203935-39-1

Basic information

• Product Name: Helioxanthin derivative 5-4-2
• Synonyms: Helioxanthin derivative 5-4-2
• CAS NO: 203935-39-1
• Molecular Formula: C20H13NO5
• Molecular Weight: 347.32092
• Mol File: 203935-39-1.mol

Chemical Properties

• Melting Point: 252-254 °C
• Boiling Point: 671.3±55.0 °C(Predicted)
• Appearance: /
• Density: 1.491±0.06 g/cm3(Predicted)
• Solubility: Soluble in DMSO
• PKA: 13.14±0.20(Predicted)
• CAS DataBase Reference: Helioxanthin derivative 5-4-2(CAS DataBase Reference)
• NIST Chemistry Reference: Helioxanthin derivative 5-4-2(203935-39-1)
• EPA Substance Registry System: Helioxanthin derivative 5-4-2(203935-39-1)

Safety Data

• Hazardous Substances Data: 203935-39-1(Hazardous Substances Data)

Usage

Biological Activity

helioxanthin derivative 5-4-2, an analogue of helioxanthin (ach126447), is a small-molecule inhibitor of hbv, hsv-1and hsv-2 virus with ec50 values of 0.08 μm, 0.29 μm and 0.16 μm, respectively [1].helioxanthin derivative 5-4-2 is a lactam and has been reported to inhibit the hbv dna and rna and viral protein expression [2]. helioxanthin derivative 5-4-2 has significant anti-virus activity with ec50 values of 0.08 μm, 0.29 μm and 0.16 μm for hbv(hepatitis b virus), hsv-1(herpes simplex virus type 1) and hsv-2(herpes simplex virus type 2), respectively [1]. in addition, helioxanthin derivative 5-4-2 inhibited hbv replication by post-transcriptional down-regulation of necessary transcription factors [3]. helioxanthin derivative 5-4-2 has also exhibited potent anti-hcv (hepatitis c virus) activity with 55% inhibition at 1.0 μm and 80%inhibition at 3.0 μm [1].

references

[1] yeo h1, li y, fu l, zhu jl, gullen ea, dutschman ge, lee y, chung r, huang es, austin dj, cheng yc. synthesis and antiviral activity of helioxanthin analogues. j med chem. 2005 jan 27;48(2):534-46.[2] li y1, fu l, yeo h, zhu jl, chou ck, kou yh, yeh sf, gullen e, austin d, chengyc.inhibition of hepatitis b virus gene expression and replication by helioxanthin and its derivative. antivir chem chemother. 2005;16(3):193-201.[3] stein ll1, loomba r. drug targets in hepatitis b virus infection. infect disord drug targets. 2009 apr;9(2):105-16.

Upstream product

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Relevant articles and documents

Process research on arylnaphthalene lignan aza-analogues: a new palladium-catalyzed benzannulation of α,β-bisbenzylidenesuccinic acid derivatives

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Synthesis and antiviral activity of helioxanthin analogues

A series of natural product analogues based on helioxanthin (2), with particular attention to modification of the lactone ring and methylenedioxy group, were synthesized and evaluated for their antiviral activities. Among them, lactam derivative 18 and helioxanthin cyclic hydrazide 28 exhibited significant in vitro antiviral activity against hepatitis B virus (EC 50 = 0.08 and 0.03 μM, respectively). Compound 18 showed the most potent antiviral activity against hepatitis C virus (55% inhibition at 1.0 μM). Compound 12, an acid-hydrolyzed product of helioxanthin cyclic imide derivative 9, was found to exhibit broad-spectrum antiviral activity against hepatitis B virus (EC50 = 0.8 μM), herpes simplex virus type 1 (EC50 = 0.15 μM) and type 2 (EC50 50 = 9.0 μM), and cytomegalovirus (EC 50 = 0.45 μM). Helioxanthin lactam derivative 18 also showed marked inhibition of herpes simplex virus type 1 (EC50 = 0.29 μM) and type 2 (EC50 = 0.16 μM). The cyclic hydrazide derivative of helioxanthin 28 and its brominated product 42 exhibited moderately potent activities against human immunodeficiency virus (EC50 = 2.7 and 2.5 μM, respectively). Collectively, these molecules represent a novel set of antiviral compounds with unique structural features.

NOVEL ANTIVIRAL HELIOXANTHIN ANALOGS

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