83816-53-9

Usage

Uses

Used in Dye Production:
2-Hydroxy-3-propyl-benzaldehyde is used as a chemical intermediate for the synthesis of dyes, due to its ability to undergo various chemical reactions that can lead to the formation of colored compounds.
Used in Perfumery:
In the fragrance industry, 2-Hydroxy-3-propyl-benzaldehyde is used as a scent ingredient, leveraging its aromatic properties to contribute to the creation of unique and complex fragrances.
Used in Pharmaceutical Industry:
2-Hydroxy-3-propyl-benzaldehyde is used as a building block in the synthesis of pharmaceutical compounds, owing to its potential to be incorporated into the molecular structures of various drugs, enhancing their therapeutic properties.

InChI:InChI=1/C10H12O2/c1-2-4-8-5-3-6-9(7-11)10(8)12/h3,5-7,12H,2,4H2,1H3

Upstream product

• 50-00-0 formaldehyd 
• 644-35-9 5-propylphenol 
• 24019-66-7 3-allylsalicylaldehyde 
• 90-02-8 salicylaldehyde 
• 28752-82-1 2-(allyloxy)benzaldehyde 

Downstream Products

• 148674-49-1 3-propyl-2-<(trifluoromethyl)sulfonoxy>benzaldehyde 
• 83816-56-2 2-Hydroxy-5-iodo-3-propyl-benzaldehyde 
• 1554475-84-1 N′-[(2-hydroxy-3-propylphenyl )methylene]-4-[4-(trifluoromethyl)benzoyl]-1-piperazineacetohydrazide 
• 1554475-82-9 N′-[(2-hydroxy-3-propylphenyl)methylene]-4-[[4-(trifluoromethyl)phenyl]methyl]-1-piperazineacetohydrazide 
• 1554475-80-7 N′-[(2-hydroxy-3-propylphenyl)methylene]-4-(4-fluorobenzoyl)-1-piperazineacetohydrazide 
• 1554475-77-2 N′-[(2-hydroxy-3-propylphenyl )methylene]-4-[(4-fluorophenyl)methyl]-1-piperazineacetohydrazide 
• 1554475-75-0 N′-[(2-hydroxy-3-propylphenyl)methylene]-4-(4-cyanobenzoyl)-1-piperazineacetohydrazide 
• 1554475-72-7 N′-[(2-hydroxy-3-propylphenyl )methylene]-4-[(4-cyanophenyl)methyl]-1-piperazineacetohydrazide 
• 1554475-70-5 N′-[(2-hydroxy-3-propylphenyl)methylene]-4-benzoyl-1-piperazineacetohydrazide 
• 1554475-68-1 4-{[4-[[[N′-[(2-hydroxy-3-propylphenyl)methylene]-hydrazine]carbonyl]methyl ]-1-piperazinyl]methyl}-benzenesulfonamide 
• 383676-27-5 2-hydroxy-5-nitro-3-propylbenzaldehyde 
• 83816-63-1 2-[(3-Dimethylamino-propylamino)-methyl]-4-iodo-6-propyl-phenol 
• 148674-62-8 Trifluoro-methanesulfonic acid 2-[(Z)-cyclohexyliminomethyl]-6-propyl-phenyl ester 

Relevant academic research and scientific papers

Cobalt-Nitrenoid Insertion-Mediated Amidative Carbon Rearrangement via Alkyl-Walking on Arenes

We herein disclose the Cp*Co(III)(LX)-catalyzed amidative alkyl migration using 2,6-disubstituted phenyl azidoformates. Upon the cobalt-nitrenoid insertion toward the substituted ortho carbon, an arenium cationic species bearing a quaternary carbon is generated, and a subsequent alkyl migration process is suggested to occur through an unforeseen alkyl-walking mechanism. A quinolinol ligand of the cobalt catalyst system is proposed to facilitate the final product-releasing rearomatization process by serving as an internal base. This new mechanistic mode enabled both [1,2]- and [1,4]-alkyl rearrangements to allow the structural variation of N-heterocyclic compounds.

Removal of metabolic liabilities enables development of derivatives of procaspase-activating compound 1 (PAC-1) with improved pharmacokinetics

Procaspase-activating compound 1 (PAC-1) is an o-hydroxy-N-acylhydrazone that induces apoptosis in cancer cells by chelation of labile inhibitory zinc from procaspase-3. PAC-1 has been assessed in a wide variety of cell culture experiments and in vivo models of cancer, with promising results, and a phase 1 clinical trial in cancer patients has been initiated (NCT02355535). For certain applications, however, the in vivo half-life of PAC-1 could be limiting. Thus, with the goal of developing a compound with enhanced metabolic stability, a series of PAC-1 analogues were designed containing modifications that systematically block sites of metabolic vulnerability. Evaluation of the library of compounds identified four potentially superior candidates with comparable anticancer activity in cell culture, enhanced metabolic stability in liver microsomes, and improved tolerability in mice. In head-to-head experiments with PAC-1, pharmacokinetic evaluation in mice demonstrated extended elimination half-lives and greater area under the curve values for each of the four compounds, suggesting them as promising candidates for further development.

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.

ENZYME-ACTIVATING COMPOUNDS AND COMPOSITIONS

The invention provides compounds and compositions useful for the modulation of certain enzymes. The compounds and compositions can induce of cell death, particularly cancer cell death. The invention also provides methods for the synthesis and use of the c

Non-metallocene compounds, method for the production thereof and use of the same for the polymerisation of olefins

The invention relates to a method for producing special transition metal compounds, to novel transition metal compounds and to the use of the same for the polymerisation of olefins.

Benzoxazepinones and their use as squalene synthase inhibitors

There is disclosed a compound represented by the formula [I]: wherein R1 is optionally substituted 1-carboxyethyl group, optionally substituted alkyl-sulfonyl group, optionally substituted (carboxy-cycloalkyl)-alkyl group, -X1-X2-Ar-X3-X4-COOH (wherein X1 and X4 are a bond or alkylene group, X2 and X3 are a bond, -O-, -S-, Ar is divalent aromatic group etc.), R2 is alkyl group optionally substituted with alkanoyloxy group and/or hydroxy group, R3 is alkyl group, and W is halogen atom, etc., or a salt thereof. The compound has the cholesterol lowering activity and the triglyceride lowering activity and is useful for preventing and/or treating hyperlipidemia.

Potent Nonpeptide Angiotensin II Receptor Antagonists. 2. (1-Carboxybenzyl)imidazole-5-acrylic Acids

The further evolution of the imidazole-5-acrylic acid series of nonpeptide angiotensin II receptor antagonists is detailed (for Part 1, see: J.Med.Chem. 1992, 35, 3858).Modifications of the N-benzyl ring substitution were undertaken in an effort to mimic the Tyr4 residue of angiotensin II.Introduction of a p-carboxylic acid on the N-benzyl ring resulted in the discovery of compounds with nanomolar affinity for the receptor and good oral activity.SAR studies of these potent antagonists revealed that the thienyl ring, the (E)-acrylic acid, and the imidazole ring in addition to the two acid groups were important for high potency.Also, overlay comparisons of the parent diacid with both angiotensin II and a representative biphenylyltetrazole nonpeptide angiotensin II receptor antagonist are presented.The parent diacid analog, SKF 108566 or (E)-3--2-propenoic acid, is currently in clinical development for the treatment of hypertension.

Radioiodine-Labeled N,N-Dimethyl-N'-(2-hydroxy-3-alkyl-5-iodobenzyl)-1,3-propanediamines for Brain Perfusion Imaging

In developing new brain-imaging agents for single photon emission computed tomography (SPECT), we synthesized five radioiodinated N,N-dimethyl-N'-(2-hydroxy-3-alkyl-5-iodobenzyl)-1,3-propanediamines (12-16).The appropriate o-alkylphenol was formylated via a tin(IV) chloride catalyzed reaction.Iodination with iodine monochloride gave the required 3-alkyl-5-iodosalicylaldehyde, which was reductively aminated with 3-(dimethylamino)propylamine and sodium borohydride.The radioactive labeling (>95percent yield) can be achieved by a rapid aqueous exchange reaction in a serum vial at 100 deg C.Biodistribution in rats exhibited high initial brain uptake (0.9 to 1.8percent dose in brain at 2 min), and the brain activity remained about the same at 1 h for all the compounds.The best brain-imaging agent was N,N-dimethyl-N'-(2-hydroxy-3-methyl-5-iodobenzyl)-1,3-propanediamine (12), which showed the highest uptake of 1.80 and 2.02percent dose in brain at 2 min and 1 h, respectively.The brain uptake increases when the specific activity of 125I-labeled 12 decreases.An imaging study of 12 in a monkey showed high initial brain uptake as well as high uptake in lungs and liver.The brain uptake persists for at least 1 h.Autoradiography of rat brain sections showed a regional distribution that reflects the cerebral perfusion pattern (high activity in gray matter and low activity in white matter).It is apparent that 12 is readily prepared and is potentially useful for brain perfusion imaging in conjunction with SPECT devices.