144464-64-2

Basic information

• Product Name: Methanesulfonic acid, 1,1,1-trifluoro-, 5,6,7,8-tetrahydro-5-oxo-2-naphthalenyl ester
• Synonyms: Methanesulfonic acid, 1,1,1-trifluoro-, 5,6,7,8-tetrahydro-5-oxo-2-naphthalenyl ester;trifluoro-methanesulfonic acid 5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl ester;5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate
• CAS NO: 144464-64-2
• Molecular Formula: C₁₁H₉F₃O₄S
• Molecular Weight: 294.2469696
• Mol File: 144464-64-2.mol
• Article Data: 60

Chemical Properties

• Boiling Point: 384.4±42.0 °C(Predicted)
• Appearance: /
• Density: 1.515±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Methanesulfonic acid, 1,1,1-trifluoro-, 5,6,7,8-tetrahydro-5-oxo-2-naphthalenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Methanesulfonic acid, 1,1,1-trifluoro-, 5,6,7,8-tetrahydro-5-oxo-2-naphthalenyl ester(144464-64-2)
• EPA Substance Registry System: Methanesulfonic acid, 1,1,1-trifluoro-, 5,6,7,8-tetrahydro-5-oxo-2-naphthalenyl ester(144464-64-2)

Safety Data

• Hazardous Substances Data: 144464-64-2(Hazardous Substances Data)

Upstream product

• 3470-50-6 6-Hydroxy-1-tetralone 
• 407-25-0 trifluoroacetic anhydride 
• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 1025373-45-8 trifluoromethanesulfonic acid anhydride 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 1493-13-6 trifluorormethanesulfonic acid 
• 1078-19-9 6-methoxy-3,4-dihydro-1(2H)-naphthalenone 

Downstream Products

• 144464-66-4 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid methyl ester 
• 101110-09-2 6-(4-hydroxyphenyl)-3,4-dihydronaphthalen-1(2H)-one 
• 90401-84-6 6-cyano-1-tetralone 
• 3470-46-0 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid 
• 51015-29-3 6-methyl-3,4-dihydronaphthalen-1(2H)-one 
• 1213846-17-3 6-methyl-1,2,3,4-tetrahydronaphthalen-1-amine 
• 847585-96-0 6-[(4-isobutylphenyl)ethyl]-1-methyl-1,2,3,4-tetrahydronaphthalen-1-ol 
• 847585-95-9 6-[(4-isobutylphenyl)ethynyl]-1-methyl-1,2,3,4-tetrahydronaphthalen-1-ol 
• 847585-97-1 7-[2-(4-isobutylphenyl)ethyl]-4-methyl-1,2-dihydronaphthalene 
• 1242848-60-7 N-[6-(methylaminomethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]-2-[2-(p-tolylsulfonyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-1-yl]acetamide 
• 945632-79-1 2-acetylamino-2-(6-octyl-1-oxo-1,2,3,4-tetrahydro-naphthalen-2-yl)-malonic acid diethyl ester 
• 945632-81-5 2-acetylamino-2-(6-octyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-malonic acid diethyl ester 
• 1118948-68-7 N-[2-hydroxy-1-hydroxymethyl-1-(6-octyl-1,2,3,4-tetrahydro-naphthalen-2-yl)ethyl]-acetamide 
• 945632-77-9 2-bromo-6-octyl-3,4-dihydro-2H-naphthalen-1-one 

Relevant articles and documents

A short, efficient synthesis of 6-cyano-1-tetralones

A new, short and high-yield synthesis of 6-cyano-1-tetralones is described. Triflate intermediates 8 and 9 are versatile intermediates for the synthesis of other 6-substituted tetralones.

Design, synthesis, and biological evaluation of Cyclobentinib (CB1107) as a potential anti-CML agent

Cyclobentinib was designed and synthesized as a novel anti-CML agent, its in vitro activity against K562 cells was evaluated by MTT assay. CB1107 showed remarkable cytotoxicity against K562 cell line with an IC50 of 0.037 ± 0.028 μmol/L, and thus it was 17-fold more potent than the reference drug Imatinib. Inducing cell apoptosis and affecting cell cycling of this compound in K562 cells were estimated by using flow cytometry and Acridine Orange/Ethidium Bromide (AO/EB) staining. The results showed that CB1107 was capable of arresting cell cycle at G0/G1 phase as well as inducing cell apoptosis significantly. Molecular mechanism of CB1107 was detected by the protein expression of Bcr-AblP210 using western blotting analysis. Downregulation of expression of Bcr-AblP210 was obviously revealed in the treatment of this tetralin amide compound. Of note, the results of these investigations suggested that CB1107 is more potent than the reference drug Imatinib against K562 cells. Additionally, in vivo results indicated that CB1107 significantly decreased tumor growth in K562 tumor-bearing Non-obese Diabetic/Severe Combined Immunodeficiency (NOD/SCID) mice. Histopathological investigation revealed that CB1107 without notable toxicity in a given dose range. These findings collectively demonstrate CB1107 is a promising candidate as a novel anti-CML agent.

PROCESSES AND INTERMEDIATES FOR PREPARING MCL1 INHIBITORS

The present disclosure provides methods for preparing MCL1 inhibitors or a salt thereof and related key intermediates.

Discovery of Tetralones as Potent and Selective Inhibitors of Acyl-CoA:Diacylglycerol Acyltransferase 1

Acyl-CoA:diacylglycerol acyltransferase 1 (DGAT1) plays an important role in triglyceride synthesis and is a target of interest for the treatment of metabolic disorders. Herein we describe the structure-activity relationship of a novel tetralone series of DGAT1 inhibitors and our strategies for overcoming genotoxic liability of the anilines embedded in the chemical structures, leading to the discovery of a candidate compound, (S)-2-(6-(5-(3-(3,4-difluorophenyl)ureido)pyrazin-2-yl)-1-oxo-2-(2,2,2-trifluoroethyl)-1,2,3,4-tetrahydronaphthalen-2-yl)acetic acid (GSK2973980A, 26d). Compound 26d is a potent and selective DGAT1 inhibitor with excellent DMPK profiles and in vivo efficacy in a postprandial lipid excursion model in mice. Based on the overall biological and developability profiles and acceptable safety profiles in the 7-day toxicity studies in rats and dogs, compound 26d was selected as a candidate compound for further development in the treatment of metabolic disorders.