Preparation and Reactions of 2-azidoquinoline-3-carboxaldehyde with Primary Amines and Active Methylene Compounds

Ibrahim, Nabila M.; Yosef, Hisham Abdallah A.; Mahran, M. R.

doi:10.3184/030823409x435900

Cited by 7 publications

(3 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In a previous investigation 8 Perkin‐type condensation between tetraethyl methylenebisphosphonate ( 1 ) and 2‐azidoquinolines‐3‐carbaldehyde ( 3 ) led to tetrazoloquinoline‐based ethylene‐bisphosphonates 4 and 5 with anti‐inflammatory properties (Scheme ). The investigation reported notwithstanding the azide 3 reacts with phosphorus reagents mainly in the tautomeric‐tetrazole form, the involvement of N 3 group in some reactions was also reported 8, 17. The results reflected the versatility of the azido group and the phosphorus reagents as well.…”

Section: Resultsmentioning

confidence: 80%

Elaborating on Efficient Anti‐Proliferation Agents of Cancer Cells and Anti‐Inflammatory‐Based N‐Bisphosphonic Acids

Abdou

Khidre

Kamel

2011

Archiv der Pharmazie

View full text Add to dashboard Cite

Methylenebisphosponic acid tetraethyl ester (1) was added to 2-azido-7a-e and 2-chloroquinoline-3-chalcones 10a-e in boiling sodium ethanolate solution to give, via Michael addition, tetrazolo[1,5-a]quinoline-8a-d, 13a and 2-chloroquinoline-based bisphosphonates 11a-d, 14a in E-configuration. Further acid hydrolysis afforded the respective BP-acid analogues E-9a-d, 12a-d, 13b, and 14b in excellent yields. Anti-tumor activity screening for the new BP-acids at a dose of 10 µM utilizing 44 different human tumor cell lines representing breast, ovary, prostate, lung, and CNS cancer as well as leukemia and melanoma was carried out. Eight of ten tested compounds exhibited remarkable anti-tumor activity against breast and prostate cancer, and a promising anti-tumor sensitivity toward ovarian cancer and melanoma. Conversely, there was only scattered activity against leukemia and no noticeable action of these BP-acids on CNS or lung cancer. Based on the prediction results (PASS program), anti-inflammatory activity of the new acids was also determined in vivo, by the acute carrageenin induced paw edema in rats. Many of these compounds showed anti-inflammatory properties at a dose of 50 mg/kg body weight.

show abstract

Section: Resultsmentioning

confidence: 80%

Elaborating on Efficient Anti‐Proliferation Agents of Cancer Cells and Anti‐Inflammatory‐Based N‐Bisphosphonic Acids

Abdou

Khidre

Kamel

2011

Archiv der Pharmazie

View full text Add to dashboard Cite

show abstract

“…α,β‐Unsaturated carbonyl derivatives 16a , b and 17a , b were synthesized via condensation of 8 with the appropriate aryl or heteroaryl ketone. Hydrazone 18 was prepared by the reported method from 8 . It was then reacted with the appropriate iso(thio)‐cyanate to yield 19a – f , respectively (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…To a solution of compound 18 (2.12 g, 0.01 mol) in tetrahydrofuran (THF) (50 ml), the appropriate iso(thio)cyanate (0.012 mol) was added. The mixture was allowed to stir overnight.…”

Section: Methodsmentioning

confidence: 99%

Design, synthesis, and docking study of new quinoline derivatives as antitumor agents

Nasr

Mostafa

El‐Sayed

et al. 2019

Archiv der Pharmazie

View full text Add to dashboard Cite

New quinolines substituted with various heterocycles and chalcone moieties were synthesized and evaluated as antitumor agents. All the synthesized compounds were in vitro screened against 60 human cancer cell lines. Compound 13 showed the highest cytotoxicity toward 58 cell lines, exhibiting distinct growth inhibition values (GI 50 ) against the majority of them, including SR, HL-60 (TB) strains (leukemia), and MDA-MB-435 strains (melanoma), with GI 50 values of 0.232, 0.260, and 0.300 µM, respectively. It exhibited great selectivity toward cancer cell lines, with less toxic effect against normal cells represented by skin fibroblast (BJ) and breast epithelial cell lines (MCF-10F). The enzyme inhibitory activity of compound 13 was evaluated against topoisomerase 1 (Topo 1), epidermal growth factor receptor and vascular endothelial growth factor receptor 2, where it displayed worthy Topo 1 inhibition activity with an IC 50 value of 0.278 µM compared with camptothecin as a reference drug (IC 50 0.224 µM). Docking studies were performed to investigate the recognition profile of compound 13 with the Topo 1 enzyme binding site. K E Y W O R D S antitumor activity, chalcones, docking, EGFR, quinolone, Topo 1, VEGFR2

show abstract

ChemInform Abstract: Preparation and Reactions of 2‐Azidoquinoline‐3‐carboxaldehyde (II) with Primary Amines and Active Methylene Compounds.

Ibrahim¹,

Yosef²,

Mahran³

2009

ChemInform

View full text Add to dashboard Cite

show abstract

Preparation and Reactions of 2-azidoquinoline-3-carboxaldehyde with Primary Amines and Active Methylene Compounds

Cited by 7 publications

References 21 publications

Elaborating on Efficient Anti‐Proliferation Agents of Cancer Cells and Anti‐Inflammatory‐Based N‐Bisphosphonic Acids

Elaborating on Efficient Anti‐Proliferation Agents of Cancer Cells and Anti‐Inflammatory‐Based N‐Bisphosphonic Acids

Design, synthesis, and docking study of new quinoline derivatives as antitumor agents

ChemInform Abstract: Preparation and Reactions of 2‐Azidoquinoline‐3‐carboxaldehyde (II) with Primary Amines and Active Methylene Compounds.

Contact Info

Product

Resources

About