322399-95-1

Basic information

• Product Name: 4-butyl-1,3,5-tris(4-methoxyphenyl)-1H-pyrazole
• Synonyms: 4-butyl-1,3,5-tris(4-methoxyphenyl)-1H-pyrazole
• CAS NO: 322399-95-1
• Molecular Weight: 442.558
• Mol File: 322399-95-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-butyl-1,3,5-tris(4-methoxyphenyl)-1H-pyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-butyl-1,3,5-tris(4-methoxyphenyl)-1H-pyrazole(322399-95-1)
• EPA Substance Registry System: 4-butyl-1,3,5-tris(4-methoxyphenyl)-1H-pyrazole(322399-95-1)

Safety Data

• Hazardous Substances Data: 322399-95-1(Hazardous Substances Data)

Upstream product

• 142-62-1 hexanoic acid 
• 100-66-3 methoxybenzene 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 322399-91-7 2-n-butyl-1,3-bis(4-methoxyphenyl)propane-1,3-dione 
• 100-09-4 4-methoxybenzoic acid 
• 7464-46-2 p-nitrophenyl p-methoxybenzoate 
• 6397-82-6 4'-methoxyhexanophenone 

Relevant articles and documents

Pyrazole ligands: Structure - Affinity/activity relationships and estrogen receptor-α-selective agonists

We have found that certain tetrasubstituted pyrazoles are high-affinity ligands for the estrogen receptor (ER) (Fink et al. Chem. Biol. 1999, 6, 205-219) and that one pyrazole is considerably more potent as an agonist on the ERα than on the ERβ subtype (Sun et al. Endocrinology 1999, 140, 800-804). To investigate what substituent pattern provides optimal ER binding affinity and the greatest enhancement of potency as an ERα-selective agonist, we prepared a number of tetrasubstituted pyrazole analogues with defined variations at certain substituent positions. Analysis of their binding affinity pattern shows that a C(4)-propyl substituent is optimal and that a p-hydroxyl group on the N(1)-phenyl group also enhances affinity and selectivity for ERα. The best compound in this series, a propylpyrazole triol (PPT, compound 4g), binds to ERα with high affinity (ca. 50% that of estradiol), and it has a 410-fold binding affinity preference for ERα. It also activates gene transcription only through ERα. Thus, this compound represents the first ERα-specific agonist. We investigated the molecular basis for the exceptional ERα binding affinity and potency selectivity of pyrazole 4g by a further study of structure-affinity relationships in this series and by molecular modeling. These investigations suggest that the pyrazole triols prefer to bind to ERα with their C(3)-phenol in the estradiol A-ring binding pocket and that binding selectivity results from differences in the interaction of the pyrazole core and C(4)-propyl group with portions of the receptor where ERα has a smaller residue than ERβ. These ER subtype-specific interactions and the ER subtype-selective ligands that can be derived from them should prove useful in defining those biological activities in estrogen target cells that can be selectively activated through ERα.