2887-61-8

Usage

Uses

Used in Pharmaceutical Industry:
2'-Hydroxybutyrophenone is used as a prescription medication for its anxiolytic and sedative effects, primarily to treat anxiety disorders, insomnia, and other mood-related conditions. Its ability to modulate the GABAergic system contributes to its therapeutic benefits in these areas.
Used in Recreational Contexts:
Although not intended for recreational use, 2'-Hydroxybutyrophenone has gained popularity as a recreational drug due to its calming and euphoric effects. However, this use is associated with significant risks, including the potential for tolerance, dependence, and withdrawal symptoms.
Used in Regulatory Contexts:
Due to the potential for abuse and the associated health risks, 2'-Hydroxybutyrophenone has been subject to regulation or outright banning in some countries to mitigate the risks of misuse and addiction.

Upstream product

• 5751-48-4 2-methylchromone 
• 4346-18-3 phenyl butanoate 
• 141-75-3 butyryl chloride 
• 108-95-2 phenol 
• 107-92-6 butyric acid 
• 7446-70-0 aluminium trichloride 
• 142-82-5 n-heptane 
• 79-34-5 1,1,2,2-tetrachloroethane 
• 63314-77-2 α-propyl-2-hydroxybenzylalcohol 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 611-20-1 salicylonitrile 
• 106-94-5 propyl bromide 
• 995-25-5 chlorotripropylsilane 
• 19311-91-2 N,N-diethylsalicylamide 

Downstream Products

• 3180-09-4 ortho-butylphenol 
• 31414-62-7 1-[2-(2-diethylamino-ethoxy)-phenyl]-butan-1-one 
• 6734-08-3 1-(2-allyloxy-phenyl)-butan-1-one 
• 65627-57-8 (2-butyryl-phenoxy)-acetic acid 
• 115322-31-1 (2-butyryl-phenyl)-[tetra-O-acetyl-β-D-glucopyranoside 
• 92300-55-5 2-<1-Propylpenten-(1)-yl>-phenol 
• 119304-75-5 1-(2-Hydroxy-phenyl)-2-morpholin-4-ylmethyl-butan-1-one 
• 119304-78-8 2-Diethylaminomethyl-1-(2-hydroxy-phenyl)-butan-1-one 
• 71289-72-0 1-[2-(3,4-Dibromo-benzyloxy)-phenyl]-butan-1-one 
• 71289-68-4 1-[2-(2,4-Dichloro-benzyloxy)-phenyl]-butan-1-one 
• 71289-71-9 1-[2-(4-Bromo-benzyloxy)-phenyl]-butan-1-one 
• 71289-73-1 1-[2-(3-Trifluoromethyl-benzyloxy)-phenyl]-butan-1-one 
• 13404-83-6 1-(2-methoxyphenyl)butan-1-one 
• 37631-10-0 o-(4-octyl)phenol 

Relevant academic research and scientific papers

THIOSEMICARBAZONES INHIBITORS OF LYSOPHOSPHATIDIC ACID ACYLTRANSFERASE AND USES THEREOF

Lysophosphatidic acid acyltransferase-beta (LPAAT-β) catalyzes the production of phosphatidic acid (PA) from lysophosphatidic acid (LPA). The lipid cofactor PA contributes to the activation of c-Raf, BRAF, mTOR and PKC-ζ. LPAAT-β expression is a prognostic factor in gynecologic malignancies and is being investigated as a therapeutic target in a variety of tumor types. A class of thiosemicarbazones was identified as inhibitors of LPAAT-β from a screen of a library of small molecules. A focused library of thiosemicarbazones derivatives was prepared and led to the development of compounds which potently inhibit LPAAT-β and inhibit the growth of MiaPaCa2 human pancreatic cancer cells.

The insertion of arynes into the O-H bond of aliphatic carboxylic acids

The insertion of arynes into the O-H bond of aliphatic carboxylic acids promoted by sodium carboxylates is described. The reactions led to the formation of aryl carboxylates in good yields with good chemoselectivities under mild conditions.

Structure-activity relationships of novel salicylaldehyde isonicotinoyl hydrazone (SIH) analogs: Iron chelation, anti-oxidant and cytotoxic properties

Salicylaldehyde isonicotinoyl hydrazone (SIH) is a lipophilic, tridentate iron chelator with marked anti-oxidant and modest cytotoxic activity against neoplastic cells. However, it has poor stability in an aqueous environment due to the rapid hydrolysis of its hydrazone bond. In this study, we synthesized a series of new SIH analogs (based on previously described aromatic ketones with improved hydrolytic stability). Their structure-activity relationships were assessed with respect to their stability in plasma, iron chelation efficacy, redox effects and cytotoxic activity against MCF-7 breast adenocarcinoma cells. Furthermore, studies assessed the cytotoxicity of these chelators and their ability to afford protection against hydrogen peroxide-induced oxidative injury in H9c2 cardiomyoblasts. The ligands with a reduced hydrazone bond, or the presence of bulky alkyl substituents near the hydrazone bond, showed severely limited biological activity. The introduction of a bromine substituent increased ligand-induced cytotoxicity to both cancer cells and H9c2 cardiomyoblasts. A similar effect was observed when the phenolic ring was exchanged with pyridine (i.e., changing the ligating site from O, N, O to N, N, O), which led to pro-oxidative effects. In contrast, compounds with long, flexible alkyl chains adjacent to the hydrazone bond exhibited specific cytotoxic effects against MCF-7 breast adenocarcinoma cells and low toxicity against H9c2 cardiomyoblasts. Hence, this study highlights important structure-activity relationships and provides insight into the further development of aroylhydrazone iron chelators with more potent and selective anti-neoplastic effects.

Lithiation of a silyl ether: Formation of an ortho-fries hydroxyketone

A hydroxy-directed alkylation of an N,N-diethylarylamide using CIPE-assisted α-silyl carbanions (CIPE=complex-induced proximity effect) has been developed using a simple reagent combination of LDA (lithium diisopropylamide) and chlorosilane. A study of the mechanism, and the application of the procedure to an anionic Snieckus-Fries rearrangement for a highly efficient synthesis of the potent phosphatidylinositol 3-kinase (PI3K) inhibitor LY294002, are reported.

Intermolecular C-O addition of carboxylic acids to arynes: Synthesis of o-hydroxyaryl ketones, xanthones, 4-chromanones, and flavones

An efficient and simple route to biologically and pharmaceutically important o-hydroxyaryl ketones, xanthones, 4-chromanones, and flavones has been developed utilizing readily available carboxylic acids and commercially available o-(trimethylsilyl)aryl tr

An improved synthesis of hydroxy aryl ketones by fries rearrangement with methanesulfonic acid/methanesulfonic anhydride

Methanesulfonic acid treated with methanesulfonic anhydride effectively mediates the Fries rearrangement of aryl esters to give hydroxy aryl ketones with high yields. Georg Thieme Verlag Stuttgart · New York.

Intermolecular C-O addition of carboxylic acids to arynes

(Figure Presented) A novel, efficient, and expedient route to biologically and pharmaceutically important o-hydroxyaryl ketones, xanthones, 4-chromanones, and flavones has been developed starting from readily available carboxylic acids and commercially available o-(trimethylsilyl)aryl triflates.

PYRIDAZINONE COMPOUNDS AS CALCILYTICS

Various calcilytic compounds and pharmaceutical compositions containing these compounds are disclosed. Calcilytic compounds are compounds capable of inhibiting calcium receptor activity. Methods for preparing calcilytic compounds, oral bioavailability of calcilytic compounds, and their use as calcium receptor antagonists are also disclosed.

Targeting the gatekeeper residue in phosphoinositide 3-kinases

A single residue in the ATP binding pocket of protein kinases-termed the gatekeeper-has been shown to control sensitivity to a wide range of small molecule inhibitors (Chem. Biol. 2004, 11, 691; Chem. Biol. 1999, 6, 671). Kinases that possess a small side chain at this position (Thr, Ala, or Gly) are readily targeted by structurally diverse classes of inhibitors, whereas kinases that possess a larger residue at this position are broadly resistant. Recently, lipid kinases of the phosphoinositide 3-kinase (PI3-K) family have become the focus of intense research interest as potential drug targets (Chem. Biol. 2003, 10, 207; Curr. Opin. Pharmacol. 2003, 3, 426). In this study, we identify the residue that corresponds structurally to the gatekeeper in PI3-Ks, and explore its importance in controlling enzyme activity and small molecule sensitivity. Isoleucine 848 of p110α was mutated to alanine and glycine, but the mutated kinase was found to have severely impaired enzymatic activity. A structural bioinformatic comparison of this kinase with its yeast orthologs identified second site mutations that rescued the enzymatic activity of the I848A kinase. To probe the dimensions of the gatekeeper pocket, a focused panel of analogs of the PI3-K inhibitor LY294002 was synthesized and its activity against gatekeeper mutated and wild-type p110α was assessed.

β1- and β2-adrenoceptor antagonist activity of a series of para- substituted N-isopropylphenoxypropanolamines

To further explore the structure-activity relationships of β- adrenoceptor (β-AR) antagonists, a series of 25 para-substituted N- isopropylphenoxy-propanolamines were synthesised, nine of which are new compounds. All have been examined for their ability to antagonise β1-ARs in rat atria and β2-ARs in rat trachea. Substitution in the para-position of the phenyl ring is thought to confer β3-specificity and the selectivity of these compounds for the β1-AR ranges from 1.5-234. None of the compounds tested were selective for the β2-AR. Of the 25 compounds studied, 22 had reasonable (pA2 > 7) potencies for the rat β1-AR. Only compound 1 displayed reasonable (pA2 > 7) potency for the rat β2-AR. Twenty two compounds were used as the training set for comparative molecular field analysis (CoMFA) of antagonist potency (pA2) at the rat β1- and β2-ARs. The inclusion of a number of additional physical characteristics improved the QSAR analysis over models derived solely using the CoMFA electrostatic and steric fields. The final models predicted the β1- and β2-AR potency of the compounds in the training set with high accuracy (r2 = 0.93 and 0.86 respectively). The final β1-AR model predicted the β1-potencies of two out of the three test compounds, not included in the training set, with residual PA2 values 2-AR model (residual pA2 values -0.38).