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Usage

Uses

Used in Pharmaceutical Industry:
4-DesMethoxy-4-broMo TriMethopriM is used as an inhibitor for the enzyme dihydrofolate reductase, which plays a crucial role in the biosynthesis of nucleotides and, consequently, DNA and RNA synthesis. Its inhibitory action on this enzyme can be leveraged for the development of therapeutic agents targeting various diseases, particularly those involving rapid cell proliferation.
Additionally, due to its structural similarity to Trimethoprim, a well-known antibiotic, 4-DesMethoxy-4-broMo TriMethopriM may also be studied for potential applications in the development of new antibiotics or as a component in combination therapies to combat antibiotic resistance.

Upstream product

• 50-01-1 guanidine hydrochloride 
• 41833-82-3 2-(3-bromo-4,5-dimethoxy-benzyl)-3-morpholin-4-yl-acrylonitrile 
• 2973-76-4 5-bromo-4-hydroxy-3-methoxybenzaldehyde 
• 121-33-5 vanillin 
• 593-85-1 guanidine carbonate 
• 6948-30-7 5-bromoveratralaldehyde 
• 110-67-8 3-Methoxypropionitrile 
• 506-93-4 guanidine nitrate 
• 92026-15-8 2-amino-5-(3-bromo-4,5-dimethoxy-benzyl)-3H-pyrimidin-4-one 

Relevant academic research and scientific papers

Halogenated trimethoprim derivatives as multidrug-resistant Staphylococcus aureus therapeutics

Incorporation of halogen atoms to drug molecule has been shown to improve its properties such as enhanced in membrane permeability and increased hydrophobic interactions to its target. To investigate the effect of halogen substitutions on the antibacterial activity of trimethoprim (TMP), we synthesized a series of halogen substituted TMP and tested for their antibacterial activities against global predominant methicillin resistant Staphylococcus aureus (MRSA) strains. Structure-activity relationship analysis suggested a trend in potency that correlated with the ability of the halogen atom to facilitate in hydrophobic interaction to saDHFR. The most potent derivative, iodinated trimethoprim (TMP-I), inhibited pathogenic bacterial growth with MIC as low as 1.25 μg/mL while the clinically used TMP derivative, diaveridine, showed resistance. Similar to TMP, synergistic studies indicated that TMP-I functioned synergistically with sulfamethoxazole. The simplicity in the synthesis from an inexpensive starting material, vanillin, highlighted the potential of TMP-I as antibacterial agent for MRSA infections.

Photocontrol of Antibacterial Activity: Shifting from UV to Red Light Activation

The field of photopharmacology aims to introduce smart drugs that, through the incorporation of molecular photoswitches, allow for the remote spatial and temporal control of bioactivity by light. This concept could be particularly beneficial in the treatment of bacterial infections, by reducing the systemic and environmental side effects of antibiotics. A major concern in the realization of such light-responsive drugs is the wavelength of the light that is applied. Studies on the photocontrol of biologically active agents mostly rely on UV light, which is cytotoxic and poorly suited for tissue penetration. In our efforts to develop photoswitchable antibiotics, we introduce here antibacterial agents whose activity can be controlled by visible light, while getting into the therapeutic window. For that purpose, a UV-light-responsive core structure based on diaminopyrimidines with suitable antibacterial properties was identified. Subsequent modification of an azobenzene photoswitch moiety led to structures that allowed us to control their activity against Escherichia coli in both directions with light in the visible region. For the first time, full in situ photocontrol of antibacterial activity in the presence of bacteria was attained with green and violet light. Most remarkably, one of the diaminopyrimidines revealed an at least 8-fold difference in activity before and after irradiation with red light at 652 nm, showcasing the effective "activation" of a biological agent otherwise inactive within the investigated concentration range, and doing so with red light in the therapeutic window.

Preparation method of trimethoprim impurities

The invention relates to a preparation method of trimethoprim impurities. The method can be used for preparing trimethoprim impurities A, E, F and G. Cyclizing agents, such as guanidine nitrate or methylguanidine hydrochloride, are taken as raw materials, and are condensed with trimethoprim methyl ether of different structures to stably obtain various kinds of trimethoprim impurities. The method is simple and available in raw material, short in reaction time and high in yield.

[...]tritium mark method for preparing phthalic

The invention belongs to the field of radioactive chemical synthesis and particularly relates to a preparation method of tritiated diaveridine. The diaveridine is an antimicrobial synergist. According to the invention, 3,4-dimethoxy-5-bromine-benzaldehyde is used as the raw material; 3,4-dimethoxy-5-bromine-benzaldehyde is subjected to the Knoevenagel reaction and the annulation reaction to obtain 5-bromine-diaveridine; finally, by adopting a micro synthesis method and using palladium-charcoal (Pd/C) as a catalyst, the reductive debromination reaction is performed on 5-bromine-diaveridine and tritium gas and simultaneously, tritium is exchanged to generate 5-3H-diaveridine with high specific activity (22.08Ci/g), high radiochemical purity (more than or equal to 98 percent) and high chemical purity (more than or equal to 98 percent). As a radioactive tracer, the tritiated diaveridine synthesized by the preparation method provides the material basis to systematically carry out researches on the adsorption, distribution, metabolism and residue elimination rules of diaveridine in an animal body, and also provides methodological reference for tritium labeling of like medicine.

Preparation of β-anilino-α-benzylacrylonitriles

Compounds comprising selected N-substituted β-amino-α-benzyl-acrylonitriles and methods of preparing said compounds substantially free from the corresponding bensalacrylonitrile. The compounds are useful as intermediates in the preparation of antibacterial and antimalerial agents.