19749-93-0Relevant articles and documents
Design, synthesis, and biological evaluation of novel 1,3,4-thiadiazole derivatives as potential antitumor agents against chronic myelogenous leukemia: Striking effect of nitrothiazole moiety
Alt?ntop, Mehlika Dilek,Ciftci, Halil Ibrahim,Radwan, Mohamed O.,Sever, Belgin,Kaplanc?kl?, Zafer As?m,Ali, Taha F. S.,Koga, Ryoko,Fujita, Mikako,Otsuka, Masami,Zdemir, Ahmet
, (2018)
In an attempt to develop potent antitumor agents, new 1,3,4-thiadiazole derivatives were synthesized and evaluated for their cytotoxic effects on multiple human cancer cell lines, including the K562 chronic myelogenous leukemia cell line that expresses the Bcr-Abl tyrosine kinase. N-(5-Nitrothiazol-2-yl)-2-((5-((4-(trifluoromethyl)phenyl)amino)-1,3,4-thiadiazol-2-yl)thio)acetamide (2) inhibited the Abl protein kinase with an IC50 value of 7.4 μM and showed selective activity against the Bcr-Abl positive K562 cell line. Furthermore, a Bcr-Abl-compound 2 molecular modelling simulation highlighted the anchoring role of the nitrothiazole moiety in bonding and hydrophobic interaction with the key amino acid residues. These results provide promising starting points for further development of novel kinase inhibitors.
Design, synthesis, and bioassay of 4-thiazolinone derivatives as influenza neuraminidase inhibitors
Xiao, Mengwu,Xu, Lvjie,Lin, Ding,Lian, Wenwen,Cui, Manying,Zhang, Meng,Yan, Xiaowei,Li, Shuishi,Zhao, Jun,Ye, Jiao,Liu, Ailin,Hu, Aixi
, (2021/02/09)
A series of 4-thiazolinone derivatives (D1-D58) were designed and synthesized. All of the derivatives were evaluated in vitro for neuraminidase (NA) inhibitory activities against influenza virus A (H1N1), and the inhibitory activities of the five most pot
Preparation method and application of 2-(4-oxo-thiazoline-2-imino)thiazole-4-acetic acid derivative
-
Paragraph 0035; 0038; 0039, (2016/10/10)
The invention discloses a 2-(4-oxo-thiazoline-2-imino)thiazole-4-acetic acid derivative as shown in the structural formulas I and II, a pharmaceutically acceptable salt thereof, a preparation method thereof, a pharmaceutical composition comprising the derivative and the pharmaceutically acceptable salt of the derivative, as well as application of the derivative to preparation of an influenza virus neuraminidase inhibitor.
Synthesis and in vitro kinetic evaluation of N-thiazolylacetamido monoquaternary pyridinium oximes as reactivators of sarin, O-ethylsarin and VX inhibited human acetylcholinesterase (hAChE)
Valiveti, Aditya Kapil,Bhalerao, Uma M.,Acharya, Jyotiranjan,Karade, Hitendra N.,Acharya, Badri Narayan,Raviraju,Halve, Anand K.,Kaushik, Mahabir Parshad
, p. 4899 - 4910 (2015/08/03)
Presently available medications for treatment of organiphosphorus poisoning are not sufficiently effective due to various pharmacological and toxicological reasons. In this regard, herein we report the synthesis of a series of N-thiazolylacetamide monoquaternary pyridinium oximes and its analogs (1a-1b to 6a-6b) with diversely substituted thiazole ring and evaluation of their in vitro reactivation efficacies against nerve agent (sarin, O-ethylsarin and VX) inhibited human erythrocyte acetylcholinesterase (hAChE). Reactivation kinetics was performed to determine dissociation constant (KD), reactivity rate constant (kr) and the second order rate constant (kr2) for all the compounds and compared their efficacies with commercial antidotes viz. 2-PAM and obidoxime. All the newly synthesized oximes were evaluated for their physicochemical parameters (pKa) and correlated with their respective reactivation efficacies to assess the capability of the oxime reactivator. Three of these novel compounds showed promising reactivation efficacies toward OP inhibited hAChE. Molecular docking studies were performed in order to correlate the reactivation efficacies with their interactions in the active site of the AChE.
Chromophore-linked substrate (CLS405): Probing metallo-β-lactamase activity and inhibition
Makena, Anne,Van Berkel, Sander S.,Lejeune, Clarisse,Owens, Raymond J.,Verma, Anil,Salimraj, Ramya,Spencer, James,Brem, Juergen,Schofield, Christopher J.
, p. 1923 - 1929 (2014/01/06)
Serine- and metallo-β-lactamases present a threat to the clinical use of nearly all β-lactam antibiotics, including penicillins, cephalosporins, and carbapenems. Efforts to develop metallo-β-lactamase (MBL) inhibitors require suitable screening platforms to allow the rapid determination of β-lactamase activity and efficient inhibition. Unfortunately, the platforms currently available are not ideal for this purpose. Further progress in MBL inhibitor identification requires inexpensive and widely applicable assays. Herein the identification of an inexpensive and stable chromogenic substrate suitable for use in assays of clinically relevant MBLs is described. (6R,7R)-3-((4-Nitrophenoxy)methyl)-8-oxo-7-(2-phenylacetamido) -5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 5,5-dioxide (CLS405) was synthesised in a three-step protocol. CLS405 was then characterised spectroscopically, and its stability and kinetic properties evaluated. With a Δλmax value of 100 nm between the parent and hydrolysis product, a higher analytical accuracy is possible with CLS405 than with commonly used chromogenic substrates. The use of CLS405 in assays was validated by MBL activity measurements and inhibitor screening that resulted in the identification of N-hydroxythiazoles as new inhibitor scaffolds for MBLs. Further evaluation of the identified N-hydroxythiazoles against a panel of clinically relevant MBLs showed that they possess inhibitory activities in the mid- to low-micromolar range. The findings of this study provide both a useful tool compound for further inhibitor identification, and novel scaffolds for the design of improved MBL inhibitors with potential as antibiotics against resistant strains of bacteria. Monitoring MBLs! Resistance to β-lactam antibiotics, mediated by metallo-β-lactamases (MBLs), is an increasing clinical problem. While compounds that target MBLs could be useful antibacterial agents, their identification is hampered by the lack of suitable assay platforms. To this end, CLS405, a chromophore-linked MBL substrate, was developed and its applicability demonstrated by the identification of N-hydroxythiazoles as potential inhibitors against a panel of clinically relevant MBLs. Copyright
Synthesis and evaluation of antimicrobial and anticonvulsant activities of some new 3-[2-(5-aryl-1,3,4-oxadiazol-2-yl/4-carbethoxymethylthiazol-2-yl)imino- 4-thiazolidinon-5-ylidene]-5-substituted/nonsubstituted 1H-indole-2-ones and investigation of their
Altintas, Handan,Ates, Oeznur,Uydes-Dogan, B. Soenmez,Alp, F. Ilkay,Kaleli, Deniz,Oezdemir, Osman,Birteksoez, Seher,Oetuek, Guelten,Satana, Dilek,Uzun, Meltem
, p. 239 - 248 (2007/10/03)
In the present study, 20 new compounds having 3-[2-(5-aryl-1,3,4-oxadiazol- 2-yl) imino-4-thiazolidinon-5-ylidene]-5-substituted/nonsubstituted 1H-indole-2-one (I-XII) and 3-[2-(4-carbethoxymethylthiazol-2-yl)imino-4- thiazolidinon-5-ylidene]-5-substitute
Synthesis, characterization and evaluation of antimicrobial activity of Mannich bases of some 2-[(4-carbethoxymethylthiazol-2-yl)imino]-4- thiazolidinones
Altintas, Handan,Ates, Oeznur,Kocabalkanli, Ayse,Birteksoez, Seher,Oetuek, Guelten
, p. 585 - 590 (2007/10/03)
A series of 5-(N,N-disubstituted aminomethyl)-2-[(4- carbethoxymethylthiazol-2-yl)imino]-4-thiazolidinones 4a-m have been synthesized. Their structures are confirmed by elemental analyses and spectral data (IR, 1H NMR, EIMS). The antibacterial activities of the compounds against Staphylococcus aureus ATCC 6538, Staphylococcus epidermidis ATCC 12228, Escherichia coli ATCC 8739, Klebsiella pneumoniae ATCC 4352, Pseudomonas aeruginosa ATCC 1539, Salmonella typhi, Shigella flexneri, Proteus mirabilis ATCC 14153 and antifungal activity against Candida albicans ATCC 10231 are tested using disk diffusion method. Some of the compounds are found to have significant activity against S. aureus ATCC 6538.
Synthesis and antimicrobial activity of 4-phenyl/cyclohexyl-5-(1- phenoxyethyl)-3-[N-(2-thiazolyl)acetamido]thio-4H-1,2,4-triazole derivatives
Turan-Zitouni, Guelhan,Kaplancikli, Zafer Asim,Yildiz, Mehmet Taha,Chevallet, Pierre,Kaya, Demet
, p. 607 - 613 (2007/10/03)
The increasing clinical importance of drug-resistant fungal and bacterial pathogens has lent additional urgency to microbiological research and new antimicrobial compound development. For this purpose, new thiazole derivatives of triazoles were synthesize
Aminothiazole derivatives with antidegenerative activity on cartilage
Panico, Anna Maria,Geronikaki, Athina,Mgonzo, Remi,Cardile, Venera,Gentile, Barbara,Doytchinova, Irini
, p. 2983 - 2989 (2007/10/03)
A series of 2-dialkylamino-N-(4-substituted thiazolyl-2)acetamides and 3-dialkylamino-N-(4-substituted thiazolyl-2)propionamides were synthesized and evaluated for their anti-inflammatory activity. Encouraging results led us to investigate the effect of t
Synthesis and antimicrobial activity of {2-[2-(N,N-disubstituted thiocarbamoyl-sulfanyl)-acylamino]thiazol-4-yl}acetic acid ethyl esters
Ates, Oeznur,Guersoy, Aysel,Altintas, Handan,Oetuek, Guelten,Birteksoez, Seher
, p. 39 - 46 (2007/10/03)
{2-[2-(N,N-Disubstituted thiocarbamoyl-sulfanyl)acylamino]thiazol-4-yl}acetic acid ethyl esters (3 a-x) were synthesized by the reaction of potassium salts of N,N-di-substituted dithiocarbamoic acids with [2-(2-chloroalkanoyl)amino-thiazol-4-yl]acetic acid ethyl esters. The structures of the synthesized compounds were confirmed by elemental analyses, UV, IR, 1H-NMR, and EI mass spectral data. The antimicrobial activities of all the compounds were investigated by microbroth dilution technique using Mueller-Hinton broth and Mueller-Hinton agar. In this study, Staphylococcus aureus ATCC 6538, Staphylococcus epidermidis ATCC 12228, Escherichia coli ATCC 8739, Klebsiella pneumoniae ATCC 4352, Pseudomonas aeruginosa ATCC 1539, Salmonella typhi, Shigella flexneri, Proteus mirabilis ATCC 14153 and Candida albicansATCC 10231 were used as test microorganisms. Among the tested compounds 3 a, d, e, f, h, k, w showed activity against S. epidermidis ATCC 12228 (MIC: 156 mg/L, 78 mg/L, 62.5 mg/L, 78 mg/L, 62.5 mg/L, 312 mg/L, 250 mg/L, respectively), compound 3 d also had some activity against S. aureus ATCC 6538 (MIC: 156 mg/L) and C. albicans ATCC 10231 (MIC: 156 mg/L). Compounds 3 I, 3 x were also evaluated for antituberculosis activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system and BACTEC 12B medium. The preliminary results indicated that all of the tested compounds were inactive against the test organism.