165111-46-6

Basic information

• Product Name: Methyl 2-bromomethyl-4-cyanobenzoate
• Synonyms: Methyl 2-bromomethyl-4-cyanobenzoate
• CAS NO: 165111-46-6
• Molecular Formula: C₁₀H₈BrNO₂
• Molecular Weight: 254.08002
• Mol File: 165111-46-6.mol

Chemical Properties

• Boiling Point: 380.5 °C at 760 mmHg
• Flash Point: 183.9 °C
• Appearance: /
• Density: 1.53 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: Methyl 2-bromomethyl-4-cyanobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-bromomethyl-4-cyanobenzoate(165111-46-6)
• EPA Substance Registry System: Methyl 2-bromomethyl-4-cyanobenzoate(165111-46-6)

Safety Data

• Hazardous Substances Data: 165111-46-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 2-bromomethyl-4-cyanobenzoate is used as an intermediate in the synthesis of pharmaceuticals for its ability to contribute to the formation of complex organic molecules. Its presence of a bromine atom and other functional groups allows for the creation of a wide range of medicinal compounds.
Used in Agrochemical Industry:
Similarly, in the agrochemical sector, Methyl 2-bromomethyl-4-cyanobenzoate serves as an intermediate in the production of various agrochemicals, leveraging its reactivity to form compounds that can be used in crop protection and other agricultural applications.
Used in Organic Synthesis:
Methyl 2-bromomethyl-4-cyanobenzoate is used as a versatile building block in organic synthesis for its capacity to react with other compounds to form a diverse array of organic molecules. Its reactivity and the presence of multiple functional groups make it a valuable component in the synthesis of specialty chemicals.

Upstream product

• 103261-67-2 4-cyano-2-methylbenzoic acid methyl ester 
• 68837-59-2 4-bromo-2-methylbenzoic acid 
• 99548-55-7 4-bromo-2-methyl-benzoic acid methyl ester 

Downstream Products

• 678992-35-3 5-[5-(6-cyano-1-oxo-1,3-dihydro-isoindol-2-ylmethyl)-3-methyl-1H-pyrazol-4yloxy]-isophthalonitrile 
• 165111-47-7 methyl 4-cyano-2-(4-hydroxyphenoxy)methylbenzoate 
• 1134082-50-0 3-(5-Cyano-1-oxoisoindolin-2-yl)benzoic acid 
• 1440519-96-9 2-(4-methoxy-benzyl)-1-oxo-2,3-dihydro-1H-isoindole-5-carbonitrile 
• 23386-40-5 1-oxo-2,3-dihydro-1H-isoindole-5-carboxylic acid 
• 1261869-76-4 1-oxoisoindoline-5-carbonitrile 
• 1010100-27-2 2-(2,6-dioxo-piperidin-3-yl)-1-oxo-2,3-dihydro-1H-isoindole-5-carbonitrile 

Relevant articles and documents

PROTEIN-TARGETING COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS THEREOF, AND THEIR THERAPEUTIC APPLICATIONS

The present disclosure provides compounds, for example, a compound of Formula (I), that modulate a protein function and/or restore protein homeostasis. The disclosure provides a method of modulating a protein-mediated disease, disorder, condition, or response. Compositions, including in combination with other therapeutic agents, are provided.

Discovery of 3-Pyridyl Isoindolin-1-one Derivatives as Potent, Selective, and Orally Active Aldosterone Synthase (CYP11B2) Inhibitors

Aldosterone synthase (CYP11B2) inhibitors have been explored in recent years as an alternative therapeutic option to mineralocorticoid receptor (MR) antagonists to reduce elevated aldosterone levels, which are associated with deleterious effects on various organ systems including the heart, vasculature, kidney, and central nervous system (CNS). A benzamide pyridine hit derived from a focused screen was successfully developed into a series of potent and selective 3-pyridyl isoindolin-1-ones CYP11B2 inhibitors. Our systematic structure-activity relationship study enabled us to identify unique structural features that result in high selectivity against the closely homologous cortisol synthase (CYP11B1). We evaluated advanced lead molecules, exemplified by compound 52, in an in vivo cynomolgus monkey acute adrenocorticotropic hormone (ACTH) challenge model and demonstrated a superior 100-fold in vivo selectivity against CYP11B1.

Degradable hydrogel under physiological conditions

The present invention discloses a hydrogel that can be degraded under physiological conditions. The hydrogel includes at least one backbone moiety and an optional crosslinking moiety, and biodegradable linkers connecting backbone moieties and crosslinking moieties can be degraded by intramolecular cyclization.

AMINOAMIDE COMPOUNDS

Compounds with amino amide linkers and pharmaceutical compositions and medicaments comprising such compounds are disclosed. The compounds modulate protein function of 1L-1β, IL-2, IL-6, TNF-α, CK1α, GSPT1, aiolos, ikaros or helios, or combinations thereof. In addition, methods of making such compounds and their uses for treating or ameliorating diseases, disorders, or conditions associated with protein malfunction, such as cancer, are provided.

Identification of novel uracil derivatives incorporating benzoic acid moieties as highly potent Dipeptidyl Peptidase-IV inhibitors

Dipeptidyl Peptidase-IV (DPP-4) is a validated therapeutic target for type 2 diabetes. Aiming to interact with both residues Try629 and Lys554 in S2′ site, a series of novel uracil derivatives 1a–l and 2a–i incorporating benzoic acid moieties at the N3 position were designed and evaluated for their DPP-4 inhibitory activity. Structure-activity relationships (SAR) study led to the identification of the optimal compound 2b as a potent and selective DPP-4 inhibitor (IC50 = 1.7 nM). Docking study revealed the additional salt bridge formed between the carboxylic acid and primary amine of Lys554 has a key role in the enhancement of the activity. Furthermore, compound 2b exhibited no cytotoxicity in human hepatocyte LO2 cells up to 50 μM. Subsequent in vivo evaluations revealed that the ester of 2b robustly improves the glucose tolerance in normal mice. The overall results have shown that compound 2b has the potential to a safe and efficacious treatment for T2DM.

Rapid generation of novel benzoic acid–based xanthine derivatives as highly potent, selective and long acting DPP-4 inhibitors: Scaffold-hopping and prodrug study

A series of novel xanthine derivatives 2a-l incorporating benzoic acid moieties were rapidly generated by using strategy of scaffold-hopping from our previously reported scaffold uracil to xanthine, a scaffold of approved drug linagliptin. After systematic structure-activity relationship (SAR) study around benzoic acid moieties, 5 novel DPP-4 inhibitors with low picomolar potency range (IC50 50 value of 0.1 nM for DPP-4, showed 22-fold improvement in inhibitory activity compared to lead compound uracil 1, its activity was 45-fold more potent than alogliptin. 2e, 2f, 2i and 2k were selected for pharmacokinetic evaluation, and 2f and 2i showed the better pharmacokinetic profiles after iv administration, but poor oral bioavailability. To improve the oral pharmacokinetic profile, prodrug design approach was performed around 2f and 2i. Esters of 2f and 2i were synthesized and evaluated for stability, toxicity and pharmacokinetics. Compound 3e, the methyl ester of compound 2f, was identified to demonstrate good stability, low toxicity and improved oral bioavailability, with 3-fold higher blood concentration compared to 2f in rats. The following in vivo evaluations revealed 3e provided a sustained pharmacodynamics effect for 48h, and robustly improved glucose tolerance in normal ICR and db/db mice in dose-dependent manner. Chronic treatments investigations demonstrated that 3e achieved more beneficial effects on fasting blood glucose levels and glucose tolerance than alogliptin in type 2 diabetic db/db mice. The overall results have shown that compound 3e has the potential to efficacious, safety and long-acting treatment for T2DM.

OXOINDOLINE DERIVATIVES AS PROTEIN FUNCTION MODULATORS

The present invention provides chimeric compounds of formula (II) that modulate protein function, to restore protein homeostasis, including cytokine, aiolos, and/or ikaros activity, TNF-alpha activity, CKl-alpha activity and cell-cell adhesion. The invention provides methods of modulating protein-mediated diseases, such as cytokine-mediated diseases, disorders, conditions, or responses. Compositions, including in combination with other cytokine and inflammatory mediators, are provided. Methods of treatment, amelioration, or prevention of protein-mediated diseases, disorders, and conditions, such as cytokine-mediated diseases, disorders, and conditions, including inflammation, fibromyalgia, rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, psoriasis, psoriatic arthritis, inflammatory bowel diseases, Crohn's disease, ulcerative colitis, uveitis, inflammatory lung diseases, chronic obstructive pulmonary disease, Alzheimer's disease, organ transplant rejection, and cancer, are provided.

SPIRODIAMINE DERIVATIVES AS ALDOSTERONE SYNTHASE INHIBITORS

The invention provides compounds having the general formula (I) pharmaceutical compositions containing the compounds and a process for their preparation. The compounds act as aldosterone synthase inhibitors and are for use in the treatment or prevention of chronic kidney disease, congestive heart failure, hypertension, primary aldosteronism and Cushing syndrom.

CHROMAN DERIVATIVES AS TRPM8 INHIBITORS

Chroman compounds and derivatives of Formula I are useful inhibitors of TRPM8. Such compounds are useful in treating a number of TRPM8 mediated disorders and conditions and may be used to prepare medicaments and pharmaceutical compositions useful for treating such disorders and conditions. Examples of such disorders include, but are not limited to, migraines and neuropathic pain. Compounds of Formula I have the following structure: where the definitions of the variables are provided herein.

NEW 3,4-DIHYDRO-2H-ISOQUINOLINE-1-ONE AND 2,3-DIHYDRO-ISOINDOL-1-ONE COMPOUNDS

The invention provides novel compounds having the general formula (I) wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, A, B, m, n and p are as described herein compositions including the compounds and methods of using the compounds.