Synthesis and characterization of bindarit, an inhibitor of monocyte chemoattractant protein 1
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TQ463

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Program for the Innovative Talents of Higher Education Institutions of Shanxi

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    Abstract:

    In order to solve the problem that bindarit (BIN) is difficult to industrially produce, a new and efficient method for the synthesis of BIN was reported. Firstly, methyl 1H-indazole-3-carboxylate (Ⅰ) was prepared by using 1H-indazole-3-carboxylic acid as the starting material. Then, the intermediate Ⅰ reacted with benzyl bromide to obtain methyl 1-benzyl-1H-indazole-3-carboxylate (Ⅱ), and the ester group was further converted to (1-benzyl-1H-indazol-3-yl)methanol (Ⅲ) by reaction with sodium borohydride. Finally, the target product BIN was obtained by the reaction of the intermediate Ⅲ with chloroform and acetone in the presence of sodium hydroxide. The optimum conditions for the synthesis of BIN were obtained as follows: n(Ⅲ)∶n(NaOH)∶n(CHCl3) = 1∶10∶4, reaction temperature is 55 ℃, reaction time is 3 hours. The structure of the BIN was confirmed by 1H NMR, 13C NMR, HR-MS and elemental analysis. This method is characterized by high yield, simple and convenient operation, cheap and easily available raw materials and easy industrialized production.

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History
  • Received:October 20,2021
  • Revised:January 18,2022
  • Adopted:January 26,2022
  • Online: May 11,2022
  • Published:
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