In 2019,Bioorganic & Medicinal Chemistry Letters included an article by Thanh, Nguyen Dinh; Hai, Do Son; Ha, Nguyen Thi Thu; Tung, Do Tien; Le, Cao Thi; Van, Hoang Thi Kim; Toan, Vu Ngoc; Toan, Duong Ngoc; Dang, Le Hai. Synthetic Route of C7H6O2. The article was titled 《Synthesis, biological evaluation and molecular docking study of 1,2,3-1H-triazoles having 4H-pyrano[2,3-d]pyrimidine as potential Mycobacterium tuberculosis protein tyrosine phosphatase B inhibitors》. The information in the text is summarized as follows:
Some heterocycles, namely 2-amino-4H-pyran-3-carbonitriles, were synthesized in a three-component reaction from substituted benzaldehydes, malononitrile, and Et acetoacetate. These heterocycles have been converted subsequently into 4H-pyrano[2,3-d]pyrimidine ring by ring-closing reaction with acetic anhydride in the presence of the concentrated sulfuric acid as catalyst. The successive alkylation reaction of lactam N-H bond on pyrimidine-4-one ring was carried out using propargylic bromide in dry acetone in the presence of anhydrous potassium carbonate. The click chem. of 3-propargyl-4H-pyrano[2,3-d]pyrimidine compounds has been accomplished by reaction with tetra-O-acetyl-α-D-glucopyranosyl azide using the metal-organic framework Cu@MOF-5 as a catalyst in absolute ethanol. All the synthesized 1H-1,2,3-triazoles were screened for their in vitro Mycobacterium tuberculosis protein tyrosine phosphatase B (MtbPtpB) inhibition. Kinetic studies of the most active compounds I (R = 3,5-diOMe-4-OH, 3-OH-4-OEt, 3-OMe-4-OH-5-NO2) showed their competitive inhibition toward the MtbPtpB enzyme. The detailed structure-activity relationship (SAR) in vitro and in silico studies suggested that the interaction of Arg63 amino acids with anion type of para-hydroxyl group via a salt bridge of iminium cation was essential for strong inhibitory activity against MtbPtpB.3-Hydroxybenzaldehyde(cas: 100-83-4Synthetic Route of C7H6O2) was used in this study.
3-Hydroxybenzaldehyde(cas: 100-83-4) can be used as a reactant along with ethyl acetoacetate and thiourea in the synthesis of corresponding dihydropyrimidine-2-thione (monastrol), using Yb(OTf)3 as a catalyst by Biginelli cyclocondensation reaction.Synthetic Route of C7H6O2
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