5398-36-7Relevant academic research and scientific papers
Iron(II)-promoted synthesis of 2-aminothiazoles via C-N bond formation from vinyl azides and potassium thiocyanate
Zhang, Guolin,Chen, Binhui,Guo, Xiao,Guo, Shanshan,Yu, Yongping
, p. 1065 - 1069 (2015)
A simple protocol to prepare the privileged 2-aminothiazoles promoted by ferrous sulfate heptahydrate via C-N bond formation from vinyl azides and commercially available potassium thiocyanate has been developed. A wide range of vinyl azides are tolerated to afford the expected polysubstituted 2-aminothiazoles in reasonably good yields. The use of the non-toxic substrates and catalyst renders the reaction more environmentally friendly than traditional approaches.
A fluorescence probe based on 6-phenylimidazo[2,1-: B] thiazole and salicylaldehyde for the relay discerning of In3+ and Cr3+
Li, Bing,Shang, Xiaodong,Li, Linlin,Xu, Yuankang,Wang, Hanyu,Yang, Xiaofeng,Pei, Meishan,Zhang, Ruiqing,Zhang, Guangyou
, p. 951 - 957 (2020)
A new fluorescence probe, (E)-N′-(2-hydroxybenzylidene)-6-phenylimidazo[2,1-b]thiazole-3-carbohydrazide (LB1), based on 6-phenylimidazo[2,1-b]thiazole and salicylaldehyde was designed and synthesized. The chemical structures of LB1 and its intermediate we
Synthesis of lathyrane diterpenoid nitrogen-containing heterocyclic derivatives and evaluation of their anti-inflammatory activities
Wang, Wang,Xiong, Liangliang,Li, Yutong,Song, Zhuorui,Sun, Dejuan,Li, Hua,Chen, Lixia
, (2022/01/24)
As our ongoing work on lathyrane diterpenoid derivatization, three series of lathyrane diterpenoid derivatives were designed and synthesized based combination principles, including pyrazole, thiazole and furoxan moieties. Biological evaluation indicated t
Design, Synthesis, and Cytotoxic Activity of New Tubulysin Analogues
Le, Hai Van,Tran, Loc Van,Tran, Anh Tuan,Tran, Thao Thi Phuong,Tran, Sung Van,Tran, Chien Van
supporting information, p. 187 - 195 (2021/12/03)
Synthesis of tubulysin analogues, containing an N-methyl substituent on tubuvaline-amide together with the replacement of either the hydrophobic N-terminal N-methyl pipecolic acid (Mep) or at both N- and C- terminal peptides with available heteroaromatic
Synthesis process of thiazole medical intermediate
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Paragraph 0013; 0015, (2021/06/09)
The invention discloses a synthesis process of thiazole medical intermediate.The synthesis process comprises the following steps: step 1, mixing ethyl pyruvate and dichloromethane of which the volume is 2 times that of the ethyl pyruvate at room temperature, adding an obtained mixture into a reactor, starting stirring, and keeping the temperature of a system at about 20 DEG C; step 2, starting to dropwise add a dichloromethane solution of bromine, controlling the temperature to enable the system to be about 20-30 DEG C, sealing the reactor, and introducing a strong alkali solution to absorb acid gas HBr; and step 3, after dropwise adding is completed, closing a cold well, performing stirring at normal temperature for about 2 hours until the color of the reaction liquid gradually becomes light yellow to light brown, monitoring that no raw material exists through TLC, and concentrating the obtained reaction liquid. According to the synthesis process of the thiazole medical intermediate, by introducing the defoaming agent n-hexane, generated gas foam can be quickly dissolved out and released from the solvent, and the phenomenon of one-time flushing is avoided; and by introducing the n-hexane solvent, solids can be effectively separated out at low temperature, the impurity content can be controlled to be about 1%, the purification difficulty is greatly reduced, and crystallization is facilitated.
A one-pot synthesis of 2-aminothiazoles via the coupling of ketones and thiourea using I2/dimethyl sulfoxide as a catalytic oxidative system
Zhang, Qian,Wu, Jiefei,Pan, Zexi,Zhang, Wen,Zhou, Wei
, p. 89 - 94 (2020/06/17)
A series of 2-aminothiazoles is prepared in moderate-to-good yields by the direct coupling of ketones and thiourea using I2/dimethyl sulfoxide as a catalytic oxidative system. This method avoids the preparation of lachrymatory and toxic α-haloketones and the use of an acid-binding agent, thus providing a more convenient approach to 2-aminothiazoles compared to the Hantzsch reaction.
Amino acid conjugates of aminothiazole and aminopyridine as potential anticancer agents: Synthesis, molecular docking and in vitro evaluation
Ali, Tahir,Imran, Muhammad,Li, Jing Bo,Li, Shupeng,Nadeem, Humaira,Naz, Shagufta,Sarwar, Sadia,Shah, Fawad Ali,Tan, Zhen
, p. 1459 - 1476 (2021/04/19)
Purpose: The development of resistance to available anticancer drugs is increasingly becoming a major challenge and new chemical entities could be unveiled to compensate this therapeutic failure. The current study demonstrated the synthesis of 2-aminothiazole [S3 (a-d) and S5(a-d)] and 2-aminopyridine [S4(a-d) and S6(a-d)] derivatives that can target multiple cellular networks implicated in cancer development. Methods: Biological assays were performed to investigate the antioxidant and anticancer potential of synthesized compounds. Redox imbalance and oxidative stress are hallmarks of cancer, therefore, synthesized compounds were preliminarily screened for their antioxidant activity using DPPH assay, and further five derivatives S3b, S3c, S4c, S5b, and S6c, with significant antioxidant potential, were selected for investigation of in vitro anticancer potential. The cytotoxic activities were evaluated against the parent (A2780) and cisplatin-resistant (A2780CISR) ovarian cancer cell lines. Further, Molecular docking studies of active compounds were performed to determine binding affinities. Results: Results revealed that S3c, S5b, and S6c displayed promising inhibition in cisplatin-resistant cell lines in comparison to parent cells in terms of both resistance factor (RF) and IC50 values. Moreover, S3c proved to be most active compound in both parent and resistant cell lines with IC50 values 15.57 μM and 11.52 μM respectively. Our docking studies demonstrated that compounds S3c, S5b, and S6c exhibited significant binding affinity with multiple protein targets of the signaling cascade. Conclusion: Anticancer activities of compounds S3c, S5b, and S6c in cisplatin-resistant cell lines suggested that these ligands may contribute as lead compounds for the development of new anticancer drugs.
ω-Quinazolinonylalkyl aryl ureas as reversible inhibitors of monoacylglycerol lipase
Dato, Florian M.,Neud?rfl, J?rg-Martin,Gütschow, Michael,Goldfuss, Bernd,Pietsch, Markus
supporting information, (2019/11/13)
The serine hydrolase monoacylglycerol lipase (MAGL) is involved in a plethora of pathological conditions, in particular pain and inflammation, various types of cancer, metabolic, neurological and cardiovascular disorders, and is therefore a promising target for drug development. Although a large number of irreversible-acting MAGL inhibitors have been discovered over the past years, there are only few compounds known so far which inhibit the enzyme in a reversible manner. Therefore, much effort is put into the development of novel chemical entities showing reversible inhibitory behavior, which is thought to cause less undesired side effects. To explore a wide range of chemical structures as MAGL binders, we have applied a virtual screening approach by docking small molecules into the crystal structure of human MAGL (hMAGL) and envisaged a library of 45 selected compounds which were then synthesized. Biochemical investigations included the determination of the inhibitory potency on hMAGL and two related hydrolases, i.e. human fatty acid amide hydrolase (hFAAH) and murine cholesterol esterase (mCEase). The most promising candidates from theses analyses, i.e. three ω-quinazolinonylalkyl aryl ureas bearing alkyl spacers of three to five methylene groups, exhibited IC50 values of 20–41 μM and reversible, detergent-insensitive behavior towards hMAGL. Among these compounds, the inhibitor 1-(3,5-bis(trifluoromethyl)phenyl)-3-(4-(4-oxo-3,4-dihydroquinazolin-2-yl)butyl)urea (96) was selected for further kinetic characterization, yielding a dissociation constant Ki = 15.4 μM and a mixed-type inhibition with a pronounced competitive component (α = 8.94). This mode of inhibition was further supported by a docking experiment, which suggested that the inhibitor occupies the substrate binding pocket of hMAGL.
Synthesis and biological evaluation of imidazo[2,1-b]thiazole based sulfonyl piperazines as novel carbonic anhydrase ii inhibitors
Alvala, Mallika,Angeli, Andrea,Manasa, Kesari Lakshmi,Mohammed, Arifuddin,Pujitha, Sravya,Sethi, Aaftaab,Supuran, Claudiu T.
, (2020/04/17)
A novel series of imidazo[2,1-b]thiazole-sulfonyl piperazine conjugates (9aa-ee) has been synthesized and evaluated for carbonic anhydrase (CA, EC 4.2.1.1) inhibitory potency against four isoforms: The cytosolic isozyme hCA I, II and trans-membrane tumor-
Target-Directed Azide-Alkyne Cycloaddition for Assembling HIV-1 TAR RNA Binding Ligands
Dash, Jyotirmayee,Dutta, Debasish,Paul, Raj,Paul, Rakesh
supporting information, p. 12407 - 12411 (2020/06/01)
The highly conserved HIV-1 transactivation response element (TAR) binds to the trans-activator protein Tat and facilitates viral replication in its latent state. The inhibition of Tat–TAR interactions by selectively targeting TAR RNA has been used as a strategy to develop potent antiviral agents. Therefore, HIV-1 TAR RNA represents a paradigmatic system for therapeutic intervention. Herein, we have employed biotin-tagged TAR RNA to assemble its own ligands from a pool of reactive azide and alkyne building blocks. To identify the binding sites and selectivity of the ligands, the in situ cycloaddition has been further performed using control nucleotide (TAR DNA and TAR RNA without bulge) templates. The hit triazole-linked thiazole peptidomimetic products have been isolated from the biotin-tagged target templates using streptavidin beads. The major triazole lead generated by the TAR RNA presumably binds in the bulge region, shows specificity for TAR RNA over TAR DNA, and inhibits Tat–TAR interactions.
