Category: 3034-22-8

《Discovery of MFH290: A Potent and Highly Selective Covalent Inhibitor for Cyclin-Dependent Kinase 12/13》 was published in Journal of Medicinal Chemistry in 2020. These research results belong to Liu, Yao; Hao, Mingfeng; Leggett, Alan L.; Gao, Yang; Ficarro, Scott B.; Che, Jianwei; He, Zhixiang; Olson, Calla M.; Marto, Jarrod A.; Kwiatkowski, Nicholas P.; Zhang, Tinghu; Gray, Nathanael S.. Quality Control of 5-Bromothiazol-2-amine The article mentions the following:

Genetic depletion of cyclin-dependent kinase 12 (CDK12) or selective inhibition of an analog-sensitive CDK12 reduces DNA damage repair gene expression, but selective inhibition of endogenous CDK12 is difficult. Here, we report the development of MFH290(I), a novel cysteine (Cys)-directed covalent inhibitor of CDK12/13. MFH290 forms a covalent bond with Cys-1039 of CDK12, exhibits excellent kinome selectivity, inhibits the phosphorylation of serine-2 in the C-terminal domain (CTD) of RNA-polymerase II (Pol II), and reduces the expression of key DNA damage repair genes. Importantly, these effects were demonstrated to be CDK12-dependent as mutation of Cys-1039 rendered the kinase refractory to MFH290 and restored Pol II CTD phosphorylation and DNA damage repair gene expression. Consistent with its effect on DNA damage repair gene expression, MFH290 augments the antiproliferative effect of the PARP inhibitor olaparib.5-Bromothiazol-2-amine(cas: 3034-22-8Quality Control of 5-Bromothiazol-2-amine) was used in this study.

5-Bromothiazol-2-amine(cas: 3034-22-8) belongs to anime. Many important products require amines as part of their syntheses. Methylamine is utilized in the production of the analgesic meperidine (trade name Demerol) and the photographic developer Metol (trademark), and dimethylamine is used in the synthesis of the antihistamine diphenhydramine (trade name Benadryl), the solvent dimethylformamide (DMF), and the rocket propellant 1,1-dimethylhydrazine. The synthesis of the insect repellent N,N-diethyl-m-toluamide (DEET) incorporates diethylamine while that of the synthetic fibre Kevlar requires aromatic amines.Quality Control of 5-Bromothiazol-2-amine

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Formula: C3H3BrN2SIn 2014 ,《Structure-Function Relationship of Thiazolide-Induced Apoptosis in Colorectal Tumor Cells》 was published in ACS Chemical Biology. The article was written by Brockmann, Anette; Strittmatter, Tobias; May, Sarah; Stemmer, Kerstin; Marx, Andreas; Brunner, Thomas. The article contains the following contents:

Thiazolides are a novel class of anti-infectious agents against intestinal intracellular and extracellular protozoan parasites, bacteria, and viruses. While the parent compound nitazoxanide (NTZ; 2-(acetolyloxy)-N-(5-nitro-2-thiazolyl)benzamide) has potent antimicrobial activity, the bromo-thiazolide RM4819 (N-(5-bromothiazol-2-yl)-2-hydroxy-3-methylbenzamide) shows only reduced activity. Interestingly, both mols. are able to induce cell death in colon carcinoma cell lines, indicating that the mol. target in intestinal pathogens and in colon cancer cells is different. The detoxification enzyme glutathione S-transferase of class Pi 1 (GSTP1) is frequently overexpressed in various tumors, including colon carcinomas, and limits the efficacy of antitumor chemotherapeutic drugs due to its detoxifying activities. In colorectal tumor cells RM4819 has been shown to interact with GSTP1, and GSTP1 enzymic activity is required for thiazolide-induced apoptosis. At present it is unclear which mol. structures of RM4819 are required to interact with GSTP1 and to induce cell death in colon carcinoma cell lines. Here, we demonstrate that novel thiazolide derivatives with variation in their substituents of the benzene ring do not significantly affect apoptosis induction in Caco-2 cells, whereas removal of the bromide atom on the thiazole ring leads to a strong reduction of cell death induction in colon cancer cells. We further show that active thiazolides require caspase activation and GSTP1 expression in order to induce apoptosis. We demonstrate that increased glutathione (GSH) levels sensitize colon cancer cells to thiazolides, indicating that both GSTP1 enzymic activity as well as GSH levels are critical factors in thiazolide-induced cell death. After reading the article, we found that the author used 5-Bromothiazol-2-amine(cas: 3034-22-8Formula: C3H3BrN2S)

5-Bromothiazol-2-amine(cas: 3034-22-8) belongs to anime. The reaction of alkyl halides, R―X, where X is a halogen, or analogous reagents with ammonia (or amines) is useful with certain compounds. Not all alkyl halides are effective reagents; the reaction is sluggish with secondary alkyl groups and fails with tertiary ones. Its usefulness is largely confined to primary alkyl halides (those having two hydrogen atoms on the reacting site).Formula: C3H3BrN2S

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

In 2014,Liu, X. W.; Zhang, H.; Yang, Y. J.; Li, J. Y.; Li, B.; Zhou, X. Z.; Zhang, J. Y. published 《Synthesis, antibacterial evaluation and molecular docking study of nitazoxanide analogues》.Asian Journal of Chemistry published the findings.Reference of 5-Bromothiazol-2-amine The information in the text is summarized as follows:

A series of nitazoxanide analogs I, II (R = 2,4-F2, 3,4-F2, 2-CF3, 4-CF3; X = NO2, Cl, Br) were synthesized. The antibacterial activities of synthesized compounds against Clostridium difficile were evaluated and I (R = 4-CF3) was the most promising compound The preliminary results showed that compounds containing nitro-substituted thiazole ring displayed notable activities. Compounds with thiazole moiety replaced by a pyrimidine ring exhibited moderate activities. Mol. docking study of nitazoxanide and I (R = 4-CF3) with pyruvate ferredoxin oxidoreductase suggested that the nitro group interacts with thiamine pyrophosphate and surrounding amino acids, which were almost same compared with pyruvate. The results revealed that nitazoxanide may be a competitive inhibitor of pyruvate and nitro-group is necessary for thiazolide’s activities against anaerobic organisms containing pyruvate ferredoxin oxidoreductase enzyme. In the experiment, the researchers used many compounds, for example, 5-Bromothiazol-2-amine(cas: 3034-22-8Reference of 5-Bromothiazol-2-amine)

5-Bromothiazol-2-amine(cas: 3034-22-8) belongs to anime. Left-handed and right-handed forms (mirror-image configurations, known as optical isomers or enantiomers) are possible when all the substituents on the central nitrogen atom are different (i.e., the nitrogen is chiral). With amines, there is extremely rapid inversion in which the two configurations are interconverted.Reference of 5-Bromothiazol-2-amine

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

COA of Formula: C3H3BrN2SIn 2017 ,《Synthesis of Brominated Thiazoles via Sequential Bromination-Debromination Methods》 was published in Journal of Organic Chemistry. The article was written by Uzelac, Eric J.; Rasmussen, Seth C.. The article contains the following contents:

The synthesis of the full family of bromothiazoles has been revisited in order to update and optimize their production The species reported include 2-bromothiazole, 4-bromothiazole, 5-bromothiazole, 2,4-dibromothiazole, 2,5-dibromothiazole, 4,5-dibromothiazole, and 2,4,5-tribromothiazole, the majority of which are produced via sequential bromination and debromination steps. This complete family can now be produced without the use of elemental bromine, and the presented methods have allowed the phys. and NMR spectroscopic characterization of the full family to be reported for the first time. In the experimental materials used by the author, we found 5-Bromothiazol-2-amine(cas: 3034-22-8COA of Formula: C3H3BrN2S)

5-Bromothiazol-2-amine(cas: 3034-22-8) belongs to anime. The reaction of alkyl halides, R―X, where X is a halogen, or analogous reagents with ammonia (or amines) is useful with certain compounds. Not all alkyl halides are effective reagents; the reaction is sluggish with secondary alkyl groups and fails with tertiary ones. Its usefulness is largely confined to primary alkyl halides (those having two hydrogen atoms on the reacting site).COA of Formula: C3H3BrN2S

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Recommanded Product: 5-Bromothiazol-2-amineIn 2002 ,《Synthesis and Structure-Activity Relationships of Novel 7-Substituted 1,4-Dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic Acids as Antitumor Agents. Part 1》 was published in Journal of Medicinal Chemistry. The article was written by Tomita, Kyoji; Tsuzuki, Yasunori; Shibamori, Koh-ichiro; Tashima, Masanori; Kajikawa, Fumie; Sato, Yuji; Kashimoto, Shigeki; Chiba, Katsumi; Hino, Katsuhiko. The article contains the following contents:

Title compounds, e.g. I (R = H2NCH2CH2NH, 1-pyrrolidinyl, 3-hydroxy-1-pyrrolidinyl), possess moderate cytotoxic activity. Structure-activity relationships of title compounds were investigated by changing substituents at N-1 and C-7 positions and the core ring structure itself and evaluated the synthesized compounds against several murine and human tumor cell lines. The 2-thiazolyl group at the N-1 position of the naphthyridine structure is the best substituent for antitumor activity and regarding core ring structure, the naphthyridine derivative is the most active followed by pyridopyrimidine analog. At the C-7 position, aminopyrrolidine derivatives are more effective than other amines or thioether derivatives I (R = 3-amino-4-methoxy-1-pyrrolidinyl, 3-amino-3-methyl-1-pyrrolidinyl, 3-aminopyrrolidinyl) were determined to be effective in vitro and in vivo antitumor assays, and their activity was comparable to that of etoposide.5-Bromothiazol-2-amine(cas: 3034-22-8Recommanded Product: 5-Bromothiazol-2-amine) was used in this study.

5-Bromothiazol-2-amine(cas: 3034-22-8) belongs to anime. Halogenation, in which one or more hydrogen atoms of an amine is replaced by a halogen atom, occurs with chlorine, bromine, and iodine, as well as with some other reagents, notably hypochlorous acid (HClO). With primary amines the reaction proceeds in two stages, producing N-chloro- and N,N-dichloro-amines, RNHCl and RNCl2, respectively. With tertiary amines, an alkyl group may be displaced by a halogen.Recommanded Product: 5-Bromothiazol-2-amine

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Name: 5-Bromothiazol-2-amineIn 2014 ,《Development of radamide analogs as Grp94 inhibitors》 appeared in Bioorganic & Medicinal Chemistry. The author of the article were Muth, Aaron; Crowley, Vincent; Khandelwal, Anuj; Mishra, Sanket; Zhao, Jinbo; Hall, Jessica; Blagg, Brian S. J.. The article conveys some information:

Hsp90 isoform-selective inhibition is highly desired as it can potentially avoid the toxic side-effects of pan-inhibition. The current study developed selective inhibitors of one such isoform, Grp94, predicated on the chimeric and pan-Hsp90 inhibitor, radamide (RDA). Replacement of the quinone moiety of RDA with a Ph ring (2) was found to be better suited for Grp94 inhibition as it can fully interact with a unique hydrophobic pocket present in Grp94. An extensive SAR for this scaffold showed that substitutions at the 2- and 4-positions (8 and 27, resp.) manifested excellent Grp94 affinity and selectivity. Introduction of heteroatoms into the ring also proved beneficial, with a 2-pyridine derivative (38) exhibiting the highest Grp94 affinity (Kd = 820 nM). Subsequent cell-based assays showed that these Grp94 inhibitors inhibit migration of the metastatic breast cancer cell line, MDA-MB-231, as well as exhibit an anti-proliferative affect against the multiple myeloma cell line, RPMI 8226. After reading the article, we found that the author used 5-Bromothiazol-2-amine(cas: 3034-22-8Name: 5-Bromothiazol-2-amine)

5-Bromothiazol-2-amine(cas: 3034-22-8) belongs to anime. Acylation is one of the most important reactions of primary and secondary amines; a hydrogen atom is replaced by an acyl group (a group derived from an acid, such as RCOOH or RSO3H, by removal of ―OH, such as RC(=O)―, RS(O)2―, and so on). Reagents may be acid chlorides (RCOC1, RSO2C1), anhydrides ((RCO)2O), or even esters (RCOOR′); the products are amides of the corresponding acids.Name: 5-Bromothiazol-2-amine

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

In 2005,Kuo, Gee-Hong; Wang, Aihua; Emanuel, Stuart; DeAngelis, Alan; Zhang, Rui; Connolly, Peter J.; Murray, William V.; Gruninger, Robert H.; Sechler, Jan; Fuentes-Pesquera, Angel; Johnson, Dana; Middleton, Steven A.; Jolliffe, Linda; Chen, Xin published 《Synthesis and Discovery of Pyrazine-Pyridine Biheteroaryl as a Novel Series of Potent Vascular Endothelial Growth Factor Receptor-2 Inhibitors》.Journal of Medicinal Chemistry published the findings.Product Details of 3034-22-8 The information in the text is summarized as follows:

Pathol. angiogenesis is associated with disease states such as cancer, diabetic retinopathy, rheumatoid arthritis, endometriosis, and psoriasis. There is much evidence that direct inhibition of the kinase activity of vascular endothelial growth factor receptor-2 (VEGFR-2) will result in the reduction of angiogenesis and the suppression of tumor growth. Attempts to optimize a cyclin-dependent kinase-1 (CDK1) inhibitor by using palladium-catalyzed C-C bond, C-N bond formation reactions to assemble diverse biheteroaryl mols. led to the unexpected discovery of a pyrazine-pyridine biheteroaryl as a novel series of potent VEGFR-2 inhibitors. The pyridinylpyrazine I, which had IC50 = 0.084 μM at VEGFR-2, showed very modest selectivity against fibroblast growth factor receptor-2 (IC50 = 0.21 μM), platelet-derived growth factor receptor (IC50 = 0.36 μM), and glycogen synthase kinase-3 (IC50 = 0.478 μM), while it exhibited more than 10-fold selectivity against epidermal growth factor receptor (IC50 = 1.36 μM) and insulin-R kinase (IC50 = 1.69 μM). On the other hand, I exhibited > 100-fold selectivity against calmodulin kinase 2; casein kinase-1 and -2; CDK1 and -4; mitogen-activated protein kinase; and protein kinase A, Cβ2, and Cγ (IC50 >10 μM). I also displayed high inhibitory potency on VEGF-stimulated human umbilical vein endothelial cell (HUVEC) proliferation (IC50 = 0.005 μM) and good selectivity against cell lines such as HUVEC, human aortic smooth muscle cells, and MRC5 lung fibroblasts. Mol. docking studies were conducted in an attempt to rationalize the unexpected high VEGFR-2 selectivity of I. In addition to this study using 5-Bromothiazol-2-amine, there are many other studies that have used 5-Bromothiazol-2-amine(cas: 3034-22-8Product Details of 3034-22-8) was used in this study.

5-Bromothiazol-2-amine(cas: 3034-22-8) belongs to anime. Many important products require amines as part of their syntheses. Methylamine is utilized in the production of the analgesic meperidine (trade name Demerol) and the photographic developer Metol (trademark), and dimethylamine is used in the synthesis of the antihistamine diphenhydramine (trade name Benadryl), the solvent dimethylformamide (DMF), and the rocket propellant 1,1-dimethylhydrazine. The synthesis of the insect repellent N,N-diethyl-m-toluamide (DEET) incorporates diethylamine while that of the synthetic fibre Kevlar requires aromatic amines.Product Details of 3034-22-8

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

In 2005,Stanetty, Peter; Schnuerch, Michael; Mereiter, Kurt; Mihovilovic, Marko D. published 《Investigations of the Halogen Dance Reaction on N-Substituted 2-Thiazolamines》.Journal of Organic Chemistry published the findings.Related Products of 3034-22-8 The information in the text is summarized as follows:

The halogen dance (HD) reaction on various 2-thiazolamine systems was investigated and provided an easy access to a series of 5-substituted 4-bromo-2-thiazolamine derivatives The authors show that HD is a very favored process for the investigated systems and that prevention of HD is only possible when optimized reaction conditions and selected electrophiles are applied. In addition to this study using 5-Bromothiazol-2-amine, there are many other studies that have used 5-Bromothiazol-2-amine(cas: 3034-22-8Related Products of 3034-22-8) was used in this study.

5-Bromothiazol-2-amine(cas: 3034-22-8) belongs to anime. Many important products require amines as part of their syntheses. Methylamine is utilized in the production of the analgesic meperidine (trade name Demerol) and the photographic developer Metol (trademark), and dimethylamine is used in the synthesis of the antihistamine diphenhydramine (trade name Benadryl), the solvent dimethylformamide (DMF), and the rocket propellant 1,1-dimethylhydrazine. The synthesis of the insect repellent N,N-diethyl-m-toluamide (DEET) incorporates diethylamine while that of the synthetic fibre Kevlar requires aromatic amines.Related Products of 3034-22-8

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

In 2019,Organic Chemistry Frontiers included an article by Zhou, Zhao-Zhao; Zhao, Jia-Hui; Gou, Xue-Ya; Chen, Xi-Meng; Liang, Yong-Min. Recommanded Product: 3034-22-8. The article was titled 《Visible-light-mediated hydrodehalogenation and Br/D exchange of inactivated aryl and alkyl halides with a palladium complex》. The information in the text is summarized as follows:

Herein, a novel photo-induced amine-free radical reductive dehalogenation of inactivated aryl/alkyl bromides and chlorides with a palladium complex is described,. Which reveals excellent functional group compatibility and broad substrate scope. Extensional transformations for reductive cyclization, dehalogenative deuteration, and intra- and intermol. radical addition can be achieved smoothly. Mechanistic studies indicate a single-electron photoredox catalytic system with inactivated solvent as the hydrogen atom donor. The experimental process involved the reaction of 5-Bromothiazol-2-amine(cas: 3034-22-8Recommanded Product: 3034-22-8)

5-Bromothiazol-2-amine(cas: 3034-22-8) belongs to anime. The methylamines occur in small amounts in some plants. Many polyfunctional amines (i.e., those having other functional groups in the molecule) occur as alkaloids in plants—for example, mescaline, 2-(3,4,5-trimethoxyphenyl)ethylamine; the cyclic amines nicotine, atropine, morphine, and cocaine; and the quaternary salt choline, N-(2-hydroxyethyl)trimethylammonium chloride, which is present in nerve synapses and in plant and animal cells.Recommanded Product: 3034-22-8

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

In 2014,Jashari, Ahmed; Imeri, Faik; Ballazhi, Lulzime; Shabani, Agim; Mikhova, Bozhana; Drager, Gerald; Popovski, Emil; Huwiler, Andrea published 《Synthesis and cellular characterization of novel isoxazolo- and thiazolohydrazinylidene-chroman-2,4-diones on cancer and non-cancer cell growth and death》.Bioorganic & Medicinal Chemistry published the findings.Product Details of 3034-22-8 The information in the text is summarized as follows:

Coumarins are extensively studied anticoagulants that exert addnl. effects such as anticancerogenic and even anti-inflammatory. To find new drugs with anticancer activities, the authors report the synthesis and the structural anal. of new coumarin derivatives which combine the coumarin core and five member heterocycles in hydrazinylidene-chroman-2,4-diones. The derivatives were prepared by derivatization of the appropriate heterocyclic amines which were used as electrophiles to attack the coumarin ring. The structures were characterized by spectroscopic techniques including IR, NMR, 2D-NMR and MS. These derivatives were further characterized especially in terms of a potential cytotoxic and apoptogenic effect in several cancer cell lines including the breast and prostate cancer cell lines MCF-7, MDA-MB-231, PC-3, LNCaP, and the monocytic leukemia cell line U937. Cell viability was determined after 48 h and 72 h of treatment with the novel compounds by MTT assay and the 50% inhibitory concentrations (EC50 values) were determined Out of the 8 novel compounds screened for reduced cell viability, I, II and III were found to be the most promising and effective ones having EC50 values that were several fold reduced when compared to the reference substance 4-hydroxycoumarin. However, the effects were cancer cell line dependent. The breast cancer MDA-MB-231 cells, the prostate cancer LNCaP cells, and U937 cells were most sensitive, MCF-7 cells were less sensitive, and PC-3 cells were more resistant. Reduced cell viability was accompanied by increased apoptosis as shown by PARP-1 cleavage and reduced activity of the survival protein kinase Akt. In summary, this study has identified three novel coumarin derivatives that in comparison to 4-hydroxycoumarin have a higher efficiency to reduce cancer cell viability and trigger apoptosis and therefore may represent interesting novel drug candidates.5-Bromothiazol-2-amine(cas: 3034-22-8Product Details of 3034-22-8) was used in this study.

5-Bromothiazol-2-amine(cas: 3034-22-8) belongs to anime. Amines have a free lone pair with which they can coordinate to metal centers. Amine–metal bonds are weaker because amines are incapable of backbonding, but they are still important for sensing applications.While stronger than hydrogen bonds, amine–metal bonds are still weaker than both covalent and ionic bonds.Product Details of 3034-22-8

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica