80054-01-9

Usage

Uses

Used in Organic Synthesis:
1-(bromomethyl)-2,3,4-trimethoxybenzene is used as a reagent in the field of organic synthesis for its ability to facilitate the creation of new chemical compounds. Its unique structure allows it to serve as a key intermediate in the synthesis process, enabling the development of a wide range of products.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 1-(bromomethyl)-2,3,4-trimethoxybenzene is utilized as an intermediate. Its role is crucial in the development of new drugs, as its properties can be harnessed to create novel pharmaceutical compounds with potential therapeutic applications.
Used in Research and Development:
Due to its potential biological activity, 1-(bromomethyl)-2,3,4-trimethoxybenzene is also employed in research and development. Scientists and researchers use 1-(bromomethyl)-2,3,4-trimethoxybenzene to explore its possible applications in therapeutics, potentially leading to the discovery of new treatments for various health conditions.
Overall, 1-(bromomethyl)-2,3,4-trimethoxybenzene is a versatile chemical with a broad spectrum of applications across different industries, including organic synthesis, pharmaceutical research, and broader scientific exploration. Its unique properties and potential make it a valuable asset in the ongoing pursuit of new chemical and pharmaceutical innovations.

Upstream product

• 71989-96-3 2,3,4-trimethoxybenzylalcohol 
• 2103-57-3 2,3,4-trimethoxybenzaldehyde 

Downstream Products

• 105544-84-1 (3R*,4R*)-3-(2,3,4-trimethoxybenzyl)-4-(3,4-dimethoxybenzyl)-4,5-dihydro-2(3H)-furanone 
• 667936-12-1 4-[6,6-bis-(4-fluoro-phenyl)-hexanoyl]-1-(3,4,5,-trimethoxy-benzyl)-piperazin-2-one 
• 156727-93-4 ethyl 4-(3,4,5-trimethoxybenzyl)piperazine-2-carboxylate 
• 1013916-88-5 dimethyl 2-(1,2-butadienyl)-2-(2,3,4-trimethoxybenzyl)malonate 
• 366807-41-2 C₁₂H₁₆O₅S 
• 68913-85-9 2-(2,3,4-trimethoxyphenyl)acetonitrile 
• 1400793-07-8 C₂₅H₃₉N₃O₈ 
• 61240-20-8 triphenyl-(3,4,5-trimethoxybenzyl)phosphonium bromide 

Relevant academic research and scientific papers

New 3-(1H-benzo[d]imidazol-2-yl)quinolin-2(1H)-one-based triazole derivatives: Design, synthesis, and biological evaluation as antiproliferative and apoptosis-inducing agents

A series of 1,2,3-triazole derivatives based on the quinoline–benzimidazole hybrid scaffold was designed, synthesized, and screened against a panel of NCI-60 humanoid cancer cell lines for in vitro cytotoxicity evaluation, which revealed that compound Q6 was the most potent cytotoxic agent with excellent GI50, TGI, and LC50 values on multiple cancer cell lines. Q6 was tested further on the BT-474 breast cancer line to evaluate the mechanism of action. Preliminary screening studies based on the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay revealed that compound Q6 had an excellent antiproliferative effect against human breast cancer cells, BT-474, with IC50 values of 0.59 ± 0.01 μM. The detailed study based on the acridine orange/ethidium bromide staining (AO/EB) and the 4′,6-diamidino-2-phenylindole (DAPI) assay suggested that the antiproliferative activity shown was due to the induction of apoptosis on exposure to Q6. Further, DCFDA staining showed the generation of reactive oxygen species, altering the mitochondrial potential and leading to the initiation of apoptosis. This was further supported by JC-1 staining, indicating that this scaffold can contribute to the development of more potent derivatives.

TUBULIN BINDING AGENTS

The invention provides combretastatin A-4 like compounds that are modified to have enhanced tubulin binding activity and in some embodiments the ability to promote accumulation in the vasculature undergoing angiogenesis (homing activity). The compounds are based on the combretastatin A-4 skeletal structure having a tubulin-binding pharmacophore comprising two fused rings (A and B rings) in which the B ring is substituted with (a) an aromatic ring structure (C ring) and (b) a second substituent/functional group that comes off the B ring. The aromatic ring structure is typically a six membered ring phenolic or aniline structure, or may also be a fused ring structure such as a substituted or unsubstituted naphthalene. The second substituent on the B ring may for example be a substituent which has been found to provide enhanced tubulin binding activity (for example a carbonyl group), or may be a substituent that facilitates functionalisation of the B ring (for example an hydroxyl or amine group), or it may be a binding agent for a target that is preferentially expressed on vasculature undergoing angiogenesis, and not expressed on quiescent vasculature.

Asymmetric total synthesis of mycoleptodiscin A

The first total synthesis of mycoleptodiscin A, a structurally unusual indolosesquiterpenoid possessing an ortho-benzoquinone motif, has been accomplished. A sulfone alkylation coupled two readily available fragments to give an aryl triene intermediate. The tetracyclic core of the molecule was assembled through a highly enantioselective iridium-catalyzed polyene cyclization. The benzylic homologation was achieved by a cationic cyanation. The indole motif was constructed via a copper-mediated intramolecular C-N bond formation at a late stage.

Synthesis and in vitro antibacterial activity of gemifloxacin derivatives containing a substituted benzyloxime moiety

A series of novel gemifloxacin (GMFX) derivatives containing a substituted benzyloxime moiety with remarkable improvement in lipophilicity were synthesized. The target compounds evaluated for their in vitro antibacterial activity against representative strains. Our results reveal that most of the target compounds have considerable potency against all of the tested Gram-positive strains including MRSA and MRSE (MIC: 90: 1 μg/mL) is 8-fold more active than GMFX, and 2-fold more active than GMFX and moxifloxacin against MRSE clinical isolates (MIC90: 4 μg/mL). Crown Copyright

Synthesis and biological activity of pyridopyridazin-6-one p38α MAP kinase inhibitors. Part 2

This manuscript concludes the Structure Activity Relationship (SAR) on the pyridazinone scaffold and identifies a compound with subnanomolar p38α activity and 24 h coverage in the rat arthritis efficacy model.

Regio-and stereospecific synthesis of mono-β-d-glucuronic acid derivatives of combretastatin A-1

Synthetic routes have been established for the preparation of regio-and stereoisomerically pure samples of the mono-β-d-glucuronic acid derivatives of combretastatin A-1, referred to as CA1G1 (5a) and CA1G2 (6a). Judicious choice of protecting groups for the catechol ring was required for the regiospecific introduction of the glucuronic acid moiety. The tosyl group proved advantageous in this regard. The two monoglucuronic acid analogues demonstrate low cytotoxicity (compared to CA1, 2) against selected human cancer cell lines, with CA1G1 being slightly more potent than CA1G2.

A simple and efficient synthesis of the antimigraine drug lomerizine

The synthesis of the antimigraine drug 1-[bis(4-fluorophenyl)methyl]-4-(2, 3,4-trimethoxybenzyl)piperazine has been carried out in very good yields. The five-step synthesis started from bis(4-fluorophenyl)methanone. This route can be applied for large-scale preparation of lomerizine. Georg Thieme Verlag Stuttgart.

ANTIVIRAL ETHERS OF ASPARTATE PROTEASE SUBSTRATE ISOSTERES

Antiretroviral compounds (which are effective, for example, against HIV) of the formula I STR1 in which R 1 is an acyl radical lower-alkoxyl-lower-alkanoyl whose lower alkoxy radical is unsubstituted or is substituted by halogen, phenyl, lower alkoxy or a heterocyclic radical selected from piperidinyl, pyrrolidinyl, tetrahydropyranyl, tetrahydrofuranyl, thiazolidinyl, thiazolyl, indolyl or 4H-1-benzopyranyl which is unsubstituted or substituted by oxo, hydroxyl, amine, lower alkyl, lower-alkoxycarbonyl and/or phenyl-lower-alkoxycarbonyl; lower alkanoyl which is unsubstituted or is substituted by one of the said unsubstituted or substituted heterocyclic radicals; arylcarbonyl or heterocyclylcarbonyl which are substituted by heterocyclyl or heterocyclyl-lower-alkyl; phenyl-lower-alkanoyl which is substituted by hydroxyl and lower alkyl; or arylsulfonyl;or the residue of an amino acid which is defined in accordance with the description (and which may be acylated on the amino nitrogen by one of the abovementioned acyl radicals);R 2 and R 3 are in each case cyclohexyl, cyclohexenyl, phenyl, naphthyl or tetrahydronaphthyl which are unsubstituted or substituted by lower alkyl, phenyl, cyanophenyl, phenyl-lower-alkyl, halogen, halo-lower-alkyl, cyano, hydroxyl, lower alkoxy, phenyl-lower-alkoxyl, pyridyl-lower-alkoxy, lower-alkoxy-lower-alkoxy, lower-alkoxycarbonyl-lower-alkoxy, carboxyl-lower-alkoxy, hydroxyl-lower-alkoxy, carbamoyl-lower-alkoxy, cyano-lower-alkoxy, and phenyl-lower-alkanesulfonyl which is unsubstituted or substituted by halogen;R 4 is lower alkyl, cyclohexyl or phenyl; and R 5 is lower alkyl; and n is 1 or 2, or salts thereof, are novel.

Synthesis of potent and orally active HIV-protease inhibitors

A series of potent HIV-protease inhibitors has been prepared. Several of the newly synthesized compounds showed high plasma levels after oral administration to animals. Based on the overall biological profile, CGP 61755 was chosen for further preclinical evaluation. For this compound, a 10 step synthesis potentially suitable for large scale production was developed.

LE TETRAKIS(TRIFLUOROACETATE) DE RUTHENIUM(IV), NOUVEAU CATALYSEUR A TEMPERATURE AMBIANTE DU COUPLAGE BIARYLIQUE OXIDANT NON PHENOLIQUE-PREMIERE SYNTHESE TOTALE BIOMIMETIQUE DU NEOISOSTEGANE-

In situ generated Ruthenium(IV) tetrakis(trifluoroacetate) -a new organometallic reagent- was used in intramolecular non-phenolic oxydative biaryl coupling of dibenzylbutanolides, and an application to the first total synthesis of neoisostegane was perfor