5469-45-4

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 5469-45-4 differently. You can refer to the following data:
1. A protein kinase C inhibitor
2. test substance for asymmetric hydrogenations

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 4603, 1983 DOI: 10.1016/S0040-4039(00)85967-5Synthesis, p. 418, 1984 DOI: 10.1055/s-1984-30859

Purification Methods

It crystallises from H2O as the dihydrate, and on drying at 100o it forms the anhydrous compound which is hygroscopic. Alkaline hydrolysis yields NH3

InChI:InChI=1/C11H11NO3/c1-8(13)12-10(11(14)15)7-9-5-3-2-4-6-9/h2-7H,1H3,(H,12,13)(H,14,15)/b10-7-

Upstream product

• 110-86-1 pyridine 
• 17238-33-4 N-hydroxy-phenylalanine 
• 108-24-7 acetic anhydride 
• 60-35-5 acetamide 
• 156-06-9 2-oxo-3-(phenyl)propionic acid 
• 881-90-3 4-benzylidene-2-methyl-2-oxazolin-5-one 
• 67-64-1 acetone 
• 127-09-3 sodium acetate 
• 100-52-7 benzaldehyde 
• 56-40-6 glycine 
• 52386-78-4 N-acetyl dehydrophenylalanine methyl ester 
• 60676-51-9 methyl (Z)-2-(acetylamino)-3-phenylpropenoate 
• 116212-73-8 2,2,2-trifluoroethyl α-(N-acetylamino)cinnamate 
• 7732-18-5 water 

Downstream Products

• 304668-72-2 2-(methylcarboxamido)-3-phenyl-1-(piperidin-1-yl)prop-2-en-1-one 
• 150-30-1 Phenylalanine 
• 156-06-9 2-oxo-3-(phenyl)propionic acid 
• 2901-75-9 (R,S)-N-acetyl phenylalanine 
• 100400-96-2 2-acetylamino-3-cyclohexylpropanoic acid 
• 38879-46-8 (Z)-4-benzylidene-2-methyl-5(4H)-oxazolone 
• 64044-89-9 Methyl-N-acetyl-2-N-methylaminocinnamat 
• 2361-96-8 ethyl N-acetyl-(L)-phenylalaninate 
• 2361-96-8 (R)-ethyl N-acetylphenylalanine 
• 91751-54-1 N-((2S,3R)-1-Ethyl-4-oxo-2-phenyl-2,3,4,6,7,12-hexahydro-indolo[2,3-a]quinolizin-3-yl)-acetamide 
• 91751-54-1 N-((2S,3S)-1-Ethyl-4-oxo-2-phenyl-2,3,4,6,7,12-hexahydro-indolo[2,3-a]quinolizin-3-yl)-acetamide 
• 19505-57-8 5-benzylidene-3-phenyl-2-styryl-3,5-dihydro-imidazol-4-one 
• 7664-41-7 ammonia 
• 22278-80-4 4-amino-6-benzyl-3-mercapto-1,2,4-triazine-5(4H)-one 

Relevant academic research and scientific papers

2H-thiazolo [3, 2-b]-1, 2, 4-triazine-3, 7-diketone derivative and application thereof

The invention discloses a 2Hthiazolo [3, 2b] 1, 2, 4triazine 3, 7diketone derivative as shown in a general formula I or pharmaceutically acceptable hydrate and salt thereof, the 2Hthiazolo [3, 2b] 1,2, 4triazine 3, 7diketone derivative comprises stereoisomers or tautomers thereof, and R1 and R2 in the general formula I can be optionally selected from one, two or three independently selected fromhydrogen, alkyl, alkoxy, halogen, hydroxyl, acetyl, propionyl, nitro or trifluoromethyl. The 1, 2, 4-triazine 3, 7diketone derivative has an obvious inhibiting effect on acetylcholin esterase, and isused for enhancing the memory of a patient suffering from dementia and Alzheimer's disease. The invention also relates to a preparation method of the compound and the application of the compound in preparation of drugs for treating Alzheimer's disease.

Scope and limitations of reductive amination catalyzed by half-sandwich iridium complexes under mild reaction conditions

The conversion of aldehydes and ketones to 1° amines could be promoted by half-sandwich iridium complexes using ammonium formate as both the nitrogen and hydride source. To optimize this method for green chemical synthesis, we tested various carbonyl substrates in common polar solvents at physiological temperature (37 °C) and ambient pressure. We found that in methanol, excellent selectivity for the amine over alcohol/amide products could be achieved for a broad assortment of carbonyl-containing compounds. In aqueous media, selective reduction of carbonyls to 1° amines was achieved in the absence of acids. Unfortunately, at Ir catalyst concentrations of 1 mM in water, reductive amination efficiency dropped significantly, which suggest that this catalytic methodology might be not suitable for aqueous applications where very low catalyst concentration is required (e.g., inside living cells).

Biocatalytic retrosynthesis approaches to d-(2,4,5-trifluorophenyl)alanine, key precursor of the antidiabetic sitagliptin

The integration of biocatalytic steps in retrosynthetic analysis of a target molecule offers multiple advantages, such as reduction of the environmental footprint of the process, viability of milder and safer reaction conditions, and accessibility of transformations that are challenging with traditional chemical synthesis. Herein, six chemo-enzymatic routes are described for the synthesis of a fluorinated d-phenylalanine derivative, precursor of the blockbuster antidiabetic drug sitagliptin. All routes start from the same aldehyde precursor and involve at least one biocatalytic step, including reductive amination, transamination, deracemisation, hydroamination, and alkene reduction. The target molecule was obtained in 2-5 steps from the aldehyde, with ee up to >99% and in 36-62% isolated yield. Furthermore, as part of one of the routes, the first example of a fully biocatalytic conversion of a cinnamic acid derivative to the corresponding d-phenylalanine (formal d-selective hydroamination) is reported.

Synthesis, β-catenin translocation capability and ALP activation activity of 7h-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives

Background: Osteoporosis (OP) is a common bone disease, most often diagnosed in post-menopausal women. The majority of OP treatments are focused on manipulation of the patient's hormone levels, therefore, they are associated with significant adverse effects. Objective: The study aimed to design, synthesize and evaluate the β-Catenin translocation capability and the alkaline phosphatase (ALP) activation activity of 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives. Method: The styrene derivatives were synthesized as raw materials, followed by oxidation and condensation reactions, in which 6-aryl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one derivatives (1) were obtained. The 3,6-diaryl-7H-thiazolo[3,2-b]-1,2,4-triazin-7-ones (2) were obtained by a condensation reaction of compound 1 with substituted phenacyl chlorides in acetic acid. The target compounds 3,6-diaryl-7H-thiazolo[3,2-b]-1,2,4-triazin-7-ones (3a-3c) were prepared by compound 2 with substituted alkyl chloride by Williamson reaction. As to 6-benzyl-3-aryl-7H-thiazolo[3,2- b]-1,2,4-triazin-7-one derivatives as the target compounds, the benzaldehyde and acetylglycine used as raw materials, followed by Erlenmeyer-Pl?chl reaction, condensation reaction, hydrolysis reaction, condensation reaction, 6-benzyl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one derivatives were obtained, and were converted to the target compounds 6-benzyl-3-(hydroxylaryl)-7Hthiazolo[ 3,2-b]-1,2,4-triazin-7-one derivatives (5a-5d) using reaction with substituted β-phenacyl chlorides. Finally, Williamson reaction were used to yield 6-benzyl-3-aryl-7H-thiazolo[3,2-b]- 1,2,4-triazin-7-ones as target compounds (6a-6e). The β-Catenin translocation capability and the ALP activation activity were tested, and the glycogen synthase kinase-3 (GSK-3) inhibition was simulated by molecular docking. Results: Fourteen 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives were synthesized and characterized by mass spectra, proton NMR and infrared spectra, the β-Catenin translocation capability and the ALP activation activities of the target compounds were tested and calculated. The EC50 value of the ALP activation activity of 6-(4-chlorobenzyl)-3-{4-[(2-dimethylamino)-2- oxoethoxy]phenyl}-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one (6b) was 11.283 μM. The molecular docking results have showed that the target compounds would be GSK-3 inhibitors. Conclusion: Based on the results of the biological activity test, the target compounds have exhibited the β-Catenin translocation capability and the ALP activation activity.

BABIPhos Family of Biaryl Dihydrobenzooxaphosphole Ligands for Asymmetric Hydrogenation

Novel bidentate phosphine ligands BABIPhos featuring a biaryl bis-dihydrobenzooxaphosphole core are presented. Their synthesis was achieved via Pd-catalyzed reductive homocoupling of dihydrobenzooxaphosphole aryl triflates. An efficient route toward various analogues was also established, giving access to phosphines with different electronic and steric properties. The newly obtained ligands demonstrated high efficiency and selectivity in Rh-catalyzed asymmetric hydrogenation of di- and trisubstituted enamides. This new class of ligands is complementary to previously described bidentate benzooxaphosphole ligands BIBOP.

Thiazole[3,2-b]-1,2,4-thiazole derivatives and application thereof

The invention belongs to the technical field of medicine and relates to thiazole[3,2-b]-1,2,4-thiazole derivatives and an application thereof. The thiazole[3,2-b]-1,2,4-thiazole derivatives comprise thiazole[3,2-b]-1,2,4-thiazole derivative compounds as well as stereoisomers and pharmaceutically applicable salts of the compounds, and a general structural formula of the compounds is represented in the specification; the thiazole[3,2-b]-1,2,4-thiazole derivatives and the pharmaceutically applicable acid-addition salts of the compounds can be combined with existing drugs or separately utilized to serve as glucose concentration dependent type insulin secretion accelerants for treatment of type II diabetes. Compared with the prior art, the compounds are the glucose concentration dependent type insulin secretion accelerants, can promote insulin secretion under high glucose concentration and do not influence insulin secretion under low glucose concentration, so that the side effect of hypoglycemia is avoided.

Synthesis and biological evaluation of 7H-thiazolo[3,2-b]-1,2,4-triazin-7- one derivatives as dual binding site acetylcholinesterase inhibitors

A series of 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives 7a-i were synthesized and evaluated as novel acetylcholinesterase (AChE) inhibitors. All target compounds were evaluated in vitro for the inhibitory activities against AChE via Ellman colorimetric assay. Compound 7c showed an excellent (89.82%) inhibitory activity. The molecular docking studies revealed that 7c, 7d and 7g, with the lateral chain in the para position of the phenyl ring, possessed an optimal docking pose and can perfectly fit into the catalytic active site (CAS) and peripheral anionic site (PAS), simultaneously, and, consequently, exhibited higher inhibitory potency than 7b that bears the same lateral chain as 7g, but in the ortho position of the phenyl ring.

Asymmetric synthesis of unnatural amino acids and tamsulosin chiral intermediate

An efficient and enantioselective hydrogenation of N-acetylamino phenyl acrylic acids was successfully developed by using ruthenium catalyst. This methodology is important in the field of pharmaceuticals and provides a new process for the preparation of unnatural amino acids and tamsulosin chiral intermediate.

Design, synthesis, and biological evaluation of 7H-thiazolo[3,2-b]-1,2,4- triazin-7-one derivatives as dual binding site acetylcholinesterase inhibitors

A series of 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives were designed, synthesized and evaluated as dual binding site acetylcholinesterase inhibitors. The target compounds exhibited promising inhibitory activity for AChE. The structure-activity relationships were discussed and their binding conformation and simultaneous interactions mode were further clarified by the molecular docking studies.

Synthesis of oxazoles from enamides via phenyliodine diacetate-mediated intramolecular oxidative cyclization

A group of functionalized oxazoles were synthesized in moderate to good yields from enamides via phenyliodine diacetate (PIDA)-mediated intramolecular cyclization. The main advantageous features of the present method include its broad substrate scope and the heavy-metal-free characteristic of the oxidative carbon-oxygen bond formation process.