927-58-2

Usage

Uses

Used in Organic Synthesis:
4-Bromobutyryl chloride is used as a precursor for the synthesis of carolic acid by reacting with ethoxymagnesiomalonic ester. It is widely utilized as an intermediate in organic synthesis due to its reactivity and ability to form various chemical compounds.
Used in Pharmaceutical Industry:
4-Bromobutyryl chloride is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its acylating properties make it a valuable building block for the development of new drugs and therapeutic agents.

InChI:InChI=1/C4H6BrClO/c5-3-1-2-4(6)7/h1-3H2

Upstream product

• 2623-87-2 bromobutyric acid 
• 18340-00-6 4-Brombuttersaeure-trimethylsilylester 

Downstream Products

• 2969-81-5 Ethyl 4-bromobutyrate 
• 7661-18-9 4-bromo-N-(4-chlorophenyl)butyramide 
• 24070-52-8 4-bromo-1-phenyl-1-butanone 
• 40132-01-2 1-(4-fluorophenyl)-4-bromo-1-butanone 
• 100129-05-3 γ-Brom-N-benzyl-butyramid 
• 7578-45-2 N-phenyl-4-chlorobutyramide 
• 72709-39-8 N-Benzyl-4-chlorobutananilide 
• 72709-37-6 1,12-Dichloro-5,6,7,8-tetraphenyl-5,8-diazadodecane-4,9-dione 
• 100-52-7 benzaldehyde 
• 97559-23-4 N-(β-phenethyl)-4-bromobutyramide 
• 123337-33-7 <(2,4-dioxo-5,5-diphenyl-3-imidazolidinyl)methyl>-4-bromobutyrate 
• 170798-05-7 (S)-2-(4-Bromo-butyrylamino)-3-phenyl-propionic acid ethyl ester 
• 4897-84-1 Methyl 4-bromobutyrate 
• 211922-28-0 2-Cyano-2-[dihydro-furan-(2Z)-ylidene]-N-phenyl-acetamide 

Relevant academic research and scientific papers

Gemfibrozil derivatives as activators of soluble guanylyl cyclase – A structure-activity study

Previous studies demonstrated that anti-hyperlipidemic drug gemfibrozil acts as NO- and heme-independent activator of NO receptor soluble guanylyl cyclase. A series of new gemfibrozil derivatives were synthesized and evaluated for sGC activation. The structure-activity relationship study identified the positions in gemfibrozil's scaffold that are detrimental for sGC activation and those that are amendable for optimizing modifications. Compared with gemfibrozil, compounds 7c and 15b were more potent activators of cGMP-forming activity of purified sGC and exhibited enhanced relaxation of preconstricted mouse thoracic aorta rings. These studies established the overall framework needed for futher improvement of sGC activators based on gemfibrozil scaffold.

Targeted Delivery of mRNA with One-Component Ionizable Amphiphilic Janus Dendrimers

Targeted and efficient delivery of nucleic acids with viral and synthetic vectors is the key step of genetic nanomedicine. The four-component lipid nanoparticle synthetic delivery systems consisting of ionizable lipids, phospholipids, cholesterol, and a PEG-conjugated lipid, assembled by microfluidic or T-tube technology, have been extraordinarily successful for delivery of mRNA to provide Covid-19 vaccines. Recently, we reported a one-component multifunctional sequence-defined ionizable amphiphilic Janus dendrimer (IAJD) synthetic delivery system for mRNA relying on amphiphilic Janus dendrimers and glycodendrimers developed in our laboratory. Amphiphilic Janus dendrimers consist of functional hydrophilic dendrons conjugated to hydrophobic dendrons. Co-assembly of IAJDs with mRNA into dendrimersome nanoparticles (DNPs) occurs by simple injection in acetate buffer, rather than by microfluidic devices, and provides a very efficient system for delivery of mRNA to lung. Here we report the replacement of most of the hydrophilic fragment of the dendron from IAJDs, maintaining only its ionizable amine, while changing its interconnecting group to the hydrophobic dendron from amide to ester. The resulting IAJDs demonstrated that protonated ionizable amines play dual roles of hydrophilic fragment and binding ligand for mRNA, changing delivery from lung to spleen and/or liver. Replacing the interconnecting ester with the amide switched the delivery back to lung. Delivery predominantly to liver is favored by pairs of odd and even alkyl groups in the hydrophobic dendron. This simple structural change transformed the targeted delivery of mRNA mediated with IAJDs, from lung to liver and spleen, and expands the utility of DNPs from therapeutics to vaccines.

POLYCYCLIC COMPOUNDS AND METHODS FOR THE TARGETED DEGRADATION OF RAPIDLY ACCELERATED FIBROSARCOMA POLYPEPTIDES

The present disclosure relates to bifunctional compounds, ULM— L—PTM, which find utility as modulators of Rapidly Accelerated Fibrosarcoma (RAF, such as c-RAF, A- RAF and/or B-RAF; the target protein). In particular, the present disclosure is directed to bifunctional compounds, which contain on one end a Von Hippel-Lindau, cereblon, Inhibitors of Apotosis Proteins or mouse double-minute homolog 2 ligand which binds to the respective E3 ubiquitin ligase and on the other end a moiety which binds the target protein RAF, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of target protein. The present disclosure exhibits a broad range of pharmacological activities associated with degradation/inhibition of target protein. Diseases or disorders that result from aggregation or accumulation of the target protein, or the constitutive activation of the target protein, are treated or prevented with compounds and compositions of the present disclosure.

LIPIDS FOR LIPID NANOPARTICLE DELIVERY OF ACTIVE AGENTS

Compounds are provided having the following structure: (I) or a pharmaceutically acceptable salt, tautomer, or stereoisomer thereof, wherein R1, R2, R3, R4, R5, L1, L2, L3, G1, G2, and G3 are as defined herein. Use of the compounds as a component of lipid nanoparticle formulations for delivery of a therapeutic agent, compositions comprising the compounds and methods for their use and preparation are also provided.

Intramolecular Cyclization of Brominated Oxime Ether Promoted with Ytterbium(0) to the Synthesis of Cyclic Imines

The first utility of ytterbium(0) as a mediating-metal in the intramolecular cyclization of brominated oxime ether was reported in this paper. In contrast to the prior methods, the N–O bond was used as a receptor of nucleophilic reagent, rather than as a source of N-centered radicals. Cyclic imines were obtained in this one-pot reaction with a broad scope of substrates and feasible reaction conditions.

Highly frustrated liquid crystal phases in optically active dimers: Synthesis and rich phase transitional behavior

Herein we report on the synthesis and characterization of four new series of optically active, nonsymmetric dimers in which cholesterol is covalently linked to a Schiff base core through an ω-oxyalkanoyl spacer. While the Schiff base core is substituted with n-butyloxy, n-hexyloxy, n-octyloxy, n-decyloxy and n-dodecyloxy tails, three even-parity spacers, namely, 4-oxybutanoyl, 6-oxyhexanoyl, 8-oxyoctanoyl, and an odd-parity spacer, namely, 5-oxypentanoyl, have been used to join the two cores. The experimental results show that the length and parity of the spacer and the length of the terminal tail play a vital role in deciding the phase sequences of the dimers. In general, the dimers possessing an even-parity spacer display enantiotropic LC phases such as chiral nematic (N?), twist grain boundary (TGB), smectic A (SmA), chiral smectic C (SmC?) and twist grain boundary phase with SmC? slabs (TGBC?). Some of these dimers display TGBC? over a wide temperature range. The dimers with an odd-parity (5-oxypentanoyl) spacer display, unlike their even-membered counterparts, blue phases (BPIII/II/I); besides, they stabilize N? and/or unknown smectic (SmX) phases. The circular dichroism (CD) measurements were carried out as a function of temperature on the planar texture formed by three even-membered dimers and an odd-membered dimer. The occurrence of a strong negative CD band in the N? phase of the even-membered dimers suggests a left-handed screw sense of the macroscopic helical structure, and the scenario is opposite in the case of an odd-membered dimer.

MACROCYCLIC COMPOUNDS AS PROTEASOME INHIBITORS

The compounds of the present invention are represented by the following compounds having Formula I and Formula (I'): where the substituents R1, R2, R2', R3, R4, R5, R', R", X, Y, and Z are as defined herein and where the substituents R1, R2, R3, R4, R5, R', R", X, Y, and Z are as defined herein. These compounds are used in the treatment of bacterial infections, parasite infections, fungal infections, cancer, immunologic disorders, autoimmune disorders, neurodegenerative diseases and disorders, inflammatory disorders, or muscular dystrophy or for providing immunosuppression for transplanted organs or tissues.

Iminyl Radicals by Reductive Cleavage of N-O Bond in Oxime Ether Promoted by SmI2: A Straightforward Synthesis of Five-Membered Cyclic Imines

A new generation method of N-centered radicals from the reductive cleavage of the N-O bond in oxime ether promoted by SmI2 is reported for the first time. The in-situ-generated N-centered radicals underwent intramolecular cyclization to afford five-membered cyclic imines in two manners: N-centered radical addition and N-centered anion nucleophilic substitution. From a synthetic point of view, an efficient synthetic method of five-membered cyclic imines was developed. A mechanism of the transformation was proposed.

Discovery of a Small-Molecule Inhibitor of Interleukin 15: Pharmacophore-Based Virtual Screening and Hit Optimization

Interleukin (IL)-15 is a pleiotropic cytokine, which is structurally close to IL-2 and shares with it the IL-2 β and γ receptor (R) subunits. By promoting the activation and proliferation of NK, NK-T, and CD8+ T cells, IL-15 plays important roles in innate and adaptative immunity. Moreover, the association of high levels of IL-15 expression with inflammatory and autoimmune diseases has led to the development of various antagonistic approaches targeting IL-15. This study is an original approach aimed at discovering small-molecule inhibitors impeding IL-15/IL-15R interaction. A pharmacophore and docking-based virtual screening of compound libraries led to the selection of 240 high-scoring compounds, 36 of which were found to bind IL-15, to inhibit the binding of IL-15 to the IL-2Rβ chain or the proliferation of IL-15-dependent cells or both. One of them was selected as a hit and optimized by a structure-activity relationship approach, leading to the first small-molecule IL-15 inhibitor with sub-micromolar activity.

Photoinduced, Copper-Catalyzed Decarboxylative C-N Coupling to Generate Protected Amines: An Alternative to the Curtius Rearrangement

The Curtius rearrangement is a classic, powerful method for converting carboxylic acids into protected amines, but its widespread use is impeded by safety issues (the need to handle azides). We have developed an alternative to the Curtius rearrangement that employs a copper catalyst in combination with blue-LED irradiation to achieve the decarboxylative coupling of aliphatic carboxylic acid derivatives (specifically, readily available N-hydroxyphthalimide esters) to afford protected amines under mild conditions. This C-N bond-forming process is compatible with a wide array of functional groups, including an alcohol, aldehyde, epoxide, indole, nitroalkane, and sulfide. Control reactions and mechanistic studies are consistent with the hypothesis that copper species are engaged in both the photochemistry and the key bond-forming step, which occurs through out-of-cage coupling of an alkyl radical.