Aryl morpholino triazenes inhibit cytochrome P450 1A1 and 1B1

Lee, Daniel; Perez, Pedro A.; Jackson, W. P. U.; Chin, Taylor; Galbreath, Michael; Fronczek, Frank R.; Isovitsch, Ralph; Iimoto, Devin S.

doi:10.1016/j.bmcl.2016.05.064

Cited by 13 publications

(4 citation statements)

References 36 publications

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“…The same behavior in bond distances is observed for triazene 3 (Figure ). These differences in bond distances at the triazene system have been described as certain degree of π-delocalization across the linear triazene moiety …”

Section: Resultsmentioning

confidence: 99%

“…These differences in bond distances at the triazene system have been described as certain degree of π-delocalization across the linear triazene moiety. 11 Treatment of a solution of 2 or 3 in dry THF with K[N(SiMe 3 ) 2 ] led to the formation of a potassium triazenide, which can be directly converted into complexes 4−7 by a transmetalation reaction with [MCp*Cl 2 ] 2 (Scheme 1). The 1 H and 13 C NMR of complexes 4 and 5 showed a very similar spectrum, as can be expected from their hypothetical structures.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Rh^(III)Cp* and Ir^(III)Cp* Complexes of 1-[(4-Methyl)phenyl]-3-[(2-methyl-4′-R)imidazol-1-yl]triazenide (R = t-Bu or H): Synthesis, Structure, and Catalytic Activity

Camarena-Díaz

Iglesias²,

Chávez

et al. 2019

Organometallics

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A series of iridium and rhodium complexes have been synthesized using as ligand a triazenide monofunctionalized with an imidazole substituent. Steric hindrance at the imidazole moiety induced differences in the coordination modes as well in the catalytic behavior of complexes 4−7. Complexes 4−7 were tested in the transfer hydrogenation of acetophenone and 5-alken-2-ones. The hydrogenation of either the double bond or the carbonyl group in 5-alken-2-ones, showed to be selective in the presence of 6, 7, and 10 and has a dependence on the presence or absence of base. Control experiments point out that the imidazole moiety in the structure of complexes 4−7 speeds-up the catalysis.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Rh^(III)Cp* and Ir^(III)Cp* Complexes of 1-[(4-Methyl)phenyl]-3-[(2-methyl-4′-R)imidazol-1-yl]triazenide (R = t-Bu or H): Synthesis, Structure, and Catalytic Activity

Camarena-Díaz

Iglesias²,

Chávez

et al. 2019

Organometallics

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“…First, (E)-1-[4-(morpholinodiazenyl)phenyl]ethan-1-one (A) was synthesized at 0-5°C by adding an aqueous NaNO 2 solution to a 4-aminoacetophenone in 6 M HCl, the formed diazonium ion underwent coupling with morpholine to give A in 81.89% yield. [40] Based on the existing methodology, the corresponding chalcone derivatives were synthesized via Claisen-Schmidt condensation [28,33] by reacting A with different substituted aryl aldehydes. Finally, MCs (MC-1 to MC-25) were obtained in good yields ranging from 85% to 98%.…”

Section: Synthesis Of Mcsmentioning

confidence: 99%

Morpholinodiazenyl chalcone blocks influenza A virus capsid uncoating by perturbing the clathrin‐mediated vesicular trafficking pathway

Thottasseri,

Kaur,

Ramesh

et al. 2024

Archiv der Pharmazie

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Influenza A virus (IAV) is a highly contagious respiratory pathogen that significantly threatens global health by causing seasonal epidemics and occasional, unpredictable pandemics. To identify new compounds with therapeutic potential against IAV, we designed and synthesized a series of 4′‐morpholinodiazenyl chalcones using the molecular hybridization method, performed a high‐content screen against IAV, and found that (E)‐1‐{4‐[(E)‐morpholinodiazenyl]phenyl}‐3‐(3,4,5‐trimethoxyphenyl)prop‐2‐en‐1‐one (MC‐22) completely neutralized IAV infection. While MC‐22 allowed IAV to successfully internalize into the cell and fuse at the acidic late endosomes, it prevented viral capsid uncoating and genome release. Since IAV majorly utilizes clathrin‐mediated endocytosis (CME) for cellular entry, we examined whether MC‐22 had any effect on CME, using nonviral cargoes that enter cells via clathrin‐dependent or ‐independent pathways. Although MC‐22 showed no effect on the uptake of choleratoxin B, a cargo that enters cells majorly via the clathrin‐independent pathway, it significantly attenuated the clathrin‐dependent internalization of both epidermal growth factor and transferrin. Cell biological analyses revealed a marked increase in the size of early endosomes upon MC‐22 treatment, indicating an endosomal trafficking/maturation defect. This study reports the identification of MC‐22 as a novel CME‐targeting, highly potent IAV entry inhibitor, which is expected to neutralize a broad spectrum of viruses that enter the host cells via CME.

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“…Arylmorpholino 1,2,3-triazenes have structural characteristics like those of compound I and contain a 1,2,3triazine unit consisting of three consecutive conjugated nitrogen atoms, as seen in I. Examination of the structure of EMUDEX (Lee et al, 2016) suggests that a degree ofdelocalization across the linear triazene moiety of I was observed. The N2-N3 double-bond distance of 1.2679 (13) A ånd the N1-N2 single-bond distance of 1.3501 (12) A ˚in EMUDEX are in accordance with those reported for OFUBUO (Mukai et al, 2013), EZEXEN (Gholivand et al, 2010), FUZLUI (Pye et al, 2010).…”

Section: Database Surveymentioning

confidence: 99%

Syntheses and crystal structure of 4-[(pyridin-3-yl)diazenyl]morpholine and 1-[(pyridin-3-yl)diazenyl]-1,2,3,4-tetrahydroquinoline

Sokhna¹,

Seck²,

Thiam³

et al. 2023

Acta Cryst E

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Two new heterocyclic 1,2,3-triazenes were synthesized by diazotation of 3-aminopyridine following respectively by coupling with morpholine or 1,2,3,4-tetrahydroquinoline. 4-[(Pyridin-3-yl)diazenyl]morpholine (I), C9H12N4O, has monoclinic P21/c symmetry at 100 K, while 1-[(pyridin-3-yl)diazenyl]-1,2,3,4-tetrahydroquinoline (II), C14H14N4, has monoclinic P21/n symmetry at 100 K. These 1,2,3-triazene derivatives were synthesized by the organic medium method by coupling reactions of 3-aminopyridine with morpholine and 1,2,3,4-tetrahydroquinoline, respectively, and characterized by 1H NMR, 13C NMR, IR, mass spectrometry, and single-crystal X-ray diffraction. The molecule of compound I consists of pyridine and morpholine rings connected by an azo moiety (–N=N–). In the molecule of II, the pyridine ring and the 1,2,3,4-tetrahydroquinoline unit are also connected by an azo moiety. The double- and single-bond distances in the triazene chain are comparable for the two compounds. In both crystal structures, the molecules are connected by C—H...N interactions, forming infinite chains for I and layers parallel to the bc plane for II.

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Aryl morpholino triazenes inhibit cytochrome P450 1A1 and 1B1

Cited by 13 publications

References 36 publications

Rh^(III)Cp* and Ir^(III)Cp* Complexes of 1-[(4-Methyl)phenyl]-3-[(2-methyl-4′-R)imidazol-1-yl]triazenide (R = t-Bu or H): Synthesis, Structure, and Catalytic Activity

Rh^(III)Cp* and Ir^(III)Cp* Complexes of 1-[(4-Methyl)phenyl]-3-[(2-methyl-4′-R)imidazol-1-yl]triazenide (R = t-Bu or H): Synthesis, Structure, and Catalytic Activity

Morpholinodiazenyl chalcone blocks influenza A virus capsid uncoating by perturbing the clathrin‐mediated vesicular trafficking pathway

Syntheses and crystal structure of 4-[(pyridin-3-yl)diazenyl]morpholine and 1-[(pyridin-3-yl)diazenyl]-1,2,3,4-tetrahydroquinoline

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Aryl morpholino triazenes inhibit cytochrome P450 1A1 and 1B1

Cited by 13 publications

References 36 publications

Rh(III)Cp* and Ir(III)Cp* Complexes of 1-[(4-Methyl)phenyl]-3-[(2-methyl-4′-R)imidazol-1-yl]triazenide (R = t-Bu or H): Synthesis, Structure, and Catalytic Activity

Rh(III)Cp* and Ir(III)Cp* Complexes of 1-[(4-Methyl)phenyl]-3-[(2-methyl-4′-R)imidazol-1-yl]triazenide (R = t-Bu or H): Synthesis, Structure, and Catalytic Activity

Morpholinodiazenyl chalcone blocks influenza A virus capsid uncoating by perturbing the clathrin‐mediated vesicular trafficking pathway

Syntheses and crystal structure of 4-[(pyridin-3-yl)diazenyl]morpholine and 1-[(pyridin-3-yl)diazenyl]-1,2,3,4-tetrahydroquinoline

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Rh^(III)Cp* and Ir^(III)Cp* Complexes of 1-[(4-Methyl)phenyl]-3-[(2-methyl-4′-R)imidazol-1-yl]triazenide (R = t-Bu or H): Synthesis, Structure, and Catalytic Activity

Rh^(III)Cp* and Ir^(III)Cp* Complexes of 1-[(4-Methyl)phenyl]-3-[(2-methyl-4′-R)imidazol-1-yl]triazenide (R = t-Bu or H): Synthesis, Structure, and Catalytic Activity