Day: January 6, 2023

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

Pyridyl and thiazolyl bisamide CSF-1R inhibitors for the treatment of cancer was written by Scott, David A.;Aquila, Brian M.;Bebernitz, Geraldine A.;Cook, Donald J.;Dakin, Les A.;Deegan, Tracy L.;Hattersley, Maureen M.;Ioannidis, Stephanos;Lyne, Paul D.;Omer, Charles A.;Ye, Minwei;Zheng, XiaoLan. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2008.Electric Literature of C4H6N2S This article mentions the following:

The bisamide class of kinase inhibitors was identified as being active against CSF-1R. The synthesis and SAR of pyridyl and thiazolyl bisamides are reported, along with the pharmacokinetic properties and in vivo activity of selected examples. In the experiment, the researchers used many compounds, for example, 2-Methylthiazol-5-amine (cas: 89281-44-7Electric Literature of C4H6N2S).

2-Methylthiazol-5-amine (cas: 89281-44-7) 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. 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.Electric Literature of C4H6N2S

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

Experimental and theoretical study of the reactivity of thiazole and 4,5-dimethylthiazole towards free phenyl and substituted phenyl radicals was written by Vitry-Raymond, Jacqueline;Metzger, Jacques. And the article was included in Bulletin de la Societe Chimique de France in 1963.Synthetic Route of C9H7NS This article mentions the following:

The reactivity of thiazole (I) towards free phenyl and p-nitrophenyl radicals (obtained by the thermal decomposition of Bz₂O₂ and p-nitrophenyldiazonium salts, resp.) was investigated. The results are interpreted on the basis of the radical polarization energies calculated by the mol. orbital method. I and Bz₂O₂ in a molar ratio of 55:1 heated at 80° under N, excess I removed, the residue hydrolyzed, and the mixture steam distilled gave a mixture of 52% 2- (II), 37% 5- (III), and 11% 4-phenylthiazole (IV). The crude residue from a similar run extracted with C₆H₆, the extract successively reextracted with concentrated HCl and concentrated aqueous NaOH, the acidic extract neutralized and extracted with Et₂O, and the extract evaporated yielded 8% mixture of 54-6% II, 29-31% III, and 13-17% IV; the alk. extract neutralized gave BzOH, m. 122°, and p-PhC₆H₄CO₂H, m. 114°. These results show that the steam distillation apparently caused a reduction of the yields of IV and that in all runs the decreasing order of reactivity of the various positions in I was 2 > 5 > 4. The spectroscopic analysis of the steam-distilled product showed the presence of 60% II, 24% III, and 16% IV. I treated with p-nitrodiazonium salts under the conditions described previously for the reaction with 4,5-dimethylthiazole (CA 55, 22288c) gave 14% of a mixture of 3 isomeric monosubstitution products. The electron distribution in 2-, 4-, and 5-methylthiazole and in 4,5-dimethylthiazole was calculated In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Synthetic Route of C9H7NS).

5-Phenylthiazole (cas: 1826-13-7) 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 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.Synthetic Route of C9H7NS

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

Importance of substituents in ring opening: a DFT study on a model reaction of thiazole to thioamide was written by Bai, Xue;Qin, Dan;Yang, Lijun. And the article was included in Journal of Molecular Modeling in 2021.Recommanded Product: 2-Methylthiazol-5-amine This article mentions the following:

Thiazole ring is an important active mol. skeleton of drugs. Thiazole in natural products and drugs are usually harmlessly eliminated. However, hepatotoxic reactions may occur due to the biol. activation of thiazole to produce reactive thioamide. A typical example is hepatotoxic sudoxicam and safety meloxicam. The only structural difference between them is a Me group on C5 position of thiazole in meloxicam. The mol. basis for the difference remains unknown and the bioactivation mechanism of the thiazole ring is still obscure. Quantum chem. calculations were performed to elucidate the activation mechanism of the thiazole ring under P 450 catalysis, and the influence of the substituents on the activation pathways of thiazole ring was also studied. The calculated results show that the activation of thiazole is closely related to the substituents on the thiazole and spin state of Cpd I. The thiazole and substituted thiazole directly open the ring when catalyzed by doublet spin state Cpd I that catalyzed by the quartet spin state Cpd I can open the ring directly or indirectly, which is related to the substituents. Thiazoles modified with electron-donating substituents mainly undergo direct ring opening, while thiazoles modified with electron-withdrawing groups or weak electron-donating groups mainly undergo indirect ring-opening process accompanied by intermediate formation. The research results laid the foundation for the design of thiazole ring drugs, and also laid a theor. foundation for the study of reducing the toxicity of thiazole ring drugs. In the experiment, the researchers used many compounds, for example, 2-Methylthiazol-5-amine (cas: 89281-44-7Recommanded Product: 2-Methylthiazol-5-amine).

2-Methylthiazol-5-amine (cas: 89281-44-7) 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. 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.Recommanded Product: 2-Methylthiazol-5-amine

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

Experimental model of renal tumors in polycystic kidneys: effects of long-term 2-amino-4,5-diphenylthiazole administration in rats treated with N-ethyl-N-hydroxyethylnitrosamine was written by Tsumatani, Kenichi;Nakagawa, Yoshinori;Kitahori, Yoshiteru;Konishi, Noboru;Uemura, Hirotsugu;Ozono, Seiichiro;Hirao, Yoshihiko;Okajima, Eigoro;Hirao, Kazuya;Hiasa, Yoshio. And the article was included in Toxicologic Pathology in 1997.Category: thiazole This article mentions the following:

The present study was undertaken to examine the effects of long-term 2-amino-4,5-diphenylthiazole (DPT) treatment after initiation of kidney carcinogenesis with N-ethyl-N-hydroxyethylnitrosamine (EHEN) in Wistar rats. One hundred forty-four 6-wk-old male Wistar rats were divided into 6 equal receiving groups: 1000 ppm EHEN or normal tap water for 2 wk followed by 1.06% DPT or basal diet for the subsequent 14 or 30 wk. Controls were maintained without treatment throughout. Subgroups of 6 animals from each group were sacrificed after 8, 16, 24, and 32 wk for histopathol. assessment of lesion development in the kidneys and liver. Animals treated with DPT first developed cystic changes of the kidneys (primarily at the corticomedullary border) after 8 wk of treatment, and these changes progressed with time thereafter. In the groups in which DPT treatment was discontinued after 14 wk, cysts then gradually decreased in size. All tumors detected in the kidneys were histopathol. diagnosed as renal cell adenomas. The tumor multiplicity after 32 wk of treatment was significantly higher in Group I, receiving EHEN + DPT for 30 wk (6.33±4.46), and Group III, receiving EHEN + DPT for 14 wk (3.83±1.57), than in Group V, EHEN alone (1.00±0.58). Renal cell tumors within cysts were only seen in Groups I and III. The general bromodeoxyuridine labeling indexes for the kidneys at week 32 were significantly higher in Group I (55.94±21.08 cells/mm²) and Group III (53.75±12.38 cells/mm²) than in Group V (22.38±6.98 cells/mm²). In conclusion, DPT caused cystic changes in rat kidneys, which, however, gradually decreased in size after the treatment was discontinued, suggesting a reversible nature. DPT clearly also promotes renal tumor development after EHEN initiation, and this effect persists, to a certain extent, even after the insult is removed. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Category: thiazole).

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. 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.Category: thiazole

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

A one-pot strategy for the synthesis of 2-aminobenzothiazole in water by copper catalysis was written by Khatun, Nilufa;Jamir, Latonglila;Ganesh, Majji;Patel, Bhisma K.. And the article was included in RSC Advances in 2012.Quality Control of N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

A straightforward, efficient and sustainable method (green chem.) for the synthesis of 2-aminobenzothiazole derivatives has been achieved from in-situ generated 2-halo thioureas using a copper(I) catalyst in water as a reaction medium. The present study demonstrates that copper iodide (CuI) exhibits better efficiency in water towards intramol. S-arylation compared to other organic solvents. While (2-iodoaryl)thioureas are smoothly converted to the desired product in high yield with only a catalytic quantity of CuI, addition of base and ligand are essential for bromo analogs and chloro analogs. The title compounds thus formed included N-(2-methoxyphenyl)-2-benzothiazolamine (I) [N-(2-methoxyphenyl)-6-methyl-2-benzotiazolamine]. An unprecedented demethoxylation of a (2-methoxyphenyl)thiourea intermediate followed by a Friedel-Crafts type methylation (para to nitrogen) was observed in the aryl ring possessing the original methoxy group and the product thus formed was N-(2-iodo-4-methylphenyl)-6-methyl-2-benzotiazolamine (II). The synthesis of the target compounds was also achieved by a reaction of 1-iodo-2-(isothiocyanato)benzene with morpholine, piperidine, pyrrolidine and the products thus formed included 2-(4-morpholinyl)benzothiazole, 2-(1-piperidinyl)benzothiazole and 2-(1-pyrrolidinyl)benzothiazole. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Quality Control of N-Phenylbenzo[d]thiazol-2-amine).

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. 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.Quality Control of N-Phenylbenzo[d]thiazol-2-amine

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

Molecular search of new active drugs against Toxoplasma gondii was written by Gozalbes, R.;Galvez, J.;Garcia-Domenech, R.;Derouin, F.. And the article was included in SAR and QSAR in Environmental Research in 1999.Application In Synthesis of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride This article mentions the following:

Mol. connectivity has been applied to the search of new compounds with activity against the protozoan Toxoplasma gondii, using a stepwise linear discriminant anal. (SLDA) which is able to classify a compound according to its activity either as active or as inactive. Among the selected compounds, andrographolide and dibenzothiophene sulfone stand out, both with IC₅₀ values lower than 1 μg/mL, which are comparable to these of drugs such as sulfamethoxazole, pyrimethamine and trimethoprim, with IC₅₀ values equal to 1.1, 0.04 and 2.31 μg/mL, resp. These results confirm the usefulness of this topol. approach for the selection and design of new-lead drugs active against Toxoplasma gondii. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Application In Synthesis of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride).

2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) 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. 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 In Synthesis of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride

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

Metal-Free Synthesis of 2-Aminobenzothiazoles via Iodine-Catalyzed and Oxygen-Promoted Cascade Reactions of Isothiocyanatobenzenes with Amines was written by Xu, Yuanshuang;Li, Bin;Zhang, Xinying;Fan, Xuesen. And the article was included in Journal of Organic Chemistry in 2017.Formula: C13H10N2S This article mentions the following:

In this paper, a highly efficient and sustainable synthesis of 2-aminobenzothiazoles through the cascade reactions of isothiocyanatobenzenes with primary or secondary amines by using iodine as a catalyst and oxygen as an oxidant is presented. Mechanistically, the formation of the title compounds involves the in situ formation of the required benzothiourea intermediate followed by its intramol. cross dehydrogenative coupling of a C(sp²)-H bond and a S-H bond. To our knowledge, this should be the first example in which 2-aminobenzothiazoles are efficiently prepared from simple and cheap isothiocyanates and amines under metal-free conditions by using iodine as a catalyst and mol. oxygen as an oxidant with water as the byproduct. Compared with literature protocols, this method eliminates the use of ortho-halo-substituted precursors, expensive transition-metal catalysts, and hazardous oxidants. 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. 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. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Formula: C13H10N2S

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