- Design, synthesis and bioactivity evaluation of novel pyrazole linked phenylthiazole derivatives in context of antibacterial activity
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Methicillin-resistant Staphylococcus aureus (MRSA) infections are a significant burden both clinically and economically worldwide. Increasing resistance to current antibiotics requires an urgent investigation into novel classes of antimicrobial agents. This study presents a structure–activity relationship (SAR) rationale for pyrazole linked phenylthiazole analogues as new antibacterial agents. A library of 23 novel pyrazole linked phenylthiazole compounds were synthesised, followed by screening for antimicrobial activity against five bacterial species and two fungi. The most active compound 14b has shown promising antibacterial activity against the Gram-positive methicillin-resistant Staphylococcus aureus (MRSA, ATCC 43300) strain (MIC 4 μg/mL). Furthermore, the active pyrazole linked phenylthiazole compound exhibited a better toxicity profile than standard antibiotics. In summary, these results demonstrate that a pyrazole linked phenylthiazole scaffold has potential as a lead for further investigation to afford novel antibacterial agents.
- Patel, Bhautikkumar,Zunk, Matthew,Grant, Gary,Rudrawar, Santosh
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- A efficient protocol for the synthesis of thioamides in [DBUH][OAc] at room temperature
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A novel, simple and eco-friendly method to synthesize thioamides from aryl nitriles and sodium sulfide (Na2S·9H2O) catalyzed by 1,8-diazabicyclo[5,4,0]undec-7-enium acetate ([DBUH][OAc]) ionic liquid (IL) at room temperature was developed in this paper. In this reaction, readily available inorganic salt (Na2S·9H2O) serves as the sulfur source, and various functional groups of aryl nitriles were well tolerated at room temperature. In addition, the products were easily separated from the IL which could be reused at least five times without considerable loss of its activity and applied in the green, concise synthesis of ethionamide.
- Cao, Xian-Ting,Qiao, Li,Zheng, Hui,Yang, Hui-Yong,Zhang, Peng-Fei
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p. 170 - 175
(2018/01/17)
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- A simple method for synthesis of thioamides and application in synthesis of 1,2,4-thiadiazoles
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A novel, simple protocol is disclosed for the synthesis of 1,2,4-thiadiazoles starting from thioamides with Na2-eosin Y-sensitized titanium dioxide as catalyst through visible light irradiation (7 W blue LED light) and only 0.3 mol% catalysts were used. The raw material thioamides is prepared by aryl nitriles and sodium sulfide (Na2S9H2O) in DMF and in this reaction, readily available, inexpensive inorganic salt (Na2S9H2O) serves as the sulfur source and various functional groups of aryl nitriles were well and thioamides were synthesized successfully in gram-scale.
- Cao, Xian Ting,Yang, Huiyong,Zheng, Hui,Zhang, Pengfei
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p. 509 - 517
(2018/03/27)
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- Discovery and characterization of potent thiazoles versus methicillin- and vancomycin-resistant Staphylococcus aureus
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Methicillin- and vancomycin-resistant Staphylococcus aureus (MRSA and VRSA) infections are growing global health concerns. Structure-activity relationships of phenylthiazoles as a new antimicrobial class have been addressed. We present 10 thiazole derivatives that exhibit strong activity against 18 clinical strains of MRSA and VRSA with acceptable PK profile. Three derivatives revealed an advantage over vancomycin by rapidly eliminating MRSA growth within 6 h, and no derivatives are toxic to HeLa cells at 11 μg/mL.
- Mohammad, Haroon,Mayhoub, Abdelrahman S.,Ghafoor, Adil,Soofi, Muhammad,Alajlouni, Ruba A.,Cushman, Mark,Seleem, Mohamed N.
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supporting information
p. 1609 - 1615
(2014/03/21)
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- ANTIMICROBIAL SUBSTITUTED THIAZOLES AND METHODS OF USE
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Disclosed are compositions having activity against MRSA and/or VRSA, and methods of using the compositions to treat microbial infections.
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Paragraph 0061
(2014/05/08)
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- One-step conversion of alcohols into thioesters
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A one-step conversion of alcohols into thioesters under solvent-free conditions is reported. The alcohols were reacted with primary thioamides in the presence of p-toluenesulfonic acid under solvent-free conditions to produce the corresponding thioesters in good to excellent yields. Georg Thieme Verlag Stuttgart - New York.
- Boeini, Hassan Zali,Mobin, Mehdi
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supporting information; experimental part
p. 2861 - 2866
(2011/02/16)
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- Modulators of peroxisome proliferator activated receptors
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The present invention is directed to compounds represented by Structural Formula I and pharmaceutically acceptable salts, solvates and hydrates thereof, and methods of making, methods of using and pharmaceutical compositions having compounds represented b
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- Alternative synthesis of dibenzo-and dipyrido-[1,3]diazepines from thioamides and o,o'-diaminobiaryls
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Thioamides were treated with iodomethane, and then o,o'-diaminobiphenyl or bipyridyl to afford 6-substituted-5H-dibenzo- or dipyrido [1,3]diazepines in good yields.
- Matsuda, Koyo,Yanagisawa, Isao,Isomura, Yasuo,Mase, Toshiyasu,Shibanuma, Tadao
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p. 2393 - 2402
(2007/10/03)
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- Syntheses and selective inhibitory activities of terphenyl-bisamidines for serine proteases
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Biphenyl nitriles 5a-c, terphenyl dinitriles 11a-d, and naphthalene-bis(benzonitrile) 11e were prepared by palladium-catalyzed cross coupling reactions and subsequently converted to biphenyl amidines 8a-c and bis(benzamidines) 4a-e. Among the biphenyl amidines 8 only the meta-derivative 8b inhibits factor Xa and trypsin (K(i) = 10 μM). The terphenyl bisamidine 4c does not inhibit factor Xa, trypsin, thrombin, and plasmin, while 4a and 4d are almost equipotent inhibitors of theses enzymes (K(i) 1-6 μM), and 4b and 4e are selective for trypsin (K(i) = 0.2 and 0.3 μM; but K(i) > 1 μM for factor Xa, thrombin, and plasmin). X-ray analysis of crystals of 4b complexed with bovine trypsin revealed a unique binding mode: one benzamidino group binds in the S1 site to the side chain carboxylate of Arg 189. The central phenyl group is twisted away from the S2/S3 sites and the second amidino group contacts the Asn 143 side chain.
- Von Der Saal, Wolfgang,Engh, Richard A.,Eichinger, Andreas,Gabriel, Bernhard,Kucznierz, Ralf,Sauer, Juergen
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