Tag: 200-300

Copper-Catalyzed Thiolation of Terminal Alkynes Employing Thiocyanate as the Sulfur Source Leading to Enaminone-Based Alkynyl Sulfides under Ambient Conditions was written by R., Chandran;Pise, Ashwini;Shah, Suraj Kumar;D., Rahul;V., Suman;Tiwari, Keshri Nath. And the article was included in Organic Letters in 2020.SDS of cas: 6294-52-6 This article mentions the following:

A highly efficient protocol for copper-catalyzed thio-alkynylation of enaminone-based thiocyanates with terminal alkynes under mild conditions has been developed. This scalable amino group-directed thio-alkynylation proceeds in the open air with a broad substrate scope and an excellent yield. The demonstrated synthetic transformation creates the opportunity for a wide variety of sulfur-containing useful materials. Gram-scale synthesis and further synthetic transformations of alkynyl sulfides highlight the potential utility of the method. In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6SDS of cas: 6294-52-6).

5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6) 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. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.SDS of cas: 6294-52-6

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

[Chemical-induced polycyst with renal tumor and expression of 8-OHdG in kidney tissue]. was written by Huang, X;Wang, X;Zhu, J;Hou, S;Dong, J. And the article was included in Zhonghua wai ke za zhi [Chinese journal of surgery] in 2000.Application of 6318-74-7 This article mentions the following:

OBJECTIVE: To induce the rat model of polycyst with renal tumor and investigate the expression of 8-OHdG in the kidney tissues. METHODS: The rat model of polycyst with renal tumor, similar to human acquired cystic disease of the kidney (ACDK), was induced by oral administration of 2-amino-4, 5-diphenylthiazole (DPT) and N-nitrosomorpholine (NNM). Immunohistochemical method (LSAB) was used to assay the expression of 8-hydroxydeoxyguanosine (8-OHdG) in the rat kidney tissue. RESULTS: Three of 10 rats in the NNM group had renal solid adenomatous lesions. Bilateral polycysts were observed in all 9 rats of the DPT/NNM group. Seven of the 9 rats had cystic multistage renal tumor. In the DPT/NNM group, 4 rats had cystic adenomatous lesions, but none in the other groups showed this lesion. In the model, adenomatous lesions derived from polycysts in the rats were closely consistent to human ACDK in morphology. The significant expression of 8-OHdG was found on renal tubular cell, cystic epithelial cell, stromal cell and tumor cell in all rats of the NNM and DPT/NNM group. CONCLUSION: A rat model of polycysts with renal tumor, similar to human ACDK, induced by DPT and NNM provides evidences for further study on pathogenic mechanism in human ACDK with renal cell carcinoma. The expression of 8-OHdG, a DNA damage marker, in the renal tissues of rat model might help to explain the mechanism of cysticogenesis and carcinogenesis in human ACDK. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Application of 6318-74-7).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) 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. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Application of 6318-74-7

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

Use of molecular oxygen as a reoxidant in the synthesis of 2-substituted benzothiazoles via palladium-catalyzed C-H functionalization/intramolecular C-S bond formation was written by Inamoto, Kiyofumi;Hasegawa, Chisa;Kawasaki, Junpei;Hiroya, Kou;Doi, Takayuki. And the article was included in Advanced Synthesis & Catalysis in 2010.Safety of N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

Mol. oxygen (O₂) was successfully employed as a reoxidant in cyclizations of thiobenzanilides through a palladium-catalyzed C-H functionalization/intramol. C-S bond formation process, leading to an efficient, green method for the synthesis of 2-arylbenzothiazoles I (R¹ = 6-CN, 6-EtOCO, 6-NO₂, 6-MeO, 5-MeO, 4-Me, 6-Cl, 6-Br, 5-Br, 6-I, 4-F, 5-N, 6-N, R² = H; R¹ = H, R² = 4-CN, 4-Cl, 4-MeO, 3-MeO; R¹ =6-CN, R² = 4-MeO). Addition of cesium fluoride (CsF) greatly enhanced the reactions, which produced variously substituted 2-aryl-benzothiazoles with good functional group tolerance. Thioureas were also found to be suitable substrates for the cyclization process using a palladium/O₂ catalyst system, thus generating 2-aminobenzothiazoles II (R¹ = H, R² = 4-MeO-Bn, 4-NO₂-Bn, 2-Me-Bn, Ph, 1-Ph-Et, R³ = H ; R¹ = H, 6-MeO, 6-CN, 4-Me, R² = Bn, R³ = H; R¹ = H, R², R³ = morpholinyl). One-pot syntheses of 2-aminobenzothiazoles II from aryl isothiocyanates and amines were also successful. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Safety of N-Phenylbenzo[d]thiazol-2-amine).

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. 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.Safety of N-Phenylbenzo[d]thiazol-2-amine

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

Stereoselective formation of (Z)-2-fluoroalkenoates via Julia-Kocienski reaction of aldehydes with pyrimidinyl-fluoro-sulfones was written by Larnaud, Florent;Pfund, Emmanuel;Linclau, Bruno;Lequeux, Thierry. And the article was included in Tetrahedron in 2014.Name: 5-Nitrobenzothiazole-2-thiol This article mentions the following:

The selective synthesis of fluoroalkenoates is reported using a pyrimidine-fluoro-sulfone as a starting material. This sulfone allowed the preparation of (Z)-fluoroalkenoates with very high stereoselectivity from both aromatic and aliphatic aldehydes. The nature of the heterocycle on the course of the Julia-Kocienski reaction is discussed. A Julia-Kocienski reaction involves the formation of alkenes by a reaction of sulfones with aldehyde derivatives In this work the synthesis of the target compounds was achieved using 4-bromobenzaldehyde, 2,5-dibromobenzaldehyde, 2-thiophenecarboxaldehyde, 2-furancarboxaldehyde, heptanal, nonanal, 10-undecanal, (S)-citronellal, benzenepropanal, cyclohexanecarboxaldehyde, (1S,3R)-3-formyl-2,2-dimethylcyclopropanecarboxylic acid ester as aldehyde components. Sulfone components contained a fluorine group, such as 2-[(2-benzothiazolyl)sulfonyl]-2-(fluoro)acetic acid Et ester, 2-fluoro-2-[(2-pyridinyl)sulfonyl]acetic acid Et ester, 2-fluoro-2-[(2-pyrimidinyl)sulfonyl]acetic acid Et ester. The title compounds thus formed included (2Z)-3-(4-bromophenyl)-2-fluoro-2-propenoic acid ester, (2Z)-2-fluoro-3-(2-thienyl)-2-propenoic acid ester, (2Z)-2-fluoro-3-(2-furanyl)-2-propenoic acid ester, (2Z)-2-fluoro-2-nonenoic acid ester, (1S,3S)-3-[(1Z)-3-ethoxy-2-fluoro-3-oxo-1-propen-1-yl]-2,2-dimethylcyclopropanecarboxylic acid ester. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0Name: 5-Nitrobenzothiazole-2-thiol).

5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0) 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.Name: 5-Nitrobenzothiazole-2-thiol

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

Gold nanoparticle catalyzed intramolecular C-S bond formation/C-H bond functionalization/cyclization cascades was written by Gogoi, Prasanta;Paul, Bappi;Hazarika, Sukanya;Barman, Pranjit. And the article was included in RSC Advances in 2015.Reference of 1843-21-6 This article mentions the following:

An efficient synthesis of 2-(N-aryl)aminobenzo[d]-1,3-thiazoles via intramol. C-S bond formation/C-H bond functionalization utilizing an unusual cocatalytic Au-NPs/KMnO₄ system under an oxygen atm. at 80° was presented. Au-NPs could be easily prepared by using HAuCl₄ with reductive potential of Kayea assamica (sia nahor) aqueous fruit extract The catalyst could be easily separated and recycled eight times without any appreciable loss of activity. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Reference of 1843-21-6).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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.Reference of 1843-21-6

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

A New, Efficient and Recyclable Lanthanum(III) Oxide- Catalyzed C-N Cross-Coupling was written by Murthy, S. Narayana;Madhav, B.;Reddy, V. Prakash;Nageswar, Y. V. D.. And the article was included in Advanced Synthesis & Catalysis in 2010.Recommanded Product: 1843-21-6 This article mentions the following:

A new and efficient protocol for the C-N cross-coupling of aryl halides with heteroaromatic amines using lanthanum(III) oxide (10 mol%) as a recyclable catalyst, N,N’-dimethylethylenediamine (DMEDA) (20 mol%)as a ligand, and potassium hydroxide (KOH) as a base in DMSO at 110 °C has been developed. This inexpensive catalytic system is highly effective towards the amination of aryl halides with various nitrogen nucleophiles and is significantly tolerant towards other functional groups in the substrates. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Recommanded Product: 1843-21-6).

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

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

Synthesis and structure-activity relationship of aminoarylthiazole derivatives as correctors of the chloride transport defect in cystic fibrosis was written by Pesce, Emanuela;Bellotti, Marta;Liessi, Nara;Guariento, Sara;Damonte, Gianluca;Cichero, Elena;Galatini, Andrea;Salis, Annalisa;Gianotti, Ambra;Pedemonte, Nicoletta;Zegarra-Moran, Olga;Fossa, Paola;Galietta, Luis J. V.;Millo, Enrico. And the article was included in European Journal of Medicinal Chemistry in 2015.Name: 6-Bromo-2-chlorobenzothiazole This article mentions the following:

(Arylamino)arylthiazoles such as I were prepared and tested for their ability to correct mutations in the folding and function of the cystic fibrosis transmembrane conductance regulator (CFTR) and to determine general structure-activity relationships for correcting folding (processing) mutations and functional mutations (potentiation) of the CFTR. I acted as both a corrector and potentiator for the CTFR; its efficacy was improved and marked synergy was present when used in combination with the corrector VX-809. Mol. docking of I and two other (arylamino)arylthiazoles to the nucleotide binding domain NBD1 of the CFTR was performed to determine their binding sites to the CTFR. In the experiment, the researchers used many compounds, for example, 6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4Name: 6-Bromo-2-chlorobenzothiazole).

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. 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.Name: 6-Bromo-2-chlorobenzothiazole

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

Small molecules enhance functional O-mannosylation of Alpha-dystroglycan was written by Lv, Fengping;Li, Zhi-fang;Hu, Wenhao;Wu, Xiaohua. And the article was included in Bioorganic & Medicinal Chemistry in 2015.Reference of 58759-63-0 This article mentions the following:

Alpha-dystroglycan (α-DG), a highly glycosylated receptor for extracellular matrix proteins, plays a critical role in many biol. processes. Hypoglycosylation of α-DG results in various types of muscular dystrophies and is also highly associated with progression of majority of cancers. Currently, there are no effective treatments for those devastating diseases. Enhancing functional O-mannosyl glycans (FOG) of α-DG on the cell surfaces is a potential approach to address this unmet challenge. Based on the hypothesis that the cells can up-regulate FOG of α-DG in response to certain chem. stimuli, the authors developed a cell-based high-throughput screening (HTS) platform for searching chem. enhancers of FOG of α-DG from a large chem. library with 364,168 compounds Sequential validation of the hits from a primary screening campaign and chem. works led to identification of a cluster of compounds that pos. modulate FOG of α-DG on various cell surfaces including patient-derived myoblasts. These compounds enhance FOG of α-DG by almost ten folds, which provide us powerful tools for O-mannosylation studies and potential starting points for the development of drug to treat dystroglycanopathy. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0Reference of 58759-63-0).

5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0) 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 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.Reference of 58759-63-0

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

Environment-friendly and efficient synthesis of 2-aminobenzo-oxazoles and 2-aminobenzothiazoles catalyzed by Vitreoscilla hemoglobin incorporating a cobalt porphyrin cofactor was written by Xu, Yaning;Li, Fengxi;Zhao, Nan;Su, Jiali;Wang, Chunyu;Wang, Ciduo;Li, Zhengqiang;Wang, Lei. And the article was included in Green Chemistry in 2021.Category: thiazole This article mentions the following:

In this study, an environment-friendly and efficient artificial Vitreoscilla Hb (VHb) for the synthesis of 2-aminobenzoxazoles and 2-aminobenzothiazoles has been reported. Authors demonstrate an expression-based porphyrin substitution strategy to produce VHb containing cobalt porphyrin instead of native hemin, which can catalyze the oxidative cyclization of corresponding 2-aminobenzoxazoles and 2-aminobenthiazoles with up to 97% yield and 4850 catalytic turnovers in water under aerobic conditions. Hence, authors provide a green and mild method for the synthesis of 2-aminobenzoxazoles and 2-aminobenzothiazoles. In addition, authors indicate the value of porphyrin ligand substitution as a strategy to tune and enhance the catalytic properties of hemoproteins in non-natural reactions. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Category: thiazole).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.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

2-Amino-4-methyl-5-thiazolesulfonamide and some derivatives was written by Backer, H. J.;de Jonge, J.. And the article was included in Recueil des Travaux Chimiques des Pays-Bas et de la Belgique in 1943.Application of 69812-29-9 This article mentions the following:

ClSO₃H (300 g.) was added to 50 g. of 2-acetamido-4-methylthiazole below 10° with agitation; the mixture was heated for 3 h. at 50°, for 3 h. at 60°, and then poured into a mixture of ice and water. Extraction with 1.5 l. of Et₂O left 14 g. of insoluble 2-acetamido-4-methyl-5-thiazolesulfonic acid (XVI), soluble in H₂O but only slightly soluble in 25% H₂SO₄. The ether solution when washed with water, dried, and distilled yielded 27 g. of 2-acetamido-4-methyl-5-thiazolesulfonyl chloride (XVII), crystals from C₆H₆, m. 159-60°. The Na salt of XVI with ClSO₃H gave XVII. Dry NH₃ passed into 6 g. of XVII in 35 cc. of C₅H₅N gave 4.1 g. of 2-acetamido-4-methyl-5-thiazolesulfonamide, crystals from AcOH, m. 230-1° after drying at 100°, 1 g. of which, heated for 0.25 h. with 6 cc. of 25% HCl, gave 0.5 g. of 2-amino-4-Me 5-thiazolesulfonamide, crystals from H₂O, m. 175-6°. Heating 2.5 g. of XVII with 5 cc. of C₆H₆NH₂ for 0.25 h. at 60° gave 2.7 g. of 2-acetamido-4-methyl-5-thiazolesulfonanilide, crystals from dilute EtOH, m. 198-9°, 2.5 g. of which heated with 20 cc. of 3 N HCl gave 0.9 g. of 2-amino-4-methyl-5-thiazolesulfonanilide (XVIII), crystals from H₂O, m. 135-6°. Heating 5.1 g. of XVII with 1.9 g. of 2-aminopyridine in 30 cc. of C₅H₅N on a water bath for 2 h. gave 3.9 g. 2-(2-acetamido-4-methyl-5-thiazolylsulfonamido)pyridine, crystals from EtOH, m. 229-30° after drying at 105°, 1 g. of which heated with 6 cc. of 3 N HCl for 0.5 h. gave 2-(2-amino-4-methyl-5-thiazolylsulfonamido)pyridine, crystals from H₂O, m. 208-9° (crystals from EtOH contained 1 mol. of EtOH). Heating 7.65 g. of XVII with 3.42 g. of I in 45 cc. of C₅H₅N for 2 h. on a water bath gave 3.4 g. of 2-(2-acetamido-4-methyl-5-thiazolylsulfonamido)-4-methylthiazole, crystals from H₂O, m. 235-6.5°, 1.2 g. of which boiled with 12 cc. of 3 N HCl for 0.5 h. gave 2-(2-amino-4-methyl-5-thiazolylsulfonamido)-4-methylthiazole, crystals from dilute EtOH, decompose near 241°. The compounds were not active against pneumococcal infections in mice. XVIII was very toxic. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Application of 69812-29-9).

2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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.Application of 69812-29-9

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