Effect of 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole-5-carboxhydrazides on photosynthetic processes

Katarína Kráľová,Renata Gašparová,Martin Moncman

doi:10.36547/nbc.1367

Abstract

A new series of carboxhydrazides 6-8 was synthesized under microwave irradiation by reaction of carboxhydrazide 1 with heterocyclic aldehydes 2-4 in the presence of p-toluenesulfonic acid in ethanol. N-Benzoylcarboxhydrazide 9 was prepared by reaction of 1 with benzoylchlorid 5 in THF at room temperature. The effects of 6-9 on inhibition of photosynthetic electron transport in spinach chloroplasts and chlorophyll content in the antialgal suspensions of Chlorella vulgaris were investigated.

Highlights

Carboxhydrazides and their derivatives represent an interesting class of compounds which exhibits antimicrobial (EL-SHAAER et al, 1998), antifungal (DUTTA et al, 1986), analgesic and anti-inflammatory (SANTOS et al, 1997) activities
The present study is a follow-up paper to our previous research dealing with the synthesis and reactions of furo[3,2-b]pyrrole system and the study of its biological activity (GAŠPAROVÁ et al, 2005; MONCMAN, 2006)
The photosynthetic electron transport (PET)-inhibitory activity of the compounds studied was expressed in term of IC50 values as their negative logarithms corresponding to molar concentrations of inhibitors causing a 50% decrease of oxygen evolution rate (OER) with respect to the untreated control sample

Summary

Introduction

Carboxhydrazides and their derivatives represent an interesting class of compounds which exhibits antimicrobial (EL-SHAAER et al, 1998), antifungal (DUTTA et al, 1986), analgesic and anti-inflammatory (SANTOS et al, 1997) activities. The presence of trifluoromethyl group in the molecule leads often to the biologically active compounds. Many heterocycles bearing the trifluoromethyl group possess antiprotozoal (NAVARRETE-VAZQUEZ et al, 2006), antimalarial (MADRID et al, 2005) or antibacterial (WOLFART et al, 2004) activities. 5-Substituted furan-2-carboxaldehydes and some of their derivatives show antibacterial (SHINDHAR et al, 1980) or antiviral (SHIGETAKA et al, 1970) activities. The present study is a follow-up paper to our previous research dealing with the synthesis and reactions of furo[3,2-b]pyrrole system and the study of its biological activity (GAŠPAROVÁ et al, 2005; MONCMAN, 2006)

General procedure for synthesis of 6-8

Synthesis of 9

Study of chlorophyll content in Chlorella vulgaris

Results and discussion

Conclusions