Thiophene S-Oxides

Thiemann, Thies; Dongol, Krishna Gopal

doi:10.5772/intechopen.79080

Cited by 5 publications

(7 citation statements)

References 129 publications

(150 reference statements)

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“…S-Oxidation of the nitro building block has the disadvantage that the more polar groups (especially the sulfoxides) are present in subsequent synthetic steps, which complicates purification of the products by normal phase column chromatography. S-Oxidation after the final coupling step has not been investigated since the thiophene groups are also prone to oxidation …”

Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of Phenylalanine Amides Active against Mycobacterium abscessus and Other Mycobacteria

et al. 2023

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Nα-2-thiophenoyl-d-phenylalanine-2-morpholinoanilide [MMV688845, Pathogen Box; Medicines for Malaria Venture; IUPAC: (2R)-N-(1-((2-morpholinophenyl)amino)-1-oxo-3-phenylpropan-2-yl)thiophene-2-carboxamide)] is a hit compound, which shows activity against Mycobacterium abscessus (MIC90 6.25–12.5 μM) and other mycobacteria. This work describes derivatization of MMV688845 by introducing a thiomorpholine moiety and the preparation of the corresponding sulfones and sulfoxides. The molecular structures of three analogs are confirmed by X-ray crystallography. Conservation of the essential R configuration during synthesis is proven by chiral HPLC for an exemplary compound. All analogs were characterized in a MIC assay against M. abscessus, Mycobacterium intracellulare, Mycobacterium smegmatis, and Mycobacterium tuberculosis. The sulfone derivatives exhibit lower MIC90 values (M. abscessus: 0.78 μM), and the sulfoxides show higher aqueous solubility than the hit compound. The most potent derivatives possess bactericidal activity (99% inactivation of M. abscessus at 12.5 μM), while they are not cytotoxic against mammalian cell lines.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of Phenylalanine Amides Active against Mycobacterium abscessus and Other Mycobacteria

et al. 2023

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“…The system is novel in that the compound incorporates photocleavable S-N and S-O bonds for a tandem process. Other work has been published on nitrenes, carbenes and atomic O from photolysis of sulfilimines, sulfoxides, pyridine N-oxide and related compounds (13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25), but by nature are one-step processes. Relatedly, simultaneous formation of reactive intermediates has also been reported.…”

Section: Commentarymentioning

confidence: 99%

Two‐step Two‐intermediate Photorelease Bolm‐McCulla Reaction: Dual Release of Nitrene and Atomic Oxygen Reactive Intermediates

Rashid

Baker

Greer

2021

Photochem & Photobiology

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This article is a highlight of the paper by Isor et al. in this issue of Photochemistry and Photobiology. It describes the photolysis of a dibenzothiophene sulfoximine (bearing Nphenyl imino and S-oxide groups) to produce two reactive intermediates in tandem. The sulfoximine undergoes a S-N and S-O photocleavage to release phenyl nitrene and atomic oxygen [O( 3 P)]. The phenyl nitrene dimerizes to azobenzene or is trapped by diethylamine to reach an azepine. From there, atomic oxygen arises in a secondary photolysis of dibenzothiophene sulfoxide. A computational analysis also reveals that the S-N bond is labile for initial nitrene release, with the secondary release of atomic oxygen by S-O cleavage. Whether future sulfoximine scaffolds can produce the reverse order release of O( 3 P) then nitrene, or release both simultaneously, is yet to be established. Nonetheless, molecules with dual-intermediate release, such as coupled photoaffinity labeling and cellular oxidation, are worth pursuing.

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“…Many soil erosion models have been developed concerning the estimation and the prediction of soil loss and degradation. Estimation of soil erosion consists of physical‐based models like Water Erosion Prediction Project, [ 29 , 30 ] European Soil Erosion Soil Model, [ 31 , 32 , 33 ] and empirical‐based models like universal soil loss equation (USLE). [ 44 , 47 ] The USLE and its revised version RUSLE are two of the empirical models that have been most commonly used, and RUSLE is an empirically based model that can estimate and forecast the long‐term average annual rate of soil erosion.…”

Section: Introductionmentioning

confidence: 99%

The Spatiotemporal Dynamics of Land Use Land Cover Change, and Its Impact on Soil Erosion in Tagaw Watershed, Blue Nile Basin, Ethiopia

et al. 2021

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The Blue Nile basin is one of the hot‐spots of soil erosion areas in Ethiopia. However, the impact of land use changes on soil erosion is poorly understood in the Tagaw watershed. Hence, the objective of the study is to assess the impact of land use changes on soil erosion in Tagaw watershed over the last 31 years. Rainfall, soil, satellite images and topographic data are acquired from field survey and secondary sources. A Revised Universal Soil Loss Equation (RUSLE) model is used to estimate soil erosion. The mean annual and total potential soil losses of the watershed are 19.3, 22.9, 26 and 0.06–503.56, 0.11–516.67, and 0.00–543.5 tons ha −1 yr −1 for 1995, 2006 and 2016 respectively. The highest soil loss is found for bare land. The RUSLE model further showed that the highest soil erosion occurred in 2016 whereas the lowest soil erosion occurred in 1995.

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Thiophene S-Oxides

Cited by 5 publications

References 129 publications

Synthesis and Characterization of Phenylalanine Amides Active against Mycobacterium abscessus and Other Mycobacteria

Synthesis and Characterization of Phenylalanine Amides Active against Mycobacterium abscessus and Other Mycobacteria

Two‐step Two‐intermediate Photorelease Bolm‐McCulla Reaction: Dual Release of Nitrene and Atomic Oxygen Reactive Intermediates

The Spatiotemporal Dynamics of Land Use Land Cover Change, and Its Impact on Soil Erosion in Tagaw Watershed, Blue Nile Basin, Ethiopia

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