Benzoylphenylurea

Benzoylphenylurea
Names
	IUPAC name N-carbamoyl-N-phenylbenzamide
	Other names N-(aminocarbonyl)-N-phenylbenzamide
Identifiers
CAS Number	1195179-46-4 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL4650348;
ChemSpider	14672653;
PubChem CID	19851629;
UNII	M10I9SO6RR;
	InChI InChI=1S/C14H12N2O2/c15-14(18)16(12-9-5-2-6-10-12)13(17)11-7-3-1-4-8-11/h1-10H,(H2,15,18) Key: XYFMGGWVGACNEC-UHFFFAOYSA-N;
	SMILES C1=CC=C(C=C1)C(=O)N(C2=CC=CC=C2)C(=O)N;
Properties
Chemical formula	C14H12N2O2
Molar mass	240.262 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Benzoylphenylurea (BPU) is a class of chemical compounds known for its insecticidal properties and applications in cancer treatment.

Insecticidal use

Benzoylphenylurea was first identified in the 1970s as an effective inhibitor of chitin biosynthesis in insects. These compounds disrupt molting and development, making them useful as insect growth regulators. BPUs such as lufenuron and diflubenzuron are commonly used for pest control due to their selectivity and low toxicity to vertebrates.^[1]

Antitumor activity

BPUs have also demonstrated antitumor activity. Studies have shown that BPU analogues can inhibit tubulin polymerization, thereby disrupting cell division in cancer cells. These compounds, especially sulfur analogues, have exhibited significant potency against various cancer cell lines, including pancreatic and prostate cancers.^[2]

Mechanism of action

In insects, BPUs inhibit chitin synthesis by targeting chitin synthase, preventing proper exoskeleton formation. In cancer treatment, BPU analogues interfere with microtubule formation, disrupting the proliferation of cancer cells.^[3]

References

^ Chen, Li (2007). "Insecticidal Benzoylphenylurea-S-Carbamate: A New Propesticide with Two Effects of Both Benzoylphenylureas and Carbamates". Journal of Agricultural and Food Chemistry. 55 (7): 2659–2663. doi:10.1021/jf063564g. PMID 17348679.
^ Hallur, Gurulingappa (2006). "Benzoylphenylurea Sulfur Analogues with Potent Antitumor Activity". Journal of Medicinal Chemistry. 49 (7): 2357–2360. doi:10.1021/jm051261s. PMID 16570932.
^ Gangishetti, Umesh (2009). "Effects of Benzoylphenylurea on Chitin Synthesis and Orientation in the Cuticle of the Drosophila Larva". European Journal of Cell Biology. 88 (2): 167–180. doi:10.1016/j.ejcb.2008.09.002. PMID 18996617.

[chen2007-1] Chen, Li (2007). "Insecticidal Benzoylphenylurea-S-Carbamate: A New Propesticide with Two Effects of Both Benzoylphenylureas and Carbamates". Journal of Agricultural and Food Chemistry. 55 (7): 2659–2663. doi:10.1021/jf063564g. PMID 17348679.

[hallur2006-2] Hallur, Gurulingappa (2006). "Benzoylphenylurea Sulfur Analogues with Potent Antitumor Activity". Journal of Medicinal Chemistry. 49 (7): 2357–2360. doi:10.1021/jm051261s. PMID 16570932.

[gangishetti2009-3] Gangishetti, Umesh (2009). "Effects of Benzoylphenylurea on Chitin Synthesis and Orientation in the Cuticle of the Drosophila Larva". European Journal of Cell Biology. 88 (2): 167–180. doi:10.1016/j.ejcb.2008.09.002. PMID 18996617.

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