205117-47-1

Usage

Uses

Used in Pharmaceutical Industry:
Bifendate Impurity E is used as a synthetic intermediate for the development of anti-HBV drugs, specifically for the treatment of chronic hepatitis B. Its role in the pharmaceutical industry is crucial, as it contributes to the creation of medications that combat hepatitis B virus and improve the health outcomes of patients suffering from this chronic condition.

Upstream product

• 111897-21-3 dimethyl-4,4'-dimethoxy-5,6,5',6'-dimethylenedioxybiphenyl-2,2'-dicarboxylic acid 
• 111897-19-9 DDB 
• 67-56-1 methanol 

Downstream Products

• 1350363-27-7 (Z)-5-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)-2-ethoxyphenyl) 5'-methyl 7,7'-dimethoxy-4,4'-bibenzo[d][1,3]dioxole-5,5'-dicarboxylate 
• 1350363-28-8 (Z)-5-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)-2-methoxyphenyl) 5'-methyl 7,7'-dimethoxy-4,4'-bibenzo[d][1,3]dioxole-5,5'-dicarboxylate 
• 1350363-29-9 (E)-5-(3-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl) 5'-methyl 7,7'-dimethoxy-4,4'-bibenzo[d][1,3]dioxole-5,5'-dicarboxylate 
• 1350363-30-2 (Z)-5-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)-2,6-dimethoxyphenyl) 5'-methyl 7,7'-dimethoxy-4,4'-bibenzo[d][1,3]dioxole-5,5'-dicarboxylate 
• 1350363-31-3 (E)-5-(2,4-dichloro-6-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl) 5'-methyl 7,7'-dimethoxy-4,4'-bibenzo[d][1,3]dioxole-5,5'-dicarboxylate 
• 1350363-32-4 (Z)-5-(2-bromo-4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl) 5'-methyl 7,7'-dimethoxy-4,4'-bibenzo[d][1,3]dioxole-5,5'-dicarboxylate 
• 1350363-33-5 (Z)-5-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)-2-fluorophenyl) 5'-methyl 7,7'-dimethoxy-4,4'-bibenzo[d][1,3]dioxole-5,5'-dicarboxylate 
• 1350363-34-6 (E)-5-(2,4-dibromo-6-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl) 5'-methyl 7,7'-dimethoxy-4,4'-bibenzo[d][1,3]dioxole-5,5'-dicarboxylate 
• 1350363-35-7 (E)-5-(5-((2,4-dioxothiazolidin-5-ylidene)methyl)-2-methoxyphenyl) 5'-methyl 7,7'-dimethoxy-4,4'-bibenzo[d][1,3]dioxole-5,5'-dicarboxylate 
• 1350363-36-8 (E)-5-(2-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl) 5'-methyl 7,7'-dimethoxy-4,4'-bibenzo[d][1,3]dioxole-5,5'-dicarboxylate 
• 1350363-37-9 (Z)-5-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl) 5'-methyl 7,7'-dimethoxy-4,4'-bibenzo[d][1,3]dioxole-5,5'-dicarboxylate 
• 1350363-38-0 (E)-5-(4-chloro-2-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl) 5'-methyl 7,7'-dimethoxy-4,4'-bibenzo[d][1,3]dioxole-5,5'-dicarboxylate 
• 1350363-25-5 5-(4-formylphenyl) 5'-methyl 7,7'-dimethoxy-4,4'-bibenzo[d][1,3]dioxole-5,5'-dicarboxylate 
• 1350363-26-6 5-(4-chloro-2-formylphenyl) 5'-methyl 7,7'-dimethoxy-4,4'-bibenzo-[d][1,3]dioxole-5,5'-dicarboxylate 

Relevant academic research and scientific papers

Alkoxybiphenyl alpha, beta-unsaturated amide compound and preparing method and medical application thereof

The invention relates to an alkoxybiphenyl alpha, beta-unsaturated amide compound and a preparing method and medical application thereof, and belongs to the fields of medicinal chemistry and pharmacotherapeutics. The invention provides application of the compound shown in the formula I or pharmaceutically acceptable salt thereof in preparing drugs for antioxidation related diseases, especially theapplication in preparing anti-inflammatory drugs or antioxidant drugs. (The formula is shown in the description.).

Development of tacrine-bifendate conjugates with improved cholinesterase inhibitory and pro-cognitive efficacy and reduced hepatotoxicity

A novel series of tacrine-bifendate (THA-DDB) conjugates (7a-e) were synthesized and evaluated as potential anti-Alzheimer's agents. These compounds showed potent cholinesterase and self-induced β-amyloid (Aβ) aggregation inhibitory activities. A Lineweaver–Burk plot and molecular modeling study showed that these compounds can target both catalytic active site (CAS) and peripheral anionic site (PAS) of acetylcholinesterase (AChE). The cytotoxicity of the conjugate 7d against PC12 and HepG2 cells and hepatotoxicity against human hepatocyte cell line (HL-7702) were found to be considerably less compared to THA. Moreover, treatment with 7d did not exhibit significant hepatotoxicity in mice. Finally, in vivo studies confirmed that 7d significantly ameliorates the cognitive performances of scopolamine-treated ICR mice. Therefore, 7d has high potential for the treatment of Alzheimer's disease and warrants further investigation.

Synthesis and evaluation of substituted dibenzo[c,e]azepine-5-ones as P-glycoprotein-mediated multidrug resistance reversal agents

A series of substituted dibenzo[c,e]azepine-5-ones (7a-h) were synthesized and evaluated as P-glycoprotein (P-gp)-mediated multidrug resistance (MDR) reversal agents. The most potent compound 7h could significantly and selectively enhance the chemo-sensit

Synthesis and evaluation of nitric oxide-releasing DDB derivatives as potential Pgp-mediated MDR reversal agents in MCF-7/Adr cells

Novel furoxan-based nitric oxide (NO)-releasing DDB derivatives (7a-j) were synthesized. Compounds 7i and 7j significantly reversed the resistance of MCF-7/Adr cells to doxorubicin in the combination treatment, and markedly increased the intracellular accumulation of doxorubicin probably via inhibiting Pgp-mediated intracellular drug efflux as well as down-regulating doxorubicin-induced Pgp expression. It was demonstrated that NO released by 7i and 7j played an important role in increasing intracellular doxorubicin accumulation and chemo-sensitizing MCF-7/Adr cells to doxorubicin, and the synergic effects of DDB and NO-donor moieties in 7i and 7j may contribute to reversing Pgp-mediated MDR in MCF-7/Adr cells to doxorubicin.

Synthesis and biological evaluation of bifendate-chalcone hybrids as a new class of potential P-glycoprotein inhibitors

Overexpression of P-glycoprotein (P-gp) is one of the major problems to successful cancer chemotherapy. To find novel effective P-gp inhibitors, a series of bifendate-chalcone hybrids were synthesized and evaluated. Among them, the most active compound 8g

Synthesis and biological evaluation of novel dimethyl[1,1′-biphenyl]- 2,2′-dicarboxylate derivatives containing thiazolidine-2,4-dione for the treatment of concanavalin A-induced acute liver injury of BALB/c mice

In this paper, we reported the synthesis of bifendate derivatives and evaluation of anti-inflammatory activity by detecting the production of the Nitric Oxide (NO) in the lipopolysaccharide(LPS)-stimulated RAW 264.7 cell lines. Among the newly derivatives

A solid-phase approach to DDB derivatives

Since the discovery of 2,2′-dimethoxycarbonyl-4,4-dimethoxy-5,6, 5′,6′-biomethylenedioxy-biphenyl (DDB) as a potent anti-HBV agent, we have studied the structure-activity relationships of 4,4′-dimethoxy-5, 6,5′,6′-dimethenedioxy-2-alkyloxycarbonyl-2′-(4-substituted benzyl piperazin-1-yl)carbonyl-biphenyl as anti-HBV agents. Therefore, it is rational to extend this study to the 3,3′-disustituted-4,4′- dimethoxy-5,6,5′,6′-dimethenedioxy-2-alkyloxycarbonyl-2′- Serine derivatives. Thus, in an attempt to develop an efficient method for the preparation of a large number of DDB derivatives, the reaction between a DDB acid chloride and serine derivatives on solid support was studied. The structure of resulted compounds was confirmed by LC-MS and 1H NMR analysis. Compounds 2a, 2d, 2f, 2j showed in vitro anti-HBV activity without significant toxicity up to 100 μM.