Category: 6294-52-6

Inoue, Hirozumi et al. published their research in Chemical & Pharmaceutical Bulletin in 1997 | CAS: 6294-52-6

5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6) 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 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.Quality Control of 5,6-Dimethoxybenzo[d]thiazol-2-amine

Synthesis and biological evaluation of alkyl, alkoxy, alkylthio, or amino-substituted 2,3-dihydro-1,5-benzothiazepin-4(5H)-ones was written by Inoue, Hirozumi;Konda, Mikihiko;Hashiyama, Tomiki;Otsuka, Hisao;Watanabe, Akishige;Gaino, Mitsunori;Takahashi, Kaoru;Date, Tadamasa;Okamura, Kimio;Takeda, Mikio;Narita, Hiroshi;Murata, Sakae;Odawara, Akio;Sasaki, Haruhiko;Nagao, Taku. And the article was included in Chemical & Pharmaceutical Bulletin in 1997.Quality Control of 5,6-Dimethoxybenzo[d]thiazol-2-amine This article mentions the following:

2,3-Dihydro-1,5-benzothiazepin-4(5H)-ones,e.g., I (R1 = 6-, 7-, 8-Me, 7-CF3, 7-OMe, etc., R2 = OMe, OCF3, Me, etc.), substituted with an alkyl, alkoxy, alkylthio, hydroxy, or amino group on the fused benzene ring of the 1,5-benzothiazepine skeleton were synthesized and their vasodilating, antihypertensive, and platelet aggregation-inhibitory activities were investigated. (-)-Cis-3-Acetoxy-5-[2-(dimethylamino)ethyl]-2,3-dihydro-8-methyl-2-(4-m ethylphenyl)-1,5-benzothiazepin-4(5H)-one was selected for further studies as a potent inhibitor of platelet aggregation. In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6Quality Control of 5,6-Dimethoxybenzo[d]thiazol-2-amine).

5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6) 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 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.Quality Control of 5,6-Dimethoxybenzo[d]thiazol-2-amine

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

Buchholz, Mirko et al. published their research in Journal of Medicinal Chemistry in 2006 | CAS: 6294-52-6

5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6) 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.Computed Properties of C9H10N2O2S

The first potent inhibitors for human glutaminyl cyclase: synthesis and structure-activity relationship was written by Buchholz, Mirko;Heiser, Ulrich;Schilling, Stephan;Niestroj, Andre J.;Zunkel, Katrin;Demuth, Hans-Ulrich. And the article was included in Journal of Medicinal Chemistry in 2006.Computed Properties of C9H10N2O2S This article mentions the following:

The first effective inhibitors for human glutaminyl cyclase (QC) are described. The structures are developed by applying a ligand-based optimization approach starting from imidazole. Screening of derivatives of that heterocycle led to compounds of the imidazol-1-yl-alkyl thiourea type as a lead scaffold. A library of thiourea derivatives was synthesized, resulting in an inhibitory improvement by 2 orders of magnitude, leading to 1-(3-(1H-imidazol-1-yl)propyl)-3-(3,4-dimethoxyphenyl)thiourea as a potent inhibitor. Systematic exploitation of the scaffold revealed a strong impact on the inhibitory efficacy and resulted in the development of imidazole-propyl-thioamides as another new class of potent inhibitors. A flexible alignment of the most potent compounds of the thioamide and thiourea class and a QC substrate revealed a good match of characteristic features of the mols., which suggests a similar binding mode of both inhibitors and the substrate to the active site of QC. In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6Computed Properties of C9H10N2O2S).

5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6) 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.Computed Properties of C9H10N2O2S

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

Trapani, G. et al. published their research in European Journal of Pharmaceutical Sciences in 2001 | CAS: 6294-52-6

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. 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.Recommanded Product: 5,6-Dimethoxybenzo[d]thiazol-2-amine

Synthesis, in vitro and in vivo cytotoxicity, and prediction of the intestinal absorption of substituted 2-ethoxycarbonyl-imidazo[2,1-b]benzothiazoles was written by Trapani, G.;Franco, M.;Latrofa, A.;Reho, A.;Liso, G.. And the article was included in European Journal of Pharmaceutical Sciences in 2001.Recommanded Product: 5,6-Dimethoxybenzo[d]thiazol-2-amine This article mentions the following:

The imidazobenzothiazole compounds together with an imidazobenzoxazole, and an imidazobenzoimidazole were prepared and their cytotoxic activity evaluated at the National Cancer Institute (NCI) for testing against a panel of approx. 60 tumor cell lines. Four compounds exhibited interesting in vitro cytotoxic activity. The most active imidazobenzothiazole derivative I was further evaluated as a cytotoxic agent in the hollow fiber assay and showed a score greater than the min. values for xenograft testing together with a net cell kill. Comparison with the results displayed in the in vivo assay by standard antitumor drugs in clin. use revealed a significant in vivo activity of the benzothiazole compound COMPARE analyses for 16 of the compounds against the NCI’s standard agent database show poor or no correlation, and it might suggest for these compounds a mechanism of action unrelated to that of any known drug. Furthermore, the benzothiazole I did not show significant antitumor activity in a panel of two xenotransplanted tumors (i.e. colon and non-small cell lung tumors). By computing the polar surface area of the compounds with the MAREA computer program it was established that the most active compounds should experience good intestinal permeability. In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6Recommanded Product: 5,6-Dimethoxybenzo[d]thiazol-2-amine).

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. 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.Recommanded Product: 5,6-Dimethoxybenzo[d]thiazol-2-amine

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

Some tips on 6294-52-6

The synthetic route of 6294-52-6 has been constantly updated, and we look forward to future research findings.

6294-52-6, 5,6-Dimethoxybenzo[d]thiazol-2-amine is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,6294-52-6

General procedure: Chloroacetyl chloride(33 mmol, 2.63 mL) was added dropwise with stirring to a mixtureof triethylamine (33 mmol, 4.63 mL) and 2-aminobenzothiazole oraniline derivative (30 mmol) in THF (100 mL) at 0 C. After thecompletion of dropping, the mixturewas allowed to stir for 1 h. Thesolvent was evaporated under reduced pressure. The residue waswashed with water to remove trimethylamine hydrochloride, driedand recrystallized from EtOH [59,60].

The synthetic route of 6294-52-6 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Sa?l?k, Beguem Nurpelin; Ilg?n, Sinem; Oezkay, Yusuf; European Journal of Medicinal Chemistry; vol. 124; (2016); p. 1026 – 1040;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

New learning discoveries about 6294-52-6

6294-52-6 5,6-Dimethoxybenzo[d]thiazol-2-amine 94938, athiazole compound, is more and more widely used in various fields.

6294-52-6, 5,6-Dimethoxybenzo[d]thiazol-2-amine is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6294-52-6, 2-Chloro-N-(5,6-dimethoxybenzo[d]thiazol-2-yl)acetamide (Compound 53) To the reaction mixture of 5,6-dimethoxybenzo[d]thiazol-2-amine (50 mg, 0.238 mmol), TEA (0.100 mL, 0.713 mmol) in DCM (1 mL) was added 2-chloroacetyl chloride (0.023 mL, 0.285 mmol) at room temperature. Overnight, concentration and purification on combiflash (4 g, MeOH/DCM) gave 2-chloro-N-(5,6-dimethoxybenzo[d]thiazol-2-yl)acetamide (15 mg, 0.052 mmol, 22.00% yield). 1HNMR (400 MHz, CDCl3), 9.73 (s, 1H), 7.26 (s, 1H), 7.25 (s, 1H), 4.30 (s, 2H), 3.969s, 6H) ESI-MS: m/z 286.94 (M+H)+

6294-52-6 5,6-Dimethoxybenzo[d]thiazol-2-amine 94938, athiazole compound, is more and more widely used in various fields.

Reference：
Patent; Stingray Therapeutics, Inc.; The University of Utah; Vankayalapati, Hariprasad; Liu, Xiaohui; Ramamoorthy, Gurusankar; Sharma, Sunil; Kaadige, Mohan Rao; Weston, Alexis; Thode, Trason; (59 pag.)US2019/31655; (2019); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

Downstream synthetic route of 6294-52-6

6294-52-6 5,6-Dimethoxybenzo[d]thiazol-2-amine 94938, athiazole compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6294-52-6,5,6-Dimethoxybenzo[d]thiazol-2-amine,as a common compound, the synthetic route is as follows.

General procedure: Corresponding benzo[d]thiazol-2-amine (3 and 4) (0.025 mol) and triethylamine (0.030 mol,4.24 mL) were dissolved in THF (50 mL). This mixture was kept on an ice bath andchloroacetyl chloride (0.030 mol, 2.37 mL) in THF (10 ml) was added dropwise with constantstirring. After this stage, the content was allowed to stir for an additional 1 h at roomtemperature. THF was evaporated, the raw product was washed with water, dried andrecrystallized from ethanol.2,3, 6294-52-6

6294-52-6 5,6-Dimethoxybenzo[d]thiazol-2-amine 94938, athiazole compound, is more and more widely used in various fields.

Reference：
Article; Demir Oezkay, Uemide; Can, Oezguer Devrim; Sa?l?k, Beguem Nurpelin; Acar Cevik, Ulviye; Levent, Serkan; Oezkay, Yusuf; Ilg?n, Sinem; Atl?, Oezlem; Bioorganic and Medicinal Chemistry Letters; vol. 26; 22; (2016); p. 5387 – 5394;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

Analyzing the synthesis route of 6294-52-6

As the paragraph descriping shows that 6294-52-6 is playing an increasingly important role.

6294-52-6, 5,6-Dimethoxybenzo[d]thiazol-2-amine is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6294-52-6, 4.1.1.4 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-N-(5,6-dimethoxybenzo[d]thiazol-2-yl)benzamide 4d Obtained from the reaction of 2d with 3, yellow solid, yield 82% (072?gm), mp 155-156?C. 1HNMR (400?MHz, DMSO-d6) delta 9.97 (s, 1H, NH exchanged with D2O), 7.72 (s, 1H, Ar H), 7.62 (d, J?=?1.8, 8.2, 1H, Ar H), 7.40 (s, 1H, Ar H), 7.31 (d, J?=?1.8, 1H, Ar H), 7.22 (d, J?=?8.2, 1H, Ar H), 7.02 (s, 1H, CHF2), 3.98 (d, J?=?6.92, 2H, CH2), 3.81 (s, 3H, OCH3), 3.76 (s, 3H, OCH3), 1.30 (m, 1H, CH), 0.61 (m, 2H, 2 CH), 0.38 (m, 2H, 2 CH). 13C NMR (100?MHz, DMSO-d6) delta 164.80, 149.97, 148.64, 148.45, 142.84, 132.44, 129.51, 120.94, 119.56, 116.99, 115.45, 114.42, 114.03, 113.10, 111.59, 73.72, 56.50, 56.31, 10.43, 3.52. IR (KBr) upsilonmax?cm-1: 3259 (NH), 1647 (C=O). Elemental analysis calcd (%) for C21H20F2N2O5S (450.46): C, 55.99; H, 4.48; N, 6.22. Found: C, 56.23; H, 4.62; N, 6.39.

As the paragraph descriping shows that 6294-52-6 is playing an increasingly important role.

Reference：
Article; Moussa, Bahia A.; El-Zaher, Asmaa A.; El-Ashrey, Mohamed K.; Fouad, Marwa A.; European Journal of Medicinal Chemistry; vol. 148; (2018); p. 477 – 486;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

Brief introduction of 6294-52-6

As the paragraph descriping shows that 6294-52-6 is playing an increasingly important role.

6294-52-6,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6294-52-6,5,6-Dimethoxybenzo[d]thiazol-2-amine,as a common compound, the synthetic route is as follows.

To the reaction mixture of 5,6-dimethoxybenzo[d]thiazol-2-amine (50 mg, 0.238 mmol), TEA (0.100 mL, 0.713 mmol) in DCM (1 mL) was added 2-chloroacetyl chloride (0.023 mL, 0.285 mmol) at room temperature. Overnight, concentration and purification on combiflash (4 g, MeOH/DCM) gave 2-chloro-N-(5,6-dimethoxybenzo[d]thiazol-2-yl)acetamide (15 mg, 0.052 mmol, 22.00% yield). 1HNMR (400 MHz, CDCl3), 9.73 (s, 1H), 7.26 (s, 1H), 7.25 (s, 1H), 4.30 (s, 2H), 3.969s, 6H) ESI-MS: m/z 286.94 (M+H)+

As the paragraph descriping shows that 6294-52-6 is playing an increasingly important role.

Reference：
Patent; Stingray Therapeutics, Inc.; Vankayalapati, Hariprasad; Sharma, Sunil; Kaadige, Mohan Rao; Weston, Alexis; Thode, Trason; (117 pag.)US2020/39979; (2020); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica