43009-17-2Relevant academic research and scientific papers
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.
p-Aromatic Isothiocyanates: Synthesis and Anti Plant Pathogen Activity
Tang,Niu,Wang,Huo,Li,Luo,Cao
, p. 1252 - 1257 (2018/08/16)
In this study, a series of p-aromatic isothiocyanates are prepared by reacting p-aromatic amines with carbon disulphide and further treating with molecular iodine to yield corresponding isothiocyanate derivatives. The structures of newly synthesized compounds are confirmed by IR, NMR, and MS data. Activity of the products against plant pathogenic fungi and bacteria is tested and the structure-activity relationship is approached. p-Nitrophenyl isothiocyanate most efficiently inhibits Rhizoctonia solani and Erwinia carotovora. The order of seven aromatic isothiocyanates antifungicidal activity is following: p-nitrophenyl > p-methoxyphenyl > p-chlorophenyl > p-methylphenyl > p-ethylphenyl > phenyl > p-fluorophenyl. For antibacterial activity, the order was p-nitrophenyl > p-chlorophenyl > p-methylphenyl > p-ethylphenyl > p-fluorophenyl > phenyl > p-methoxyphenyl. The present study indicates that some of the compounds exhibit promising antimicrobial activity and can be used as an alternative to the traditional synthetic fungicides for controlling R. solani and E. carotovora.
Na2S2O8-mediated efficient synthesis of isothiocyanates from primary amines in water
Fu, Zhicheng,Yuan, Wenhao,Chen, Ning,Yang, Zhanhui,Xu, Jiaxi
, 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.
Copper promoted desulfurization towards the synthesis of isothiocyanates
Mandapati, UshaRani,Pinapati, Srinivasarao,Rudraraju, RameshRaju
supporting information, p. 125 - 128 (2016/12/26)
The cheap, readily available and air stable catalyst was used as the desulfurization agent for the conversion of aniline to isothiocyanates in one pot two step reaction under mild reaction conditions.
Synthesis and supramolecular self-assembly of thioxothiazolidinone derivatives driven by H-bonding and diverse π–hole interactions: A combined experimental and theoretical analysis
Andleeb, Hina,Khan, Imtiaz,Bauzá, Antonio,Tahir, Muhammad Nawaz,Simpson, Jim,Hameed, Shahid,Frontera, Antonio
, p. 209 - 221 (2017/03/22)
Two new 3-aryl-5-(4-nitrobenzylidene)-2-thioxothiazolidin-4-one derivatives (1 & 2) were synthesized by the Knoevenagel condensation reaction of 3-(4-aryl)-2-thioxo-1,3-thiazolidin-4-ones with 4-nitrobenzaldehyde. Both products were isolated as orange cry
Double three bromo 1,3-di-pyridine salt-based propane and its preparation method, method of use, recovery method and application
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Paragraph 0207; 0208; 0209, (2016/10/07)
The invention discloses a double tribromo 1,3-bipyridine onium salt dimethylmethane, and a preparation method, an application method, a recovery method and application thereof. The preparation method comprises the following steps: dissolving 1,3-bipyridine onium salt dimethylmethane by using water, and then adding potassium bromide; adding potassium peroxymonosulfate sulfate compound brine solution to prepare a clear solution after dissolving potassium bromide, and then stirring and reacting at -10 to 0 DEG C until solid is separated out; separating out solid, so as to obtain the double tribromo 1,3-bipyridine onium salt dimethylmethane. The product can be used for preparing isothiocyanate, aromatic thiourea or acetanilide. The preparation method disclosed by the invention is mild in condition, and simple to operate the reaction process, and raw materials are easily available. The double tribromo 1,3-bipyridine onium salt dimethylmethane not only can be used as a brominating reagent, but also can be used as organic synthesis intermediates, meanwhile, the reaction efficiency is improved, and the double tribromo 1,3-bipyridine onium salt dimethylmethane is convenient to recover and can be recycled.
Identification of novel pyrazole-rhodanine hybrid scaffolds as potent inhibitors of aldose reductase: Design, synthesis, biological evaluation and molecular docking analysis
Andleeb, Hina,Tehseen, Yildiz,Ali Shah, Syed Jawad,Khan, Imtiaz,Iqbal, Jamshed,Hameed, Shahid
, p. 77688 - 77700 (2018/06/22)
In an effort to develop a new class of potent aldose reductase inhibitors, a series of 1,3-diarylpyrazole assimilated 3-substituted 4-oxo-2-thioxo-1,3-thiazolidines (9a-n) was designed, and synthesized in good to excellent yields by a pharmacophore integr
"On water": Efficient iron-catalyzed cycloaddition of aziridines with heterocumulenes
Sengoden, Mani,Punniyamurthy, Tharmalingam
supporting information, p. 572 - 575 (2013/02/23)
In suspension: The reaction of aziridines with heterocumulenes in the presence of Fe(NO3)3×9 H2O in aqueous suspension provides access to functionalized five-membered heterocycles in good to high yields. This protocol has a wide substrate scope, is simple, and uses a nontoxic and cheap catalyst. Copyright
Microwave-assisted cyclocondensation for the synthesis of 3-Aryl-2-thioquinazolin-4(3h)-ones
Patil, Suresh,Jadhav,Shejwal,Deshmukh
scheme or table, p. 1858 - 1860 (2012/08/13)
An efficient synthesis of 3-aryl-2-thioquinazolin-4(3H)-one 1a-f is given by the condensation of anthranilic acid and dithiocarbamate triethylammonium salts of substituted aniline in ethanol as solvent under microwave irradiation.
Synthesis and biological evaluation of dihydroisoquinoline-2(1H)- carbothioamide derivatives as TRPV1 antagonists
Qian, Hai,Chen, Wei,Zhang, Xiaoyan,Zhang, Huibin,Zhou, Jinpei,Huang, Wenlong,Jin,Dai, Dongyan
scheme or table, p. 235 - 237 (2011/03/18)
TRPV1 receptor is an important analgesia target. Its antagonists are expected to prevent pain perception by blocking the receptor directly. In this letter, eight dihydroisoquinoline-2(1H)-carbothioamide derivatives were designed and synthesized as TRPV1 antagonists. The benzene ring was modified with different substitutional groups. Preliminary biological tests suggested that the new compounds exhibited TRPV1 antagonist activity and different analgesia effects, some of which were promising as analgesia drugs.
