Some Hydrazones of 2‐Aroylamino‐3‐methylbutanohydrazide: Synthesis, Molecular Modeling Studies, and Identification as Stereoselective Inhibitors of HIV‐1

Abstract

In accordance with our antiviral drug development attempt, acylhydrazone derivatives bearing amino acid side chains were synthesized for the evaluation of their antiviral activity against various types of viruses. Among these compounds, 8(S) , 11(S) , and 12(S) showed anti-HIV-1 activity with a 50% inhibitory concentration (IC(50)) =123.8 µM (selectivity index, SI>3), IC(50) =12.1 µM (SI>29), IC(50) =17.4 µM (SI>19), respectively. Enantiomers 8(R) , 11(R) , and 12(R) were inactive against the HIV-1 strain III(B) . Hydrazones 8(S) , 11(S) , and 12(S) which were active against HIV-1 wild type showed no inhibition against a double mutant NNRTI-resistant strain (K103N;Y181C). Molecular docking calculations of R- and S-enantiomers of 8, 11, and 12 were performed using the hydrazone-bound novel site of HIV-1 RT.

Volatiles and fatty acid analyzes of Tripleurospermum decipiens (Fisch & C. A. Mey) Bornm and investigation of the extracts for antimicrobial and enzyme inhibitory activities

“…Herbal remedies have been considered as a dietary supplement for disease prevention and used as complementary medicine [1]. In this scope, increasing evidence and knowledge on their potential benefits have highlighted the demand for herbal products [2]. These products were reported for potential against bacterial infections, cancer [3][4][5], neurodegenerative disorders, as well as prevention of diabetes [6], and cardiovascular diseases [7].…”

“…α-Glucosidase and amylase are key enzymes that catalyze hydrolysis of carbohydrates to glucose monomers. In this case, glucosidase and -amylase inhibitor drugs reduce blood glucose levels and use in the treatment of DM [12][13]. Natural or synthetic drugs have been used to treat high blood glucose levels.…”

“…of the relationship between Alzheimer's and diabetes has not been fully revealed, a lot of factors play a role which includes genetic factors, lifestyle, socioeconomic causes, cardiovascular diseases, inflammation, diabetes, insulin resistance, and it is thought to affect different pathological processes [8][9][10].…”

“…Ethnobotanical uses of Tripleurospermum species are summarized in Table 1. Phytochemical investigations on Tripleurospermum species have generally been focused on essential oil content [20][21][22][23][24]. A summary of previous studies on essential oil chemical composition of Tripleurospermum species is reported in Table 2.…”

“…A summary of previous studies on essential oil chemical composition of Tripleurospermum species is reported in Table 2. In general, β-farnesene (22.5%), β-sesquiphellandrene (17.9%) [21], neryl acetate (12.8%), (E)-β-farnesene (12.5%), phytol (12.1%) [24], globulol (13.5%) and sesquiphellandrene (9.3%) [25]; (Z)-β-farnesene (18.2%), 1-epi-cubenol (16.1%) [22] were reported as common volatiles compounds while dioxoipran derivative [26] and flavonoids were detected as non-volatile constituents in the extracts [27]. Fatty acid compounds of Tripleurospermum species are summarized in Table 3.…”