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Promoter free allylation of trichloroacetimidates with allyltributylstannanes under thermal conditions to access the common 1,1'-diarylbutyl pharmacophore.

ABSTRACT: 1,1'-Diarylbutyl groups are a common pharmacophore found in many biologically active small molecules. To access these systems under mild conditions, the reaction of diarylmethyl trichloroacetimidates with allyltributylstannanes was explored. Simply heating allyltributylstannane with the trichloroacetimidate resulted in substitution of the imidate with an allyl group. Unlike other methods used to access these systems, no strong base, transition metal catalyst, Brønsted acid or Lewis acid promoter was required to affect the transformation. Conversions are best with electron rich benzylic trichloroacetimidate systems, where excellent yields are achieved just by refluxing the reactants together in nitromethane.

SUBMITTER: Mahajani NS

PROVIDER: S-EPMC5976556 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature

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Promoter free allylation of trichloroacetimidates with allyltributylstannanes under thermal conditions to access the common 1,1'-diarylbutyl pharmacophore.

Mahajani Nivedita S NS Chisholm John D JD

Organic & biomolecular chemistry 20180501 21

1,1'-Diarylbutyl groups are a common pharmacophore found in many biologically active small molecules. To access these systems under mild conditions, the reaction of diarylmethyl trichloroacetimidates with allyltributylstannanes was explored. Simply heating allyltributylstannane with the trichloroacetimidate resulted in substitution of the imidate with an allyl group. Unlike other methods used to access these systems, no strong base, transition metal catalyst, Brønsted acid or Lewis acid promoter ...[more]

PMID: 29766199

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Project description:BackgroundEctotherms are assumed to be strongly influenced by the surrounding ambient and environmental conditions for daily activity and movement. As such, ecological and physiological factors contribute to stimuli influencing navigation, extent of movement, and therefore habitat use. Our study focused on the intensity of activity (from acceleration data) and extent of movement (from GPS and thread trailing data) of Eastern box turtles (Terrapene carolina carolina) in a fragmented landscape near their northern population limit. First, we quantified the thermal performance curve of box turtles using activity as a measure of performance. Second, we investigated ecological factors that could influence activity and movement and characterized the movement as extensive (exploration) and intensive (foraging).ResultsIn contrast to previous lab work investigating effects of temperature on activity, we found no relationship between box turtle activity and temperature in the field. Furthermore, box turtle activity was consistent over a wide range of temperatures. Cluster analysis categorized movement recorded with GPS more as intensive than as extensive, while thread trailing had more movement categorized as extensive than intensive. Box turtle activity was higher during the morning hours and began to decrease as the day progressed. Based on the microclimate conditions tested, we found that box turtle movement was influenced by precipitation and time of day, and activity was most influenced by absolute humidity, ambient temperature, cloud cover, and time of day.ConclusionsOur model ectotherm in this study, the Eastern box turtle, had activity patterns characteristic of a thermal generalist. Sampling resolution altered the characterization of movement as intensive or extensive movement, possibly altering interpretation. More information on the resolution needed to definitively identify foraging and exploratory behavior in turtles is needed. Activity and movement were nearly independent of environmental conditions, which supports the overall interpretation that turtle performance is that of a broad environmental generalist. Future studies of movement of other turtle and reptile species are needed to determine the generality of these findings.

Project description:During development, cells may adjust their size to balance between the tissue metabolic demand and the oxygen and resource supply: Small cells may effectively absorb oxygen and nutrients, but the relatively large area of the plasma membrane requires costly maintenance. Consequently, warm and hypoxic environments should favor ectotherms with small cells to meet increased metabolic demand by oxygen supply. To test these predictions, we compared cell size (hindgut epithelium, hepatopancreas B cells, ommatidia) in common rough woodlice (Porcellio scaber) that were developed under four developmental conditions designated by two temperatures (15 or 22°C) and two air O2 concentrations (10% or 22%). To test whether small-cell woodlice cope better under increased metabolic demand, the CO2 production of each woodlouse was measured under cold, normoxic conditions and under warm, hypoxic conditions, and the magnitude of metabolic increase (MMI) was calculated. Cell sizes were highly intercorrelated, indicative of organism-wide mechanisms of cell cycle control. Cell size differences among woodlice were largely linked with body size changes (larger cells in larger woodlice) and to a lesser degree with oxygen conditions (development of smaller cells under hypoxia), but not with temperature. Developmental conditions did not affect MMI, and contrary to predictions, large woodlice with large cells showed higher MMI than small woodlice with small cells. We also observed complex patterns of sexual difference in the size of hepatopancreatic cells and the size and number of ommatidia, which are indicative of sex differences in reproductive biology. We conclude that existing theories about the adaptiveness of cell size do not satisfactorily explain the patterns in cell size and metabolic performance observed here in P. scaber. Thus, future studies addressing physiological effects of cell size variance should simultaneously consider different organismal elements that can be involved in sustaining the metabolic demands of tissue, such as the characteristics of gas-exchange organs and O2-binding proteins.

Dataset Information

Promoter free allylation of trichloroacetimidates with allyltributylstannanes under thermal conditions to access the common 1,1'-diarylbutyl pharmacophore.

Publications

Promoter free allylation of trichloroacetimidates with allyltributylstannanes under thermal conditions to access the common 1,1'-diarylbutyl pharmacophore.

Similar Datasets

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