84806-48-4

Upstream product

• 138-59-0 shikimic acid 
• 40983-58-2 methyl shikimate 
• 10534-44-8 3-dehydroquinic acid 
• 77-95-2 D-(-)-quinic acid 
• 67-56-1 methanol 
• 57764-14-4 methyl 3-dehydroquinate 
• 186581-53-3 diazomethane 
• 2922-42-1 (-)-3-dehydroshikimic acid 

Downstream Products

• 1356144-15-4 methyl 3,4-dihydroxy-5-(propylamino)benzoate 
• 1356144-05-2 methyl 3-(2,6-diethylphenylamino)-4-hydroxybenzoate 
• 1356144-01-8 methyl 3-(2,5-dichlorophenylamino)-4-hydroxybenzoate 
• 1356144-23-4 methyl 3-(hexylamino)-4,5-dihydroxybenzoate 
• 1356144-07-4 methyl 3-(2-(diphenylmethylene)hydrazinyl)-4-hydroxybenzoate 
• 1356144-21-2 methyl 3,4-dihydroxy-5-(isobutylamino)benzoate 
• 1356143-72-0 methyl 4-hydroxy-3-(4-hydroxyphenylamino)benzoate 
• 1356143-93-5 methyl 4-hydroxy-3-(2-methoxyphenylamino)benzoate 
• 1356144-25-6 methyl 3-(cyclohexylamino)-4,5-dihydroxybenzoate 
• 132653-81-7 methyl 4-hydroxy-3-(p-tolylamino)benzoate 
• 1356143-79-7 methyl 3-(4-chlorophenylamino)-4-hydroxybenzoate 
• 1356143-87-7 methyl 3-(4-acetylphenylamino)-4-hydroxybenzoate 
• 1356143-70-8 methyl 4-hydroxy-3-(4-methoxyphenylamino)benzoate 
• 1356143-99-1 3-(2-hydroxy-5-(methoxycarbonyl)phenylamino)benzoic acid 

Relevant academic research and scientific papers

Novel 4-benzamino-benzofuran[2,3-d]pyridine compound and application thereof

The invention discloses a novel 4-benzamino-benzofuran[2,3-d]pyridine compound and application thereof. The 4-benzamino-benzofuran[2,3-d]pyridine compound as shown in a general formula (I) as well asa pharmaceutically acceptable salt, a hydrate, a solvate or a predrug with anti-tumor effect. The experiment proves that the 4-benzamino-benzofuran[2,3-d]pyridine compound has a good inhibition effecton human lung adenocarcinoma cells A549, human large cell lung cancer cells H460 and Gefitinib medicine-resistant human lung adenocarcinoma cell strains H1975 (containing high-expression T790M/L858 double-mutation EGFR) and can be used for preparing anti-tumor medicines. (The formula is as shown in the description).

Biomass-involved synthesis of: N -substituted benzofuro[2,3- d] pyrimidine-4-amines and biological evaluation as novel EGFR tyrosine kinase inhibitors

Shikimic acid (1) is a renewable biomass which could be obtained sustainably through natural product isolation or metabolic engineering. Owing to its great potential in chemical conversion, the value-added utilization of this non-grain biomass has received much attention in recent years. Based on the established transformation route from shikimic acid (1) to methyl 3-dehydroshikimate (3-MDHS, 2) and to the multi-functionalized methyl 2-amino-3-cyanobenzofuran-5-carboxylate (3), we disclose a facile and transition metal-free method to access a series of N-substituted benzofuro[2,3-d]pyrimidine-4-amines in 63%-90% yields. The identification of these compounds as EGFR tyrosine kinase inhibitors has also been described. Among them, compound 5h exhibited the most potent inhibitory effect against EGFR tyrosine kinase with an IC50 of 1.7 nM and excellent antiproliferative activity against A431 and A549 cell lines with a GI50 of 5.1 and 12.3 μM, respectively.

Sequential C-C, C-O, and C-N bond-forming reaction of methyl (-)-3-dehydroshikimate, malononitrile, and bromoalkanes: Simple synthesis of 2-(alkylamino)-3-cyanobenzofurans from a biomass-derived substrate

An interesting and simple method was developed for the synthesis of 2-(alkylamino)-3-cyanobenzofurans by consecutive C-C, C-O, and C-N coupling reaction of methyl (-)-3-dehydroshikimate with malononitrile and a bromoalkane or dibromoalkane under microwave

Cascade reaction between methyl 3-dehydroshikimate, arylamines, and 2-chloroalkyl esters under microwave conditions: A practical and biomass-based synthesis of N -aryl-1,4-benzoxazin-3-ones

A biomass-based, metal- and ligand-free assembly of N-aryl-1,4-benzoxazin- 3-ones from methyl 3-dehydroshikimate (3-MHDS), involving aliphatic to aromatic transformation followed by C-O and C-N forming reactions, is presented. A variety of N-aryl-1,4-benzoxazin-3-ones were efficiently synthesized in a one-pot consecutive manner under microwave conditions. Georg Thieme Verlag Stuttgart, New York.

Bio-based synthesis of secondary arylamines from (-)-shikimic acid

A specific family of secondary arylamines, including diarylamines and arylalkylamines have been synthesized in good yields starting from the renewable and biomass-based feedstock (-)-shikimic acid (1). The tandem cross-coupling and aromatization reactions

Synthesis of the sialic acid (-)-KDN and certain epimers from (-)-3-dehydroshikimic acid or (-)-quinic acid

(-)-3-Dehydroshikimic acid (3-DHS, 4), a C7-building block now available in large quantity from corn syrup, has been converted into the sialic acid (-)-KDN (3) as well as its C-7- and C-8-epimers. (-)-Quinic acid can be used for the same purpos

Stereoselectivity in Nucleophilic Additions to the Carbonyl Group of Methyl 1,4,5-tris(trimethylsilyl)-3-dehydroquinate

Methyl 1,4,5-tris(trimethylsilyl)-3-dehydroquinate was synthesized in a three-step procedure and condensed with various nucleophiles (-CH2COOEt, -CH2SO2Ph, -CH2-CCH, H-).The diastereoselectivity of the reaction, leading to the creation of a new quaternary (or tetiary) asymmetric carbon atom was examined.The preferential axial attack on the C=O group of the cyclohexanone system is discussed.The deprotected products were evaluated as DHQase inhibitors. - Keywords: methyl 3-dehydroquinate; nucleophilic addition; diastereoselectivity.

Toluene-dioxygenase-mediated cis-dihydroxylation of aromatics in enantioselective synthesis. Iterative glycoconjugate coupling strategy and combinatorial design for the synthesis of oligomers of nor-saccharides, inositols and pseudosugars with interesting

Vinyl epoxides 18 and 31 and vinylaziridines 24 and 25 derived from chloro- or bromocyclohexadiene-cis-diols 9 have been condensed with protected cyclitols 19, 37, and 46 in an iterative manner to generate dimeric, trimeric and tetrameric conduritol or am

Intracellular mediators: Synthesis of L-α-phosphatidyl-D-myo-inositol 3,4,5-trisphosphate and glyceryl ether analogs

L-α-Phosphatidyl-D-myo-inositol 3,4,5-trisphosphate (3,4,5-PIP3), the most prominent member of a new class of intracellular second messengers, and two ether analogs were conveniently prepared from the differentially functionalized D-myo-inosito

Synthesis of Pseudosugars From Microbial Metabolites

The short syntheses of three pseudosugars, pseudo-β-D-altropyranose, pseudo-α-L-mannopyranose and pseudo-β-D-glucopyranose starting from homochiral microbial metabolites obtained from complimentary sources are described.