64657-47-2

Basic information

• Product Name: 3-Buten-2-one, 4-(5-chloro-2-hydroxyphenyl)-, (E)-
• CAS NO: 64657-47-2
• Molecular Formula: C10H9ClO2
• Molecular Weight: 196.633
• Mol File: 64657-47-2.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 3-Buten-2-one, 4-(5-chloro-2-hydroxyphenyl)-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Buten-2-one, 4-(5-chloro-2-hydroxyphenyl)-, (E)-(64657-47-2)
• EPA Substance Registry System: 3-Buten-2-one, 4-(5-chloro-2-hydroxyphenyl)-, (E)-(64657-47-2)

Safety Data

• Hazardous Substances Data: 64657-47-2(Hazardous Substances Data)

Upstream product

• 67-64-1 acetone 
• 635-93-8 5-chlorosalicyclaldehyde 
• 106-48-9 4-chloro-phenol 

Downstream Products

• 1383253-13-1 (Z)-4-chloro-2-[(3-methyl)-3-pentenyl]phenol 
• 1383253-05-1 (E)-4-chloro-2-[(3-methyl)-3-pentenyl]phenol 
• 1421330-77-9 C₁₀H₁₁ClN₂O 
• 1421330-84-8 C₁₂H₁₂BrClN₂O₂ 
• 119607-55-5 (1E,4E)-1-(5-Chloro-2-hydroxy-phenyl)-5-(4-methoxy-phenyl)-penta-1,4-dien-3-one 
• 119607-66-8 (1E,4E)-1-(5-Chloro-2-hydroxy-phenyl)-5-(9-ethyl-9H-carbazol-3-yl)-penta-1,4-dien-3-one 
• 119607-59-9 (1E,4E,6E)-1-(5-Chloro-2-hydroxy-phenyl)-7-(4-methoxy-phenyl)-hepta-1,4,6-trien-3-one 
• 123302-61-4 4-Chloro-2-((E)-2-[1,8]naphthyridin-2-yl-vinyl)-phenol 

Relevant articles and documents

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.

Design, synthesis and biological evaluation of tricyclic pyrazolo[1,5-c][1,3]benzoxazin-5(5H)-one scaffolds as selective BuChE inhibitors

Based on the structural analysis of tricyclic scaffolds as butyrylcholinesterase (BuChE) inhibitors, a series of pyrazolo[1,5-c][1,3]benzoxazin-5(5H)-one derivatives were designed, synthesized and evaluated for their acetylcholinesterase (AChE) and BuChE inhibitory activity. Compounds with 5-carbonyl and 7- or/and 9-halogen substitutions showed potential BuChE inhibitory activity, among which compounds 6a, 6c and 6g showed the best BuChE inhibition (IC50 = 1.06, 1.63 and 1.63 μM, respectively). The structure–activity relationship showed that the 5-carbonyl and halogen substituents significantly influenced BuChE activity. Compounds 6a and 6g were found nontoxic, lipophilic and exhibited remarkable neuroprotective activity and mixed-type inhibition against BuChE (Ki = 7.46 and 3.09 μM, respectively). Docking studies revealed that compound 6a can be accommodated into BuChE via five hydrogen bonds, one Pi–Sigma interaction and three Pi–Alkyl interactions.

Design and synthesis of novel 2-methyl-4,5-substitutedbenzo[f]-3,3a,4,5- tetrahydro-pyrazolo[1,5-d][1,4]oxazepin-8(7H)-one derivatives as telomerase inhibitors

Eight novel 4,5-tetrahydropyrazolo[1,5-d][1,4]oxazepine derivatives have been synthesized and purified to be screened for anticancer activity. By a modified TRAP assay, some titled compounds were tested against telomerase, and compound 4a showed the most potent inhibitory activity with IC50 value at 0.78 ± 0.22 μM. Western blot assays showed that compounds 4a and 4b could inhibit expression of Cyclin D1, TERT, phospho-AKT and PI3K/AKT pathway.