16397-19-6

Upstream product

• 5665-74-7 2-amino-1-hexanol 
• 39978-46-6 DL-norleucine ethyl ester 
• 73397-68-9 1-hydroxyhexan-2-one 
• 866531-16-0 2-Chloro-3-oxo-heptanoic acid methyl ester 
• 261963-25-1 (-)-(R)-(phenyl)(phenylmethoxycarboxylamino)acetic acid 2-oxo-hexyl ester 
• 157985-04-1 5-butyl-3R-phenyl-3,6-dihydro-[1,4]oxazin-2-one 
• 20261-68-1 1-chlorohexan-2-one 
• 157985-13-2 (-)-(3R,5S)-5-butyl-3-phenylmorpholin-2-one 
• 327-57-1 L-Norleucine 
• 501-53-1 benzyl chloroformate 
• 21754-55-2 L-norleucine methyl ester 
• 3844-54-0 norleucine methyl ester hydrochloride 
• 55704-80-8 1-acetoxy-2-chloro-hexane 
• 592-41-6 1-hexene 

Downstream Products

• 1609165-36-7 8-[(2,6-difluorobenzyl)oxy]-7-fluoro-N-[(2R)-1-hydroxyhexan-2-yl]-2-methylimidazo[1,2-a]-pyridine-3-carboxamide 
• 116640-17-6 tert-butyl (R)-(1-hydroxyhexan-2-yl)carbamate 
• 80696-28-2 (2R)-2-amino-2-butyl-1-ethanol 
• 80696-29-3 (S)-(+)-2-Amino-1-hexanol 
• 131403-16-2 (S)-(-)-2-benzyloxycarbonylaminohexan-1-ol 
• 1609164-47-7 (rac)-8-(cyclohexylmethoxy)-N-(1-hydroxyhexan-2-yl)-2-methylimidazo[1,2-a]pyridine-3-carboxamide 
• 1380510-06-4 C₂₄H₂₄Cl₂F₃N₅O₃ 
• 1609163-76-9 8-[(2,6-difluorobenzyl)oxy]-N-[(2R)-1-hydroxyhexan-2-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide 
• 1609163-91-8 8-(benzyloxy)-N-[(2R)-1-hydroxyhexan-2-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide 
• 1609164-88-6 8-[(2,6-difluorobenzyl)oxy]-6-ethynyl-N-[(2R)-hydroxyhexan-2-yl]-2-methylimidazo[1,2-a]-pyridine-3-carboxamide 

Relevant academic research and scientific papers

Data mining of amine dehydrogenases for the synthesis of enantiopure amino alcohols

Chiral amino alcohols are essential building blocks for the pharmaceutical industry, and are widely present in natural and synthetic bioactive compounds. Amine dehydrogenases (AmDHs) can asymmetrically reduce prochiral ketones with low-cost ammonia to chiral amines and water as by-products, using NAD(P)H as a cofactor under mild conditions, but hydroxy ketones with formation of chiral hydroxy amines have rarely been investigated. In this study, six new bacterial AmDHs derived from amino acid dehydrogenases (AADHs) were identified by data mining, and five out of the six enzymes were able to efficiently reduce 1-hydroxybutan-2-one (1a) to (S)-2-aminobutan-1-ol ((S)-2a) with 19-99% conversions and 99% ee. The five AmDHs were purified and biochemically characterized for reductive amination activity towards substrate 1a with the optimal pH at 8.5 or 9.0 and the optimal temperature at 45 °C, 50 °C or 55 °C, and provided reductive amination of a broad range of prochiral α-hydroxy ketones, and even of a model β-hydroxy ketone leading to β-hydroxy amine with 99% ee. Our study expands the toolbox of AmDHs in the synthesis of chiral amino alcohols.

Enantioselective Synthesis of Chiral Vicinal Amino Alcohols Using Amine Dehydrogenases

Chiral vicinal amino alcohols are an important motif found in many biologically active molecules. In this study, biocatalytic reductive amination of α-hydroxy ketones with ammonia was investigated using engineered amine dehydrogenases (AmDHs) derived from the leucine amino acid dehydrogenase (AADH) from Lysinibacillus fusiformis. The AmDHs thus identified enabled the synthesis of (S)-configured vicinal amino alcohols from the corresponding α-hydroxy ketones in up to 99% conversions and >99% ee. One of the AmDH variants was used to prepare a key intermediate for the antituberculosis pharmaceutical ethambutol.

COMPOUNDS AND METHOD OF USE

This present disclosure relates to compounds with ferroptosis inducing activity, a method of treating a subject with cancer with the compounds, and combination treatments with a second therapeutic agent.

Docking model of the nicotinic acetylcholine receptor and nitromethylene neonicotinoid derivatives with a longer chiral substituent and their biological activities

In the present study, nitromethylene neonicotinoid derivatives possessing substituents that contain a sulfur atom, oxygen atom or aromatic ring at position 5 on the imidazolidine ring were synthesized to evaluate their affinity for the nicotinic acetylcholine receptor (nAChR) and their insecticidal activity against adult female houseflies. Comparing the receptor affinity of the alkylated derivative with the receptor affinity of compounds possessing either ether or thioether groups revealed that conversion of the carbon atom to a sulfur atom did not influence the receptor affinity, whereas conversion to an oxygen atom was disadvantageous for the receptor affinity. The receptor affinity of compounds possessing a benzyl or phenyl group was lower than that of the unsubstituted compound. Analysis of the three-dimensional quantitative structure-activity relationship using comparative molecular field analysis demonstrated that steric hindrance of the receptor should exist around the C3 of an n-butyl group attached at position 5 on the imidazolidine ring. A docking study of the nAChR-ligand model suggested that the ligand-binding region expands as the length of the substituent increases by brushing against the amino acids that form the binding region. The insecticidal activity of the compounds was positively correlated with the receptor affinity by considering log P and the number of heteroatoms, including sulfur and oxygen atoms, in the substituents, suggesting that the insecticidal activity is influenced by the receptor affinity, hydrophobicity, and metabolic stability of the compounds.

COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS

The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.

Discovery of narlaprevir (SCH 900518): A potent, second generation HCV NS3 serine protease inhibitor

Boceprevir (SCH 503034), 1, a novel HCV NS3 serine protease inhibitor discovered in our laboratories, is currently undergoing phase III clinical trials. Detailed investigations toward a second generation protease inhibitor culminated in the discovery of narlaprevir (SCH 900518), 37, with improved potency (～10-fold over 1), pharmacokinetic profile and physicochemical characteristics, currently in phase II human trials. Exploration of synthetic sequence for preparation of 37 resulted in a route that required no silica gel purification for the entire synthesis.

A catalyst-free, convenient construction of eight-membered [1,4]oxazocane-5,8-dione heterocycles from aminoethanols with divinyl succinate

A convenient protocol for the synthesis of [1,4]oxazocane-5,8-dione heterocycles by direct cyclization using 2-substituted aminoethanols and divinyl succinate without any catalysts and additives was established. This strategy is quite simple and effective to obtain eight-membered rings incorporating lactone and lactam functional groups. Georg Thieme Verlag Stuttgart.

Amino alcohol derivatives, method of producing said derivatives and medicaments containing them

Compounds of formula I in which R1denotes hydrogen or methyl R2denotes lower straight-chained or branched alkyl with 1 to 10 carbon atoms R3denotes hydrogen or lower alkyl n denotes 0-12 R4denotes alkyl, alkenyl or alkinyl with 6 to 24 carbon atoms, processes for the production thereof as well as pharmaceutical agents containing these compounds for the treatment of osteoporosis.

Asymmetric synthesis of protected 1,2-amino alcohols using tert-butanesulfinyl aldimines and ketimines

tert-Butanesulfinyl aldimines and ketimines bearing an α-benzyloxy or α-silyloxy substituent serve as precursors in the synthesis of protected 1,2-amino alcohols in high yields and diastereoselectivities. General protocols are described for the addition of unbranched alkyl, branched alkyl, and aryl organometallic reagents to N-sulfinyl aldimines 1 and 2 and ketimines 5 and 6. Furthermore, the selective N- or O-deprotection of sulfinamide products 3, 4, 7, and 8 is described, enabling further synthetic transformations of the reaction products.

A general synthesis of enantiopure 1,2-aminoalcohols via chiral morpholinones

Eleven optically active 1,2-aminoalcohols 20a-i and 26b-c were prepared from D-phenylglycine via cyclic imines 7b-i (or enamine 7a). The key step of the strategy is the diastereoselective reduction of chiral oxazinones 7a-i.