2161-68-4

Usage

Uses

Used in Pharmaceutical Industry:
METHYL-(4-METHYL-THIAZOL-2-YL)-AMINE HYDROCHLORIDE is used as a reagent in the synthesis of various drugs, contributing to the development of new pharmaceuticals and improving existing ones.
Used in Organic Synthesis:
METHYL-(4-METHYL-THIAZOL-2-YL)-AMINE HYDROCHLORIDE is used as a reagent in organic synthesis for the creation of various chemical compounds, facilitating the advancement of chemical research and development.
Used in Antifungal Applications:
METHYL-(4-METHYL-THIAZOL-2-YL)-AMINE HYDROCHLORIDE is used as an antifungal agent, potentially combating fungal infections and contributing to the development of new antifungal treatments.
Used in Antibacterial Applications:
METHYL-(4-METHYL-THIAZOL-2-YL)-AMINE HYDROCHLORIDE is used as an antibacterial agent, potentially fighting bacterial infections and contributing to the development of new antibacterial treatments.

Upstream product

• 7336-53-0 N-methyl-N-(4-methyl-thiazol-2-yl)-acetamide 
• 598-52-7 1-(methyl)-thiourea 
• 78-95-5 chloroacetone 
• 110960-25-3 4-methyl-2-(N-methyl)trifluoroacetamidothiazole 
• 111558-97-5 <2-Hydroxy-2-(4-methyl-2-methylamino-5-thiazolyl)ethyl>phosphonsaeure-diethylester 
• 67-64-1 acetone 
• 7647-01-0 hydrogenchloride 
• 861517-60-4 (5-ethoxy-4-methyl-4,5-dihydro-thiazol-2-yl)-methyl-amine 
• 106-96-7 propargyl bromide 
• 1694-29-7 3-chloropentane-2,4-dione 
• 1603-91-4 4-methylthiazol-2-ylamine 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 859479-11-1 N-methyl-N-[4-methyl-5-(4-nitro-phenylsulfanyl)-thiazol-2-yl]-acetamide 
• 878890-10-9 5-bromo-N,4-dimethylthiazol-2-amine 
• 57980-82-2 1,3-dimethyl-1-(4-methyl-thiazol-2-yl)-thiourea 
• 2161-61-7 (5-cyclohexyl-4-methyl-thiazol-2-yl)-methyl-amine 
• 860180-85-4 methyl-[4-methyl-5-(4-nitro-benzenesulfonyl)-thiazol-2-yl]-amine 
• 860180-87-6 N-methyl-N-[4-methyl-5-(4-nitro-benzenesulfonyl)-thiazol-2-yl]-acetamide 
• 1391736-87-0 C₁₈H₁₇N₃OS₂ 
• 1391736-89-2 C₁₈H₁₈N₄OS₂ 
• 1391736-91-6 C₁₉H₂₀N₄OS₂ 
• 1421693-25-5 C₁₇H₂₀N₆O₂S₂ 
• 1421693-26-6 C₁₈H₂₂N₆O₂S₂ 
• 1421693-22-2 3-(5-fluoro-4-(4-methyl-2-(methylamino)thiazol-5-yl)pyrimidin-2-ylamino)benzene sulfonamide 

Relevant academic research and scientific papers

Structure-based design of highly selective 2,4,5-trisubstituted pyrimidine CDK9 inhibitors as anti-cancer agents

Cyclin-dependent kinases (CDKs) are a family of Ser/Thr kinases involved in cell cycle and transcriptional regulation. CDK9 regulates transcriptional elongation and this unique property has made it a potential target for several diseases. Due to the conserved ATP binding site, designing selective CDK9 inhibitors has been challenging. Here we report our continued efforts in the optimization of 2,4,5-tri-substituted pyrimidine compounds as potent and selective CDK9 inhibitors. The most selective compound 30m was >100-fold selective for CDK9 over CDK1 and CDK2. These compounds showed broad anti-proliferative activities in various solid tumour cell lines and patient-derived chronic lymphocytic leukaemia (CLL) cells. Decreased phosphorylation of the carboxyl terminal domain (CTD) of RNAPII at Ser-2 and down-regulation of anti-apoptotic protein Mcl-1 were confirmed in both the ovarian cancer model A2780 and patient-derived CLL cells.

Novel preparation method for 4-methylthiazole-5-carboxaldehyde

The invention discloses a novel preparation method of 4-methylthiazole-5-carboxaldehyde. The novel preparation method includes the steps of subjecting 2-amino-4-methylthiazole to amino methylation toobtain 2-methylamino-4-methylthiazole, subjecting the 2-methylamino-4-methylthiazole to Vilsmeier reaction to obtain 2-methylamino-4-methyl-5-thiazolecarboxaldehyde, and hydrogenating the 2-methylamino-4-methyl-5-thiazolecarboxaldehyde to remove methylamino to obtain the 4-methylthiazole-5-carboxaldehyde. The preparation method has the advantages of moderate reaction condition, high yield, less generated waste and suitability for mass industrial production.

A method for preparing such CDK inhibitors (by machine translation)

The invention discloses a method for preparing such CDK inhibitors, will be single-methyl thiourea and 1 - N monochloride reaction, 4 - dimethylthiazole - 2 - amine, by bromo reaction to obtain 5 - bromo - N, 4 - dimethylthiazole - 2 - amine, under the action of the catalyst after the with the borate to obtain aromatic borate intermediates; aromatic borate ester intermediate with 2, 4 - dichloro - 5 fluoro uracil in the noble metal catalytic under suzuki coupling reaction to obtain the coupling product to continue after the Buchwald - Hartwig with the aromatic amine in the reaction, ultimately to obtain the target product. (by machine translation)

Substituted 4-(thiazol-5-yl)-2-(phenylamino)pyrimidines are highly active CDK9 inhibitors: Synthesis, X-ray crystal structures, structure-activity relationship, and anticancer activities

Cancer cells often have a high demand for antiapoptotic proteins in order to resist programmed cell death. CDK9 inhibition selectively targets survival proteins and reinstates apoptosis in cancer cells. We designed a series of 4-thiazol-2-anilinopyrimidine derivatives with functional groups attached to the C5-position of the pyrimidine or to the C4-thiazol moiety and investigated their effects on CDK9 potency and selectivity. One of the most selective compounds, 12u inhibits CDK9 with IC50 = 7 nM and shows over 80-fold selectivity for CDK9 versus CDK2. X-ray crystal structures of 12u bound to CDK9 and CDK2 provide insights into the binding modes. This work, together with crystal structures of selected inhibitors in complex with both enzymes described in a companion paper,(34) provides a rationale for the observed SAR. 12u demonstrates potent anticancer activity against primary chronic lymphocytic leukemia cells with a therapeutic window 31- and 107-fold over those of normal B- and T-cells.

Domino alkylation-cyclization reaction of propargyl bromides with thioureas/thiopyrimidinones: A new facile synthesis of 2-aminothiazoles and 5H-thiazolo[3,2-α]pyrimidin-5-ones

A new synthesis of 2-aminothiazoles and 5H-thiazolo[ 3,2-α]pyrimidin- 5-ones was developed as a domino alkylation-cyclization reaction of propargyl bromides with thioureas and thiopyrimidinones, respectively. Domino reactions were performed under microwave irradiation leading to desired compounds in a few minutes and high yields. Georg Thieme Verlag Stuttgart.

THIAZOLINE DERIVATIVE AND USE OF THE SAME

A thiazoline derivative represented by Formula (I): wherein R is a cyclic hydrocarbon group which may be substituted, or a heterocyclic group which may be substituted; X is a bond or a divalent chain hydrocarbon group which may be substituted; X' is a bond or -N(R5)-; Y is a divalent hydrocarbon group which may be substituted; Y' is a bond or -C(=O)-; ring A is a nitrogen-containing heterocycle which may be substituted; Z1 and Z3 are each independently a bond or a divalent chain hydrocarbon group which may be substituted; Z2 is a bond or -N(R6)-; and B is a group represented by the formula: which is useful as a therapeutic drug for thrombosis, is provided.

Condensation of thiourea derivatives with carbonyl compounds: One-pot synthesis of N-alkyl-1, 3-thiazol-2-amines and of 3-alkyl-1, 3-thiazolimines

The reactions of ketones and AT-substituted thioureas, in the presence of HC1 (or HBr) and DMSO afford mixtures of the title compounds which are easily separated on a silica gel column. This method avoids the classical use of a-haloketones. The mechanism of these reactions involves the enolization of ketones and the activation of thiourea sulfur, probably by oxygen transfer from DMSO.

Dialkyl(2,3-Epoxy-4-oxoalkyl)phosphonates as Synthons for Thiazoles

On reaction with thioureas and thioamides, the dialkyl (2,3-epoxy-4-oxoalkyl)phosphonates 6 can be transformed either into the new phosphonates 12 - 16, or to the (thiazolylvinyl)phosphonates 17 - 21.Cleavage of both system

The Hantzsch Thiazole Synthesis under Acidic Conditions: Change of Regioselectivity

The condensation of α-halogeno ketones with N-monosubstituted thioureas in neutral solvent leads exclusively to 2-(N-substituted amino)thiazoles.In the present work it was shown that under acidic conditions mixtures of 2-(N-substituted amino)thiazoles and 3-substituted 2-imino-2,3-dihydrothiazoles are formed. (The isomers were distinguished by characteristic differences between their 5-H 1H n.m.r. signals and the i.r.CO bands of their trifluoroacetate derivatives.) The proportions of the 2-imino-2,3-dihydrothiazoles in the mixtures are influenced by experimental features and by the structures of the starting materials.Reactions in 10 M-HCl-EtOH (1:2) at 80 deg C for 20 min were found to be the most efficient for generating 2-imino-2,3-dihydrothiazoles; in the most favourable case 2-imino-3,4-dimethyl-2,3-dihydrothiazole was obtained in 73 percent yield.A possible explanation of the results is discussed.