50772-59-3

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InChI:InChI=1/C5H4ClN3O3S/c6-1-3(10)8-5-7-2-4(13-5)9(11)12/h2H,1H2,(H,7,8,10)

Upstream product

• 121-66-4 2-amino-5-nitro-1,3-thiazole 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 1228763-97-0 (Z)-2-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)-N-(5-nitrothiazol-2-yl)acetamide 

Relevant academic research and scientific papers

Antitrypanosomal activity of 5-nitro-2-aminothiazole-based compounds

A small series of 5-nitro-2-aminothiazole-based amides containing arylpiperazine-, biphenyl- or aryloxyphenyl groups in their core were synthesized and evaluated as antitrypanosomatid agents. All tested compounds were active or moderately active against T

The synthesis of novel hybrid compounds containing 5-nitrothiazole moiety as potential antiparasitic agents

A number of novel compounds containing 5-nitrothiazole moiety as potential antiparasitic agents have been synthesized through known chemical routes. The structures of the new compounds were confirmed by spectroscopic techniques, 1H NMR, 13C NMR, and mass spectrometry, and by elemental analyses. The prepared compounds were evaluated in vitro for their antigiardial and antitrichomonal activities. All tested compounds exhibited remarkable antigiardial activity with IC50 values ranging from 2.2 to 6.9 μg/cm3 as compared to the reference drug metronidazole (IC50 = 7.3 μg/cm3). In addition, three of the prepared compounds exhibited significant antitrichomonal activity with IC50 values of 4.3, 5.0, and 7.9 μg/cm3, respectively, as compared to the reference drug metronidazole (8.5 μg/cm3). Graphical abstract: [Figure not available: see fulltext.]

An extensive research on aldose reductase inhibitory effects of new 4H-1,2,4-triazole derivatives

Aldose reductase (AR) is a key enzyme, which triggers the excessive accumulation of sorbitol in insulin independent tissues leading to severe diabetes-induced microvascular complications. Substantial evidence has proven that AR inhibition is a well-establ

Benzylidene thiazolidinediones: Synthesis, in vitro investigations of antiproliferative mechanisms and in vivo efficacy determination in combination with Imatinib

Thiazolidinedione (TZD) has been an interesting scaffold due to its proven antidiabetic activity and encouraging findings in anticancer drug discovery. We synthesised benzylidene thiazolidinedione derivatives which exhibited excellent antiproliferative effects in chronic myeloid leukemic cells K562 and the most active compounds 3t and 3x had GI50 value of 0.9 and 0.23 μM respectively. Both the compound was found to arrest the growth of K562 cells in G0/G1 phase in a time and dose dependent manner. Further, western blot analysis revealed that 3t and 3x could also inhibit the expression of cell proliferation markers, PCNA and Cyclin D1 and compound 3x up-regulated apoptosis markers, cleaved PARP1 and activated caspase 3, which could be a possible mechanism for the excellent antiproliferative effects exhibited by these compounds. In vitro combination studies of 3t and 3x with Imatinib found to potentiate the antitumor effects of Imatinib. Further in vivo efficacy in K562 xenografts, of 3t and 3x alone and in combination with Imatinib was found to be promising and far better than control group and combination treatment was found to be more effective as compared to only Imatinib treated or test compound treated animals. Thus, our findings suggest that these compounds are promising antitumor agents and could help to enhance the anticancer effects of Imatinib and other tyrosine kinase inhibitors, when used in combination.

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

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, in vitro and in silico evaluation of a new series of oxadiazole-based anticancer agents as potential Akt and FAK inhibitors

In the current work, new 1,3,4-oxadiazole derivatives were synthesized and investigated for their cytotoxic effects on A549 human lung adenocarcinoma, C6 rat glioma and NIH/3T3 mouse embryonic fibroblast cell lines. Compounds 2, 6 and 9 were found to be the most potent anticancer agents against A549 and C6 cell lines and therefore their effects on apoptosis, caspase-3 activation, Akt, FAK, mitochondrial membrane potential and ultrastructural morphological changes were evaluated. N-(5-Nitrothiazol-2-yl)-2-[[5-[((5,6,7,8-tetrahydronaphthalen-2-yl)oxy)methyl]-1,3,4-oxadiazol-2-yl]thio]acetamide (9) increased early and late apoptotic cell population in A549 and C6 cells more than cisplatin and caused more mitochondrial membrane depolarization in both cell lines than cisplatin. On the other hand, N-(6-methoxybenzothiazol-2-yl)-2-[[5-[((5,6,7,8-tetrahydronaphthalen-2-yl)oxy)methyl]-1,3,4-oxadiazol-2-yl]thio]acetamide (6) caused higher caspase-3 activation than cisplatin in both cell lines. Compound 6 showed significant Akt inhibitory activity in both cell lines. Moreover, compound 6 significantly inhibited FAK (Phospho-Tyr397) activity in C6 cell line. Molecular docking simulations demonstrated that compound 6 fitted into the active sites of Akt and FAK with high affinity and substrate-specific interactions. Furthermore, compounds 2, 6 and 9 caused apoptotic morphological changes in both cell lines obtained from micrographs by transmission electron microscopy. A computational study for the prediction of ADME properties of all compounds was also performed. These compounds did not violate Lipinski's rule, making them potential orally bioavailable anticancer agents.

ANTIBACTERIAL THERAPEUTICS AND PROPHYLACTICS

The present disclosure relates generally to novel molecules, compositions, and formulations for treatment of bacterial infections in general and more specifically to bacterial infections with antibiotic resistant pathogens.

Novel thiazole compound XQH-2-92 for resisting streptococcus mutans and application of novel thiazole compound XQH-2-92

The invention discloses a novel thiazole compound XQH-2-92 for resisting streptococcus mutans. The number of the compound is XQH-2-92, the molecular formula of the compound is C16H17BrN6O4S, the molecular weight of the compound is 469.31, and the compound is named N-(3-bromophenyl)-4-(2-((5-nitrothiazole-2-base) amino)-2-oxo ethyl)piperazine-1-formamide. Experiments prove that the compound has good antibacterial activity and sterilizing activity on the streptococcus mutans type strains and clinical strains in a planktonic state. Meanwhile, when the final concentration of the compound XQH-2-92 in a culture medium reaches 4mg/L, the inhibiting rate of the compound on a streptococcus mutans biological membrane reaches more than 99%. The compound has the advantages that the compound is small in molecular weight, relatively simple in structure, capable of evidently inhibiting the formation of streptococcus mutans planktonic cells and biological membranes, capable of being used as the novel lead compound for preventing dental caries and promising in application prospect, antibacterial experiments prove that the compound is high in antibacterial effect and good in sterilizing effect, and the like.

Novel thiazole derivatives, and preparation method and application thereof

The invention relates to a structure of novel thiazole derivatives, a preparation method of the thiazole derivatives and application of the thiazole derivatives in the aspect of bioactivities. The invention also relates to pharmaceutically acceptable salts, a solvate or prodrug, and a pharmaceutical composition of the derivatives. Thiazolyl, uramido, thioureido and other active groups are introduced to obtain the series thiazole derivatives (I) and (II). The test on the activities of the compounds for some representative pathogenic bacteria and parasites shows that the series compounds have parasite resisting activities; and the CC50/IC50 of partial compounds for Toxoplasma gondii is greater than 1 or even higher, so the partial compounds have favorable inhibiting activities. Besides, the compounds XQH-2-97, XQH-3-13 and XQH-3-14 have obvious inhibitory effects on Streptococcus mutans, have obviously higher bactericidal capacities than nitazoxanide in the positive control group, and thus, are hopeful to be developed into new antibacterial compounds.

Synthesis and trypanocidal activity of novel benzimidazole derivatives

The present work reports the synthesis and biological activity of a series of 14 benzimidazole derivatives designed to act on the enzyme triosephosphate isomerase of Trypanosoma cruzi (TcTIM). This enzyme is involved in the metabolism of glucose, the only source of energy for the parasite. In this study, we found four compounds that inhibit TcTIM moderately and lack inhibitory activity against human TIM (HsTIM). In vitro studies against T. cruzi epimastigotes showed two compounds that were more active than the reference drug nifurtimox, and these presented a low cytotoxic effect in mouse macrophages (J744 cell line).