235106-62-4

Basic information

• Product Name: 2,2''-[(4-HYDROXYFENYL)METHYLEEN]BIS(4-{(E)-[(5-METHYL-1H-TETRAZOOL1-YL)IMINO]METHYL}FENOL)
• Synonyms: 2,2''-[(4-HYDROXYFENYL)METHYLEEN]BIS(4-{(E)-[(5-METHYL-1H-TETRAZOOL1-YL)IMINO]METHYL}FENOL);VP 14637;2,2'-[(4-Hydroxyphenyl)Methylene]bis[4-[[(5-Methyl-1H-tetrazol-1-yl)iMino]Methyl]phenol;(E)-2,2'-((4-Hydroxyphenyl)methylene)bis(4-((E)-(5-methyl-1H-tetrazol-1-ylimino)methyl)phenol)
• CAS NO: 235106-62-4
• Molecular Formula: C25H22N10O3
• Molecular Weight: 510.50738
• Product Categories: Aromatics;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 235106-62-4.mol

Chemical Properties

• Boiling Point: 816.7±75.0 °C(Predicted)
• Appearance: /
• Density: 1.49±0.1 g/cm3(Predicted)
• Storage Temp.: Amber Vial, Refrigerator
• Solubility: Aqueous Base (Slightly), DMSO (Slightly)
• PKA: 7.67±0.50(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: 2,2''-[(4-HYDROXYFENYL)METHYLEEN]BIS(4-{(E)-[(5-METHYL-1H-TETRAZOOL1-YL)IMINO]METHYL}FENOL)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2''-[(4-HYDROXYFENYL)METHYLEEN]BIS(4-{(E)-[(5-METHYL-1H-TETRAZOOL1-YL)IMINO]METHYL}FENOL)(235106-62-4)
• EPA Substance Registry System: 2,2''-[(4-HYDROXYFENYL)METHYLEEN]BIS(4-{(E)-[(5-METHYL-1H-TETRAZOOL1-YL)IMINO]METHYL}FENOL)(235106-62-4)

Safety Data

• Hazardous Substances Data: 235106-62-4(Hazardous Substances Data)

Usage

Uses

Used in Antiviral Applications:
2,2''-[(4-HYDROXYFENYL)METHYLEEN]BIS(4-(E)-[(5-METHYL-1H-TETRAZOOL1-YL)IMINO]METHYLFENOL) is used as an antiviral agent for inhibiting the fusion of Human respiratory syncytial virus (HRSV). It functions by binding into a small hydrophobic cavity in the inner core of the F protein, interacting simultaneously with both the HR1 and HR2 domains, which prevents the virus from fusing with host cell membranes and thus inhibits viral replication.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,2''-[(4-HYDROXYFENYL)METHYLEEN]BIS(4-(E)-[(5-METHYL-1H-TETRAZOOL1-YL)IMINO]METHYLFENOL) is used as a key intermediate compound in the development of new antiviral drugs targeting HRSV. Its unique structure and mechanism of action make it a promising candidate for creating effective treatments against this major respiratory viral pathogen, which affects a wide range of patient populations and causes moderate to severe respiratory tract infections.

Biological Activity

ec50: 5.4 nm for rsv fusionvp-14637 is an inhibitor of rsv.respiratory syncytial virus (rsv) is the leading cause of respiratory tract infections in humans. rsv f protein that mediates fusion of the viral envelope with the host cell membrane has become a target of anti-rsv treatment.

in vitro

previous study demonstrated that vp-14637 did not block rsv adsorption but inhibited rsv-induced cell-cell fusion and specifically bound to rsv-infected cells. vp-14637 was capable of specifically interacting with the rsv fusion protein. rsv variants resistant to vp-14637 were selected, in which no mutations arose in hr1, indicating a mechanism other than direct disruption of the heptad repeat interaction. the f proteins containing the resistance mutations exhibited greatly reduced binding of vp-14637 [1].

in vivo

in cotton rats, animals given as little as 126 microg/kg of vp-14637 by small droplet aerosol starting 1 day after experimental virus infection with either a rsv a or b subtype consistently had significantly lower mean pulmonary rsv titers and reduced histopathological findings than mock-treated animals or cotton rats given placebo. in addition, no cotton rat treated with vp14637 had any evident untoward responses [2].

references

[1] douglas, j. l.,panis, m.l.,ho, e., et al. inhibition of respiratory syncytial virus fusion by the small molecule vp-14637 via specific interactions with f protein. journal of virology 77(9), 5054-5064 (2003).[2] wyde pr, laquerre s, chetty sn, gilbert be, nitz tj, pevear dc. antiviral efficacy of vp14637 against respiratory syncytial virus in vitro and in cotton rats following delivery by small droplet aerosol. antiviral res. 2005 oct;68(1):18-26.