51034-34-5Relevant academic research and scientific papers
Enantioselective synthesis of 3,5-disubstituted thiohydantoins and hydantoins
Chen, Yu,Su, Li,Yang, Xinying,Pan, Wenyan,Fang, Hao
, p. 9234 - 9239 (2015)
A mild method to convert optically pure amino acid thiourea and urea derivatives to thiohydantoins and hydantoins, respectively, is described. It provides an efficient way to realize enantioselective synthesis of thiohydantoins and hydantoins with good to high isolated yields and enantiomeric purities. We found that the enantiomeric purities were highly dependent on the reaction conditions including bases, solvents, and temperature.
Dithiocarbamates combined with copper for revitalizing meropenem efficacy against NDM-1-producing Carbapenem-resistant Enterobacteriaceae
Chen, Cheng,Yang, Ke-Wu,Zhai, Le,Ding, Huan-Huan,Chigan, Jia-Zhu
supporting information, (2021/11/20)
The worldwide prevalence of NDM-1-producing Gram-negative pathogens has drastically undermined the clinical efficacy of carbapenems, prompting a need to devise an effective strategy to preserve their clinical value. Here we constructed a focused compound library of dithiocarbamates and systematically evaluated their potential synergistic antibacterial activities combined with copper. SA09-Cu exhibited excellent inhibition against a series of clinical NDM-1-producing carbapenem-resistant Enterobacteriaceae (CRE) in restoring meropenem effect, and slowed down the development of carbapenem resistance. Enzymatic kinetic and isothermal titration calorimetry studies demonstrated that SA09-Cu was a noncompetitive NDM-1 inhibitor. The electron paramagnetic resonance (EPR) and X-ray photoelectron spectroscopy (XPS) revealed a novel inhibition mechanism, which is that SA09-Cu could convert NDM-1 into an inactive state by oxidizing the Zn(II)-thiolate site of the enzyme. Importantly, SA09-Cu showed a unique redox tuning ability, and avoided to be reduced by intracellular thiols of bacteria. In vivo experiments indicated that SA09 combined with CuGlu could effectively potentiate MER's effect against NDM-1-producing E. coli (EC23) in the murine infection model. This study provides a highly promising scaffold in developing novel inhibitors to combat NDM-1-producing CREs.
An efficient one-pot strategy for the synthesis of 4- methylene-2-thiazolidinethiones in water
Hou, Chang-Long,Wei, Mei-Hong,Chen, Li-Li,Liu, Xiao-Ling,Sheng, Shou-Ri
, p. 1561 - 1566 (2020/04/09)
A simple and efficient, one-pot strategy for the preparation of 4-methylene-2-thiazolidinethiones has been developed. This protocol involved condensation of primary amines with carbon disulfide in water to generate the dithiocarbamate salts in situ, which coupled with 2,3-dibromopropene, followed by intramolecular cyclization to the corresponding heterocycles in moderate to good yields.
Novel 1,3,5-thiadiazine-2-thione derivatives containing a hydrazide moiety: Design, synthesis and bioactive evaluation against phytopathogenic fungi in vitro and in vivo
Wang, Xiaobin,Fu, Xincan,Chen, Min,Wang, An,Yan, Jinghua,Mei, Yudong,Wang, Mengqi,Yang, Chunlong
supporting information, p. 1419 - 1422 (2019/04/10)
A series of novel 1,3,5-thiadiazine-2-thione derivatives bearing a hydrazide moiety were designed, synthesized and evaluated for their antifungal activities against Rhizoctonia solani (Rs), Fusarium graminearum (Fg), Botrytis cinerea (Bc) and Colletotrichum capsici (Cc). The in vitro antifungal bioassays indicated that most of title compounds displayed good selectivity and specificity aganist Rs relative to Fg, Bc and Cc. Strikingly, the title compound N'-(4-chlorophenyl)-2-(5-phenyl-6-thioxo-1,3,5-thiadiazinan-3-yl)acethydrazide (5b) obviously inhibited the Rs growth in vitro with the EC50 value of 0.24 μg/mL, which is approximately 2-folds more effective than the commercialized fungicide carbendazim (0.55 μg/mL). The in vivo anti-Rs effects of title compound 5b were further evaluated on rice leaves with control efficacies of 98.58% at 200 μg/mL and 61.27% at 100 μg/mL. The above researches provide a significant reference for the further structural optimization of 1,3,5-thiadiazine-2-thione derivatives bearing a hydrazide moiety as potential fungicides.
Synthesis, in vitro urease inhibitory activity and molecular docking of 3,5-disubstituted thiadiazine-2-thiones
Shah, Muhammad Ishaq Ali,Khan, Rasool,Arfan, Mohammad,Wadood, Abdul,Ghufran, Mehreen
, p. 3073 - 3080 (2019/09/16)
A series of 3,5-disubstituted-tetrahydro-thiadiazine-2-thione (1-16) have been synthesized, characterized by elemental analysis, infrared (IR), UV-visible, 1H NMR, 13C NMR, and MS spectroscopic techniques, and screened against jack bean urease. Among 16 compounds, compounds (1), (2), (3), (4), (6), (7), and (9) demonstrated excellent urease inhibitory activity with IC50 values (9.8?±?0.5, 11.0?±?0.6, 16.0?±?1.5, 17.2?±?0.5, 15.4?±?0.5, 19.7?±?0.4, and 15.8?±?0.2μM), respectively, even better than the standard thiourea (IC50?=?21?±?0.01μM). However, compound (8) shows an almost same level of inhibition (IC50?=?22.9?±?0.3μM), as like standard. In this work, we reported for the first time urease inhibitory activity of thiadiazine thiones and its molecular docking studies.
Na2S2O8-mediated efficient synthesis of isothiocyanates from primary amines in water
Fu, Zhicheng,Yuan, Wenhao,Chen, Ning,Yang, Zhanhui,Xu, Jiaxi
supporting information, p. 4484 - 4491 (2018/10/17)
We have developed two green, practical, and efficient procedures, including a one-pot one, to synthesize isothiocyanates from amines and carbon disulfide via desulfurization with sodium persulfate. Water is used as the solvent. Basic conditions are necessary for good chemoselectivity for isothiocyanates. Structurally diverse linear and branched alkyl amines and aryl amines are readily converted to isothiocyanates by the two procedures in satisfactory yields. Halogens, benzylic C-H bonds, methylthio, nitro, ester, alkenyl, electron-rich or -deficient (hetero)aryls, acetylenyl, and even phenolic and alcoholic hydroxyls are well tolerated. The one-pot procedure in water can also be used to realize the preparation of chiral isothiocyanates from chiral amines, and the modification of bioactive structures with free amino groups. In large-scale preparation, simple and practical purification procedures independent of column chromatography are developed.
NOVEL FLAVONE BASED EGFR INHIBITORS AND PROCESS FOR PREPARATION THEREOF
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Page/Page column 13, (2016/09/22)
The present invention discloses a novel EGFR inhibitor compound of formula (1), process for preparation thereof and methods of treating abnormal cell growth in mammals by administering the compounds of formula (1). wherein, R is selected from hydrogen, alkyl, nitro, halogens such as chlorine, bromine, fluorine and iodine; Rl= hydrogen, alkyl, alkoxy, aryl, nitro, halogens such as chlorine, bromine, fluorine and iodine, trifluoromethyl, thioalkyl, trifluromethoxy, trialkylsilyl.
Synthesis and antimicrobial activities of 2-thione-3-substituted-5-(4-carboxycyclohexyl-methyl)-tetrahydro-2H-1, 3, 5-thiadiazine derivatives
?z?elik, Azime Berna,Yilmaz, Günseli,?zkan, Semiha,Ersan, Seyhan
, p. 1059 - 1064 (2016/07/15)
(Formula Presented) In this study, 3-substituted-5-(4-carboxycyclohexyl-methyl)-tetrahydro-2H-1, 3, 5-thiadiazine-2-thione which have phenylethyl (1), octyl (2), cyclopropyl (3), 4-methoxybenzyl (4), phenyl (5) groups in position 3 have been synthesized and examined for antimicrobial activities. Their structures were elucidated by spectral method. Antibacterial activities of these compounds against Gram-positive bacteria (Staphylococcus aureus ATCC 29213, Enterococcus faecalis ATCC 29212), gram-negative bacteria (Escherichia coli ATCC 2592, Pseudomonas aeruginosa ATCC 27853) and yeast-like fungi (Candida albicans ATCC 10231, Candida parapsilosis ATCC 90018) were investigated by the micro-dilution method and compared with the activity of sulbentine, ciprofloxacin and flucanozole. By this way their minimal inhibitory concentration (MIC) values were determinated. Compounds 1-4 exhibited almost equally potent activity against Staphylococcus aureus ATCC 29213 (MIC: 31.2 μg/mL). Compounds 1, 3, 4 showed similar antibacterial activity against Enterococcus faecalis ATCC 29212) (MIC: 62.5 μg/mL). None of the compounds exhibited activity against Gram-negative bacteria. On the other hand, all compounds had potent antifungal activities against the yeast utilized. Compounds 1-4 displayed significant antifungal activity against Candida parapsilosis ATCC 90018 at 7.8 μg/mL concentration while sulbentine was active at 125 μg/mL. Among the synthesized compounds, 3-cyclopropyl-5-(4-carboxycyclohexyl-methyl)-tetrahydro-2H-1, 3, 5-thiadiazine-2-thione(3) seems to be the most effective compound with antibacterial and antifungal activity.
Structure-activity studies of 4-phenyl-substituted 2′-benzoylpyridine thiosemicarbazones with potent and selective anti-tumour activity
Lukmantara, Adeline Y.,Kalinowski, Danuta S.,Kumar, Naresh,Richardson, Des R.
, p. 6414 - 6425 (2013/09/23)
2′-Benzoylpyridine thiosemicarbazones (BpT) are effective iron chelators and display potent anti-proliferative activity against tumour cells. In order to gain greater insight into the structure-activity relationships of the BpT chelators, ten new analogue
5-Nitrofuran-2-yl derivatives: Synthesis and inhibitory activities against growing and dormant mycobacterium species
Sriram, Dharmarajan,Yogeeswari, Perumal,Dhakla, Prathiba,Senthilkumar, Palaniappan,Banerjee, Debjani,Manjashetty, Thimmappa H.
body text, p. 1152 - 1154 (2009/08/07)
Eighteen 5-nitrofuran-2-yl derivatives were prepared by reacting 5-nitro-2-furfural with various (sub)phenyl/pyridyl thiosemicarbazide using microwave irradiation. The compounds were tested for their in vitro activity against tubercular and various non-tubercular mycobacterium species in log-phase and 6-week-starved cultures. Compound N-(3,5-dibromopyridin-2-yl)-2-((5-nitrofuran-2-yl)methylene)hydrazinecarbothioamide (4r) was found to be the most potent compound (MIC: 0.22 μM) and was 3 times more active than standard isoniazid (INH) and equally active as rifampicin (RIF) in log-phase culture of Mycobacterium tuberculosis H37Rv. In starved M. tuberculosis H37Rv, 4r inhibited with MIC of 13.9 μM and was found to be 50 times more active than INH and slightly more active than RIF.
