62297-35-2

Basic information

• Product Name: (Z)-2-(4-nitrophenyl)-3-(p-tolyl)acrylonitrile
• Synonyms: (Z)-2-(4-nitrophenyl)-3-(p-tolyl)acrylonitrile
• CAS NO: 62297-35-2
• Molecular Weight: 264.283
• Mol File: 62297-35-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (Z)-2-(4-nitrophenyl)-3-(p-tolyl)acrylonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-2-(4-nitrophenyl)-3-(p-tolyl)acrylonitrile(62297-35-2)
• EPA Substance Registry System: (Z)-2-(4-nitrophenyl)-3-(p-tolyl)acrylonitrile(62297-35-2)

Safety Data

• Hazardous Substances Data: 62297-35-2(Hazardous Substances Data)

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 555-21-5 4-Nitrophenylacetonitrile 

Relevant articles and documents

Synthesis and evaluation of (Z)-2,3-diphenylacrylonitrile analogs as anti-cancer and anti-microbial agents

In the present study, a series of (Z)-2,3-diphenylacrylonitrile analogs were synthesized and then evaluated in terms of their cytotoxic activities against four human cancer cell lines, e.g. lung cancer (A549), ovarian cancer (SK-OV-3), skin cancer (SK-MEL-2), and colon cancer (HCT15), as well as anti-microbial activities against three microbes, e.g. Staphylococcus aureus, Salmonella typhi, and Aspergillus niger. The title compounds were synthesized by Knoevenagel condensation reaction of benzyl cyanide or p-nitrobenzyl cyanide with substituted benzaldehydes in good yields. Most of the compounds exhibited significant suppressive activities against the growth of all cancer cell lines. Compound 3c was most active in inhibiting the growth of A549, SK-OV-3, SK-MEL-2, and HCT15 cells lines with IC50 values of 0.57, 0.14, 0.65, and 0.34 mg/mL, respectively, followed by compounds 3f, 3i, and 3h. Compound 3c exhibited 2.4 times greater cytotoxic activity against HCT15 cells, whereas it showed similar potency against SK-OV-3 cells to that of the standard anti-cancer agent doxorubicin. Structure-activity relationship study revealed that electron-donating groups at the para-position of phenyl ring B were more favorable for improved cytotoxic activity, whereas the presence of electron-withdrawing groups was unfavorable compare to unsubstituted acrylonitrile. An optimal electron density on phenyl ring A of (Z)-2,3-diphenylacrylonitrile analogs was crucial for their cytotoxic activities against human cancer cell lines used in the present study. Qualitative structure-cytotoxic activity relationships were studied using physicochemical parameters; a good correlation between calculated polar surface area (PSA), a lipophobic parameter, and cytotoxic activity was found. Moreover, all compounds showed significant anti-bacterial activities against S. typhi, whereas compound 3k showed potent inhibition against both S. aureus and S. typhi bacterial strains.