- Gamma-bifendate intermediate, synthesis method thereof, and synthesis method of gamma-bifendate
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The invention discloses a gamma-bifendate intermediate, a synthesis method thereof, and a synthesis method of gamma-bifendate. The gamma-bifendate intermediate is 4-methoxy-5, 6-methylenedioxy-2-methoxycarbonyl phenylboronic acid, and based on the gamma-bifendate intermediate, the invention further provides a novel synthesis method of gamma-bifendate. Ullmann reaction is not adopted, and Suzuki-Miyaura reaction is introduced as a key step of asymmetric synthesis, so that synthesis is simple, isomeride does not occur, the preparation process is optimized and upgraded, reaction steps are reduced, and reaction conditions are optimized.
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Paragraph 0016; 0045; 0048
(2021/08/07)
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- Nitrogen-containing biaromatic ring compounds as well as preparation method and application thereof
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The invention relates to nitrogen-containing biaromatic ring compounds, a preparation method and an application, namely a pharmaceutical composition consisting of the compound as an effective component, a preparation method and an application of the compound in resisting liver cancer. A series of nitrogen-containing biaromatic ring compounds with novel structures are synthesized, generation of miRNA is induced by regulating TRBP, a good anti-liver cancer effect is shown, small molecules have a relatively strong inhibiting effect on proliferation of liver cancer cells, individual compounds even have a better curative effect than enoxacin, no similar structure has the effect before, and the compounds have good development prospects.
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- Towards the Total Synthesis of Schisandrene: Stereoselective Synthesis of the Dibenzocyclooctadiene Lignan Core
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A stereoselective synthesis of the dibenzocyclooctadiene lignan core of the natural product schisandrene is described. Starting from readily available gallic acid, the synthetic strategy involves Suzuki-Miyaura cross-coupling, Stille reaction, and ring-closing metathesis (RCM) in the reaction sequence. The required asymmetric center at C-7′ was established by an asymmetric reduction of a keto compound using the Corey-Bakshi-Shibata (CBS) catalyst. In our approach, the eight-membered ring was achieved by RCM for the first time.
- Venkanna, Arramshetti,Poornima, Borra,Siva, Bandi,Babu, B. Hari,Babu, K. Suresh
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p. 908 - 911
(2018/02/26)
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- Nitrogen-Containing Biphenyl Compounds, Pharmaceutical Compositions of Same, Preparation Methods and Anti-HIV-1 Uses Thereof
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Nitrogen-containing biphenyl compounds as represented by formula (I), pharmaceutically acceptable salts or derivatives thereof, pharmaceutical compositions, and preparation methods therefore, and anti-HIV-1 use of the compound. Each substituent group in formula (I) is as defined in the description.
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Paragraph 0049-0053
(2014/01/08)
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- An improved method for the synthesis of γ-DDB
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A mild and efficient method for the synthesis γ-DDB has been developed through anhydride-linker assisted intramolecular Ullmann reaction. Highly regioselective bromination of differentially protected gallate was realized by virtue of the introduction of NBS.
- Song, Chuanjun,Zhao, Peng,Hu, Zhiqiang,Shi, Shuai,Cui, Yanmei,Chang, Junbiao
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supporting information; experimental part
p. 2297 - 2298
(2010/06/16)
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- Asymmetrie synthesis of (+)- and (-)-wuweizisu C stereoisomers and their chemosensitizing effects on multidrug-resistant cancer cells
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Total syntheses of the dibenzocyclooctadiene natural product wuweizisu C in its (-)-form [(S)-1] and its (+)-form [(R)-l] were achieved in 19 steps, starting from commercially available gallic acid. In the key step, the asymmetric biphenyl axis was constructed by an oxazoline-mediated Ullmann reaction to provide either the P or Mbiaryl product in 68% yield and >99% de, depending on the configuration of the oxazoline. The efficiency of this total synthesis was excellent, as the syntheses of (S)-1 and (R)-1 from, intermediate 7 each proceeded in 13 steps with an overall yield of 6.8%. (S)-1 and (R)-1 were evaluated as chemosensitizers for multidrug-resistant cancers.
- Li, Yanfeng,Wang, Qiang,Dong, Lihong,Guo, Xiaohe,Wang, Wei,Xie, Jingxi,Chang, Junbiao
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scheme or table
p. 3383 - 3390
(2010/02/28)
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- Synthesis of unsymmetrical biphenyls as potent cytotoxic agents
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Twenty-six unsymmetrical biphenyls were synthesized and evaluated for cytotoxic activity against DU145, A549, KB and KB-Vin tumor cell lines. Three compounds 27, 35 and 40 showed very potent activity against the HTCL panel with an IC50 value range of 0.04-3.23 μM. In addition, fourteen active compounds were all more potent against the drug-resistant KB-Vin cell line than the parental KB cell line. Preliminary SAR analysis indicated that two bulky substituents on the 2,2′-positions of unsymmetrical biphenyl skeleton are necessary and crucial for in vitro anticancer activity, thus providing a good starting point to develop unsymmetrical biphenyls as novel anticancer agents.
- Wu, Gang,Guo, Huan-Fang,Gao, Kun,Liu, Yi-Nan,Bastow, Kenneth F.,Morris-Natschke, Susan L.,Lee, Kuo-Hsiung,Xie, Lan
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scheme or table
p. 5272 - 5276
(2009/05/07)
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- Multi-functionalization of gallic acid towards improved synthesis of α- and β-DDB
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The synthesis of mono-, di- and trisubstituted gallic acids and their ester with similar or different groups including different acetal and ketals is described. Regioselective bromination on two ortho-positions of methyl gallate, which is very crucial for many organic syntheses, was achieved in high yield and purity. The α- and β-DDB were synthesized in high overall yield and purity from the regioselective bromoderivatives.
- Alam, Ashraful,Takaguchi, Yutaka,Ito, Hideyuki,Yoshida, Takashi,Tsuboi, Sadao
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p. 1909 - 1918
(2007/10/03)
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- Efficient synthesis of γ-DDB
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Synthesis of γ-DDB, which is another family member of α-DDB (dimethyl 4,4′-dimethoxy-5,6,5′,6 ′- dimethylenedioxybiphenyl-2,2′- dicarboxylate), is described. The unsymmetric isomer (γ-DDB) was constructed by a linker-directed intramolecular Ullmann coupling reaction, followed by the cleavage of the linker and re-esterification.
- Chang, Junbiao,Guo, Xiaohe,Cheng, Senxiang,Guo, Ruiyun,Chen, Rongfeng,Zhao, Kang
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p. 2131 - 2136
(2007/10/03)
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- Synthesis, separation, and theoretical studies of chiral biphenyl lignans (α- and β-DDB)
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Two biphenyl lignans, α- and β-DDB (1 and 2, respectively) were efficiently synthesized without contamination by other regio-isomers. The different yields of the Ullmann coupling reactions for the synthesis of 1 and 2 were rationalized by calculating steric hindrance, stability, entropy change, and heat-of-formation values. The enantiomers of 1 and 2 were readily separated by HPLC on a chiral stationary phase. Their configurations were assigned based on the Cotton effect of the authentic natural products.
- Chang, Junbiao,Chen, Rongfeng,Guo, Ruiyun,Dong, Chunhong,Zhao, Kang
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p. 2239 - 2246
(2007/10/03)
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- Biphenyl derivative useful in the treatment of liver diseases
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The present invention relates to a novel biphenyl derivative having a liver ailment-moderating action, which is effective for the remedy of liver diseases such as acute hepatitis and chronic hepatitis, a process for the preparation of this derivative and a liver ailment-moderating agent comprising this derivative as an active ingredient. Moreover, the present invention relates to a compound valuable as the intermediate compound for the synthesis of this derivative and a process for efficiently preparing this intermediate compound.
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