- Improved synthesis of a Smad3 phosphorylation inhibitor lingzhifuran A via condensation reaction
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A facile and high-efficient synthesis of lingzhifuran A, a Smad3 phosphorylation inhibitor isolated from Ganoderma lucidum, was developed from commercially available dibenzo[b,d]furan. The crucial step of this strategy was achieved via condensation reaction using key intermediate 8-hydroxydibenzo[b,d]furan-4-carbaldehyde and commercially available (E)-2-methylbut-2-enal. By this strategy, lingzhifuran A was obtained in 5 steps with up to 57.6% yield.
- Chen, Weiming,Xu, Xiaoling,Sun, Mingfeng,Huang, Xuelong,Ma, Weiping,Jiang, Feng
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p. 122 - 128
(2021/02/12)
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- Preparation method of ganoderma lucidum furan A
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The invention belongs to the technical field of chemical synthesis, and particularly relates to a preparation method of ganoderma lucidum furan A. According to the preparation method of the ganodermalucidum furan A, a compound shown in a general formula II and a compound shown in a general formula III are subjected to condensation reaction to obtain a compound shown in a general formula I, and the reaction equation is as shown in the specification. According to the technical scheme provided by the invention, a synthetic route which is particularly suitable for amplifying and synthesizing theganoderma lucidum furan A is provided; the selected raw materials, namely dibenzofuran and 2-methyl-2-butenal, are mature chemical products; the method has the advantages of simple process, wide source, low price, mild reaction conditions of the whole reaction route and no special requirements, the obtained intermediate can be directly subjected to subsequent reactions without purification, the route completely overcomes the defects of the synthesis route in the prior art due to the elements, and the method has the prospect of industrial large-scale production.
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Paragraph 0033-0038
(2020/09/20)
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- Fused imidazole compounds with indoleamine 2,3-dioxygenase inhibition activity
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The invention relates to fused imidazole compounds, and a preparation method and application thereof. The structure of the compounds is shown in a general formula I, wherein the definitions of each group are as described in the specification. The compounds are capable of selectively inhibiting indoleamine 2,3-dioxygenase (IDO). The compounds provided by the invention can be used as IDO inhibitorsfor the treatment and/or prevention of diseases with the pathological characteristics of IDO mediated tryptophan metabolism pathways, such as cancer, eye diseases, autoimmune diseases, psychological disorders, depression, anxiety and other diseases.
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Paragraph 0410-0413
(2018/07/10)
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- Synthesis and antitubercular evaluation of amidoalkyl dibenzofuranols and 1H-benzo[2,3]benzofuro[4,5-e][1,3]oxazin-3(2H)-ones
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A new class of amidoalkyl dibenzofuranols and 1H-benzo[2,3]benzofuro[4,5-e] [1,3]oxazin-3(2H)-ones was synthesized in very good yields through polyphosphoric acid supported on silica (PPA-SiO2) catalyzed one-pot three component condensation of 2-dibenzofuranol; aromatic aldehydes and acetamide or benzamide or urea under solvent free conditions. At 125 °C the reaction led to the formation of amidoalkyl dibenzofuranols 5a-k where as at 160 °C cyclization take place to give oxazin-3(2H)-one analogues 6a-e. Screening all the 16 compounds for in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB) resulted 1-((4-chlorophenyl)(2- hydroxydibenzo[b,d]furanyl)methyl)urea 5h; 1-((4-bromophenyl)(2- hydroxydibenzo[b,d]furanyl)methyl)urea 5i; 1-phenyl-1H-benzo[2,3]benzo furo[4,5-e][1,3]oxazin-3(2H)-one 6a (MIC 3.13 μg/mL) and 1-(4-chlorophenyl)- 1H-benzo[2,3]benzofuro[4,5-e][1,3]oxazin-3(2H)-one 6b; 1-(4-bromophenyl)-1H- benzo[2,3]benzofuro [4,5-e][1,3]oxazin-3(2H)-one 6c (MIC 1.56 μg/mL) as most active antitubercular agents.
- Kantevari, Srinivas,Yempala, Thirumal,Yogeeswari, Perumal,Sriram, Dharmarajan,Sridhar, Balasubramanian
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supporting information; experimental part
p. 4316 - 4319
(2011/08/09)
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- Fries rearrangement of dibenzofuran-2-yl ethanoate under photochemical and Lewis-acid-catalysed conditions
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The Fries rearrangement of dibenzofuran-2-yl ethanoate as a route to o-hydroxyacetyldibenzofurans has been investigated, both under thermal Lewis-acid catalysed and non-catalysed photochemical conditions. The reactions were examined theoretically at semi-empirical (PM3 and ZINDO/S) and density functional theory (DFT) levels. The correct selection of reaction conditions provides viable preparative routes to ortho-acylated hydroxydibenzofurans.
- Oliveira, Ana M. A. G.,Oliveira-Campos, Ana M. F.,Raposo, M. Manuela M.,Griffiths, John,Machado, Antonio E. H.
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p. 6145 - 6154
(2007/10/03)
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