1692-41-7

Basic information

• Product Name: 1-(3-(2-hydroxyphenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)ethanone
• Synonyms: 1-(3-(2-hydroxyphenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)ethanone
• CAS NO: 1692-41-7
• Molecular Weight: 280.326
• Mol File: 1692-41-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1-(3-(2-hydroxyphenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-(2-hydroxyphenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)ethanone(1692-41-7)
• EPA Substance Registry System: 1-(3-(2-hydroxyphenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)ethanone(1692-41-7)

Safety Data

• Hazardous Substances Data: 1692-41-7(Hazardous Substances Data)

Upstream product

• 888-12-0 (E)-2'-hydroxy-chalcone 
• 64-19-7 acetic acid 
• 4702-96-9 3-(2-hydroxyphenyl)-5-phenyl-4,5-dihydro-1H-pyrazole 
• 100-52-7 benzaldehyde 
• 118-93-4 o-hydroxyacetophenone 
• 108-24-7 acetic anhydride 
• 1214-47-7 1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one 
• 98499-05-9 2'-hydroxychalcone hydrazone 

Downstream Products

• 2726-54-7 3-(2-acetoxy-phenyl)-1-acetyl-5-phenyl-4,5-dihydro-1H-pyrazole 

Relevant articles and documents

Anti-inflammatory, analgesic and antipyretic N-acetyl-Δ2-pyrazolines and dihydrothienocoumarines

1-Acetyl-3-(2-hydroxyphenyl)-5-(R,R′-aryl)-4,5-dihydro-(1H)pyrazoles (2a-o) were synthesized and showed anti-inflammatory and analgesic activity. The substituents on the 5-aryl group were necessary for biological activity. R-R′-aryl-2-dihydro-1,2(4H)thieno(2,3-c)benzo(e)pyranone-4 derivatives (3a-f) also showed analgesic and anti-inflammatory activity. The position and the number of the substituents caused a modulation of analgesic or anti-inflammatory activity of the N-acetyl-Δ2-pyrazoline2 and dihydrothienocoumarines 3. All compounds showed low antipyretic activity.

Design, Synthesis, and Biological Evaluation of Pyrazoline-Based Hydroxamic Acid Derivatives as Aminopeptidase N (APN) Inhibitors

Aminopeptidase N (APN) has been recognized as a target for anticancer treatment due to its overexpression on diverse malignant tumor cells and association with cancer invasion, metastasis and angiogenesis. Herein we describe the synthesis, biological evaluation, and structure–activity relationship study of two new series of pyrazoline analogues as APN inhibitors. Among these compounds, 5-(2-(2-(hydroxyamino)-2-oxoethoxy)phenyl)-3-phenyl-4,5-dihydro-1H-pyrazole-1-carboxamide (compound 13 e) showed the best APN inhibition with an IC50 value of 0.16±0.02 μm, which is more than one order of magnitude lower than that of bestatin (IC50=9.4±0.5 μm). Moreover, compound 13 e was found to inhibit the proliferation of diverse carcinoma cells and to show potent anti-angiogenesis activity. At the same concentration, compound 13 e presents significantly higher anti-angiogenesis activity than bestatin in human umbilical vein endothelial cells (HUVECs) capillary tube formation assays. The putative binding mode of 13 e in the active site of APN is also discussed.

Synthesis of Isomeric Δ2-Pyrazolines

2'-Hydroxychalkones (I) react with hydrazine hydrate in ethanol to give 5-aryl-3-(2-hydroxyphenyl)-Δ2-pyrazolines (II) while in acetic acid the corresponding 5-aryl-1-acetyl-3-(2-hydroxyphenyl)-Δ2-pyrazolines (III) are obtained contr