Identification of 4-isopropyl–thiotropolone as a novel anti-microbial: regioselective synthesis, NMR characterization, and biological evaluation

Abstract

We have synthesized and separated tosylated thujaplicin isomers for the first time, and elucidated their structures using 1D, 2D-NMR techniques and X-ray crystallography. The tosylated isomers were used to synthesize 4-isopropyl-thiotropolone and 6-isopropyl-thiotropolone in a regioselective manner. 27853)). 4-Isopropyl-thiotropolone was found to inhibit Staphylococcus aureus in a low micro molar range and exhibit good therapeutic index and ADME properties. This compound can be used for future lead optimization to design inhibitors against Staphylococcus aureus (ATCC 29213).

Carbon Dot-like Molecular Nanoparticles, Their Photophysical Properties, and Implications for LEDs

“…A group of peaks between 110 and 150 ppm shows that the structure of the CMPs is mainly aromatic with pyridinic nitrogen. 22,23 Peaks corresponding to aliphatic carbon are also present in the 13 C NMR spectrum. In addition, the peaks at around 170 and 75 ppm are attributed to carbon having a double and single bond with oxygen, respectively.…”

“…The 13 C NMR spectrum of the CMPs dispersed in dimethyl sulfoxide (DMSO) is presented in Figure b. A group of peaks between 110 and 150 ppm shows that the structure of the CMPs is mainly aromatic with pyridinic nitrogen. , Peaks corresponding to aliphatic carbon are also present in the 13 C NMR spectrum. In addition, the peaks at around 170 and 75 ppm are attributed to carbon having a double and single bond with oxygen, respectively. , An X-ray photoelectron spectroscopy (XPS) survey scan of the CMPs drop-cast from water on the Si substrate confirms that the CMPs contain oxygen (31%) and nitrogen (9%) in addition to carbon (60%); see Figure c.…”

Novel synthesis of benzotriazolyl alkyl esters: an unprecedented CH2 insertion

“…One of our ongoing research programs is to develop tropolones as antibacterial agents. 27,28 While developing aminoacid conjugates of aminotropones 1a, we used acyl benzotriazole as an acylating reagent. Aminotropones were reported to couple with similar acylating reagents such as acid chlorides under conventional reaction conditions.…”

Design, synthesis and biological evaluation of 2-quinolyl-1,3-tropolone derivatives as new anti-cancer agents

“…For example, some of the best-known representatives are colchicine, colchamine and b-thujaplicin (hinokitiol), which have antitumor, antibacterial, antiviral, antifungal, anti-inammatory and antioxidant properties. [10][11][12] In particular, high anti-bacterial and anti-inammatory effects of natural alkaloids cordytropolone and stipitalide against Propionibacterium acnes have been recently shown. 13 3-Isopropenyl-tropolone has high activity against antibiotic-resistant bacteria Staphylococcus aureus, 14 while hinokitiol was effective against MRSA, Aggregatibacter actinomycetemcomitans, Streptococcus mutans, and Candida albicans.…”