Abstract
We describe the microwave-assisted synthesis of thirteen functionalized peptoids and evaluate their in vitro antileishmanial activity against forms of Leishmania (Leishmania) amazonensis promastigotes. Synthesis via the Ugi four-component reaction (Ugi 4CR) reaction furnished the compounds of interest in 55-80% yield; reactions were conducted in a microwave reactor and lasted only 10 min. We then screened the antileishmanial activity of the synthesized compounds in vitro. To determine the IC50 (inhibitory concentration necessary to inhibit the growth of 50% of parasites) values, we selected the compounds that inhibited L. (L.) amazonensis growth by more than 50%. The seven selected compounds displayed IC50 values ranging from 2.6 to 72 µM after incubation for 48 h. Three peptoids gave IC50 values between 2.6 and 7.9 µM and can be considered as bioreactive molecules (hit criteria).
Highlights
Protozoan parasites of the Leishmania genus cause a group of diseases known as leishmaniasis, a parasitosis that is transmitted by the bite of infected female phlebotomine sandflies in tropical and subtropical countries.[1]
The infection manifests in three main typical ways: cutaneous leishmaniasis (LC), which presents skin lesions, mostly ulcers, on exposed body parts, leading to life-long scars and serious disability; mucocutaneous leishmaniasis (MCL), which partially or totally destroys mucous membranes; and visceral leishmaniasis (LV), which may be lethal if left untreated.[1,2,3]
When we compared the percentage of L. (L.) amazonensis promastigote growth inhibition by the peptoids 5a-m (Table 2), we observed that the antileishmanial activity decreased when a benzenoid aromatic ring was replaced by a furan ring, as in the case of compounds 5a and 5k
Summary
Protozoan parasites of the Leishmania genus cause a group of diseases known as leishmaniasis, a parasitosis that is transmitted by the bite of infected female phlebotomine sandflies in tropical and subtropical countries.[1]. These non-natural molecules are being increasingly investigated because they are easy to synthesize, and various functionalities can be incorporated into their amide side-chains, which may generate new compounds with several biological activities and interesting pharmaceutical properties.[9,10,11,12]
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