Reaction of Hexamethylene Diisocyanate with Amines

Skrylkova, A. S.; Egorov, D. M.; Tarabanov, R. V.

doi:10.1134/s1070363222100176

Cited by 1 publication

(2 citation statements)

References 32 publications

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“…3-Phenyl-1-{6-[(phenylcarbamoyl)amino]hexyl}urea ( D4 ). 1H and 13C NMR and HRMS are in agreement with previously reported data [ 20 ].…”

Section: Methodssupporting

confidence: 91%

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Fatty Acid-Activated Proton Transport by Bisaryl Anion Transporters Depolarises Mitochondria and Reduces the Viability of MDA-MB-231 Breast Cancer Cells

York,

McNaughton,

Duman

et al. 2023

Biomolecules

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In respiring mitochondria, the proton gradient across the inner mitochondrial membrane is used to drive ATP production. Mitochondrial uncouplers, which are typically weak acid protonophores, can disrupt this process to induce mitochondrial dysfunction and apoptosis in cancer cells. We have shown that bisaryl urea-based anion transporters can also mediate mitochondrial uncoupling through a novel fatty acid-activated proton transport mechanism, where the bisaryl urea promotes the transbilayer movement of deprotonated fatty acids and proton transport. In this paper, we investigated the impact of replacing the urea group with squaramide, amide and diurea anion binding motifs. Bisaryl squaramides were found to depolarise mitochondria and reduce MDA-MB-231 breast cancer cell viability to similar extents as their urea counterpart. Bisaryl amides and diureas were less active and required higher concentrations to produce these effects. For all scaffolds, the substitution of the bisaryl rings with lipophilic electron-withdrawing groups was required for activity. An investigation of the proton transport mechanism in vesicles showed that active compounds participate in fatty acid-activated proton transport, except for a squaramide analogue, which was sufficiently acidic to act as a classical protonophore and transport protons in the absence of free fatty acids.

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“…3-Phenyl-1-{6-[(phenylcarbamoyl)amino]hexyl}urea ( D4 ). 1H and 13C NMR and HRMS are in agreement with previously reported data [ 20 ].…”

Section: Methodssupporting

confidence: 91%

“…13 C NMR (100 MHz, DMSO-d6) δ 154.8 (2C), 144.3 (2C), 125.9 (2C), 124.7 (q, J = 269 Hz, 2C), 120.8 (q, J = 32 Hz, 2C), 117.1 (2C), 39.0 (2C), 29 3-Phenyl-1-{6-[(phenylcarbamoyl)amino]hexyl}urea (D4). 1H and 13C NMR and HRMS are in agreement with previously reported data [20].…”

Section: -[3-chloro-5-(trifluoromethyl)phenyl]-1-[6-({[3-chloro-5-(tr...supporting

confidence: 91%