Tag: 100-200

The author of 《Catalyst-free oxidative N-N coupling for the synthesis of 1,2,3-triazole compounds with tBuONO》 were Cai, Yue-Ming; Zhang, Xin; An, Cui; Yang, Ye-Fei; Liu, Wei; Gao, Wen-Xia; Huang, Xiao-Bo; Zhou, Yun-Bing; Liu, Miao-Chang; Wu, Hua-Yue. And the article was published in Organic Chemistry Frontiers in 2019. Application of 95-24-9 The author mentioned the following in the article:

A catalyst-free method was developed to synthesize 1,2,3-benzotriazinones I [R = H, 6-Cl, 6-Br, etc.] and 1,2,3-benzothiadiazoles II [R1 = H, 6-Cl, 6-Br, etc.] from 2-amino-benzamides and 2-amino thiols. Of particular note was that the one-step synthesis route to access [1,2,3]triazolo[1,5-a]pyridines III [R2 = H, Ph, 4-ClC6H4; R3 = H, 7-Me, 7-Br] from pyridin-2-ylmethanamine was reported for the first time. This approach featured no use of catalyst, extremely mild conditions and excellent efficiency. In addition to this study using 6-Chlorobenzothiazol-2-ylamine, there are many other studies that have used 6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9Application of 95-24-9) was used in this study.

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Application of 95-24-9The thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone.

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

《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

The author of 《Synthesis, structure and reactivity with phosphines of Hg(II) ortho-cyano-aminothiophenolate complexes formed via C-S bond cleavage and dehydrogenation of 2-aminobenzothiazoles》 were Al-Jibori, Subhi A.; Irzoqi, Ahmed A.; Al-Janabi, Ahmed S. M.; Al-Nassiry, Amenah I. A.; Basak-Modi, Sucharita; Ghosh, Shishir; Wagner, Christoph; Hogarth, Graeme. And the article was published in Dalton Transactions in 2022. Synthetic Route of C7H5ClN2S The author mentioned the following in the article:

Addition of 2-aminobenzothiazole (abt) and substituted derivatives to Hg(OAc)2 leads to the high yield formation of ortho-cyano-aminothiophenolate (ocap) complexes [Hg{SC6H3XN(CN)}]n (X = H, Me, Cl, Br, NO2) resulting from dehydrogenation and C-S bond cleavage. The reaction appears to be unique to Hg(OAc)2 and with HgCl2 the product [HgCl2(abt)]n contains an intact abt ligand, but reacts with acetate to afford the ocap complex [Hg{SC6H4N(CN)}]n. Binding of abt to Hg(II) was previously probed in mol. structures of [Hg(sac)2(abt)L] (L = MeOH, DMSO) and these were reexamined to understand the perturbation of abt upon coordination. When the reaction of abt and Hg(OAc)2 was carried out at low temperatures the intermediate [Hg(κ2-OAc)(EtOH)(μ-HNCNSC6H4)]2 was isolated resulting from a single ligand deprotonation thus allowing a mechanism for ring-opening to be proposed. Reactions of [Hg{SC6H3XN(CN)}]n with mono- and bidentate phosphines were studied, affording a series of complexes in which the ocap ligands adopt four different binding modes in the solid state, as shown by a number of crystallog. studies. In all, the ligand chelates to a single mercury center but spans to the second via either: (i) a simple S,N-chelate, (ii) coordination through nitrogen of the CN group, (iii) the sulfur acting as a thiolate-bridge, (iv) both thiolate bridging and cyanide coordination. With PPh3 two different binding modes are seen in complexes [Hg{SC6H3XN(CN)}(PPh3)]2 being dependant upon the nature of the arene-substituent, while addition of excess PPh3 affords mononuclear [Hg{SC6H3XN(CN)}(PPh3)2]. With dppm, binuclear [Hg{SC6H3XN(CN)}(κ1-dppm)]2 result in which the diphosphine binds in a monodentate fashion. With the more flexible diphosphines, dppe and dppb, coordination polymers [Hg{SC6H3XN(CN)}(κ1,κ1-diphosphine)]n result in which ocap binds in a simple chelate fashion. Somewhat unexpectedly, with dppp, binuclear complexes [Hg2{SC6H3XN(CN)}2(μ,κ1,κ1-dppp)] result in which two diphosphines bridge the Hg2 center, while with dppf mononuclear chelates are proposed to result. Thus, the simple and high-yielding ring-opening of 2-aminobenzothiazole and substituted derivatives by mercuric acetate provides ready access to a range of novel ortho-cyano-aminothiophenolate complexes, being shown to be a highly versatile ligand that can adopt a number of different coordination modes. In the part of experimental materials, we found many familiar compounds, such as 6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9Synthetic Route of C7H5ClN2S)

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Synthetic Route of C7H5ClN2STheir presence in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications.

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

de Oliveira Lima Filho, Edson; Malvestiti, Ivani published their research in ACS Omega on December 29 ,2020. The article was titled 《Mechanochemical Thiocyanation of Aryl Compounds via C-H Functionalization》.Synthetic Route of C7H5ClN2S The article contains the following contents:

Aryl thiocyanate compounds are important building blocks for the synthesis of bioactive compounds and intermediates for several functional groups. Reported thiocyanation reactions via C-H functionalization have limited substrate scope and low RME. The ball-milling method reported here uses ammonium persulfate and ammonium thiocyanate as reagents and silica as a grinding auxiliary. It afforded aryl thiocyanates with moderate to excellent yields for a wide variety of aryl compounds (36 examples, 8-96% yield), such as anilines, phenols, anisoles, thioanisole, and indole, thus tolerating substrates with sensitive functional groups. New products such as benzo[d][1,3]oxathiol-2-ones were obtained with C-4 substituted phenols. Thus, to our knowledge, we report, for the first time, aryl thiocyanation reaction by ball-milling at room temperature and solvent-free conditions, with short reaction times and no workup. Anal. of several mass-based green metrics indicates that it is an efficient greener method.6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9Synthetic Route of C7H5ClN2S) was used in this study.

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Synthetic Route of C7H5ClN2SThe thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone.

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

Walker, Erin Joanne; Heydet, Deborah; Veldre, Timothy; Ghildyal, Reena published their research in Scientific Reports on December 31 ,2019. The article was titled 《Transcriptomic changes during TGF-β-mediated differentiation of airway fibroblasts to myofibroblasts》.Formula: C7H5ClN2S The article contains the following contents:

In this study, we have used next generation sequencing to delineate changes in transcriptome induced by TGF-β treatment of WI-38 airway fibroblasts in both short term and after differentiation into myofibroblasts. The data obtained from RNAseq anal. was confirmed by quant. PCR and protein expression by western blotting. We found that genes coding for intermediates in TGF-β signalling pathways (SMADs) were differentially expressed after TGF-β treatment, SMAD2 being upregulated and SMAD3 being downregulated. Genes involved in cytoskeletal pathways (FN1, LAMA, ITGB1) were upregulated in myofibroblasts. Genes that were previously shown to be changed in asthmatic lungs (ADAMTS1, DSP, TIMPs, MMPs) were similarly differentially expressed in myofibroblasts, strongly suggesting that TGF-β mediated differentiation of fibroblasts to myofibroblasts may underlie important changes in the asthmatic airway. We also identified new intermediates of signalling pathways (PKB, PTEN) that are changed in myofibroblasts compared to fibroblasts. We have found a significant number of genes that are altered after TGF-β induced transdifferentiation of WI-38 fibroblasts into myofibroblasts, many of which were expected or predicted. We also identified novel genes and pathways that were affected after TGF-β treatment, suggesting addnl. pathways are activated during the transition between fibroblasts and myofibroblasts and may contribute to the asthma phenotype. In the part of experimental materials, we found many familiar compounds, such as 6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9Formula: C7H5ClN2S)

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Formula: C7H5ClN2STheir presence in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications.

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

The author of 《Organocatalytic asymmetric synthesis of benzothiazolopyrimidines via a [4+2] cycloaddition of azlactones with 2-benzothiazolimines》 were Ke, Chaoqi; Liu, Zhenzhong; Ruan, Sai; Feng, Xiaoming; Liu, Xiaohua. And the article was published in Organic Chemistry Frontiers in 2021. Safety of 6-Chlorobenzothiazol-2-ylamine The author mentioned the following in the article:

An easily available L-proline-derived guanidine-amide were found to be efficient at catalyzing a [4+2] cycloaddition of azlactones with 2-benzothiazolimines by affording various benzothiazolopyrimidines bearing adjacent tertiary and quaternary stereogenic centers in excellent yields at 2 mol% loading. The diastereoisomers of the main adducts differed from those in a previous bifunctional organocatalytic system. In the experiment, the researchers used 6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9Safety of 6-Chlorobenzothiazol-2-ylamine)

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Safety of 6-Chlorobenzothiazol-2-ylamineTheir presence in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications.

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

In 2021,Heterocyclic Letters included an article by Prajapat, Prakash; Pappula, Venkata Narayana; Vaghani, Hasit; Agarwal, Shikha; Samota, Jayanti; Talesara, Ganpat L.. Name: 6-Chlorobenzothiazol-2-ylamine. The article was titled 《Synthesis of biologically potent alkoxyphthalimido plugged N-(2,4-dioxo-1,4-dihydroquinazolin)-3(2H)-yl)-4-oxo-4H-benzo[4,5]thiazolo[3,2-a]pyrimidine-3-carboxamide via Gould Jacobs reaction》. The information in the text is summarized as follows:

Convenient methods for the synthesis of new alkoxyphthalimidoquinazolinedione and their pyrimidobenzothiazole derivatives I [R1 = H, Cl, O2N; R2 = H, 2-(1,3-dioxoisoindolin-2-yl)oxyethyl] were reported. A series of benzothiazolopyrimidine-3-carboxamides I were prepared starting from substituted 2-aminobenzothiazoles via solvent free multi-component Gould-Jacobs reaction. Structures of newly synthesized compounds were established based on IR, 1H-NMR, mass, anal. studies and fluorescence tests. Some of synthesized mols. I were assayed for their antimalarial activity. IC50 values of antimalarial activity of compounds were also determined The results came from multiple reactions, including the reaction of 6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9Name: 6-Chlorobenzothiazol-2-ylamine)

6-Chlorobenzothiazol-2-ylamine(cas: 95-24-9) belongs to thiazoles. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Name: 6-Chlorobenzothiazol-2-ylamineThe thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone.

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

Name: 5-Bromothiazol-2-amineIn 2020 ,《Novel small molecule retrograde transport blocker confers post-exposure protection against ricin intoxication》 appeared in Acta Pharmaceutica Sinica B. The author of the article were Zhao, Xu; Li, Haixia; Li, Jia; Liu, Kunlu; Wang, Bo; Wang, Yuxia; Li, Xingzhou; Zhong, Wu. The article conveys some information:

Ricin is a highly toxic type 2 ribosome-inactivating protein (RIP) which is extracted from the seeds of castor beans. Ricin is considered a potential bioterror agent and no effective antidote for ricin exists so far. In this study, by structural modification of a retrograde transport blocker Retro-2cycl, a series of novel compounds were obtained. The primary screen revealed that compound I has an improved antiricin activity compare to pos. control. In vitro pre-exposure evaluation in Madine-Darby Canine Kidney (MDCK) cells demonstrated that compound I is a powerful anti-ricin compound with an EC50 of 41.05 nmol/L against one LC (lethal concentration, 5.56 ng/mL) of ricin. Further studies surprisingly indicated that compound I confers post-exposure activity against ricin intoxication. An in vivo study showed that 1 h post-exposure administration of compound I can improve the survival rate as well as delay the death of ricin-intoxicated mice. A drug combination of compound I with monoclonal antibody mAb4C13 rescued mice from one LD (LD) ricin challenge and the survival rate of tested animals is 100%. These results represent, for the first time, indication that small mol. retrograde transport blocker confers both in vitro and in vivo post-exposure protection against ricin and therefore provides a promising candidate for the development of anti-ricin medicines. In the part of experimental materials, we found many familiar compounds, such as 5-Bromothiazol-2-amine(cas: 3034-22-8Name: 5-Bromothiazol-2-amine)

5-Bromothiazol-2-amine(cas: 3034-22-8) belongs to anime. To avoid the problem of multiple alkylation, methods have been devised for “blocking” substitution so that only one alkyl group is introduced. The Gabriel synthesis is one such method; it utilizes phthalimide, C6H4(CO)2NH, whose one acidic hydrogen atom has been removed upon the addition of a base such as KOH to form a salt.Name: 5-Bromothiazol-2-amine

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