178445-81-3

Basic information

• Product Name: (E)-1-(3-hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• Synonyms: (E)-1-(3-hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS NO: 178445-81-3
• Molecular Weight: 314.338
• Mol File: 178445-81-3.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (E)-1-(3-hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-(3-hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one(178445-81-3)
• EPA Substance Registry System: (E)-1-(3-hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one(178445-81-3)

Safety Data

• Hazardous Substances Data: 178445-81-3(Hazardous Substances Data)

Upstream product

• 121-71-1 3-Hydroxyacetophenone 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 178445-80-2 (E)-1-(3,4-dimethoxyphenyl)-3-(3-hydroxyphenyl)prop-2-en-1-one 

Downstream Products

• 178445-84-6 1-(3-hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)-1-propanone 
• 110049-40-6 1-(3-methoxy-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propan-1-one 
• 902120-07-4 C₂₅H₃₈O₇SSi 
• 902120-02-9 (R)-(+)-3-[1-hydroxy-3-(3,4,5-trimethoxyphenyl)propyl]phenol 
• 902119-94-2 (R)-(+)-1-[3-(tert-butyldimethylsilyloxy)phenyl]-3-(3,4,5-trimethoxyphenyl)propan-1-ol 
• 902119-93-1 1-[3-(tert-butyldimethylsilyloxy)phenyl]-3-(3,4,5-trimethoxyphenyl)propan-1-one 
• 902120-08-5 C₂₄H₃₇NO₄Si 
• 902119-95-3 (S)-(-)-1-azido-[3-(tert-butyldimetylsilyloxy)phenyl]-3-(3,4,5-trimethoxyphenyl)propane 
• 875018-27-2 (S)-(-)-N-[1-[3-(tert-butyldimethylsilyloxy)phenyl]-3-(3,4,5-trimethoxyphenyl)propyl]acetamide 
• 178446-58-7 (1R)-1-[3-[2-(1,1-dimethylethoxy)-2-oxoethoxy]phenyl]-3-(3,4,5-trimethoxyphenyl)-1-propanyl (2S)-1-(3,3-dimethyl-1,2-dioxopentyl)-2-piperidinecarboxylate 
• 178446-03-2 (S)-1-(3,3-Dimethyl-2-oxo-pentanoyl)-piperidine-2-carboxylic acid (R)-1-(3-carboxymethoxy-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propyl ester 
• 178445-90-4 tert-butyl (R)-2-(3-(1-hydroxy-3-(3,4,5-trimethoxyphenyl)propyl)phenoxy)acetate 
• 178445-87-9 tert-butyl 2-(3-(3-(3,4,5-trimethoxyphenyl)propanoyl)phenoxy)acetate 

Relevant articles and documents

RAPAFUCIN DERIVATIVE COMPOUNDS AND METHODS OF USE THEREOF

The present disclosure provides macrocyclic compounds inspired by the immunophilin ligand family of natural products FK506 and rapamycin. The generation of a Rapafucin library of macrocyles that contain FK506 and rapamycin binding domains should have grea

Discovery of novel human inosine 5′-monophosphate dehydrogenase 2 (hIMPDH2) inhibitors as potential anticancer agents

The enzyme inosine 5′-monophosphate dehydrogenase (IMPDH) catalyzes an essential step in the de novo biosynthesis of guanine nucleotides, and thus regulates the guanine nucleotide pool required for cell proliferation. Of the two isoforms, human IMPDH type 2 (hIMPDH2) is a validated molecular target for potential immunosuppressive, antiviral and anticancer chemotherapy. In search of newer hIMPDH2 inhibitors as potential anticancer agents, three novel series (A: 5-aminoisobenzofuran-1(3H)-one, B: 3,4-dimethoxyaniline and C: benzo[d]-[1,3]dioxol-5-ylmethanamine) were synthesized and evaluated for in vitro and cell-based activities. A total of 37 molecules (29–65) were screened for their in vitro hIMPDH2 inhibition, with particular emphasis on establishing their structure–activity relationship (SAR) trends. Eight compounds (hits, 30, 31, 33–35, 37, 41 and 43) demonstrated significant enzyme inhibition (>70% @ 10 μM); especially the A series molecules were more potent than B series (50 values for the hits ranged from 0.36 to 7.38 μM. The hits displaying >80% hIMPDH2 inhibition (30, 33, 35, 41 and 43) were further assessed for their cytotoxic activity against cancer cell lines such as MDA-MB-231 (breast adenocarcinoma), DU145 (prostate carcinoma), U87 MG (glioblastoma astrocytoma) and a normal cell line, NIH-3T3 (mouse embryonic fibroblast) using MTT assay. Most of the compounds exhibited higher cellular potency against cancer cell lines and notably lower toxicity towards NIH-3T3 cells compared to mycophenolic acid (MPA), a prototypical hIMPDH2 inhibitor. Two of the series A hits (30 and 35) were evaluated in human peripheral blood mononuclear cells (hPBMC) assay and found to be better tolerated than MPA. The calculated/predicted molecular and physicochemical properties were satisfactory with reference to drug-likeness. The molecular docking studies clearly demonstrated crucial interactions of the hits with the cofactor-binding site of hIMPDH2, further providing critical information for refining the design strategy. The present study reports the design and discovery of structurally novel hIMPDH2 inhibitors as potential anticancer agents and provides a guide for further research on the development of safe and effective anticancer agents, especially against glioblastoma.

Synthetic multimerizing agents

New compounds are disclosed for multimerizing immunophilins and proteins containing immunophilin or immunophilin-related domains. The compounds are of the formulaM-L-Qwhere M is a synthetic ligand for an FKBP protein