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7,7'-DIMETHOXY-[4,4']BI[BENZO[1,3]DIOXOLYL]-5,5'-DICARBOXYLIC ACID is a carboxylic acid derivative of Bifendate (B382890), a synthetic intermediate of Schisandrin C. It is also an anti-HBV drug used in the treatment of chronic hepatitis B.

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  • 105868-34-6 Structure
  • Basic information

    1. Product Name: 7,7'-DIMETHOXY-[4,4']BI[BENZO[1,3]DIOXOLYL]-5,5'-DICARBOXYLIC ACID
    2. Synonyms: Bifendate Dicarboxylic Acid;[4,4'-Bi-1,3-benzodioxole]-5,5'-dicarboxylic acid, 7,7'-dimethoxy-;Bifendate Impurity 3;Bifendate Impurity 4;Bifendate Impurity 1;7,7'-dimethoxy-[4,4'-bibenzo[d][1,3]dioxole]-5,5'-dicarboxylic acid;Bicyclol Impurity C
    3. CAS NO:105868-34-6
    4. Molecular Formula: C18H14O10
    5. Molecular Weight: 390.3
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 105868-34-6.mol
  • Chemical Properties

    1. Melting Point: 260-262 °C
    2. Boiling Point: 574.2°Cat760mmHg
    3. Flash Point: 209.3°C
    4. Appearance: /
    5. Density: 1.56g/cm3
    6. Refractive Index: N/A
    7. Storage Temp.: Refrigerator
    8. Solubility: Aqueous Base (Slightly), DMSO (Slightly)
    9. PKA: 3.39±0.20(Predicted)
    10. CAS DataBase Reference: 7,7'-DIMETHOXY-[4,4']BI[BENZO[1,3]DIOXOLYL]-5,5'-DICARBOXYLIC ACID(CAS DataBase Reference)
    11. NIST Chemistry Reference: 7,7'-DIMETHOXY-[4,4']BI[BENZO[1,3]DIOXOLYL]-5,5'-DICARBOXYLIC ACID(105868-34-6)
    12. EPA Substance Registry System: 7,7'-DIMETHOXY-[4,4']BI[BENZO[1,3]DIOXOLYL]-5,5'-DICARBOXYLIC ACID(105868-34-6)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 105868-34-6(Hazardous Substances Data)

105868-34-6 Usage

Uses

Used in Pharmaceutical Industry:
7,7'-DIMETHOXY-[4,4']BI[BENZO[1,3]DIOXOLYL]-5,5'-DICARBOXYLIC ACID is used as an anti-HBV drug for the treatment of chronic hepatitis B. It serves as a synthetic intermediate of Schisandrin C, which is known for its potential therapeutic properties.

Check Digit Verification of cas no

The CAS Registry Mumber 105868-34-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,5,8,6 and 8 respectively; the second part has 2 digits, 3 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 105868-34:
(8*1)+(7*0)+(6*5)+(5*8)+(4*6)+(3*8)+(2*3)+(1*4)=136
136 % 10 = 6
So 105868-34-6 is a valid CAS Registry Number.

105868-34-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-(5-carboxy-7-methoxy-1,3-benzodioxol-4-yl)-7-methoxy-1,3-benzodioxole-5-carboxylic acid

1.2 Other means of identification

Product number -
Other names dimethyl-4,4'-dimethoxy-5,6,5',6'-dimethylenedioxybiphenyl-2,2'-dicarboxylic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:105868-34-6 SDS

105868-34-6Downstream Products

105868-34-6Relevant articles and documents

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

Tang, Xiaobo,Gu, Xiaoke,Ren, Zhiguang,Ma, Yuanfang,Lai, Yisheng,Peng, Hui,Peng, Sixun,Zhang, Yihua

, p. 2675 - 2680 (2012)

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

New synthesis of (S)-dimethyl-4,4′-dimethoxy-5,6,5′,6′- dimethenedioxy-biphenyl-2,2′-dicarboxylate by configuration transform

Cheng, Sen-Xiang,Chang, Jun-Biao,Qu, Ling-Bo,Chen, Rong-Feng

, p. 1665 - 1667 (2004)

(R/S)-4,4′-Dimethoxy-5,6,5′,6′-dimethenedioxy-2, 2′-di-(4(S)-methyl-oxazoline-1)-biphenyl has been synthesized from dimethyl-4,4′-dimethoxy-5,6,5′,6′-dimethenedioxy-biphenyl-2, 2′-dicarboxylate, and then the diastereoisomer mixture was almost fully converted to a single diastereoisomer with S-configuration ((S)-3) through the key configuration transform promoted by CuI, which was confirmed by CD, HPLC and 13C NMR. The C2-symmetric biphenyl, (S)-dimethyl-4,4′-dimethoxy-5,6,5′,6′-dimethenedioxy-biphenyl- 2,2′-dicarboxylate was prepared easily via the hydrolysis and ester exchange of (S)-3.

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

Cen, Juan,Guo, Huiyan,Hong, Chen,Lv, Jianwu,Yang, Yacheng,Wang, Ting,Fang, Dong,Luo, Wen,Wang, Chaojie

, p. 128 - 136 (2018)

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.

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

-

Paragraph 0123; 0125, (2018/10/19)

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.).

Method for preparing bicyclol by using bifendate

-

Paragraph 0081; 0086; 0091; 0097, (2017/10/26)

The invention discloses a method for preparing bicyclol by using bifendate, and belongs to the technical field of the chemical synthesis. The method comprises the following steps: using the bifendate as an initial raw material, hydrolyzing by using strong base, acidizing to obtain biphenyl dioic acid, dehydrating the biphenyl dioic acid to obtain biphenyl anhydride, reducing the biphenyl anhydride to obtain biphenyl alcohol acid, and finally esterifying to obtain the bicyclol. A product synthesized by the method is white solid, and the melting point of the white solid is 138-140 DEG C. The white solid can be determined as the pure bicyclol through a liquid chromatography-mass spectrometry and a nuclear magnetic resonance spectrometry. The method has the characteristics of cheap cost, short synthetic route, high yield, moderate reaction condition, simple post-treatment, and larger industrialized potential.

Bifendate derivatives, preparation method and its in the treatment of autoimmune diseases

-

Paragraph 0274; 0275; 0276, (2016/10/09)

The invention belongs to the chemical medicine technical field, and especially relates to a bifendate derivative, a preparation method and an application of the bifendate derivative for treating autoimmune disease. A structure of the bifendate derivative

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

Tang, Xiaobo,Gu, Xiaoke,Ai, Hua,Wang, Guangji,Peng, Hui,Lai, Yisheng,Zhang, Yihua

scheme or table, p. 801 - 805 (2012/03/11)

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

Gu, Xiaoke,Ren, Zhiguang,Tang, Xiaobo,Peng, Hui,Ma, Yuanfang,Lai, Yisheng,Peng, Sixun,Zhang, Yihua

scheme or table, p. 2540 - 2548 (2012/05/31)

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

Wang, Guangcheng,Deng, Chongyang,Xie, Caifeng,Ma, Liang,Yang, Jincheng,Qiu, Neng,Xu, Qinyuan,Chen, Tao,Peng, Fei,Chen, Jinying,Qiu, Jingxiang,Peng, Aihua,Wei, Yuquan,Chen, Lijuan

experimental part, p. 5941 - 5948 (2012/01/03)

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

Liquid chromatography resolution of biphenyl dimethyl dicarboxylate (DDB) and its analogues on a chiral stationary phase

Hyun, Myung Ho,Lee, Gil Soo,Han, Sang Cheol,Cho, Yoon Jae

, p. 313 - 318 (2007/10/03)

Racemic biphenyl dimethyl dicarboxylate (DDB) and its analogues have been successfully resolved on a commercial HPLC chiral column, (3R,4S)-Whelk-O 1. In general, cyclic amide analogues of DDB, which were derived from pyrrolidine or piperidine, showed greater enantioselectivity and greater retention than the corresponding N,N-dialkyl amide or N-alkyl amide or ester analogues. From these results, it was concluded that the carbonyl oxygen of the DDB analogues plays an important role as a hydrogen bond acceptor, though the steric bulkiness of the amide functionality of DDB analogues may be another factor governing chiral recognition. The conformational stability of the two enantiomers of DDB and its analogues was also found to be high enough for the two enantiomers to be resolvable on (3R,4S)-Whelk-O 1.

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