Synthesis and biological evaluation of 5-fatty-acylamido-1, 3, 4-thiadiazole-2-thioglycosides

Vudhgiri, Srikanth; Koude, Dhevendar; Veeragoni, Dileep K; Misra, Sunil; Prasad, R. B. N.; Jala, Ram Chandra Reddy

doi:10.1016/j.bmcl.2017.06.004

Cited by 38 publications

(12 citation statements)

References 26 publications

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“…Our study demonstrated a higher concentration of gamma-tocopherol in the control group, which is a derivative of vitamin E. Notably, this lipid is important for the vaginal epithelial tissue homeostasis as it acts as a protector against disorders in the local microenvironment, such as the oxidative stress caused by infections and dysbioses. Another antioxidant lipid biomarker found in the control group was myristic acid, which has been described as improving the bioavailability of polar antioxidant molecules in the organism [ 59 ], besides exerting antimicrobial activities [ 60 ].…”

Section: Discussionmentioning

confidence: 99%

Vaginal lipidomics of women with vulvovaginal candidiasis and cytolytic vaginosis: A non-targeted LC-MS pilot study

et al. 2018

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ObjectiveTo characterize the lipid profile in vaginal discharge of women with vulvovaginal candidiasis, cytolytic vaginosis, or no vaginal infection or dysbiosis.DesignCross-sectional study.SettingGenital Infections Ambulatory, Department of Tocogynecology, University of Campinas, Campinas, São Paulo–Brazil.SampleTwenty-four women were included in this study: eight with vulvovaginal candidiasis, eight with cytolytic vaginosis and eight with no vaginal infections or dysbiosis (control group).MethodsThe lipid profile in vaginal discharge of the different study groups was determined by liquid chromatography-mass spectrometry and further analyzed with MetaboAnalyst 3.0 platform.Main outcome measuresVaginal lipids concentration and its correlation with vulvovaginal candidiasis and cytolytic vaginosis.ResultsPCA, PLS-DA and hierarchical clustering analyses indicated 38 potential lipid biomarkers for the different groups, correlating with oxidative stress, inflammation, apoptosis and integrity of the vaginal epithelial tissue. Among these, greater concentrations were found for Glycochenodeoxycholic acid-7-sulfate, O-adipoylcarnitine, 1-eicosyl-2-heptadecanoyl-glycero-3-phosphoserine, undecanoic acid, formyl dodecanoate and lipoic acid in the vulvovaginal candidiasis group; N–(tetradecanoyl)-sphinganine, DL-PPMP, 1-oleoyl-cyclic phosphatidic, palmitic acid and 5-aminopentanoic acid in the cytolytic vaginosis group; and 1-nonadecanoyl-glycero-3-phosphate, eicosadienoic acid, 1-stearoyl-cyclic-phosphatidic acid, 1-(9Z,12Z-heptadecadienoyl)-glycero-3-phosphate, formyl 9Z-tetradecenoate and 7Z,10Z-hexadecadienoic acid in the control group.ConclusionsLipids related to oxidative stress and apoptosis were found in higher concentrations in women with vulvovaginal candidiasis and cytolytic vaginosis, while lipids related to epithelial tissue integrity were more pronounced in the control group. Furthermore, in women with cytolytic vaginosis, we observed higher concentrations of lipids related to bacterial overgrowth.

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Section: Discussionmentioning

confidence: 99%

Vaginal lipidomics of women with vulvovaginal candidiasis and cytolytic vaginosis: A non-targeted LC-MS pilot study

et al. 2018

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“…The most active compound ( 59 ) is presented in Figure 30 . Acylated compounds were less active than compounds with a free hydroxyl group [ 39 ].…”

Section: Derivatives Of 25-disubstituted-134-thiadiazolementioning

confidence: 99%

“…Figure20. The structures of 5-(9-chloro-6,7-dihydro-5H-benzo[7]annulen-8-yl)-2-(N-phenylamino)-1,3,4thiadiazole(38) and 5-(9-chloro-2,3-dimethyl-6,7-dihydro-5H-benzo[7]annulen-8-yl)-2-(N-phenylamino)-1,3,4-thiadiazole(39) Plech et al (2015). reported anticancer activity of a series of 2,5-disubstituted-1,3,4-thiadiazole.…”

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confidence: 99%

Cytotoxic Properties of 1,3,4-Thiadiazole Derivatives—A Review

2020

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“…The synthesis protocol was divided into five steps (Scheme 1). Firstly, 2-amino-5-mercapto-1,3,4-thiadiazole (intermediate 1 ) was obtained according to the previously reported method [24]. Secondly, intermediates 2a – 2p were synthesized from intermediate 1 and various benzyl chlorides via substitution reaction.…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, and Biological Activity of Novel Myricetin Derivatives Containing Amide, Thioether, and 1,3,4-Thiadiazole Moieties

et al. 2018

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A series of myricetin derivatives containing amide, thioether, and 1,3,4-thiadiazole moieties were designed and synthesized, and their antiviral and antibacterial activities were assessed. The bioassays showed that all the title compounds exhibited potent in vitro antibacterial activities against Xanthomonas citri (Xac), Ralstonia solanacearum (Rs), and Xanthomonas oryzae pv. Oryzae (Xoo). In particular, the compounds 5a, 5f, 5g, 5h, 5i, and 5l, with EC50 values of 11.5–27.3 μg/mL, showed potent antibacterial activity against Xac that was better than the commercial bactericides Bismerthiazol (34.7 μg/mL) and Thiodiazole copper (41.1% μg/mL). Moreover, the in vivo antiviral activities against tobacco mosaic virus (TMV) of the target compounds were also tested. Among these compounds, the curative, protection, and inactivation activities of 5g were 49.9, 52.9, and 73.3%, respectively, which were better than that of the commercial antiviral Ribavirin (40.6, 51.1, and 71.1%, respectively). This study demonstrates that myricetin derivatives bearing amide, thioether, and 1,3,4-thiadiazole moieties can serve as potential alternative templates for the development of novel, highly efficient inhibitors against plant pathogenic bacteria and viruses.

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Synthesis and biological evaluation of 5-fatty-acylamido-1, 3, 4-thiadiazole-2-thioglycosides

Cited by 38 publications

References 26 publications

Vaginal lipidomics of women with vulvovaginal candidiasis and cytolytic vaginosis: A non-targeted LC-MS pilot study

Vaginal lipidomics of women with vulvovaginal candidiasis and cytolytic vaginosis: A non-targeted LC-MS pilot study

Cytotoxic Properties of 1,3,4-Thiadiazole Derivatives—A Review

Design, Synthesis, and Biological Activity of Novel Myricetin Derivatives Containing Amide, Thioether, and 1,3,4-Thiadiazole Moieties

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