29173-65-7

Usage

Uses

Used in Pharmaceutical Industry:
4-(Chloromethyl)phenyl isocyanate is used as a key intermediate in the synthesis of carbamate derivatives of Hoechst 33258, which are potential anticancer agents. Its role in the development of these compounds highlights its importance in the fight against cancer.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4-(Chloromethyl)phenyl isocyanate is used as a valuable building block for the creation of various complex organic molecules. Its unique structure and reactivity make it a versatile component in the synthesis of different compounds, contributing to the advancement of chemical research and development.

InChI:InChI=1/C8H6ClNO/c9-5-7-1-3-8(4-2-7)10-6-11/h1-4H,5H2

Upstream product

• 622-58-2 p-Tolylisocyanate 
• 1260104-72-0 C₈H₆ClN₃O 
• 1642-81-5 p-(chloromethyl)benzoic acid 

Downstream Products

• 778643-67-7 C₂₇H₂₃N₂O₄⁽¹⁺⁾ 
• 88465-69-4 C₉H₁₁ClN₂O 
• 221531-96-0 (4-chloromethylphenyl)-carbamic acid 2-trimethylsilanyl-ethyl ester 
• 1373331-85-1 1-(4-(chloromethyl)phenyl)-3-(prop-2-yn-1-yl)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.