82575-52-8

Usage

InChI:InChI=1/C9H7NO/c10-7-1-2-8-3-5-9(11)6-4-8/h1-6,11H/b2-1+

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 372-09-8 cyanoacetic acid 
• 540-38-5 p-Iodophenol 
• 107-13-1 acrylonitrile 
• 14482-11-2 (E)-p-methoxycinnamonitrile 
• 590-17-0 cyanomethyl bromide 
• 71-43-2 benzene 
• 4360-47-8 cinnamonitrile 
• 122520-77-8 (E)-2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 

Downstream Products

• 59576-98-6 (E)-p-coumaric amide 
• 1207604-15-6 3-(4-(2-(1,7'-dimethyl-2'-propyl-1H,3H'-2,5'-bibenzo[d]imidazol-3'-yl)ethoxy)phenyl)acrylonitrile 
• 1314759-67-5 C₁₉H₂₀O₂ 
• 1314759-68-6 C₂₀H₂₂O₂ 
• 1314839-77-4 C₂₂H₂₇NO₃ 
• 1314839-78-5 C₂₃H₂₉NO₃ 
• 1314759-76-6 C₂₂H₂₇NO₃*ClH 
• 1314759-78-8 C₂₃H₂₉NO₃*ClH 
• 20711-53-9 p-hydroxy-cinnamaldehyde 
• 1176235-31-6 C₁₂H₁₁NO₃S 
• 17362-17-3 3-(p-hydroxyphenyl)propiononitrile 
• 107223-57-4 1-<2-hydroxy-3-propyl-4-<<4-<2-(1H-tetrazol-5-yl)ethenyl>phenoxy>methyl>phenyl>ethanone 
• 58187-52-3 N-(3-(4-hydroxyphenyl)propyl)acetamide 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of 8-(2-amino-1-hydroxyethyl)-6-hydroxy-1,4-benzoxazine-3(4H)-one derivatives as potent β2-adrenoceptor agonists

A series of β2-adrenoceptor agonists with an 8-(2-amino-1-hydroxyethyl)-6-hydroxy-1,4-benzoxazine-3(4H)-one moiety is presented. The stimulatory effects of the compounds on human β2-adrenoceptor and β1-adrenoceptor were characterized by a cell-based assay. Their smooth muscle relaxant activities were tested on isolated guinea pig trachea. Most of the compounds were found to be potent and selective agonists of the β2-adrenoceptor. One of the compounds, (R)-18c, possessed a strong β2-adrenoceptor agonistic effect with an EC50 value of 24 pM. It produced a full and potent airway smooth muscle relaxant effect same as olodaterol. Its onset of action was 3.5 min and its duration of action was more than 12 h in an in vitro guinea pig trachea model of bronchodilation. These results suggest that (R)-18c is a potential candidate for long-acting β2-AR agonists.

METHOD FOR THE SYNTHESIS AND PRODUCTION OF ALKENYL COMPOUND

PROBLEM TO BE SOLVED: To provide a method for producing an efficient alkenyl compound conveniently and inexpensively. SOLUTION: A first compound represented by formula (1) reacts with a second compound represented by formula (3), in the presence of amino acid, in solvent containing amine, in a range of 50-200°C, to produce an alkenyl compound represented by formula (A) [where R1 is hydrogen or an optionally substituted C1-C30 alkyl group, R2 is a carboxyl group or the like, R3 and R4 are hydrogen, an optionally substituted C1-C30 alkyl group or the like]. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Development of simple firefly luciferin analogs emitting blue, green, red, and near-infrared biological window light

Simple firefly luciferin analogs emitting blue, green, and red light were developed. The longest emission maximum was observed at 675 nm, which belongs to the NIR biological window (650-900 nm), useful for deep site bioimaging of living animals. The analogs showed a slow rise of emission intensity compared with the rapid emission of natural luciferin. The light emission of the adenylated analogs was strongly enhanced compared with those of analogs themselves.

Small molecule perimeter defense in entomopathogenic bacteria

Two Gram-negative insect pathogens, Xenorhabdus nematophila and Photorhabdus luminescens, produce rhabduscin, an amidoglycosyl- and vinyl-isonitrile-functionalized tyrosine derivative. Heterologous expression of the rhabduscin pathway in Escherichia coli, precursor-directed biosynthesis of rhabduscin analogs, biochemical assays, and visualization using both stimulated Raman scattering and confocal fluorescence microscopy established rhabduscin's role as a potent nanomolar-level inhibitor of phenoloxidase, a key component of the insect's innate immune system, as well as rhabduscin's localization at the bacterial cell surface. Stimulated Raman scattering microscopy visualized rhabduscin at the periphery of wild-type X. nematophila cells and E. coli cells heterologously expressing the rhabduscin pathway. Precursor-directed biosynthesis created rhabduscin mimics in X. nematophila pathway mutants that could be accessed at the bacterial cell surface by an extracellular bioorthogonal probe, as judged by confocal fluorescence microscopy. Biochemical assays using both wild-type and mutant X. nematophila cells showed that rhabduscin was necessary and sufficient for potent inhibition (low nM) of phenoloxidases, the enzymes responsible for producing melanin (the hard black polymer insects generate to seal off microbial pathogens). These observations suggest a model in which rhabduscin's physical association at the bacterial cell surface provides a highly effective inhibitor concentration directly at the site of phenoloxidase contact. This class of molecules is not limited to insect pathogens, as the human pathogen Vibrio cholerae also encodes rhabduscin's aglycone, and bacterial cell-coated immunosuppressants could be a general strategy to combat host defenses.

Discovery of S1P agonists with a dihydronaphthalene scaffold

Structure-activity relationship of sphingosine-1-phosphate receptor agonists was examined. Cinnamyl derivative 1 was modified to improve S1P 1 agonistic activity as well as selectivity over S1P3 agonistic activity. Dihydronaphthalene derivative 10d was identified as a potent S1P1 receptor agonist with high selectivity against S1P3 and enhanced efficacy in lowering peripheral lymphocyte counts in mice.

Design, synthesis, and docking studies of novel benzimidazoles for the treatment of metabolic syndrome

In addition to lowering blood pressure, telmisartan, an angiotensin (AT1) receptor blocker, has recently been shown to exert pleiotropic effects as a partial agonist of nuclear peroxisome proliferator-activated receptor γ (PPARγ). On the basis of these findings and docking pose similarity between telmisartan and rosiglitazone in PPARγ active site, two classes of benzimidazole derivatives were designed and synthesized as dual PPARγ agonist/angiotensin II antagonists for the possible treatment of metabolic syndrome. Compound 4, a bisbenzimidazole derivative showed the best affinity for the AT1 receptor with a Ki=13.4 nM, but it was devoid of PPARγ activity. On the other hand 9, a monobenzimidazole derivative, showed the highest activity in PPARγ transactivation assay (69% activation) with no affinity for the AT1 receptor. Docking studies lead to the designing of a molecule with dual activity, 10, with moderate PPARγ activity (29%) and affinity for the AT1 receptor (Ki=2.5 μM).

One-pot Wittig reactions in aqueous media: A rapid and environmentally benign synthesis of α,β-unsaturated carboxylic esters and nitriles

One-pot Wittig reactions of ethyl bromoacetate and bromoacetonitrile with aldehydes in the presence of PPh3 and LiOH in water were investigated. Most of the olefination reactions completed within 5-120 min in refluxing water containing 1.2 M LiCl to afford the olefin products in 71-97% yields with 100:0-55:45 ratios of E:Z isomers. Copyright Taylor & Francis Group, LLC.

Cosmetic composition

A composition suitable for topical application to mammalian skin and hair for inducing, maintaining or increasing hair growth comprises a hair growth promoter chosen from glutamine derivatives and salts thereof. The composition preferably also comprises an activity enhancer which may be chosen from hair growth stimulants, penetration enhancers and cationic polymers.

Cosmetic composition containing DOPA derivatives

A composition for topical application to human hair or skin contains a chemical analogue of dihydroxyphenyl alanine (DOPA). This chemical analogue can be absorbed by skin or by a hair follicle and metabolised in-vivo, thus leading to the formation of melanin in skin or to the growth of melanin-pigmented hair. Consequently the composition can give controlled skin darkening to mimic sun-induced tanning or can bring about the growth of dar hair in place of the grey or white hair.

Cosmestic composition

A composition suitable for topical application to mammalian skin and hair for inducing, maintaining or increasing hair growth comprises a hair growth promoter chosen from glutamic acid derivatives and salts thereof. The composition preferably also comprises an activity enhancer which may be chosen from hair growth stimulants, penetration enhancers and cationic polymers.