Category: 101080-15-3

Helal, Christopher J.; Sanner, Mark A.; Cooper, Christopher B.; Gant, Thomas; Adam, Mavis; Lucas, John C.; Kang, Zhijun; Kupchinsky, Stanley; Ahlijanian, Michael K.; Tate, Bonnie; Menniti, Frank S.; Kelly, Kristin; Peterson, Marcia published the artcile< Discovery and SAR of 2-aminothiazole inhibitors of cyclin-dependent kinase 5/p25 as a potential treatment for Alzheimer's disease>, Recommanded Product: 5-Isopropylthiazol-2-amine, the main research area is cyclin dependent kinase inhibitor thiazolyl isobutyramide structure.

High-throughput screening with cyclin-dependent kinase 5 (cdk5)/p25 led to the discovery of N-(5-isopropyl-thiazol-2-yl)isobutyramide. This compound is an equipotent inhibitor of cdk5 and cyclin-dependent kinase 2 (cdk2)/cyclin E (IC50 = ca. 320 nM). Parallel and directed synthesis techniques were utilized to explore the SAR of this series. Up to 60-fold improvements in potency at cdk5 and 12-fold selectivity over cdk2 were achieved.

Bioorganic & Medicinal Chemistry Letters published new progress about Alzheimer disease. 101080-15-3 belongs to class thiazole, and the molecular formula is C6H10N2S, Recommanded Product: 5-Isopropylthiazol-2-amine.

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

Widler, Leo; Jaeggi, Knut A.; Glatt, Markus; Mueller, Klaus; Bachmann, Rolf; Bisping, Michael; Born, Anne-Ruth; Cortesi, Reto; Guiglia, Gabriela; Jeker, Heidi; Klein, Remy; Ramseier, Ueli; Schmid, Johann; Schreiber, Gerard; Seltenmeyer, Yves; Green, Jonathan R. published the artcile< Highly Potent Geminal Bisphosphonates. From Pamidronate Disodium (Aredia) to Zoledronic Acid (Zometa)>, Recommanded Product: 5-Isopropylthiazol-2-amine, the main research area is bisphosphonate derivative preparation structure bone resorption inhibitor osteoporosis; hypercalcemia Paget’s metastasis osteolysis osteoporosis bisphosphonate derivative preparation.

Bisphosphonates (BPs) are pyrophosphate analogs in which the oxygen in P-O-P has been replaced by a carbon, resulting in a metabolically stable P-C-P structure. Pamidronate (1b, Novartis), a second-generation BP, was the starting point for extensive SAR studies. Small changes of the structure of pamidronate lead to marked improvements of the inhibition of osteoclastic resorption potency. Alendronate (1c, MSD), with an extra methylene group in the N-alkyl chain, and olpadronate (1h, Gador), the N,N-di-Me analog, are about 10 times more potent than pamidronate. Extending one of the N-Me groups of olpadronate to a pentyl substituent leads to ibandronate (1k, Roche, Boehringer-Mannheim), which is the most potent close analog of pamidronate. Even slightly better antiresorptive potency is achieved with derivatives having a Ph group linked via a short aliphatic tether of three to four atoms to nitrogen, the second substituent being preferentially a Me group (e.g., 4g, 4j, 5d, or 5r). The most potent BPs are found in the series containing a heteroaromatic moiety (with at least one nitrogen atom), which is linked via a single methylene group to the geminal bisphosphonate unit. Zoledronic acid (6i), the most potent derivative, has an ED50 of 0.07 mg/kg in the TPTX in vivo assay after s.c. administration. It not only shows by far the highest therapeutic ratio when comparing resorption inhibition with undesired inhibition of bone mineralization but also exhibits superior renal tolerability. Zoledronic acid (6i) has thus been selected for clin. development under the registered trade name Zometa. The results of the clin. trials indicate that low doses are both efficacious and safe for the treatment of tumor-induced hypercalcemia, Paget’s disease of bone, osteolytic metastases, and postmenopausal osteoporosis.

Journal of Medicinal Chemistry published new progress about Antiosteoporotic agents. 101080-15-3 belongs to class thiazole, and the molecular formula is C6H10N2S, Recommanded Product: 5-Isopropylthiazol-2-amine.

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

Wang, Ning-Yu; Xu, Ying; Zuo, Wei-Qiong; Xiao, Kun-Jie; Liu, Li; Zeng, Xiu-Xiu; You, Xin-Yu; Zhang, Li-Dan; Gao, Chao; Liu, Zhi-Hao; Ye, Ting-Hong; Xia, Yong; Xiong, Ying; Song, Xue-Jiao; Lei, Qian; Peng, Cui-Ting; Tang, Hong; Yang, Sheng-Yong; Wei, Yu-Quan; Yu, Luo-Ting published the artcile< Discovery of Imidazo[2,1-b]thiazole HCV NS4B Inhibitors Exhibiting Synergistic Effect with Other Direct-Acting Antiviral Agents>, Computed Properties of 101080-15-3, the main research area is imidazothiazole HCV NS4B inhibitor drug synergism antiviral.

The design, synthesis, and SAR studies of novel inhibitors of HCV NS4B based on the imidazo[2,1-b]thiazole scaffold were described. Optimization of potency with respect to genotype 1b resulted in the discovery of two potent leads 26f (I, EC50 = 16 nM) and 28g (II, EC50 = 31 nM). The resistance profile studies revealed that 26f and 28g targeted HCV NS4B, more precisely the second amphipathic α helix of NS4B (4BAH2). Cross-resistance between our 4BAH2 inhibitors and other direct-acting antiviral agents targeting NS3/4A, NS5A, and NS5B was not observed For the first time, the synergism of a series of combinations based on 4BAH2 inhibitors was evaluated. The results demonstrated that our 4BAH2 inhibitor 26f was synergistic with NS3/4A inhibitor simeprevir, NS5A inhibitor daclatasvir, and NS5B inhibitor sofosbuvir, and it could also reduce the dose of these drugs at almost all effect levels. Our study suggested that favorable effects could be achieved by combining 4BAH2 inhibitors such as 26f with these approved drugs and that new all-oral antiviral combinations based on 4BAH2 inhibitors were worth developing to supplement or even replace current treatment regimens for curing HCV infection.

Journal of Medicinal Chemistry published new progress about Antiviral agents. 101080-15-3 belongs to class thiazole, and the molecular formula is C6H10N2S, Computed Properties of 101080-15-3.

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

Stachulski, Andrew V.; Pidathala, Chandrakala; Row, Eleanor C.; Sharma, Raman; Berry, Neil G.; Iqbal, Mazhar; Bentley, Joanne; Allman, Sarah A.; Edwards, Geoffrey; Helm, Alison; Hellier, Jennifer; Korba, Brent E.; Semple, J. Edward; Rossignol, Jean-Francois published the artcile< Thiazolides as Novel Antiviral Agents. 1. Inhibition of Hepatitis B Virus Replication>, Formula: C6H10N2S, the main research area is thiazolide preparation Hepatitis replication inhibition antiviral human structure activity.

The syntheses and activities of a wide range of thiazolides [viz., 2-hydroxyaroyl-N-(thiazol-2-yl)amides] against hepatitis B virus replication, with results of QSAR anal. are reported. The prototypical thiazolide, nitazoxanide [2-hydroxybenzoyl-N-(5-nitrothiazol-2-yl)amide, NTZ] I, is a broad spectrum antiinfective agent effective against anaerobic bacteria, viruses, and parasites. By contrast, 2-hydroxybenzoyl-N-(5-chlorothiazol-2-yl)amide II is a novel, potent, and selective inhibitor of hepatitis B replication (EC50 = 0.33 μm) but is inactive against anaerobes. Several 4′- and 5′-substituted thiazolides show good activity against HBV; by contrast, some related salicyloylanilides show a narrower spectrum of activity. The ADME properties of II are similar to I, viz., the O-acetate is an effective prodrug, and the O-aryl glucuronide is a major metabolite. The QSAR study shows a good correlation of observed EC90 for intracellular virions with thiazolide structural parameters. Finally the mechanism of action of thiazolides in relation to the present results is discussed.

Journal of Medicinal Chemistry published new progress about Antiviral agents. 101080-15-3 belongs to class thiazole, and the molecular formula is C6H10N2S, Formula: C6H10N2S.

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

Masuda, Naoyuki; Yamamoto, Osamu; Fujii, Masahiro; Ohgami, Tetsuro; Moritomo, Ayako; Kontani, Toru; Kageyama, Shunji; Ohta, Mitsuaki published the artcile< Regioselective Alkylation of Thiazolylsulfonamides: Direct and Efficient Synthesis of 3-Alkylthiazolidene Derivatives>, Recommanded Product: 5-Isopropylthiazol-2-amine, the main research area is thiazolylsulfonamide alkyl halide regioselective alkylation; thiazolidene sulfonamide preparation; alkylthiazolidene sulfonamide preparation; sulfonyliminothiazole preparation.

Various N(3)-alkylated thiazolidene sulfonamide derivatives were efficiently prepared by the direct endo-selective alkylation of thiazolyl sulfonamides. The effects of different bases and solvents were investigated, and the NaH-THF combination was found to be the most effective at conferring high yields and endo-selectivity.

Synthetic Communications published new progress about Alkylation, regioselective. 101080-15-3 belongs to class thiazole, and the molecular formula is C6H10N2S, Recommanded Product: 5-Isopropylthiazol-2-amine.

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

Vulpetti, Anna; Casale, Elena; Roletto, Fulvia; Amici, Raffaella; Villa, Manuela; Pevarello, Paolo published the artcile< Structure-based drug design to the discovery of new 2-aminothiazole CDK2 inhibitors>, Application of C6H10N2S, the main research area is CDK2 inhibitor aminothiazole drug design crystal structure.

N-(5-Bromo-1,3-thiazol-2-yl)butanamide (compound 1) was found active (IC50 = 808 nM) in a high throughput screening (HTS) for CDK2 inhibitors. By exploiting crystal structures of several complexes between CDK2 and inhibitors and applying structure-based drug design (SBDD), we rapidly discovered a very potent and selective CDK2 inhibitor 4-[(5-isopropyl-1,3-thiazol-2-yl)amino] benzenesulfonamide (compound 4, IC50 = 20 nM). The syntheses, structure-based analog design, kinases inhibition data and x-ray crystallog. structures of CDK2/inhibitor complexes are reported.

Journal of Molecular Graphics & Modelling published new progress about Crystal structure. 101080-15-3 belongs to class thiazole, and the molecular formula is C6H10N2S, Application of C6H10N2S.

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

Nguyen, William; Jacobson, Jonathan; Jarman, Kate E.; Jousset Sabroux, Helene; Harty, Leigh; McMahon, James; Lewin, Sharon R.; Purcell, Damian F.; Sleebs, Brad E. published the artcile< Identification of 5-Substituted 2-Acylaminothiazoles That Activate Tat-Mediated Transcription in HIV-1 Latency Models>, COA of Formula: C6H10N2S, the main research area is acylaminothiazole TAT transcription HIV1 latency antiretroviral agent HIV infection.

The persistent reservoir of cells latently infected with human immunodeficiency virus (HIV)-integrated proviral DNA necessitates lifelong suppressive antiretroviral therapy (ART). Epigenetic targeted compounds have shown promise as potential latency-reversing agents; however, these drugs have undesirable toxicity and lack specificity for HIV. We utilized a novel HEK293-derived FlpIn dual-reporter cell line, which quantifies specific HIV provirus reactivation (LTR promoter) relative to nonspecific host cell gene expression (CMV promoter), to identify the 5-substituted 2-acylaminothiazole hit class. Here, we describe the optimization of the hit class, defining the functionality necessary for HIV gene activation and for improving in vitro metabolism and solubility The optimized compounds displayed enhanced HIV gene expression in HEK293 and Jurkat 10.6 latency cellular models and increased unspliced HIV RNA in resting CD4+ T cells isolated from HIV-infected individuals on ART, demonstrating the potential of the 2-acylaminothiazole class as latency-reversing agents.

Journal of Medicinal Chemistry published new progress about Anti-HIV agents. 101080-15-3 belongs to class thiazole, and the molecular formula is C6H10N2S, COA of Formula: C6H10N2S.

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

101080-15-3, 5-Isopropylthiazol-2-amine is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The thiazole amine (69 mmol) was combined with 2- (S)-tert-butoxycarbonylamino- pentanoic acid (69 mmol) in 170 mL of anhydrous DMF under N2. Triethylamine (76 mmol) was added to the reaction, followed by HOBT (76 mmol) and EDCI (76 mmol). The resultant mixture was stirred at r. t. for 16h. The reaction was then diluted with 200 mL of EtOAc and washed with 200 mL of water and brine. The organics were then dried over Na2SO4, filtered and concentrated under reduced pressure to give the desired product, [1-(5-Isopropyl-thiazol- 2-ylcarbamoyl)-butyl]-carbamic acid ter-butyl ester. The product (10.2 mmol) was purified through flash chromatography and dissolved in 15 mL of anhydrous 4.0 N HCI in dioxane and stirred at rt for 2 h. The reaction was then concentrated under reduced pressure and triturated in Et20 to give the desired amine, 2- Amino-pentanoic acid (5-isopropyl-thiazol-2-yl)-amide, 101080-15-3

The synthetic route of 101080-15-3 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; PFIZER PRODUCTS INC.; WO2005/95367; (2005); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

101080-15-3, 5-Isopropylthiazol-2-amine is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A Schlenk tube was charged with ethyl 2-iodo-phenylcarbamates (1 mmol), CuI (19mg, 0.1 mmol), and Na2S*9H2O (3 mmol). The tube was evacuated and backfilled with argon (3 times), and the 2 mL of DMF was added. The reaction mixture wasstirred at 80 C for 10-16 h, then 3 mL of AcOH was added to the cooled reaction mixture and the mixture was stirred at 130 C for another 36 h. Saturated NaHCO3 (10mL) was added and the mixture was extracted with ethyl acetate. The organic layer was washed with H2O, brine, and dried over Na2SO4. After removal of the solvent in vacuo, the residue was purified by column chromatography on silica gel to provide the desired benzothiazolone.

101080-15-3, The synthetic route of 101080-15-3 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Li, Jiaojiao; Zhang, Yihua; Jiang, Yongwen; Ma, Dawei; Tetrahedron Letters; vol. 53; 20; (2012); p. 2511 – 2513;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.101080-15-3,5-Isopropylthiazol-2-amine,as a common compound, the synthetic route is as follows.

EXAMPLE 6 Preparation of a Compound of Formula (VI): 4-nitrophenyl-5-isopropyl-1,3-thiazol-2-ylcarbamate To a solution of 4 g (28.13 mmol) of 5-isopropyl-2-amino-1,3-thiazole in 30 ml of anhydrous dichloromethane 5.7 g (28.13 mmol) of 4-nitrophenyl chloroformate were added dropwise at 0 C. under nitrogen. Then 2.3 ml of pyridine were added. The mixture was maintained at room temperature under stirring overnight and then filtered, giving 6.96 g (80% yield) of the title compound as a white solid. m.p. 157-159 C. 1H-NMR (400 MHz-DMSO-d6) deltappm: 1.23 (d, 6H, J=6.8, CH3CHCH3); 3.06 (m, 1H, CH3CHCH3); 7.05 (s, 1H, H thiazole); 6.91 (d, 2H, J=9.2, H-3′, 5′-phenyl); 8.10 (d, 2H, J=9.2, H-2′,6′-phenyl); 11.00 (bs, 1H, NH). EI-MS: m/z 307 (0.5, M+); m/z 168 ((CH3)2-CH-thiazole-NCO)+; m/z 153 (100, (CH3-CH-thiazole-NCO)+); m/z 139 (45, (OH-C6H4-NO2)+)., 101080-15-3

101080-15-3 5-Isopropylthiazol-2-amine 10486954, athiazole compound, is more and more widely used in various fields.

Reference：
Patent; Pevarello, Paolo; Amici, Raffaella; Traquandi, Gabriella; Villa, Manuela; Vulpetti, Anna; Isacchi, Antonella; US2003/187040; (2003); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica