80697-91-2

Upstream product

• 106-31-0 butanoic acid anhydride 
• 77943-39-6 4-methyl-5-phenyloxazolidin-2-one 
• 107645-17-0 (3-Methoxymethoxy-phenyl)-acetaldehyde 
• 107645-16-9 C₂₂H₃₄BNO₃ 
• 141-75-3 butyryl chloride 
• 37577-28-9 (1S,2R)-(+)-norphedrine 
• 492-39-7 (1S,2S)-2-amino-1-phenylpropanol 

Downstream Products

• 107691-84-9 (4R,5S)-3-((2S,3S,4S)-2-Ethyl-3-hydroxy-4,6-dimethyl-hept-6-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 107691-84-9 (2'R,3'S,4R,4'S,5S)-(+)-3-(2'-ethyl-3'-hydroxy-4',6'-dimethyl-1'-oxohept-6'-enyl)-4-methyl-5-phenyloxazolidin-2-one 
• 96930-29-9 <3(2R),4R,5S>-3-(2-hydroxy-1-oxobutyl)-4-methyl-5-phenyl-2-oxazolidinone 
• 79563-31-8 (4R,5S)-4-methyl-3-[2(R)-methyl-1-oxobutyl]-5-phenyloxazolidin-2-one 
• 79563-30-7 (4R,5S)-4-Methyl-3-[(S)-2-methylbutyryl]-5-phenyloxazolidin-2-one 
• 219506-89-5 (4R,5S)-3-((R)-2-Hydroxymethyl-butyryl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 219506-97-5 (4R,5S)-3-((S)-2-Iodomethyl-butyryl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 219506-93-1 Methanesulfonic acid (R)-2-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidine-3-carbonyl)-butyl ester 
• 219507-00-3 (S)-4-[(S)-2-((4R,5S)-4-Methyl-2-oxo-5-phenyl-oxazolidine-3-carbonyl)-butylsulfanyl]-2-(4-nitro-benzyloxycarbonylamino)-butyric acid methyl ester 
• 219507-03-6 (S)-4-[(S)-2-((4R,5S)-4-Methyl-2-oxo-5-phenyl-oxazolidine-3-carbonyl)-butane-1-sulfinyl]-2-(4-nitro-benzyloxycarbonylamino)-butyric acid methyl ester 
• 219507-06-9 methyl (2S)-4-{(2S)-2-[((4R,5S)-4-methyl-5-phenyl-2-oxazolidinone-3-yl)carbonyl]butyl-(R,S)-sulfonimidoyl}-2-(N-4-nitrobenzyloxycarbonylamino)butanoate 
• 1104899-97-9 C₁₉H₂₅NO₄ 

Relevant academic research and scientific papers

Thermal proteome profiling efficiently identifies ribosome destabilizing oxazolidinones

Identifying the targets of bioactive small molecules is a challenging endeavor for which no general solution currently exists. Classical affinity purification experiments suffer from the need to functionalise a bioactive compound and link it to a solid support, which may interfere with target binding. A modern mass spectrometry-based proteomics technique that has partially circumvented this problem is thermal proteome profiling (TPP), which determines the effect of an unmodified small molecule on the thermal stability of the whole proteome simultaneously. Here, we use TPP to identify the mode-of-action of a newly-discovered autophagy inhibitor based on oxazolidinones often employed as chiral auxiliaries. Surprisingly, a significant portion of all ribosomal proteins were found to be destabilized by the inhibitor, highlighting the utility of this technology for determining a challenging mode-of-action.

Conformational preference in bis(porphyrin) tweezer complexes: A versatile chirality sensor for α-chiral carboxylic acids

Metallated porphyrin tweezers have demonstrated a remarkable ability to function as reporters of absolute stereochemistry for a number of different classes of organic molecules. Flexibility in binding, however, can result in an ensemble of different Exciton Coupled Circular Dichroism (ECCD) active conformations that could lead to variable results. Linker flexibility was found to be a key determinant of binding conformation. Experimental results indicate that a balance between linker flexibility and rigidity could yield an optimum porphyrin tweezer that stabilizes a common conformation for all bound chiral guests. This leads to a more simplified approach to absolute stereochemical determination of asymmetry for small organic molecules. This was demonstrated by the use of a C3-linked zincated porphyrin tweezer that yields a common conformational preference for a variety of α-chiral carboxylic acids derivatized with a diamine carrier. Copyright

Pyran-2-ones and 5,6-dihydropyran-2-ones useful for treating hyperplasia and other diseases

Certain 2H-pyran-2-ones are useful for treating benign prostatic hypertrophy or hyperplasia, prostatic cancer, alopecia, hirsutism, acne vulgaris and seborrhea.

Thiopyrano[2,3,4-cd]indoles as 5-lipoxygenase inhibitors: Synthesis, biological profile, and resolution of 2-[2-[1-(4-chlorobenzyl)-4-methyl-6- [(5-phenylpyridin-2-yl)methoxy]-4,5-dihydro-1H-thiopyrano[2,3,4-cd]indol-2- yl]ethoxy]butanoic acid

Leukotriene biosynthesis inhibitors have potential as new therapies for asthma and inflammatory diseases. The recently disclosed thiopyrano[2,3,4- cd]indole class of 5-lipoxygenase (5-LO) inhibitors has been investigated with particular emphasis on the side chain bearing the acidic functionality. The SAR studies have shown that the inclusion of a heteroatom (O or S) in conjunction with an α-ethyl substituted acid leads to inhibitors of improved potency. The most potent inhibitor prepared contains a 2-ethoxybutanoic acid side chain. This compound, 14d (2-[2-[1-(4-chlorobenzyl)-4-methyl-6-[(5- phenylpyridin-2-yl)methoxy]-4,5-dihydro-1H-thiopyrano[2,3,4-cd]indol-2- yl]ethoxy]butanoic acid, L-699,333), inhibits 5-HPETE production by human 5- LO and LTB4 biosynthesis by human PMN leukocytes and human whole blood (IC50s of 22 nM, 7 nM and 3.8 μM, respectively). The racemic acid 14d has been shown to be functionally active in a rat pleurisy model (inhibition of LTB4, ED50 = 0.65 mg/kg, 6 h pretreatment) and in the hyperreactive rat model of antigen-induced dyspnea (50% inhibition at 2 and 4 h pretreatment; 0.5 mg/kg po). In addition, 14d shows excellent functional activity against antigen-induced bronchoconstriction in the conscious squirrel monkey [89% inhibition of the increase in R(L) and 68% inhibition in the decrease in C(dyn) (0.1 mg/kg, n = 3)] and in the conscious sheep models of asthma (iv infusion at 2.5 μg/kg/min). Acid 14d is highly selective as an inhibitor of 5-LO activity when compared to the inhibition of human 15-LO, porcine 12-LO and ram seminal vesicle cyclooxygenase (IC50 > 5 μM) or competition in a FLAP binding assay (IC50 > 10 μM). Resolution of 14d affords 14g, the most potent diastereomer, which inhibits the 5-HPETE production of human 5-LO and LTB4 biosynthesis of human PMN leukocytes and human whole blood with IC50s of 8 nM, 4 nM, and 1 μM respectively. The in vitro and in vivo profile of 14d is comparable to that of MK-0591, which has showed biochemical efficacy in inhibiting ex vivo LTB4 biosynthesis and urinary LTE4 excretion in clinical trials.

A practical method for N-acylation of bornane-2,10-sultam and 2-oxazolidinones

The N-trimethylsilyl derivatives of (+)-bornane-2,10-sultam (10,10-dimethyl-5-thia-4-azatricyclo[5.2.1.03,7]decane 5,5-dioxide) and (R)-4-benzyl-2-oxazolidinone and 4-methyl-5-phenyl-2-oxazolidinone react with acid chlorides in refluxing benzen

Stereocontrolled Synthesis of a Key Lactone Intermediate Required for the Synthesis of Salinomycin

The stereocontrolled synthesis of lactone (1b), a key intermediate required for the synthesis of the polyether antibiotic salinomycin, is described.

Syntheses of 20'-Deoxyvinblastine, 20'-Deoxyleurosidine, 20'-Deoxyvincovaline, 20'-epi-20'-Deoxyvincovaline, and 20'-Deoxyvincristine and Its 20'-Epimer through Racemic and Enantioselectively Generated Intermediates. New Syntheses of D/E-cis- and -trans-Ψ

Vindoline (20), on reaction with chloro imine derivatives of the D-seco-D/E-trans-Ψ- and -20-epi-Ψ-vincadifformines 18 and 19, followed by cyclization and debenzylation steps, provided the natural products 20'-deoxyvinblastine (4) and 20'-deoxyleurosidine