42768-45-6

Usage

Uses

Used in Organic Synthesis:
2-Bromovalerylchloride is used as a reagent in organic synthesis for its ability to participate in various chemical reactions. Its versatility in Grignard reactions and acylations makes it a valuable component in the synthesis of a wide range of organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Bromovalerylchloride is used as an intermediate in the synthesis of various drugs. Its reactivity in different types of reactions allows for the creation of complex molecular structures that are essential in the development of new medications.
Used in Chemical Research:
2-Bromovalerylchloride is also used as a research tool in chemical laboratories. Its unique properties and reactivity make it an important compound for studying reaction mechanisms and exploring new synthetic pathways in the field of organic chemistry.

Upstream product

• 584-93-0 2-Bromovaleric acid 
• 638-29-9 n-valeryl chloride 
• 109-52-4 valeric acid 
• 760-78-1 2-aminopentanoic acid 

Downstream Products

• 19129-92-1 methyl 2-bromovalerate 
• 100794-28-3 2-bromo-valeric acid-(2,4,6-trimethyl-anilide) 
• 300707-84-0 N-4'-methylphenyl-2-bromopentanamide 
• 86895-81-0 (E)-methyl 2-methyl-2-phenylthiopent-3-enoate 
• 86895-65-0 α-phenylthio methyl pentanoate 
• 99683-07-5 (E)-2-Phenylsulfanyl-pent-2-enoic acid methyl ester 
• 86895-69-4 methyl 2-phenylsulphinylpentanoate 
• 128960-23-6 2-propyl-3-thiapentanamide 
• 5632-86-0 norvaline amide 
• 208252-85-1 N-(2-bromobutyryl)glycine benzyl ester 
• 944356-95-0 2-bromo-N-(2-hydroxy-3,5-dimethylphenyl)valeramide 
• 1382859-50-8 (R)-(-)-N-(4-bromophenyl)-2-[5-(3-methoxybenzyl)-3-methyl-6-oxopyridazin-1(6H)-yl]pentanamide 
• 1382859-49-5 (S)-(+)-N-(4-bromophenyl)-2-[5-(3-methoxybenzyl)-3-methyl-6-oxopyridazin-1(6H)-yl]pentanamide 
• 1382859-61-1 (+/-)-2-bromo-N-(4-bromophenyl)pentanamide 

Relevant academic research and scientific papers

Cobalt-Catalyzed 1,4-Aryl Migration/Desulfonylation Cascade: Synthesis of α-Aryl Amides

A cobalt-catalyzed 1,4-aryl migration/disulfonylation cascade applied to α-bromo N-sulfonyl amides was developed. The reaction was highly chemoselective, allowing the preparation of α-aryl amides possessing a variety of functional groups. The method was used as the key step to synthesize an alkaloid, (±)-deoxyeseroline. Mechanistic investigations suggest a radical process.

Synthetic method of 2-substituted-1-(2-thiophene)-1-pentanone

The invention discloses a synthetic method of 2-substituted-1-(2-thiophene)-1-pentanone. The method includes the steps: taking n-pentanoic acid and bromine as raw materials, and taking phosphorus trichloride as a catalyst to prepare 2-bromovaleric acid; mixing the 2-bromovaleric acid and thionyl chloride to obtain 2-bromovaleryl chloride; taking aluminum trichloride as a catalyst, dropping thiophene into 2-bromovaleryl chloride, and stirring mixture to obtain 2-bromine-1-(2-thiophene)-1-pentanon; performing heating reflux on the 2-bromine-1-(2-thiophene)-1-pentanon and pyrrolidine or piperidine to obtain the 2-substitution-1-(2-thiophene)-1-pentanone. A target compound is a precursor compound for synthesizing drugs such as anticonvulsant drugs or vasodilator drugs and provided with an important pharmaceutical intermediate.

Benzoxazinone-containing 3,5-dimethylisoxazole derivatives as BET bromodomain inhibitors for treatment of castration-resistant prostate cancer

The bromodomain and extra-terminal proteins (BET) have emerged as promising therapeutic targets for the treatment of castration-resistant prostate cancer (CRPC). We report the design, synthesis and evaluation of a new series of benzoxazinone-containing 3,5-dimethylisoxazole derivatives as selective BET inhibitors. One of the new compounds, (R)-12 (Y02234), binds to BRD4(1) with a Kd value of 110 nM and blocks bromodomain and acetyl lysine interactions with an IC50 value of 100 nM. It also exhibits selectivity for BET over non-BET bromodomain proteins and demonstrates reasonable anti-proliferation and colony formation inhibition effect in prostate cancer cell lines such as 22Rv1 and C4-2B. The BRD4 inhibitor (R)-12 also significantly suppresses the expression of ERG, Myc and AR target gene PSA at the mRNA level in prostate cancer cells. Treatment with (R)-12 significantly suppresses the tumor growth of prostate cancer (TGI = 70%) in a 22Rv1-derived xenograft model. These data suggest that compound (R)-12 is a promising lead compound for the development of a new class of therapeutics for the treatment of CRPC.

Enantioselective synthesis of quaternary α-amino acids via l -tert-leucine-derived squaramide-catalyzed conjugate addition of α-nitrocarboxylates to enones

Enantioselective Michael addition of tertiary α-nitroesters to β-unsubstituted vinyl ketones has been carried out in the presence of an l-tert-leucine-derived squaramide as organocatalyst. The products, quaternary α-nitroesters, were formed in excellent yield and moderate to good ee's in most cases. Scale-up of the reaction and synthetic applications of the products, including transformation to representative quaternary α-amino acids, have also been demonstrated.

Enantioselective construction of tetrasubstituted stereogenic carbons through bronsted base catalyzed michael reactions: α′-hydroxy enones as key enoate equivalent

Catalytic and asymmetric Michael reactions constitute very powerful tools for the construction of new C-C bonds in synthesis, but most of the reports claiming high selectivity are limited to some specific combinations of nucleophile/electrophile compound types, and only few successful methods deal with the generation of all-carbon quaternary stereocenters. A contribution to solve this gap is presented here based on chiral bifunctional Bronsted base (BB) catalysis and the use of α′-oxy enones as enabling Michael acceptors with ambivalent H-bond acceptor/donor character, a yet unreported design element for bidentate enoate equivalents. It is found that the Michael addition of a range of enolizable carbonyl compounds that have previously demonstrated challenging (i.e., α-substituted 2-oxindoles, cyanoesters, oxazolones, thiazolones, and azlactones) to α′-oxy enones can afford the corresponding tetrasubstituted carbon stereocenters in high diastereo- and enantioselectivity in the presence of standard BB catalysts. Experiments show that the α′-oxy ketone moiety plays a key role in the above realizations, as parallel reactions under identical conditions but using the parent α,β-unsaturated ketones or esters instead proceed sluggish and/or with poor stereoselectivity. A series of trivial chemical manipulations of the ketol moiety in adducts can produce the corresponding carboxy, aldehyde, and ketone compounds under very mild conditions, giving access to a variety of enantioenriched densely functionalized building blocks containing a fully substituted carbon stereocenter. A computational investigation to rationalize the mode of substrate activation and the reaction stereochemistry is also provided, and the proposed models are compared with related systems in the literature.

Synthesis, enantioresolution, and activity profile of chiral 6-methyl-2,4-disubstituted pyridazin-3(2H)-ones as potent N-formyl peptide receptor agonists

A series of chiral pyridazin-3(2H)-ones was synthesized, separated as pure enantiomers, and evaluated for N-formyl peptide receptor (FPR) agonist activity. Characterization of the purified enantiomers using combined chiral HPLC and chiroptical studies (circular dichroism, allowed unambiguous assignment of the absolute configuration for each pair of enantiomers). Evaluation of the ability of racemic mixtures and purified enantiomers to stimulate intracellular Ca 2+ flux in FPR-transfected HL-60 cells and human neutrophils and to induce β-arrestin recruitment in FPR-transfected CHO-K1 cells showed that many enantiomers were potent agonists, inducing responses in the sub-micromolar to nanomolar range. Furthermore, FPRs exhibited enantiomer selectivity, generally preferring the R-(-)-forms over the S-(+)-enantiomers. Finally, we found that elongation of the carbon chain in the chiral center of the active compounds generally increased biological activity. Thus, these studies provide important new information regarding molecular features involved in FPR ligand preference and report the identification of a novel series of FPR agonists.

Investigation of the synthetic and mechanistic aspects of the highly stereoselective transformation of α-thioamides to α-thio-β- chloroacrylamides

Treatment of a series of α-thioamides with N-chlorosuccinimide results in efficient transformation to the analogous α-thio-β- chloroacrylamides. The mechanistic pathway has been established through isolation and characterisation of intermediate compounds. The scope of the transformation has been explored - aryl and alkylthio substituents, primary, secondary and tertiary amides can be employed. In most instances, the chloroacrylamides are formed exclusively as the Z-stereoisomer; however, with tertiary propanamides or with amides derived from butanoic or pentanoic acid a mixture of E- and Z-stereoisomers is formed. The Royal Society of Chemistry.

Carboxylic Acid Compounds and Use Thereof

Provision of a superior URAT1 activity inhibitor effective for the treatment and the like of a pathology involving uric acid, such as hyperuricemia, gouty tophus, acute gouty arthritis, chronic gouty arthritis, gouty kidney, urinary lithiasis, renal dysfunction, coronary heart disease, ischemic cardiac diseases and the like. A URAT1 activity inhibitor containing a compound represented by the following formula [1] or a pharmaceutically acceptable salt thereof, or a solvate thereof as an active ingredient: [image] wherein each symbol is as defined in the specification.

CYANOARYLAMINES

The present invention relates to a compound represented by the following formula (I) or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate thereof, or a combination thereof; wherein R°, R1, R1', R2, R2', R3 and n are defi

Carboxylic acid and phosphate ester derivatives of fluconazole: Synthesis and antifungal activities

Carboxylic acid and phosphate ester derivatives of fluconazole were synthesized and evaluated in vitro against Cryptococcus neoformans, Candida albicans, and Aspergillus niger. Two classes of fluconazole derivatives, (a) carboxylic acid esters and (b) fatty alcohol and carbohydrate phosphate esters, were synthesized and evaluated in vitro against Cryptococcus neoformans, Candida albicans, and Aspergillus niger. All carboxylic acid ester derivatives of fluconazole (1a-l), such as O-2-bromooctanoylfluconazole (1g, MIC = 111 μg/mL) and O-11-bromoundecanoylfluconazole (1j, MIC = 198 μg/mL), exhibited higher antifungal activity than fluconazole (MIC ≥ 4444 μg/mL) against C. albicans ATCC 14053 in SDB medium. Several fatty alcohol phosphate triester derivatives of fluconazole, such as 2a, 2b, 2f, 2g, and 2h, exhibited enhanced antifungal activities against C. albicans and/or A. niger compared to fluconazole in SDB medium. For example, 2-cyanoethyl-ω-undecylenyl fluconazole phosphate (2b) with MIC value of 122 μg/mL had at least 36 times greater antifungal activity than fluconazole against C. albicans in SDB medium. Methyl-undecanyl fluconazole phosphate (2f) with a MIC value of 190 μg/mL was at least 3-fold more potent than fluconazole against A. niger ATCC 16404. All compounds had higher estimated lipophilicity and dermal permeability than those for fluconazole. These results demonstrate the potential of these antifungal agents for further development as sustained-release topical antifungal chemotherapeutic agents.