4463-02-9

Usage

Uses

Used in Pharmaceutical Industry:
2,4,6-Trihydroxy-1,3-dimethyl benzene is used as a reagent for the synthesis of flavanone derivatives, which exhibit anti-tumor activities. These flavanone derivatives have potential applications in the development of new cancer treatments, targeting various types of cancer cells and contributing to the advancement of oncology research.
Used in Chemical Synthesis:
Due to its unique structure and functional groups, 2,4,6-trihydroxy-1,3-dimethyl benzene can be used as a building block in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its versatility as a chemical intermediate makes it valuable in the development of new products and materials across different industries.

InChI:InChI=1/C8H10O3/c1-4-6(9)3-7(10)5(2)8(4)11/h3,9-11H,1-2H3

Upstream product

• 55743-13-0 2,4,6-trihydroxy-3-methylbenzaldehyde 
• 23848-22-8 2,6-Dimethylphloroglucin-1-monomethylether 
• 108-73-6 3,5-dihydroxyphenol 
• 74-88-4 methyl iodide 
• 82-08-6 rottlerin 
• 94135-19-0 2,4-dimethyl-benzene-1,3,5-triyltriamine 
• 7732-18-5 water 
• 207924-64-9 1-tert-butyl-3,5-dimethyl-2,4,6-triaminobenzene 
• 39828-33-6 2,4,6-Trihydroxy-3-methyl-benzoesaeure-methylester 
• 487-70-7 2,4,6-trihydroxybenzaldehyde 
• 88-03-9 2,4,6-trihydroxytoluene 
• 4396-13-8 2,4-diformyl 2,4,6-trihydroxybenzene 
• 108-38-3 m-xylene 
• 632-92-8 2,4-dimethyl-1,3,5-trinitrobenzene 

Downstream Products

• 94632-38-9 1,3-Dihydroxy-5-methoxy-2,4-dimethyl-benzol 
• 84633-27-2 Dimethylphlorobutyrophenone 
• 95273-01-1 2,3-dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-6,8-dimethylchromen-4-one 
• 1402589-43-8 C₁₆H₁₆O₄ 
• 1402589-44-9 C₁₆H₁₅FO₄ 
• 1402589-45-0 C₁₆H₁₅ClO₄ 
• 1402589-46-1 C₁₇H₁₈O₅ 
• 1402589-48-3 C₁₆H₁₄Cl₂O₄ 
• 1402589-50-7 C₁₇H₁₈O₄ 
• 1402589-51-8 C₁₈H₂₀O₄ 
• 1402589-52-9 C₁₈H₁₉FO₄ 
• 1402589-53-0 C₁₈H₁₉ClO₄ 
• 1402589-55-2 C₁₉H₂₂O₅ 
• 1402589-56-3 C₁₈H₁₈Cl₂O₄ 

Relevant academic research and scientific papers

A Nouvel Route to Resorcinols

Hydroxylation of para-alkylated or 2,6-dialkylated phenols by hydrogen peroxide in SbF5-HF yields resorcinols, the electrophile reacting with the O-protonated substrate.

Total Syntheses of 4′,6′-Dimethoxy-2'-Hydroxy-3′,5′-Dimethylchalcone Derivatives

Chalcone derivatives afford several pharmacological activities. However, a general synthetic method for 2',4'-dihydroxy-6'-methoxy-3',5'-dimethylchalcone (DMC) derivatives has not been reported thus far. To address this, the preparation of 4',6'-dimethoxy-2'-hydroxy-3',5'-dimethylchalcone (MDMC) derivatives, modified compounds of DMC, in excellent overall yields is reported herein. These compounds have recently attracted growing attention due to their various pharmacological activities. Di-O-methyl-dimethylphloroacetophenone, the key intermediate containing the B-ring moiety, was fabricated by four efficient reaction steps from commercially available phloroglucinol in a 50.1% isolated yield overall. Our synthetic route, which constructs the chalcone skeleton in the final stage via a Claisen–Schmidt condensation of the key intermediate with the desired benzaldehyde derivative, can rapidly produce a vast library of DMC derivatives.

HALOGEN-SUBSTITUTED DIMETHYLCHALCONE DERIVATIVES AND PREPARATION METHOD THEREOF

The present invention relates to dimethylchalcone (DMC) derivatives substituted with halogen and a method for producing the same. A compound according to an embodiment of the present invention is represented by chemical formula I: [Chemical Formula I]. In Formula I, R1 and R2 are the same as or different from each other, R1, and R2 are each independently selected from the group consisting of hydrogen, methoxy, and methoxy. R3, and R4 are each independently hydrogen or halogen elements, and when R3 is hydrogen, R4 R4 is any one selected from the group consisting of halogen elements R3.

DIMETHYLCHALCONE DERIVATIVES AND PREPARATION METHOD THEREOF

The present invention relates to a dimethalcone (DMC) derivative and a method for producing the same. A compound according to an embodiment of the present invention is represented by chemical formula I: [Chemical Formula I]. In Formula I, R1, R2, and R3 are the same as or different from each other, R1 is a hydroxy group or a methoxy group, R2, and R3 are each independently hydrogen, deuterium, a nitro group, a hydroxyl group, a carbonyl group C1?C10, a nitro group, C1?C10 a hydroxyl group, an 'C2?C10 alkyloxy group', an aryloxy C2?C10 group, an aryloxy group, an alkylthioxy group, a silyl group, a boron group, an alkyl group or an C6?C20 aryl group. (C1?C10. The cycloalkyl group, alkenyl group, alkynyl group, aryl group, aralkyl group, aralkyl group, alkylaryl group, alkylamine group. The substituent may be substituted or unsubstituted with 1 or more substituents selected from the group consisting of an aralkylamine group, a heteroarylamine group, an arylamine group, an arylphosphine group, and a heterocyclic group.

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.

Biomimetic Synthesis Enables the Structure Revision of Littordials e and F and Drychampone B

Structural reassignments for littordial E, littordial F, and drychampone B are proposed on the basis of consideration of their biosynthetic origin. The key step in the proposed biosynthesis of each of these meroterpenoids is an intermolecular hetero-Diels-Alder reaction between an o-quinone methide and caryophyllene or humulene. Biomimetic total synthesis of the natural products gave sufficient material to allow their structure revision by NMR studies.

Synthesis of methylophiopogonanone a

Ophiopogon Root (root of Ophiopogon japonicus Ker-Gawler, Liliaceae) is a crude drug used as expectorant, anti-cough and tonic in Kampo medicine (traditional Japanese medicine) as well as other traditional medicines of Asian countries. It contains characteristic homoisoflavonoids with methylated ring A. We synthesized methylophiopogonanone A (1), which is a candidate marker compound for identification test of Ophiopogon Root, from phloroglucinol in 9 steps with overall yield of 11.1%.

Derivatives of Natural Product Agrimophol as Disruptors of Intrabacterial pH Homeostasis in Mycobacterium tuberculosis

This article reports the rational medicinal chemistry of a natural product, agrimophol (1), as a new disruptor of intrabacterial pH (pHIB) homeostasis in Mycobacterium tuberculosis (Mtb). Through the systematic investigation of the structure-activity relationship of 1, scaffold-hopping of the diphenylmethane scaffold, pharmacophore displacement strategies, and studies of the structure-metabolism relationship, a new derivative 5a was achieved. Compound 5a showed 100-fold increased potency in the ability to reduce pHIB to pH 6.0 and similarly improved mycobactericidal activity compared with 1 against both Mycobacterium bovis-BCG and Mtb. Compound 5a possessed improved metabolic stability in human liver microsomes and hepatocytes, lower cytotoxicity, higher selectivity index, and similar pKa value to natural 1. This study introduces a novel scaffold to an old drug, resulting in improved mycobactericidal activity through decreasing pHIB, and may contribute to the critical search for new agents to overcome drug resistance and persistence in the treatment of tuberculosis.

Chemo-enzymatic Total Synthesis of Oxosorbicillinol, Sorrentanone, Rezishanones B and C, Sorbicatechol A, Bisvertinolone, and (+)-Epoxysorbicillinol

The sorbicillinoids are a large family of fungal natural products, many of which possess highly challenging molecular architectures. Depending on their individual structures they exhibit strong biological activities ranging from radical scavenging and anti-infective properties to cytotoxicity. Despite the resulting strong biomedical potential of these natural products and the interest of synthetic chemists owing to their fascinating structures, many sorbicillinoids are currently not synthetically accessible, thus hampering in-depth biological characterization and structural diversification. By using recombinant oxidoreductase SorbC and readily accessible sorbicillin-type synthetic precursors, we have developed enantioselective, one-pot chemo-enzymatic routes to a broad range of sorbicillinoids, thereby establishing total syntheses of oxosorbicillinol, sorrentanone, rezishanones B and C, sorbicatechol A, bisvertinolone, and (+)-epoxysorbicillinol.

Aurone compound and preparation method and application thereof

The invention provides an aurone compound shown in the formula (I). Compared with the prior art, the compound has the relatively high inhibiting effect on release of PGE (prostaglandine) 2 of RAW 264.7 macrophage of a mouse induced by lipopolysaccharide, the activity is superior to ibuprofen, and the aurone compound has the anti-inflammatory related pharmacological activity.