Month: January 2023

Base and ligand free copper-catalyzed N-arylation of 2-amino-N-heterocycles with boronic acids in air was written by Rao, D. Nageswar;Rasheed, Sk.;Aravinda, S.;Vishwakarma, Ram A.;Das, Parthasarathi. And the article was included in RSC Advances in 2013.SDS of cas: 1843-21-6 This article mentions the following:

A wide range of N-arylated 2-amino-N-heterocycles were synthesized by a copper-catalyzed boronic acid cross coupling reaction at ambient temperature in air. This ligand and base free methodol. is general and could provide rapid access to a diverse array of potential bioactive heterocyclic compounds In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6SDS of cas: 1843-21-6).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at δ 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. Thiazole sulfonation occurs only under forcing conditions: the action of oleum at 250 °C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.SDS of cas: 1843-21-6

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

Synthesis and evaluation of amides surrogates of dopamine D3 receptor ligands was written by Jean, Mickael;Renault, Jacques;Levoin, Nicolas;Danvy, Denis;Calmels, Thierry;Berrebi-Bertrand, Isabelle;Robert, Philippe;Schwartz, J. C.;Lecomte, J. M.;Uriac, Philippe;Capet, Marc. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2010.Formula: C9H6ClNS This article mentions the following:

Isosteric replacement of the amide function and modulation of the arylpiperazine moiety of known dopamine D3 receptor ligands led to potent and selective compounds Enhanced bioavailability and preferential brain distribution make (piperazinyl)butanamine derivative I a good candidate for pharmacol. and clin. evaluation. In the experiment, the researchers used many compounds, for example, 2-Chloro-5-phenylthiazole (cas: 329794-40-3Formula: C9H6ClNS).

2-Chloro-5-phenylthiazole (cas: 329794-40-3) 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.Formula: C9H6ClNS

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

Photocatalytic intermolecular carboarylation of alkenes by selective C-O bond cleavage of diarylethers was written by Ji, Meishan;Chang, Chenyang;Wu, Xinxin;Zhu, Chen. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2021.COA of Formula: C7H3BrClNS This article mentions the following:

Disclosed herein is a novel radical-mediated intermol. carboarylation of alkenes by cleaving inert C-O bonds. The strategically designed arylbenzothiazolylether diazonium salts are harnessed as dual-function reagents. A vast array of alkenes are proven to be suitable substrates. The benzothiazolyl moiety in the products serves as the formyl precursor, and the OH residue provides the cross-coupling site for further product elaboration, indicating the robust transformability of the products. In the experiment, the researchers used many compounds, for example, 6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4COA of Formula: C7H3BrClNS).

6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. 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.COA of Formula: C7H3BrClNS

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

Metal-free synthesis of 2-substituted (N, O, C) benzothiazoles via an intramolecular C-S bond formation was written by Feng, Enguang;Huang, He;Zhou, Yu;Ye, Deju;Jiang, Hualiang;Liu, Hong. And the article was included in Journal of Combinatorial Chemistry in 2010.Formula: C13H10N2S This article mentions the following:

An efficient, economical, and convenient method was developed for the preparation of 2-substituted (N, O, C) benzothiazoles from N’-substituted-N-(2-halophenyl)thioureas, O’-substituted-N-(2-halophenyl) carbamothioates, or N-(2-halophenyl) thioamides via a base-promoted cyclization in dioxane without any transition metal. A one-pot variant combining the synthesis of the thiourea and the cyclization was also demonstrated. High yields were obtained, and a variety of functional groups were tolerated under these conditions. Transition-metal-free, mild reactive conditions, wide application scope, and shorter reaction times make this method superior to the reported methods for the synthesis of 2-substituted benzothiazoles and suitable for combinatorial format. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Formula: C13H10N2S).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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.Formula: C13H10N2S

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

Novel triapine derivative induces copper-dependent cell death in hematopoietic cancers was written by Chen, Ge;Niu, Chunyi;Yi, Jianhua;Sun, Lin;Cao, Hengyi;Fang, Yanjia;Jin, Taijie;Li, Ying;Lou, Chunli;Kang, Jingwu;Wei, Wanguo;Zhu, Jidong. And the article was included in Journal of Medicinal Chemistry in 2019.Category: thiazole This article mentions the following:

Triapine, an iron chelator that inhibits ribonucleotide reductase, has been evaluated in clin. trials for cancer treatment. Triapine in combination with other chemotherapeutic agents shows promising efficacy in certain hematol. malignancies; however, it is less effective against many advanced solid tumors, probably due to the unsatisfactory potency and pharmacokinetic properties. In this report, we developed a triapine derivative IC25 (10(I)) with potent antitumor activity. I preferentially inhibited the proliferation of hematopoietic cancers by inducing mitochondria reactive oxygen species production and mitochondrial dysfunction. Unlike triapine, I executed cytotoxic action in a copper-dependent manner. I-induced up-expression of thioredoxin-interacting protein resulted in decreased thioredoxin activity to permit c-Jun N-terminal kinase and p38 activation and ultimately led to the execution of the cell death program. Remarkedly, I showed good bioavailability and inhibited tumor growth in mouse xenograft models. Taken together, our study identifies I as a copper-dependent antitumor agent, which may be applied to the treatment of hematopoietic cancers. In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6Category: thiazole).

5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6) 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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Category: thiazole

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

Reversible changes of tubular cell and basement membrane in drug-induced renal cystic disease was written by Kanwar, Yashpal S.;Carone, Frank A.. And the article was included in Kidney International in 1984.Safety of 4,5-Diphenylthiazol-2-amine This article mentions the following:

To delineate changes in the development and regression of renal cystic disease, sequential studies were done in rats fed 2-amino-4,5-diphenyl thiazole (DPT). Kidneys were perfusion fixed with either aldehyde fixative alone or with the addition of ruthenium red (RR), a stain detecting the presence of proteoglycans. Tissues were processed for light and electron microscopy. Light microscopy sections were stained with alcian blue (a stain detecting acid mucopolysaccharides) and eosin and hematoxylin. Initially, cellular proliferation and, later cystic transformation of collecting tubules were observed The structural changes in tubular cells preceded alterations in the basement membrane and consisted of an increase in smooth and rough endoplasmic reticulum and free polyribosomes, prominence of Golgi complexes, and an increased number of lysosomes. These findings are suggestive of changes in the biosynthetic, secretory, and degradative mechanisms of the cell. With time, the tubular basement membranes became progressively thicker and laminated with concomitant loss of alcian-blue- nad RR-staining. When DPT-treated animals with renal cystic disease were placed on a normal diet, tubular cell and basement membrane morphol. and alcian-blue- and RR-staining returned to normal and cystic changes regressed. These findings are compatible with altered synthesis and degradation of tubular basement membranes in this model of cystic disease. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Safety of 4,5-Diphenylthiazol-2-amine).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. 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 4,5-Diphenylthiazol-2-amine

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

Iodine-catalyzed amination of benzothiazoles with KSeCN in water to access primary 2-aminobenzothiazoles was written by Zhu, Yu-Shen;Shi, Linlin;Fu, Lianrong;Chen, Xiran;Zhu, Xinju;Hao, Xin-Qi;Song, Mao-Ping. And the article was included in Chinese Chemical Letters in 2022.Application In Synthesis of 5,6-Dimethoxybenzo[d]thiazol-2-amine This article mentions the following:

A facile and sustainable approach for the amination of benzothiazoles I (X = H, N; R = H, 4-Cl, 5-OMe, 6-NO₂, 7-C(O)OMe; R¹ = H) with KSeCN using iodine as the catalyst in water has been disclosed under transition-metal free conditions. The reaction proceeded smoothly to afford various primary 2-amino benzothiazoles I (R¹ = NH₂) in up to 96% yield. A series of control experiments were performed, suggesting that a ring-opening mechanism was involved via a radical process. This protocol provides efficient synthesis of primary 2-aminobenzothiazole I (R¹ = NH₂). In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6Application In Synthesis of 5,6-Dimethoxybenzo[d]thiazol-2-amine).

5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-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. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Application In Synthesis of 5,6-Dimethoxybenzo[d]thiazol-2-amine

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

High Adsorption Capacity of an sp2/sp3-N-Rich Polymeric Network: From Molecular Iodine Capture to Catalysis was written by Gambhir, Diksha;Venkateswarulu, Mangili;Verma, Tushar;Koner, Rik Rani. And the article was included in ACS Applied Polymer Materials in 2020.Application of 1843-21-6 This article mentions the following:

Removal of volatile radioiodine from air and wastewater streams using porous materials is imperative to curb its long-term adverse effects on the environment. Herein, we report the development of a hydrogel system (PEIG) using polyethylenimine and glutaraldehyde followed by production of xerogel (PEIXG). PEIXG effectively captured iodine in its vapor form with an excellent adsorption capacity of 2.9 g/g. Addnl., PEIXG efficaciously removed dissolved iodine from water and nonpolar solvent. Moreover, the reversible nature of the uptake enabled good recyclability and utilization of I₂-PEIXG as a catalyst for the synthesis of an important class of functional heterocycle, 2-aminobenzothiazoles. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Application of 1843-21-6).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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. Thiazole sulfonation occurs only under forcing conditions: the action of oleum at 250 °C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.Application of 1843-21-6

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

Parallel solution-phase synthesis of a 2-aminothiazole library including fully automated work-up was written by Buchstaller, Hans-Peter;Anlauf, Uwe. And the article was included in Combinatorial Chemistry & High Throughput Screening in 2011.Electric Literature of C15H12N2S This article mentions the following:

A straightforward and effective procedure for a solution phase preparation of a 2-aminothiazole combinatorial library is described. The synthesis of the target compounds was achieved by a reaction, work-up and isolation of these thiazolamine derivatives as free bases by a fully automated method using the Chemspeed ASW 2000 automated synthesizer. The compounds were obtained in good yields and excellent purity without any further purification requirements. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Electric Literature of C15H12N2S).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) 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.Electric Literature of C15H12N2S

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

Regarding the synthesis of 2-mercaptobenzothiazole was written by Ivanova, V. A.;Shebuev, A. N.. And the article was included in Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation) in 1957.Application of 1843-21-6 This article mentions the following:

A series of preparations were made in an attempt to establish the progressive steps in the synthesis of 2-mercaptobenzothiazole (I) from PhNH₂, CS₂, and S at 250°. The reactions of PhNH₂ and CS₂ to form (PhNH)₂CS (II) or PhNCS (III) and H₂S are reversible. The former decompose above 160° to form the original substances and the latter, though stable, reacts with S to form I only in the presence of saponifying agents. Neither II nor III can, therefore, be intermediate steps in the synthesis of I (cf. Sebrell and Boord, C.A. 17, 3876; Bruni and Levi, C.A. 18, 2341). Their presence in the products at certain stages of the reaction is attributed to side reactions. Heating 2-aminothiophenol (IV) or 2,2′-diaminodiphenyl disulfide (V) with S failed to yield acylated compounds This was probably due to the rapid closing of the thiazole ring to give I. On the other hand, in an alk. solution, IV reacts with CS₂ at 80° to give C₁₃H₁₀N₂S₃ which reacts with Zn dust and HCl to give 4,4′-dimercaptodiphenylthiourea. By analogy it was assumed that CS₂ acylates the amino group of IV or V which pass into I. PhNH₂, CS₂, and S were heated in an autoclave 3 hrs. at 250-60° and then cooled to 20°. After treatment with dilute HCl and recrystallization from 50% EtOH, V was obtained, m. 93°. The absence of IV and the presence of a considerable quantity of anilinobenzothiazole (VI) in the products were noted. The absence of IV was ascribed to its oxidation by S; at 20° S dissolved in IV with a vigorous evolution of H₂S and the formation of V. The presence of VI was ascribed to the reversible reaction PhNH₂ + I ⇌ VI + H₂S which is shifted to the left as the normal synthesis progresses and PhNH₂ is used up. VI is not an intermediate in the synthesis of I. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Application of 1843-21-6).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. Thiazoles in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications. Electrophilic attack at nitrogen depends on the presence of electron density at nitrogen as well as the position and nature of substituent linked to the thiazole ring.Application of 1843-21-6

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