1392440-42-4

Basic information

• Product Name: N₁,N₃-bis(4-fluorobenzyl)-2-methoxyisophthalamide
• Synonyms: N₁,N₃-bis(4-fluorobenzyl)-2-methoxyisophthalamide
• CAS NO: 1392440-42-4
• Molecular Weight: 410.42
• Mol File: 1392440-42-4.mol

Chemical Properties

• CAS DataBase Reference: N₁,N₃-bis(4-fluorobenzyl)-2-methoxyisophthalamide(CAS DataBase Reference)
• NIST Chemistry Reference: N₁,N₃-bis(4-fluorobenzyl)-2-methoxyisophthalamide(1392440-42-4)
• EPA Substance Registry System: N₁,N₃-bis(4-fluorobenzyl)-2-methoxyisophthalamide(1392440-42-4)

Safety Data

• Hazardous Substances Data: 1392440-42-4(Hazardous Substances Data)

Upstream product

• 1951-38-8 2-methoxyisophthalic acid 
• 140-75-0 para-fluorobenzylamine 

Downstream Products

• 1392440-10-6 N₁,N₃-bis(4-fluorobenzyl)-2-hydroxyisophthalamide 

Relevant articles and documents

Metal-chelating 2-hydroxyphenyl amide pharmacophore for inhibition of influenza virus endonuclease

The influenza virus PA endonuclease is an attractive target for development of novel anti-influenza virus therapeutics. Reported PA inhibitors chelate the divalent metal ion(s) in the enzyme's catalytic site, which is located in the N-terminal part of PA (PA-Nter). In this work, a series of 2-hydroxybenzamide- based compounds have been synthesized and biologically evaluated in order to identify the essential pharmacophoric motif, which could be involved in functional sequestration of the metal ions (probably Mg2+) in the catalytic site of PA. By using HL1, H2L2, and HL3 as model ligands with Mg2+ ions, we isolated and fully characterized a series of complexes and tested them for inhibitory activity toward PA-Nter endonuclease. H2L2 and the corresponding Mg2+ complex showed an interesting inhibition of the endonuclease activity. The crystal structures of the uncomplexed HL1 and H 2L2 and of the isolated magnesium complex [Mg(L 3)2(MeOH)2]·2MeOH were solved by X-ray diffraction analysis. Furthermore, the speciation models for HL1, H2L2, and HL3 with Mg2+ were obtained, and the formation constants of the complexes were measured. Preliminary docking calculations were conducted to investigate the interactions of the title compounds with essential amino acids in the PA-Nter active site. These findings supported the two-metal coordination of divalent ions by a donor triad atoms chemotype as a powerful strategy to develop more potent PA endonuclease inhibitors.

Metal-chelating properties and antiviral activity of some 2-hydroxyphenyl amides

Influenza virus is an hot topic in medicinal chemistry and great efforts are ongoing for the discover of new antivirals able to overcome problems related to resistant strains and adverse side effects of current drugs. Influenza virus endonuclease is an attractive target for antiviral drug development and in particular the strategy to chelate the metal ion(s) within the active site proved to be an efficient mode to inhibit enzymatic activity. Our previous findings revealed that 2-hydroxyamide derivatives are able to chelate Mg2+ ions, forming complexes with different stoichiometric ratios. Here we report on the activity of the three ligands N-(4-fluorobenzyl)-2-hydroxybenzamide, N-(4-fluorobenzyl)-2,3-dihydroxybenzamide, and N1,N3-bis(4-fluorobenzyl)-2-hydroxyisophthalamide, containing the salicylic group, and their Mg2+ complexes (7)–(9), evaluated by means of virus yield assay in influenza virus-infected MDCK cells and vRNP reconstitution assay in HEK293T cells. In some cases, promising anti-influenza activities with EC50 values in the low micromolar range were found. As a contribute to clarify the activity in cells of the ligands, here we also present a study on the their coordinating properties towards the other essential metal ion Cu(II), carried out by potentiometric and calorimetric measurements.

HIV INTEGRASE INHIBITORS

Provided herein, inter alia, are novel compounds for the inhibition of HIV integrase. The compounds disclosed herein are useful for methods of treating HIV infection in a subject in need thereof.