13383-63-6

Usage

Preparation

Preparation by reaction of acetonitrile on 1,3-dimethyl-phloroglucinol (Hoesch reaction), (66%).

InChI:InChI=1/C10H12O4/c1-4-8(12)5(2)10(14)7(6(3)11)9(4)13/h12-14H,1-3H3

Upstream product

• 4463-02-9 2,4-dimethylbenzene-1,3,5-triol 
• 75-05-8 acetonitrile 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 74-88-4 methyl iodide 
• 58818-99-8 2,4,6-Triacetoxy-1,3-dimethylbenzene 
• 108-73-6 3,5-dihydroxyphenol 
• 4396-13-8 2,4-diformyl 2,4,6-trihydroxybenzene 
• 108-24-7 acetic anhydride 

Downstream Products

• 13197-10-9 5,6-Dihydroxy-1,3-dioxo-2,6-dimethyl-4-acetyl-cyclohexen-⁽⁴⁾ 
• 95273-00-0 6,8-dimethyl-3’-methoxy-4’,5,7-trihydroxyflavanone 
• 1204194-87-5 C₁₇H₁₅ClO₄ 
• 1204194-89-7 C₁₇H₁₅NO₆ 
• 27593-80-2 5,7-dihydroxy-6,8-dimethylflavanone 
• 95403-16-0 Farrerol 
• 95273-01-1 2,3-dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-6,8-dimethylchromen-4-one 
• 1204194-83-1 C₁₇H₁₆O₅ 
• 1252795-97-3 C₁₇H₁₆O₅ 
• 1204194-96-6 C₁₈H₁₈O₅ 
• 1204194-98-8 C₁₉H₂₀O₆ 
• 1204194-91-1 C₁₇H₁₅NO₆ 
• 95272-99-4 2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-6,8-dimethyl-chroman-4-one 
• 1204194-85-3 C₁₇H₁₅ClO₄ 

Relevant academic research and scientific papers

Discovery of Anti-TNBC Agents Targeting PTP1B: Total Synthesis, Structure-Activity Relationship, in Vitro and in Vivo Investigations of Jamunones

Twenty-three natural jamunone analogues along with a series of jamunone-based derivatives were synthesized and evaluated for their inhibitory effects against breast cancer (BC) MDA-MB-231 and MCF-7 cells. The preliminary structure-activity relationship revealed that the length of aliphatic side chain and free phenolic hydroxyl group at the scaffold played a vital role in anti-BC activities and the methyl group on chromanone affected the selectivity of molecules against MDA-MB-231 and MCF-7 cells. Among them, jamunone M (JM) was screened as the most effective anti-triple-negative breast cancer (anti-TNBC) candidate with a high selectivity against BC cells over normal human cells. Mechanistic investigations indicated that JM could induce mitochondria-mediated apoptosis and cause G0/G1 phase arrest in BC cells. Furthermore, JM significantly restrained tumor growth in MDA-MB-231 xenograft mice without apparent toxicity. Interestingly, JM could downregulate phosphatidylinositide 3-kinase (PI3K)/Akt pathway by suppressing protein-tyrosine phosphatase 1B (PTP1B) expression. These findings revealed the potential of JM as an appealing therapeutic drug candidate for TNBC.

Synthesis and biological activity of flavanone derivatives

A series of new flavanone derivatives of farrerol was synthesized by a convenient method. The in vitro anti-tumor activity of these compounds was evaluated against human Bel-7402, HL-60, BGC-823 and KB cell lines, the protein tyrosine kinase (PTK) inhibitor activity was also tested. Their cytoprotective activity was tested using hydrogen peroxide (H2O2)-induced injury in human umbilical vein endothelial cells. Their in vitro anti-atherosclerosis activity was tested on vascular smooth muscle cells by the MTT method using tetrandrine as a positive contrast drug. The structures of all compounds synthesized were confirmed by 1H, 13C NMR and ESI-MS. Most of the compounds exhibited good pharmacological activity and the preliminary structure-activity relationships were described.

A Novel Synthesis of 1-(2,4,6-Trihydroxy-3,5-dimethylphenyl)ethanone (Di-C-methylphloracetophenone) and Two New Non-Aromatic C-Benzylated Derivatives

The synthesis of the title compound 1e was achieved by an easy three-step procedure from 1,3,5-benzenetriol (1a, phloroglucinol).Compound 1a was C-methylated using MeI.The crude mixture obtained was acetylated to give 1d which was converted into 1e using BF3*AcOH complex.Benzylation of the latter with benzyl chloride afforded the new non-aromatic compound 2.Reaction of 2 with NaOH and benzoyl chloride (Scheme 1) gave the new compound 4.Its structure was established by X-ray analysis. - Keywords: Acetophenone / Di-C-methylphloracetopheneone

Pharmaceutical compositions containing compounds with a flavanone skeleton, process for the preparation of the said compound and novel compounds obtained

Compounds with a flavanone skeleton having the formula I STR1 in which R1 and R2, which may be the same or different, represent hydrogen, hydroxyl, methoxyl, thiomethyl, amino or substituted amino, are endowed with expectorant, mucolytic, mucopoietic, choleretic and hypolipaemia-producing activity.