The reaction of 2‐dimethylaminomethylene‐3‐oxo‐<i>N</i>‐phenylbutyramide with active methylene nitriles

Abdelrazek, Fathy M.; Sharaf, Mohey F.; Metz, Peter; Jaeger, Anne

doi:10.1002/jhet.356

Cited by 8 publications

(6 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The intermediate 3 was conveniently accessed via an aqueous phase reaction between 4-fluoro-3-methylaniline ( 1 ) and 2,2,6-trimethyl-4H-1,3-dioxin-4-one ( 2 ) [ 44 ]. Base-mediated addition of 2-cyanoacetamide to the intermediate 4 followed by a thermal cyclization yielded the 6-methyl pyridine derivative ZW-1840 [ 45 ]. The intermediate 4 was further diversified to rapidly generate fused heteroaromatic cores by reacting it with the corresponding amines ( 5 , 6 and 7 ) under thermal conditions [ 46 ] to yield ZW-1841, ZW-1842, and ZW-1843.…”

Section: Methodsmentioning

confidence: 99%

Discovery of New Small Molecule Hits as Hepatitis B Virus Capsid Assembly Modulators: Structure and Pharmacophore-Based Approaches

Senaweera

Zhang

et al. 2021

Viruses

View full text Add to dashboard Cite

Hepatitis B virus (HBV) capsid assembly modulators (CpAMs) have shown promise as potent anti-HBV agents in both preclinical and clinical studies. Herein, we report our efforts in identifying novel CpAM hits via a structure-based virtual screening against a small molecule protein-protein interaction (PPI) library, and pharmacophore-guided compound design and synthesis. Curated compounds were first assessed in a thermal shift assay (TSA), and the TSA hits were further evaluated in an antiviral assay. These efforts led to the discovery of two structurally distinct scaffolds, ZW-1841 and ZW-1847, as novel HBV CpAM hits, both inhibiting HBV in single-digit µM concentrations without cytotoxicity at 100 µM. In ADME assays, both hits displayed extraordinary plasma and microsomal stability. Molecular modeling suggests that these hits bind to the Cp dimer interfaces in a mode well aligned with known CpAMs.

show abstract

Section: Methodsmentioning

confidence: 99%

Discovery of New Small Molecule Hits as Hepatitis B Virus Capsid Assembly Modulators: Structure and Pharmacophore-Based Approaches

Senaweera

Zhang

et al. 2021

Viruses

View full text Add to dashboard Cite

show abstract

“…β‐Ketoanilides are versatile reagents that have been extensively utilized in heterocyclic synthesis . In this work, the prepared heterocycles are proved to be interesting for their potentiality as biodegradable agrochemicals , pharmaceuticals , as non‐peptide HIV , protease inhibitors, anti‐schistosomal agents , and intermediates for the manufacture of dyestuffs. In the past few years, we have been involved in a program aiming to develop new simple routes for the synthesis of different heterocyclic compounds of interest to be evaluated as disperse dyestuff .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Some New Thiazolo[3,2‐a]pyrimidine Derivatives and Their Applications as Disperse Dyes

Elmaaty

El‐Taweel

Abdeldayem

et al. 2019

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

A series of novel thiazolo[3,2‐a]pyrimidine derivatives were synthesized by using β‐ketoanilides 1a–c as starting materials and as key intermediates for preparation of new pyrimidinecompounds 3a–e and fused heterocyclic pyrimidine derivatives 5a–c. The new compounds were transformed to disperse dyes 6a,b and 7. The chemical structures were elucidated by spectroscopic and elemental analyses and found to be in good agreement with the proposed structures. The versatility of compounds 6a,b and 7 for textile dyeing as disperse dyes was reported. The synthesized dyes were applied to polyester fabrics by using high temperature dyeing method at 120°C. The dye uptake expressed as color strength (k/s) of the dyed samples has been measured. Moreover, the color strength was examined in detail. In addition, the position of color in CIELAB coordinates (L*, a*, b*, h, and C*) was assessed. The color fastness of the dyed samples gave excellent results for washing and rubbing; however, the light fastness was moderate. Raman spectra of dyed samples unequivocally excluded ring dyeing and found to match with the proposed structures.

show abstract

“…In the past few years, we have been involved in a program aimed at the synthesis of some new heterocyclic systems of biological interest to be tested as biodegradable agrochemicals . In the context of this program, we have previously reported several syntheses starting from 2‐bromo‐1‐phenylethanone (ω‐bromoacetophenone) 2a (obtained from acetophenone 1 by bromination; Fig.…”

Section: Introductionmentioning

confidence: 99%

Phenacyl Bromides Revisited: Facile Synthesis of Some New Pyrazoles, Pyridazines, and Their Fused Derivatives

Abdelrazek

Hassaneen

Nassar

et al. 2013

Journal of Heterocyclic Chem

Self Cite

View full text Add to dashboard Cite

The reaction of 2‐dimethylaminomethylene‐3‐oxo‐N‐phenylbutyramide with active methylene nitriles

Cited by 8 publications

References 18 publications

Discovery of New Small Molecule Hits as Hepatitis B Virus Capsid Assembly Modulators: Structure and Pharmacophore-Based Approaches

Discovery of New Small Molecule Hits as Hepatitis B Virus Capsid Assembly Modulators: Structure and Pharmacophore-Based Approaches

Synthesis of Some New Thiazolo[3,2‐a]pyrimidine Derivatives and Their Applications as Disperse Dyes

Phenacyl Bromides Revisited: Facile Synthesis of Some New Pyrazoles, Pyridazines, and Their Fused Derivatives

Contact Info

Product

Resources

About