Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C20H15N3O2 |
| Molecular Weight | 329.352 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O=C1NC(=O)C2=CC(NC3=CC=CC=C3)=C(NC4=CC=CC=C4)C=C12
InChI
InChIKey=AAALVYBICLMAMA-UHFFFAOYSA-N
InChI=1S/C20H15N3O2/c24-19-15-11-17(21-13-7-3-1-4-8-13)18(12-16(15)20(25)23-19)22-14-9-5-2-6-10-14/h1-12,21-22H,(H,23,24,25)
| Molecular Formula | C20H15N3O2 |
| Molecular Weight | 329.352 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
4,5-Dianilinophthalimide (DAPH-1) is an inhibitor of human Epithelial growth factor (IC50 0.3 microM). It was originally developed by scientists at CIBA-Geigy Limited as a potential anti tumor compound, although certain early in vivo studies have been retracted. DAPH-1 was found to be rapidly metabolized in the liver, however, a fluorinated analog (DAPH-2) was more stable in vivo. More recently DAPH-1 has found interest as an anti-amyloid compound. DAPH-1 shows specific efficacy against the yeast prion and may be a useful model for the development of other anti prion compounds.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P00533|||Q9GZX1 Gene ID: 1956.0 Gene Symbol: EGFR Target Organism: Homo sapiens (Human) |
0.3 µM [IC50] | ||
Target ID: P05453 Gene ID: 851752.0 Gene Symbol: SUP35 Target Organism: Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast) |
0.58 µM [IC50] | ||
Target ID: P05771|||Q9UE50 Gene ID: 5579.0 Gene Symbol: PRKCB Target Organism: Homo sapiens (Human) |
4.8 µM [IC50] | ||
Target ID: P17252 Gene ID: 5578.0 Gene Symbol: PRKCA Target Organism: Homo sapiens (Human) |
6.0 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Potent inhibitors of amyloid β fibrillization, 4,5-dianilinophthalimide and staurosporine aglycone, enhance degradation of preformed aggregates of mutant Notch3. | 2010-11-05 |
|
| Direct and selective elimination of specific prions and amyloids by 4,5-dianilinophthalimide and analogs. | 2008-05-20 |
|
| Retractions. | 1998-09-29 |
|
| 4-(Phenylamino)pyrrolopyrimidines: potent and selective, ATP site directed inhibitors of the EGF-receptor protein tyrosine kinase. | 1996-06-07 |
|
| 4,5-bis(4-fluoroanilino)phthalimide: A selective inhibitor of the epidermal growth factor receptor signal transduction pathway with potent in vivo antitumor activity. | 1995-08 |
|
| Dianilinophthalimides: potent and selective, ATP-competitive inhibitors of the EGF-receptor protein tyrosine kinase. | 1994-04-01 |
Patents
Sample Use Guides
Female nude mice were transfected in the left flank with human A431 epithelial carcinoma, v-sis transfected BALB/c 3T3 cells, or T24 bladder carcinoma cells. DAPH-1 was administered as a single oral dose of 100 mg/kg, unfortunately, DAPH-1 is readily metabolized by the liver and no physiological effect could be observed. Anti tumor activity was observed using fluorinated analog DAPH-2, which is not rapidly metabolized.
Route of Administration:
Oral
Prion expressing yeast cells ([PSI+] delta-PDR5) were treated with 0 - 100 microM DAPH-1 while growing in the mid-log phase. Cells were incubated in the treatment condition for 24 hours in liquid culture. The fraction of prion +/- cells was determined by plating on YPD media and by fluorescence microscopy. DAPH-1 demonstrated a dose dependent ability to cure prion positive yeast cells, which was 5 fold more effective than 1% DMSO.
| Substance Class |
Chemical
Created
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admin
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Edited
Mon Mar 31 22:17:51 GMT 2025
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on
Mon Mar 31 22:17:51 GMT 2025
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| Record UNII |
Z13D008FZ2
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| Record Status |
Validated (UNII)
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