Synthesis and biological activity of novel statine derivatives containing ferrocenyl moiety

Lijun Gu,Feilong Liu,Bingqin Yang

doi:10.1590/s0103-50532010000100010

Abstract

In a search for new aspartic protease inhibitors, conjugates of ferrocene with statine were designed and synthesized by coupling reaction using the standard N,N'-dicyclohexylcarbodiimide (DCC) and 1-hydroxybenzotriazole (HOBt) protocol. The title compounds were characterized by IR, ¹H NMR spectroscopy, MS and elemental analysis. The results of bioassay showed that some title compounds could serve as a starting point.

Highlights

Aspartic proteases are involved in many biological pathways in fungi, plants, humans, parasites, retroviruses.[1,2] Aspergillus oryzae aspartic proteinase is found to have activity for the activation of trypsinogen and for the activation of chimotrypsinogen with the cleavage of the Arg15-Ile[16] bond.[3]
We report here the search for shorter aspartic protease inhibitors resulting from introducing
The representative synthesis of various inhibitors containing ferrocenyl moiety is outlined in Scheme 1 and 2

Summary

Introduction

Aspartic proteases are involved in many biological pathways in fungi, plants, humans, parasites, retroviruses.[1,2] Aspergillus oryzae aspartic proteinase is found to have activity for the activation of trypsinogen and for the activation of chimotrypsinogen with the cleavage of the Arg15-Ile[16] bond.[3]. The amino compound (1 mmol) was dissolved in DCM (1 mL) and DMF (1 mL). The residue was dissolved in ethyl acetate, washed successively with cold 1 mol L-1 HCl, saturated NaHCO , and saturated NaCl, and dried (MgSO4). Of HCl) was stirred at room temperature and the reaction monitored by TLC. The inhibition of the tested bacteria (Aspergillus oryzae) was determined with the method of dull colony notation.[16] All. HO2C NHBoc compounds tested were dissolved in DMSO (500 μmol) and subsequently diluted in the culture medium before treatment of the suspension of the tested bacteria. The suspension at three concentrations was inoculated on the culture medium treated with compound and incubated at room temperature for 60 h.

Results and Discussion

H Bu-i N NHBoc b

Conclusions

C H FeN O