1021267-09-3

Basic information

• Product Name: 2'-hydroxy-4'-methoxyacetophenone imine
• Synonyms: 2'-hydroxy-4'-methoxyacetophenone imine
• CAS NO: 1021267-09-3
• Molecular Weight: 165.192
• Mol File: 1021267-09-3.mol

Chemical Properties

• CAS DataBase Reference: 2'-hydroxy-4'-methoxyacetophenone imine(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-hydroxy-4'-methoxyacetophenone imine(1021267-09-3)
• EPA Substance Registry System: 2'-hydroxy-4'-methoxyacetophenone imine(1021267-09-3)

Safety Data

• Hazardous Substances Data: 1021267-09-3(Hazardous Substances Data)

Upstream product

• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 

Downstream Products

• 1033425-29-4 (E)-1,1,1-trichloro-3-nitro-N-[1-(2-hydroxy-4-methoxyphenyl)ethylidene]propan-2-amine 
• 73344-39-5 6-methoxy-3-methyl-1,2-benzisoxazole 
• 23999-64-6 6-methoxy-2-methyl-benzoxazole 
• 1228553-89-6 (S)-2-(1-aminoethyl)-5-methoxyphenol 
• 1021267-65-1 2-(1-aminoethyl)-5-methoxyphenol 

Relevant articles and documents

A kind of benzo [d] different wicked zuozuo apperception compound and use thereof

The invention relates to the technical field of chemical medicine, and particularly discloses a benzo[d]isoxazole compound shown as a general formula (A) and application thereof. The compound can effectively inhibit bromodomain of BET family proteins so as to block interaction between the BET family proteins and chromatin histone to adjust genetic transcription, cause changing of a downstream signal path and exert important influence on various diseases, so that the compound and a combination thereof can be used for preparing medicine for treating or preventing diseases like tumorigenesis, inflammation, viral infection, cell proliferation disorder, autoimmune diseases and septicemia.

Synthesis and pharmacological evaluation of carboxycoumarins as a new antitumor treatment targeting lactate transport in cancer cells

Under hypoxia, cancer cells consume glucose and release lactate at a high rate. Lactate was recently documented to be recaptured by oxygenated cancer cells to fuel the TCA cycle and thereby to support tumor growth. Monocarboxylate transporters (MCT) are the main lactate carriers and therefore represent potential therapeutic targets to limit cancer progression. In this study, we have developed and implemented a stepwise in vitro screening procedure on human cancer cells to identify new potent MCT inhibitors. Various 7-substituted carboxycoumarins and quinolinone derivatives were synthesized and pharmacologically evaluated. Most active compounds were obtained using a palladium-catalyzed Buchwald-Hartwig type coupling reaction, which proved to be a quick and efficient method to obtain aminocarboxycoumarin derivatives. Inhibition of lactate flux revealed that the most active compound 19 (IC 50 11 nM) was three log orders more active than the CHC reference compound. Comparison with warfarin, a conventional anticoagulant coumarin, further showed that compound 19 did not influence the prothrombin time which, together with a good in vitro ADME profile, supports the potential of this new family of compounds to act as anticancer drugs through inhibition of lactate flux.

A divergent and selective synthesis of isomeric benzoxazoles from a single N-Cl imine

A divergent and regioselective synthesis of either 3-substituted benzisoxazoles or 2-substituted benzoxazoles from readily accessible ortho-hydroxyaryl N-H ketimines is described. The reaction proceeds in two distinct pathways through a common N-Cl imine intermediate: (a) N-O bond formation to form benzisoxazole under anhydrous conditions and (b) NaOCl mediated Beckmann-type rearrangement to form benzoxazole, respectively. The reaction path also depends on the electronic nature of the aromatic ring, with the electron-rich aromatic rings favoring the rearrangement and the electron-deficient rings favoring the N-O bond formation. A Beckmann-type rearrangement mechanism via net [1,2]-aryl migration for the formation of 2-substituted benzoxazole is proposed.

Chiral phosphoric acid-catalyzed enantioselective transfer hydrogenation of ortho-hydroxyaryl alkyl N - H ketimines

The first enantioselective chiral phosphoric acid-catalyzed transfer hydrogenation of unprotected ortho-hydroxyaryl alkyl N - H ketimines using Hantszch di-tert-butyl ester as a reductant is reported. A variety of ortho-hydroxybenzylamines were obtained in good to excellent yields and enantiomeric excesses.

A simple and convenient synthesis of 4-methyl-3-nitro-2-trihalomethyl-2H-chromenes from N-unsubstituted imines of 2-hydroxyacetophenones and trichloro(trifluoro)ethylidene nitromethanes

The reaction of N-unsubstituted imines of 2-hydroxyacetophenones with trichloro(trifluoro)ethylidene nitromethanes in the presence of DABCO proceeds via tandem oxa-Michael/aza-Henry additions (in dichloromethane) or aza-Michael addition (in benzene) to give 4-methyl-3-nitro-2-trichloro(trifluoro)methyl-2H-chromenes or 1,1,1-trichloro(trifluoro)-3-nitro-N-[1-(2-hydroxyaryl)ethylidene]propan-2-amines, respectively.