58721-63-4

Basic information

• Product Name: 2-[5-(4-methoxy-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-phenol
• Synonyms: 2-[5-(4-methoxy-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-phenol
• CAS NO: 58721-63-4
• Molecular Weight: 268.315
• Mol File: 58721-63-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-[5-(4-methoxy-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[5-(4-methoxy-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-phenol(58721-63-4)
• EPA Substance Registry System: 2-[5-(4-methoxy-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-phenol(58721-63-4)

Safety Data

• Hazardous Substances Data: 58721-63-4(Hazardous Substances Data)

Upstream product

• 90-02-8 salicylaldehyde 
• 58721-41-8 2-hydroxy-4'-methoxychalcone 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 3327-24-0 1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one 

Downstream Products

• 1621417-93-3 5-[5-(2-hydroxyphenyl)-3-(4-methoxyphenyl)-4,5-dihydropyrazol-1-ylmethylene]-3-(3-acetoxyphenyl)-2-thioxothiazolidin-4-one 
• 107095-44-3 Acetic acid 2-[5-(4-methoxy-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-phenyl ester 
• 58721-54-3 2-(4-methoxy-phenyl)-5,5-dimethyl-1,10b-dihydro-benzo[e]pyrazolo[1,5-c][1,3]oxazine 

Relevant articles and documents

Novel isoniazid-spirooxindole derivatives: design, synthesis, biological evaluation, in silico ADMET prediction and computational studies

In the present scenario, the Synthesis of new and desired antimycobacterial agent has an eternal demand to resist Mycobacterium tuberculosis (MTB). The design and identification of new molecules for the treatment of tuberculosis is an important task in organic as well as medicinal chemistry research. In the present study, we have reported the combination of the desired compound using two versatile and significant moieties, isoniazid and spirooxindole derivatives. A series of novel isoniazid-spirooxindole hybrid molecules (6a-6ao) were designed, synthesized, and well-characterized by various spectroscopic methods. We have evaluated for their in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB) strain and MDR-TB. Among them, Compound 6ab was found to be the most effective compare to other compounds. ADMET-related descriptors were to be calculated of all the compounds to predict the pharmacokinetic properties for the selection of the effective and bioavailable compounds. In addition, molecular docking and molecular dynamics studies reveal that the binding modes of all the compounds in the active site of isoniazid-resistant enoyl-ACP(COA) reductase, which helped to establish a structural basis of inhibition of Mycobacterium tuberculosis.

Design and synthesis of novel 2-pyrazoline-1-ethanone derivatives as selective MAO inhibitors

Thirty seven novel 2-pyrazoline-1-ethanone derivatives were designed, synthesized and evaluated as selective hMAO inhibitors. Among them, compounds 7h (IC50 = 2.40 μM) and 12c (IC50 = 2.00 μM) exhibited best inhibitory activity and selectivity against hMAO-A, surpassing that of the positive control Clorgyline (IC50 = 2.76 μM). Based on selective activity of hMAO-A, SAR analysis showed that the order of N1 substituent contribution was bromo (3) > piperidinyl (4) > morpholinyl (5) > imidazolyl (6), and compounds with electron-withdrawing substituents (-F, -Cl) at C3 or C5 phenyl ring of 2-pyrazoline nucleus dedicated stronger MAO-A inhibitory activity. Molecular docking showed that compounds 7h and 12c were nicely bound to hMAO-A via two hydrogen bonds (SER209, GLU216), one Pi-Pi interaction and three hydrogen bonds (SER209, GLU216, TYR69), one Sigma-Pi interaction, respectively. In addition, the substituent at C3 position of 2-pyrazoline with the N1 acetyl has little effect on MAO-A inhibitory activity. These data support further studies to assess rational design of more efficiently selective hMAO inhibitors in the future.