SML2290
ANI-7
≥98% (HPLC)
Synonym(s):
(αZ)-3,4-Dichloro-α-(1H-pyrrol-2-ylmethylene)benzeneacetonitrile, (Z)-2-(3,4-dichlorophenyl)-3-(1H-pyrrol-2-yl)acrylonitrile
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About This Item
Empirical Formula (Hill Notation):
C13H8Cl2N2
CAS Number:
Molecular Weight:
263.12
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
powder
InChI
1S/C13H8Cl2N2/c14-12-4-3-9(7-13(12)15)10(8-16)6-11-2-1-5-17-11/h1-7,17H/b10-6+
InChI key
IJJHHDLGGYDXGD-UXBLZVDNSA-N
SMILES string
ClC1=CC(/C(C#N)=C/C2=CC=CN2)=CC=C1Cl
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 2 mg/mL, clear
storage temp.
2-8°C
Biochem/physiol Actions
ANI-7 is a potent and selective activator of the aryl hydrocarbon receptor (AHR) pathway that exhibit potent cytotoxic activity against multiple cancer cell lines while spearing normal breast cells (MCF-10A). Apparently activation of AHR by ANI-7 leads to induction of CYP1 metabolising monooxygenases. ANI-7 metabolites induce DNA damage, checkpoint activation, S-phase cell cycle arrest and cell death in sensitive breast cancer cell lines.
potent and selective activator of the aryl hydrocarbon receptor (AHR) pathway that exhibit potent cytotoxic activity against multiple cancer cell lines
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Jayne Gilbert et al.
Molecular pharmacology, 93(2), 168-177 (2017-12-23)
We have previously reported the synthesis and breast cancer selectivity of (Z)-2-(3,4-dichlorophenyl)-3-(1H-pyrrol-2-yl)acrylonitrile (ANI-7) in cancer cell lines. To further evaluate the selectivity of ANI-7, we have expanded upon the initial cell line panel to now include the breast cancer cell
Abdelselam Ali et al.
Bioorganic & medicinal chemistry letters, 17(4), 993-997 (2006-12-08)
A series of 2-phenyl-3-(1H-pyrrol-2-yl)acrylonitrile derivatives were synthesized and evaluated for in vitro activity against the endoparasite Haemonchus contortus and the ectoparasite Ctenocephalides felis. Some compounds had significant in vitro activity against these parasites.
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