289038-87-5

Upstream product

• 31719-77-4 3-chloromethylbenzoic acid 

Downstream Products

• 1373331-92-0 1-(3-((4-methoxybenzylamino)methyl)phenyl)-3-(prop-2-yn-1-yl)urea 
• 1373331-84-0 1-(3-(chloromethyl)phenyl)-3-(prop-2-yn-1-yl)urea 
• 1373331-88-4 C₁₉H₁₈N₂O₄ 
• 1373331-89-5 1-(3-((benzylamino)methyl)phenyl)-3-(prop-2-yn-1-yl)urea 
• 1373331-90-8 1-(3-((4-methylbenzylamino)methyl)phenyl)-3-(prop-2-yn-1-yl)urea 
• 1373331-91-9 1-(3-((4-trifluoromethoxybenzylamino)methyl)phenyl)-3-(prop-2-yn-1-yl)urea 
• 117098-59-6 DPPA 
• 1432579-03-7 3-(4-((3-(3-chloromethylphenyl)ureido)methyl)-1H-1,2,3-triazol-1-yl)benzenesulfonamide 
• 1432579-02-6 4-(4-((3-(3-chloromethylphenyl)ureido)methyl)-1H-1,2,3-triazol-1-yl)benzenesulfonamide 
• 1432579-01-5 1-((1-(benzo[d]thiazol-6-yl)-1H-1,2,3-triazol-4-yl)methyl)-3-(3-chlormethylphenyl)urea 
• 1432579-00-4 1-((1-((2-oxo-1,2-dihydroquinolin-4-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)-3-(3-chloromethylphenyl)urea 
• 1432578-99-8 1-((1-(1-acetylindolin-6-yl)-1H-1,2,3-triazol-4-yl)methyl)-3-(3-chloromethylphenyl)urea 
• 1432578-98-7 1-((1-(2-(1,3-dioxoisoindolin-2-yl)ethyl)-1H-1,2,3-triazol-4-yl)methyl)-3-(3-chloromethylphenyl)urea 
• 1432578-97-6 3-((1-(4-morpholinosulfonylphenyl)-1H-1,2,3-triazol-4-yl)methyl)-1-(3-chloromethylphenyl)urea 

Relevant academic research and scientific papers

Synthesis and evaluation of 1-(substituted)-3-prop-2-ynylureas as antiangiogenic agents

Novel urea derivatives of alkynes have been designed, synthesized, and evaluated as potential cancer therapeutics leads. The most active 1-((3-chloromethyl)phenyl)-3-prop-2-ynylurea (1) exhibited cytotoxic effect against HELA and MCF-7 cell lines with IC50 values of 1.55 μM and 1.48 μM, respectively. Further investigation on tube formation assay in human vein umbilical cells (HUVEC) demonstrated that 1 and methyl 4-(3-(3-ethynylureido)benzyloxy) benzoate (6) possess antiangiogenic activity, with minimum effective dose of 25 nM (for 1) and 6.25 μM (for 6). The ED 50 of 1 and 6 were found to be 0.26 μM and 17.52 μM, respectively. The results from in vitro tyrosine kinase assay indicated the EGFR inhibition of 1 over other kinases (VEGFR2, FGFR1 and PDGFRβ). The cytotoxicity of 1 against EGFR overexpressing cell line A431 (IC50 36 nM) was comparable to that of erlotinib. The binding mode of 1 from docking simulation in the EGFR active site revealed that the urea motif formed hydrogen bonding with Lys745, Thr854 and Asp855 in hydrophobic pocket of EGFR. Compound 1 is considered as a potential lead for further optimization.

Novel VEGFR-2 kinase inhibitors identified by the back-to-front approach

We report a novel VEGFR-2 inhibitor, developed by the back-to-front approach. Docking experiments indicated that the 3-chloromethylphenylurea motif of the lead compound occupied the back pocket of VEGFR-2 kinase. An attempt was made to enhance the binding affinity of 1 by expanding the structure to access the front pocket using a triazole linker. A library of 1,4-(disubstituted)-1H-1, 2,3-triazoles were screened in silico, and one compound (VH02) was identified with an IC50 against VEGFR-2 of 0.56 μM. VH02 showed antiangiogenic effects, inhibiting tube formation in HUVEC cells (EA.hy926) at 0.3 μM, 13 times lower than its cytotoxic dose. These enzymatic and cellular activities suggest that VH02 has potential as a lead for further optimization.