877624-38-9

Basic information

• Product Name: methyl 5-(bromomethyl)nicotinate
• Synonyms: methyl 5-(bromomethyl)nicotinate;5-broMoMethyl-nicotinic acid Methyl ester;Methyl 5-(bromomethyl)nicotinate hydrobromide;3-Pyridinecarboxylic acid, 5-(bromomethyl)-, methyl ester
• CAS NO: 877624-38-9
• Molecular Formula: C₈H₈BrNO₂
• Molecular Weight: 230
• Mol File: 877624-38-9.mol

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: methyl 5-(bromomethyl)nicotinate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 5-(bromomethyl)nicotinate(877624-38-9)
• EPA Substance Registry System: methyl 5-(bromomethyl)nicotinate(877624-38-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 877624-38-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 5-(bromomethyl)nicotinate is used as a building block for the synthesis of various drugs, particularly in the production of antineoplastic agents, which are used to treat cancer. Its unique structure and properties make it a valuable component in the development of new pharmaceuticals.
Used in Synthesis of Biologically Active Molecules:
Methyl 5-(bromomethyl)nicotinate is used as a key intermediate in the synthesis of other biologically active molecules and pharmaceutical intermediates. Its versatile chemical properties allow for the creation of a wide range of compounds with potential therapeutic applications.
Used in Antineoplastic Agent Production:
Methyl 5-(bromomethyl)nicotinate is used as a key component in the production of antineoplastic agents, which are drugs specifically designed to treat cancer. Its presence in these agents contributes to their effectiveness in combating cancer cells and improving patient outcomes.
It is important to handle methyl 5-(bromomethyl)nicotinate with care, as it is considered hazardous and may cause irritation to the skin, eyes, and respiratory system. It is a white solid with a melting point of around 109-113°C and is moderately soluble in water.

Upstream product

• 29681-45-6 5-methylnicotinic acid methyl ester 

Downstream Products

• 912934-74-8 C₁₅H₁₅NO₃ 
• 1446322-14-0 methyl 5-((4-formyl-6-methoxyphen-3-yloxy)methyl)nicotinate 

Relevant articles and documents

Resin and Magnetic Nanoparticle-Based Free Radical Probes for Glycan Capture, Isolation, and Structural Characterization

By combining the merits of solid supports and free radical activated glycan sequencing (FRAGS) reagents, we develop a multifunctional solid-supported free radical probe (SS-FRAGS) that enables glycan enrichment and characterization. SS-FRAGS comprises a solid support, free radical precursor, disulfide bond, pyridyl, and hydrazine moieties. Thio-activated resin and magnetic nanoparticles (MNPs) are chosen as the solid support to selectively capture free glycans via the hydrazine moiety, allowing for their enrichment and isolation. The disulfide bond acts as a temporary covalent linkage between the solid support and the captured glycan, allowing the release of glycans via the cleavage of the disulfide bond by dithiothreitol. The basic pyridyl functional group provides a site for the formation of a fixed charge, enabling detection by mass spectrometry and avoiding glycan rearrangement during collisional activation. The free radical precursor generates a nascent free radical upon collisional activation and thus simultaneously induces systematic and predictable fragmentation for glycan structure elucidation. A radical-driven glycan deconstruction diagram (R-DECON) is developed to visually summarize the MS2 results and thus allow for the assembly of the glycan skeleton, making the differentiation of isobaric glycan isomers unambiguous. For application to a real-world sample, we demonstrate the efficacy of the SS-FRAGS by analyzing glycan structures enzymatically cleaved from RNase-B.

Discovery of novel ketoxime ether derivatives with potent FXR agonistic activity, oral effectiveness and high liver/blood ratio

The farnesoid X receptor (FXR) is a promising therapeutic target for nonalcoholic steatohepatitis (NASH) and other bile acid related diseases because it plays a critical role in fibrosis, inflammation and bile acid homeostasis. Obeticholic acid (OCA), a FXR agonist which was synthesized from chenodeoxycholic acid, showed desirable curative effects in clinical trials. However, the pruritus which was the main side effect of OCA limited its further applications in NASH. Although pruritus was also observed in the clinical trials of non-steroidal FXR agonists, the proportion of patients with pruritus was much smaller than that of OCA. Thus, we decided to develop non-steroidal FXR agonists and discovered a series of novel FXR agonists which were synthesized from GW4064 by replacing the stilbene group with ketoxime ether. Encouragingly, in the following biological tests, our target compounds 13j and 13z not only showed potent FXR agonistic activities in vitro, but also effectively promoted the expression of target genes in vivo. More importantly, in the pharmacokinetic experiments, compounds 13j and 13z displayed high liver/blood ratio characteristics which were helpful to reduce the potential side effects which were caused by prolonged systemic activation of FXR. In summary, our compounds were good choices for the development of non-steroidal FXR agonists and were deserved further investigation.

Biomimetic reagents for the selective free radical and acid-base chemistry of glycans: Application to glycan structure determination by mass spectrometry

Nature excels at breaking down glycans into their components, typically via enzymatic acid-base catalysis to achieve selective cleavage of the glycosidic bond. Noting the importance of proton transfer in the active site of many of these enzymes, we describe a sequestered proton reagent for acid-catalyzed glycan sequencing (PRAGS) that derivatizes the reducing terminus of glycans with a pyridine moiety possessing moderate proton affinity. Gas-phase collisional activation of PRAGS-derivatized glycans predominately generates C1-O glycosidic bond cleavages retaining the charge on the reducing terminus. The resulting systematic PRAGS-directed deconstruction of the glycan can be analyzed to extract glycan composition and sequence. Glycans are also highly susceptible to dissociation by free radicals, mainly reactive oxygen species, which inspired our development of a free radical activated glycan sequencing (FRAGS) reagent, which combines a free radical precursor with a pyridine moiety that can be coupled to the reducing terminus of target glycans. Collisional activation of FRAGS-derivatized glycans generates a free radical that reacts to yield abundant cross-ring cleavages, glycosidic bond cleavages, and combinations of these types of cleavages with retention of charge at the reducing terminus. Branched sites are identified with the FRAGS reagent by the specific fragmentation patterns that are observed only at these locations. Mechanisms of dissociation as well as application of the reagents for both linear and highly branched glycan structure analysis are investigated and discussed. The approach developed here for glycan structure analysis offers unique advantages compared to earlier studies employing mass spectrometry for this purpose.

Inhibitors of 11-beta hydroxysteroid dehydrogenase type I

Novel compounds are provided which are 11-beta-hydroxysteroid dehydrogenase type I inhibitors. 11-beta-hydroxysteroid dehydrogenase type I inhibitors are useful in treating, preventing, or slowing the progression of diseases requiring 11-beta-hydroxysteroid dehydrogenase type I inhibitor therapy. These novel compounds have the structure: or stereoisomers or prodrugs or pharmaceutically acceptable salts thereof, wherein G, L, Q, Z, R6, R7, and R8 are defined herein.

QUINAZOLINONE DERIVATIVES AND THEIR USE AS B-RAF INHIBITORS

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2-SULFANYL-BENZOIMIDAZOL-1-YL-ACETIC ACID DERIVATIVES AS CRTH2 ANTAGONISTS

The invention relates to 2-sulfanyl-benzoimidazol-1-yl-acetic acid derivatives and their use as potent "chemoattractant receptor-homologous molecule expressed on Th2 cells" antagonists in the treatment of prostaglandin mediated diseases, to pharmaceutical compositions containing these derivatives and to processes for their preparation.

[(3-Pyridylalkyl)piperidylidene]benzocycloheptapyridine derivatives as dual antagonists of PAF and histamine

A series of [(3-pyridylalkyl)piperidylidene]- and (nicotinoylpiperidylidene)benzocycloheptapyridine derivatives, Ia,b, were prepared and evaluated for PAF antagonist and H1 antihistamine activity. PAF antagonist activity was investigated by the in vitro PAF-induced platelet aggregation assay (PPA) and the in vivo PAF-induced hypotension test in rats (PH) and mortality test in mice (PM). For the evaluation of H1 antihistamine activity, the in vitro histamine-induced contraction of the guinea-pig ileum assay (HC) and the in vivo histamine-induced hypotension test (HH) in normotensive rats were used. The potential antiallergic activity of the compounds was evaluated using the active anaphylactic shock test in mice. These compounds are structurally related to loratadine (1) and were generated by replacement of the ethoxycarbonyl group of 1 with substituted 3- pyridylmethyl and nicotinoyl moieties. Both anti-PAF and H1 antihistamine activities have shown a high dependence on the exact nature and position of the substituent in the pyridine ring. Optimum structure 19 (UR-12592) incorporating a (5-methyl-3-pyridyl)methyl radical displayed an unique dual activity inhibiting both PAF-induced effects (PPA, IC50 = 3.7 μM; PH, ID50 = 0.44 mg/kg iv; PM, ID50 = 1.9 mg/kg po) and histamine-induced effects (HC, IC50 = 3.9 nM; HH, ID50 = 1.4 mg/kg iv). Furthermore, 19 was highly active in the passive cutaneous anaphylactic shock in rats (ID50 = 1.2 mg/kg po) and strongly protected mice and rats from mortality induced by endotoxin (ID50 = 1.2 and 0.5 mg/kg iv, respectively). Compound 19 showed itself to be devoid of CNS depressant effects, neither modifying spontaneous motor activity nor prolonging barbiturate-sleeping time in mice at a dose of 100 mg/kg po, and is now under development.