4405-18-9

Usage

InChI:InChI=1/C10H10O4/c1-2-8-9(14-6-13-8)5-7(1)10-11-3-4-12-10/h1-2,5,10H,3-4,6H2

Upstream product

• 120-57-0 piperonal 
• 107-21-1 ethylene glycol 
• 2916-31-6 2,2-dimethyl-1,3-dioxolane 

Downstream Products

• 120-57-0 piperonal 
• 1219694-12-8 C₃₁H₂₈O₇ 
• 1219694-11-7 C₂₅H₂₄O₇ 
• 1219694-13-9 C₁₈H₁₅F₃O₆ 
• 1219694-10-6 C₂₅H₂₄O₇ 
• 495-76-1 piperonol 
• 1428438-97-4 C₃₃H₃₇NO₇ 
• 840528-94-1 9-benzo[1,3]dioxol-5-yl-8-benzyloxymethyl-naphtho[1,2-d][1,3]dioxole-7-carboxylic acid 3-benzyloxy-propyl ester 
• 840528-92-9 9-benzo[1,3]dioxol-5-yl-8-benzyloxymethyl-naphtho[1,2-d][1,3]dioxole-7-carboxylic acid benzyl ester 
• 840528-93-0 9-benzo[1,3]dioxol-5-yl-8-benzyloxymethyl-naphtho[1,2-d][1,3]dioxole-7-carboxylic acid 
• 840529-13-7 11-benzo[1,3]dioxol-5-yl-8,9-dihydro-1,3-dioxa-8,9-diaza-cyclopenta[a]anthracene-7,10-dione 
• 840529-31-9 (3,4-dimethoxy-phenyl)-(5-[1,3]dioxolan-2-yl-benzo[1,3]dioxol-4-yl)-methanol 

Relevant academic research and scientific papers

Synthesis and biological evaluation of helioxanthin analogues

Helioxanthin and analogues have been demonstrated to suppress gene expression of human hepatitis B virus. In the continuous attempt to optimize antiviral activity, various structural motifs were grafted on the helioxanthin scaffold. Many such analogues were synthesized and evaluated for their anti-hepatitis B virus activity. Structure-activity relationships of these helioxanthin derivatives are also discussed. Among these new compounds, 15 exhibits the highest activity against HBV (EC50 = 0.06 μM). This compound can suppress viral surface antigen and DNA expression. Furthermore, viral RNA is also diminished while the core promoter is deactivated upon treatment by 15. A plausible working mechanism is postulated. Our results establish helioxanthin lignans as potent anti-HBV agents with unique mode of action. Since their antiviral mechanism is distinct from current nucleoside/nucleotide drugs, helioxanthin lignans constitute a potentially new class of anti-HBV agents for combination therapy.

Synthesis and the biological evaluation of arylnaphthalene lignans as anti-hepatitis B virus agents

We have previously shown that helioxanthin can suppress human hepatitis B virus gene expression. A series of helioxanthin analogues were synthesized and evaluated for their anti-hepatitis B virus activity. Modifications at the lactone rings and methylenedioxy unit of helioxanthin can modulate the antiviral activity. Among them, compound 32 is the most effective anti-HBV agent. Compound 32 can suppress the secretion of viral surface antigen and e antigen in HepA2 cells with EC50 values of 0.06 and 0.14 μM, respectively. Compound 32 not only inhibited HBV DNA with wild-type and lamivudine-resistant strain but also suppressed HBV mRNA, core protein and viral promoters. In this study, a full account of the preparation, structure-activity relationships of helioxanthin analogues, and the possible mechanism of anti-HBV activity of this class of compounds are presented. This type of compounds possesses unique mode of action differing from existing therapeutic drugs. They are potentially new anti-HBV agents.

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.

Silica gel-supported metallic sulfates catalyzed chemoselective acetalization of aldehydes under microwave irradiation

Silica gel - supported metallic sulfates are found to be efficient catalysts for the protection of both aromatic and aliphatic aldehydes as 1,3- dioxolanes under microwaves in solvent-free conditions. Due to the neutral reaction conditions, this method is compatible with acid sensitive substrates.

Solvent free protection of carbonyl group under microwave irradiation

Protection of aldehydes and ketones as acetals or dioxolanes catalysed by PTSA or KSF clay was readily achieved from orthoformates, 1,2-ethanediol or 2,2-dimethyl-1,3-dioxolane without solvent under microwave irradiation.

Hindered rotation in arylnaphthalene lignans

Many arylnaphthalene lignans show biological activity and although few of them contain stereogenic centers, they may nevertheless be chiral if there is hindered rotation about the aryl-naphthalene bond. A relatively high barrier to rotation may give rise to separable rotational enantiomers (atropisomers) which might have quite different pharmacological properties. In order to investigate this possibility we have synthesized the natural products justicidin A, justicidin B, retro-helioxanthin, retro-justicidin B, and helioxanthin as well as four other arylnaphthalenes lignan analogs. We have studied the aryl-naphthalene rotational barrier in these compounds by dynamic NMR and HPLC and find barriers to rotation ranging from 16.9 to 21.5 kcal/mol. This translates to half-lives for individual atropisomers of less than 10 min at room temperature. The experimentally found barriers are compared to those obtained from molecular orbital calculations.

Novel uracil derivatives, process for preparing the same and a pharmaceutical composition containing the same

Novel uracil derivatives of the formula STR1 (wherein R1, R2 R3 and X are defined in the description) and their pharmaceutically acceptable salts, process for preparing the same and pharmaceutical composition containing the same are disclosed. The uracil derivatives have good antitumor activity and, therefore, are useful as antitumor preparation.