Category: thiazole

(Hetero)arylazo-1,2,3-triazoles: “Clicked” Photoswitches for Versatile Functionalization and Electronic Decoupling was written by Fang, Dong;Zhang, Zhao-Yang;Shangguan, Zhichun;He, Yixin;Yu, Chunyang;Li, Tao. And the article was included in Journal of the American Chemical Society in 2021.Name: 4-(Methylthio)aniline This article mentions the following:

The development of light-responsive chem. systems often relies on the rational design and suitable incorporation of mol. photoswitches such as azobenzenes. Linking a photoswitch core with another 蟺-conjugated mol. entity may give rise to intramol. electronic coupling, which can dramatically impair the photoswitch function. Decoupling strategies have been developed based on addnl. inserting a linker that can disrupt the through-bond electronic communication. Here, the authors show that 1,2,3-triazole – a commonly used decoupling spacer – can be directly merged into the azoswitch core to construct a class of “self-decoupling” azoswitches called (hetero)arylazo-1,2,3-triazoles. Such azotriazole photoswitches are easily accessed and modularly functionalized by click chem. Their photoswitch property can be optimized by rational design of the substituent groups or heteroaryl rings, allowing (near-) quant. E-Z photoisomerization yields and tunable Z-isomer thermal half-lives from days to years. Combined exptl. and theor. results demonstrate that the electronic structure of the photoswitch core is not substantially affected by various substituents attached to the 1,2,3-triazole unit, benefiting from its cross-conjugated nature. The combination of clickable synthesis, tunable photoswitch property, and self-decoupling ability makes (hetero)arylazo-1,2,3-triazoles intriguing mol. tools in developing photoresponsive systems with the desired performance. In the experiment, the researchers used many compounds, for example, 4-(Methylthio)aniline (cas: 104-96-1Name: 4-(Methylthio)aniline).

4-(Methylthio)aniline (cas: 104-96-1) belongs to thiazole derivatives. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. There are numerous natural products that possess a thiazole ring with broad pharmacological activities. Thiamine, also known as vitamin B1, possesses a thiazole ring linked with 2-methylpyrimidine-4-amine as hydrochloride salt.Name: 4-(Methylthio)aniline

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

Metabolism of sulfathiazole. I. Excreted substance in human urine after administration of sulfathiazole was written by Uno, Toyozo;Ueda, Michihiro. And the article was included in Yakugaku Zasshi in 1960.Synthetic Route of C11H11N3O3S2 This article mentions the following:

The urine during oral administration of sulfathiazole (I) was examined by paper chromatography, using neutral, acid, and alk. developing solvents and by paper electrophoresis. I, acetylsulfathiazole (II), sulfathiazole N⁴-sulfonate, sulfathiazole N⁴-glucuronide, and an unknown substance (III) were detected. These products, except the III, were compared with authentic samples. In another experiment I, II, and an unknown glucuronic acid conjugate were isolated but no other substances. A new and simple apparatus for two-dimensional, ascending paper chromatography was devised, in which the filter paper was wrapped in a plastic sheet. In the experiment, the researchers used many compounds, for example, N-(4-(N-(Thiazol-2-yl)sulfamoyl)phenyl)acetamide (cas: 127-76-4Synthetic Route of C11H11N3O3S2).

N-(4-(N-(Thiazol-2-yl)sulfamoyl)phenyl)acetamide (cas: 127-76-4) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, 蟺-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Synthetic Route of C11H11N3O3S2

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

Predicting reaction conditions from limited data through active transfer learning was written by Shim, Eunjae;Kammeraad, Joshua A.;Xu, Ziping;Tewari, Ambuj;Cernak, Tim;Zimmerman, Paul M.. And the article was included in Chemical Science in 2022.Safety of 2-Bromothiazole This article mentions the following:

Transfer and active learning have the potential to accelerate the development of new chem. reactions, using prior data and new experiments to inform models that adapt to the target area of interest. This article shows how specifically tuned machine learning models, based on random forest classifiers, can expand the applicability of Pd-catalyzed cross-coupling reactions to types of nucleophiles unknown to the model. First, model transfer is shown to be effective when reaction mechanisms and substrates are closely related, even when models are trained on relatively small numbers of data points. Then, a model simplification scheme is tested and found to provide comparative predictivity on reactions of new nucleophiles that include unseen reagent combinations. Lastly, for a challenging target where model transfer only provides a modest benefit over random selection, an active transfer learning strategy is introduced to improve model predictions. Simple models, composed of a small number of decision trees with limited depths, are crucial for securing generalizability, interpretability, and performance of active transfer learning. In the experiment, the researchers used many compounds, for example, 2-Bromothiazole (cas: 3034-53-5Safety of 2-Bromothiazole).

2-Bromothiazole (cas: 3034-53-5) belongs to thiazole derivatives. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Safety of 2-Bromothiazole

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

Facile Synthesis of Amides through Transamidation with Iodine under Neat Conditions was written by Girase, Pankaj S.;Kumar, Vishal;Dhawan, Sanjeev;Karpoormath, Rajshekhar. And the article was included in ChemistrySelect in 2022.Application of 104-96-1 This article mentions the following:

Iodine and NH₂OH.HCl mediated transamidation of unactivated amides with a variety of amines under thermal/microwave irradiations was reported. The current strategy was effective for a wide variety of primary, secondary and tertiary amides and allows formylation, acylation and benzoylation of various amines. The primary advantages of the current protocol were simple, rapid, absence of metal catalyst, low-cost starting material as a solvent, and low environmental impact during the synthesis process. In the experiment, the researchers used many compounds, for example, 4-(Methylthio)aniline (cas: 104-96-1Application of 104-96-1).

4-(Methylthio)aniline (cas: 104-96-1) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.Application of 104-96-1

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

DNA – binding and cleavage studies of macrocyclic metal complexes containing heteroatomic ligands was written by Mathur, Neha;Bargotya, Sonlata. And the article was included in Chemical Science Transactions in 2016.Formula: C7H5BrN2S This article mentions the following:

Designing of improved metal complexes, irreversibly modifying the nucleic acids is important from chem. and biol. point of view. In this regard copper nucleases are of great significance, since they form an important class of artificial nucleases possessing biol. accessible redox potentials and high cleavage affinity. Therefore, they are potential reagents for cleavage of DNA. For the same, coordination compounds using Cu(II) surfactant with N and S donor ligands in a M:L (1:2) molar ratio, complexes Cu₂(C₁₅H₃₁COO)₄L₂ and Cu₂(C₇H₁₅COO)₄L₂ where L is 2-amino-6-bromobenzothiazole, were synthesized and fully characterized by elemental and spectral anal., ¹H NMR, FTIR, ESR and mass spectra. The interaction of the complexes with Lactobacillus acidophilus DNA was studied using agarose gel electrophoresis measurements and visualization of cleavage pattern was done on a UV transilluminator. Results suggest the Cu(II) complexes bind to DNA via different modes. Gel electrophoresis study reveals the fact that the Cu complexes involving N and S donor moieties cleave super-coiled DNA to nicked linear forms. In the experiment, the researchers used many compounds, for example, 2-Amino-6-bromobenzothiazole (cas: 15864-32-1Formula: C7H5BrN2S).

2-Amino-6-bromobenzothiazole (cas: 15864-32-1) belongs to thiazole derivatives. The thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone. There are numerous natural products that possess a thiazole ring with broad pharmacological activities. Thiamine, also known as vitamin B1, possesses a thiazole ring linked with 2-methylpyrimidine-4-amine as hydrochloride salt.Formula: C7H5BrN2S

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

Cesium carbonate-promoted synthesis of aryl methyl sulfides using S-methylisothiourea sulfate under transition-metal-free conditions was written by Zhang, Caiyang;Zhou, You;Huang, Jintao;Tu, Canhui;Zhou, Xiaoai;Yin, Guodong. And the article was included in Organic & Biomolecular Chemistry in 2018.HPLC of Formula: 3034-53-5 This article mentions the following:

In the presence of cesium carbonate, an efficient synthesis of aryl Me sulfides by the reactions of aryl halides with com. available S-methylisothiourea sulfate was developed. This odourless and highly crystalline solid was used as the substitute for malodorous methanethiol. The gram-scale reaction also proceeded smoothly without the use of column chromatog. separation Similarly, 2-(dimethylamino)ethylthio and cyclopropylmethylthio groups were easily introduced into the aromatic rings from the corresponding S-[2-(dimethylamino)ethyl]isothiourea dihydrochloride and S-cyclopropylmethylisothiourea hydrobromide. The possible reaction mechanism was proposed. It was believed that this route to aryl alkyl sulfides were well competitive with currently known methods due to its wide substrate scope, excellent yields, easy operation and transition-metal-free conditions. In the experiment, the researchers used many compounds, for example, 2-Bromothiazole (cas: 3034-53-5HPLC of Formula: 3034-53-5).

2-Bromothiazole (cas: 3034-53-5) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.HPLC of Formula: 3034-53-5

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

Preparation of Novel Chiral Stationary Phases Based on the Chiral Porous Organic Cage by Thiol-ene Click Chemistry for Enantioseparation in HPLC was written by Wang, Ying;Chen, Ji-Kai;Xiong, Ling-Xiao;Wang, Bang-Jin;Xie, Sheng-Ming;Zhang, Jun-Hui;Yuan, Li-Ming. And the article was included in Analytical Chemistry (Washington, DC, United States) in 2022.COA of Formula: C11H12N2S This article mentions the following:

Porous organic cages (POCs) are an emerging class of porous materials that have aroused considerable research interest because of their unique characteristics, including good solubility and a well-defined intrinsic cavity. However, there have so far been no reports of chiral POCs as chiral stationary phases (CSPs) for enantioseparation by high-performance liquid chromatog. (HPLC). Herein, we report the first immobilization of a chiral POC, NC1-R, on thiol-functionalized silica using a mild thiol-ene click reaction to prepare novel CSPs for HPLC. Two CSPs (CSP-1 and CSP-2) with different spacers have been prepared CSP-1, with a cationic imidazolium spacer, exhibited excellent enantioselectivity for the resolution of various racemates. Twenty-three and 12 racemic compounds or chiral drugs were well enantiosepd. on the CSP-1-packed column under normal-phase and reversed-phase conditions, resp., including alcs., diols, esters, ethers, ketones, epoxides, organic acids, and amines. In contrast, chiral resolution using CSP-2 (without a cationic imidazolium spacer)-packed column B was inferior to that of column A, demonstrating the important role of the cationic imidazolium spacer for chiral separation The chiral separation capability of column A was also compared with that of two most popular com. chiral columns, Chiralpak AD-H and Chiralcel OD-H, which exhibits good chiral recognition complementarity with the two com. chiral columns. In addition, five positional isomers dinitrobenzene, nitroaniline, chloroaniline, bromoaniline, and iodoaniline were also well separated on column A. The effects of temperature, mobile phase composition, and injected analyte mass for separation on column A were investigated. Column A also showed good stability and reproducibility after repeated injections. This work demonstrates that chiral POCs are promising chiral materials for HPLC enantioseparation In the experiment, the researchers used many compounds, for example, (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole (cas: 14769-73-4COA of Formula: C11H12N2S).

(S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole (cas: 14769-73-4) belongs to thiazole derivatives. Thiazoles frequently appear in peptide studies. Thiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis. The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.COA of Formula: C11H12N2S

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

Hexahydrophthalimide-benzothiazole hybrids as a new class of protoporphyrinogen oxidase inhibitors: synthesis, structure-activity relationship, and DFT calculations was written by Wu, Qiong-You;Jiang, Li-Li;Yang, Sheng-Gang;Zuo, Yang;Wang, Zhi-Fang;Xi, Zhen;Yang, Guang-Fu. And the article was included in New Journal of Chemistry in 2014.Name: 6-Fluorobenzo[d]thiazole-2(3H)-thione This article mentions the following:

Protoporphyrinogen oxidase (PPO, EC 1.3.3.4) has attracted continuous interest during the last few decades not only because of its unique biochem. characteristics but also because of its biomedical significance. As a continuation of our research work on the development of new PPO inhibitors, N-(benzothiazol-5-yl)-hexahydro-2H-isoindole-1,3-dithione (1a-j) and N-(benzothiazol-5-yl)-octahydro-3-thioxoisoindol-1-one derivatives (2a-i) were designed and synthesized. These newly prepared compounds were characterized by elemental analyses, ¹H NMR and ESI-MS spectroscopy. The in vitro assay indicated that these compounds displayed good inhibition activity against human PPO (hPPO) with K_i values ranging from 0.38 渭M to 6.83 渭M. Notably, most of the monothionated products (1a-j) displayed a higher or comparable PPO-inhibition activity compared with the com. control sulfentrazone. The comparison of the dihedral angles of the representative compound with that of acifluorfen (ACF) complexed with hPPO clearly indicated that the dihedral angle between the thionyl amide or carbonyl amide ring and the benzothiazole ring was closely related to the variation of the PPO inhibition activity of different types of inhibitors. In the experiment, the researchers used many compounds, for example, 6-Fluorobenzo[d]thiazole-2(3H)-thione (cas: 80087-71-4Name: 6-Fluorobenzo[d]thiazole-2(3H)-thione).

6-Fluorobenzo[d]thiazole-2(3H)-thione (cas: 80087-71-4) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). The nitrogen in thiazole is sp2 hybridized and the lone pair of electrons localized on the nitrogen is less reactive due to increased aromatic character and decreased basicity. It is protonated and alkylated/acylated at nitrogen forming hydrochloride and quaternary thiazolium salt.Name: 6-Fluorobenzo[d]thiazole-2(3H)-thione

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

Synthesis and in silico analysis of some new N-phosphorylated 1,2,4-triazole derivatives as potential mycocidal agents was written by Gumber, Khushbu;Sidhu, Anjali;Sharma, Vineet K.. And the article was included in Indian Journal of Heterocyclic Chemistry in 2017.Safety of 6-Fluorobenzo[d]thiazole-2(3H)-thione This article mentions the following:

Ten new biheterocyclic compounds were synthesized by two-step reaction protocol via formation of intermediate Ph phosphorodichloridate, followed by addition of triazole and the addnl. heterocyclic substituent to obtain the final product. The in vitro mycocidal potential of novel synthesized N-phosphorylated 1,2,4-triazole derivatives were examined on phytopathogens, namely, Blumeria graminis tritici, Puccinia striiformis, Puccinia triticina, and Ustilago tritici. Structure elucidation of the compounds was made on the basis of elemental anal., Fourier transform IR, ¹H NMR, and ³¹P NMR spectral data. Most of the compounds with addnl. thiazole/benzothiazole moieties inflicted appreciable potential, comparable to standards and in silico anal. rationale the in vitro antifungal potential of the test compounds In the experiment, the researchers used many compounds, for example, 6-Fluorobenzo[d]thiazole-2(3H)-thione (cas: 80087-71-4Safety of 6-Fluorobenzo[d]thiazole-2(3H)-thione).

6-Fluorobenzo[d]thiazole-2(3H)-thione (cas: 80087-71-4) belongs to thiazole derivatives. Thiazoles frequently appear in peptide studies. Thiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis. Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.Safety of 6-Fluorobenzo[d]thiazole-2(3H)-thione

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

Study on the new synthetic method of 1,2-pentanediol and process optimization thereof was written by Xu, Bao-ming;Tang, Qiang;Luo, Yan;Cheng, Qian;Chen, Kun. And the article was included in Gaoxiao Huaxue Gongcheng Xuebao in 2014.SDS of cas: 32446-47-2 This article mentions the following:

A new feasible synthetic route for the synthesis of 1,2-pentanediol was designed and optimized in this paper with butyraldehyde and paraformaldehyde as the starting material. The effects of feed ratio, reaction temperature, catalyst dosage and reaction pressure on the yield of product were studied. The reaction was divided into two steps. The first step, using 3-Et benzothiazole bromide as catalyst, the intermediate product 1-hydroxy-2-pentanone was synthesized by cross-acyloin condensation between n-butyraldehyde and paraformaldehyde. The optimum condition is: n (butyraldehyde): n (paraformaldehyde) = 1:1.5, n (Bu aldehyde): n (catalytic agent) = 1:0.1, temperature 70掳C, the average yield obtained by six repeated experiments is 56.6%. In the second step, the final product 1,2-pentanediol was synthesized with hydrogenation reduction of 1-hydroxy-2-pentanone by using Pd/C as catalyst. The optimum condition is: Pd/C catalyst dosage 3.5% (relative to the 1-hydroxy-2-pentanone quality), hydrogen pressure 1.5 MPa, temperature 55掳C, the average yield obtained by six repeated experiments is 91.6%. Total yield of two steps is 51.8%, the cost of material is only 40,000 yuan/ton. The structures of product were analyzed and characterized by IR, ¹H-NMR, MS. This process has advantages of easy available raw material, simple technol. with mild reaction conditions, high content of the product and suitable for industrialized production In the experiment, the researchers used many compounds, for example, 3-Ethylbenzo[d]thiazol-3-ium bromide (cas: 32446-47-2SDS of cas: 32446-47-2).

3-Ethylbenzo[d]thiazol-3-ium bromide (cas: 32446-47-2) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. Thiazole sulfonation occurs only under forcing conditions: the action of oleum at 250 掳C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.SDS of cas: 32446-47-2

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