Biological Activity in Compounds Possessing Thiophen Rings

Martin‐Smith, M.; Reid, S. T.

doi:10.1021/jm50007a001

Cited by 35 publications

(2 citation statements)

References 153 publications

(33 reference statements)

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“…32 Bearing this in mind, we decided to include both phenyl and p-hydroxyphenyl substituents for derivatization and screening. Despite knowing that even minor changes result in activity loss, 2-and 3thiophenyl substituents were included because these structures are bioisosteric to phenyl 60 and therefore offer a hopefully tolerable change to the molecule without activity loss.…”

Section: Low Et Al (12 μM)mentioning

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: Low Et Al (12 μM)mentioning

confidence: 99%

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

et al. 2023

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“…Functionalized derivatives of thiophene have massively contributed to the growth of chemistry materials which have shown promising developments towards new technologies in electronics [1][2][3][4][5]. At the same time, thiophene-derived small organic molecules have shown a wide variety of applications including agrochemical [6,7] and pharmaceutical [8][9][10] fields. The model organic compound 4-Bromo-3-formyl-N-phenyl-5propylthiophene-2-carboxamide (Figure 1) is very useful, with functionalization that allows facile downhill derivation, as well as handles that themselves can be derivatized to the target material.…”

Section: Introductionmentioning

confidence: 99%