupational), and/or oral (e.g. environmental) routes.