19013-07-1

Basic information

• Product Name: 2,2-Dimethyl-6-acetyl-2H-1-benzopyran
• Synonyms: 2,2-Dimethyl-6-acetyl-2H-1-benzopyran;6-Acetyl-2,2-dimethyl-2H-1-benzopyran;6-Acetyl-2,2-dimethyl-3-chromene;Demethoxyencecalin;Desmethoxyencecalin;Methyl(2,2-dimethyl-2H-1-benzopyran-6-yl) ketone;1-(2,2-Dimethyl-2H-chromen-6-yl)-ethanone;2,2-diMethyl-2H-chroMene
• CAS NO: 19013-07-1
• Molecular Formula: C₁₃H₁₄O₂
• Molecular Weight: 202.2491
• Mol File: 19013-07-1.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 329.775 °C at 760 mmHg
• Flash Point: 147.718 °C
• Appearance: colorless transparent liquid or white solid
• Density: 1.061 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.531
• CAS DataBase Reference: 2,2-Dimethyl-6-acetyl-2H-1-benzopyran(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Dimethyl-6-acetyl-2H-1-benzopyran(19013-07-1)
• EPA Substance Registry System: 2,2-Dimethyl-6-acetyl-2H-1-benzopyran(19013-07-1)

Safety Data

• Hazardous Substances Data: 19013-07-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 32, p. 219, 1995 DOI: 10.1002/jhet.5570320136Synthesis, p. 144, 1979 DOI: 10.1055/s-1979-28595

InChI:InChI=1/C13H14O2/c1-9(14)10-4-5-12-11(8-10)6-7-13(2,3)15-12/h4-8H,1-3H3

Upstream product

• 2513-25-9 2,2-dimethyl-2H-chromene 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 78-79-5 isoprene 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 122-51-0 orthoformic acid triethyl ester 
• 99-93-4 4-Hydroxyacetophenone 
• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 33143-29-2 6-cyano-2,2-dimethylchromene 
• 155853-32-0 3-methyl-1-<2(tetrahydropyran-4-yloxy)-5-(2-methyl-(1,3)-dithian-2-yl)phenyl>-2-butenol 
• 155853-31-9 2-methyl-2-(4-tetrahydropyran-4-yloxy)-(1,3)-dithiane 
• 155853-29-5 2-methyl-2-(4-methoxymethylenoxyphenyl)-(1,3)dioxolane 
• 155853-28-4 2-methyl-2-(4-hydroxyphenyl)-1,3-dithiane 
• 36881-01-3 2-(4-hydroxyphenyl)-2-methyl-1,3-dioxolane 

Downstream Products

• 32333-31-6 2,2-dimethyl-6-acetylchroman 
• 171596-62-6 (3R,4R)-6-acetyl-2,2-dimethyl-3,4-epoxy-2H-1-benzopyran 
• 178458-56-5 (3S,4S)-6-acetyl-2,2-dimethyl-3,4-epoxy-2H-1-benzopyran 
• 77346-67-9 4-hydroxy-2,2-dimethyl-6-acetylchromane 
• 71822-00-9 <1-hydroxyethyl>-2,2-dimethylchromene 

Relevant articles and documents

A New Electrosynthesis of 2,2-Dimethylchromenes from 2-(1-Bromo-1-methylethyl)benzofurans

Electrolytic reduction of 2-(1-bromo-1-methylethyl)benzofurans in acetonitrile affords the corresponding 2,2-dimethylchromenes in good yields even in the absence of a proton donor and comprises the cleavage of a carbon-bromine bond followed by ring expansion.

Identification of anticancer agents based on the thieno[2,3-b]pyridine and 1H-pyrazole molecular scaffolds

Structural similarity search of commercially available analogues of thieno[2,3-b]pyridine and 1H-pyrazole derivatives, known anticancer agents, resulted in 717 hits. These were docked into the phosphoinositide specific-phospholipase C (PLC) binding pocket, the putative target of the compounds, to further focus the selection. Thirteen derivatives of the thieno[2,3-b]pyridines were identified and tested against the NCI60 panel of human tumour cell lines. The most active derivative 1 was most potent against the MDA-MB-435 melanoma cell line with GI50at 30?nM. Also, it was found that a piperidine moiety is tolerated on the thieno[2,3-b]pyridine scaffold with GI50?=?296?nM (MDA-MB-435) for derivative 10 considerably expanding the structure activity relationship for the series. For the 1H-pyrazoles four derivatives were identified using the in silico approach and additionally ten were synthesised with various substituents on the phenyl moiety to extend the structural activity relationship but only modest anticancer activity was found.

NOVEL COMPOUND OR PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PHARMACEUTICAL COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENT

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