91012-97-4

Upstream product

• 118-55-8 phenyl Salicylate 
• 156-87-6 propan-1-ol-3-amine 
• 61141-14-8 anionic phenyl salicylate 
• 118-61-6 2-hydroxy-benzoic acid ethyl ester 
• 119-36-8 methyl salicylate 

Downstream Products

• 90922-09-1 2-(2′-hydroxyphenyl)-5,6-dihydro-1,3-oxazine 

Relevant academic research and scientific papers

Novel derivatives of salicylanilide: Synthesis, characterization, PPO inhibitory activity and cytotoxicity

Two series of novel salicylanilide analogues (4a-4 g) and (4h-4t) were designed, synthesized, and characterized, especially the structure of compound 4q was further confirmed by single X-ray diffraction. The inhibitory activity on polyphenoloxidase (PPO)

Fast synthesis of amides from ethyl salicylate under microwave radiation in a solvent-free system

In this study, amide bond formation, one of the most important reactions in organic chemistry, it was evaluated using ethyl salicylate and ten different primary amines. Under the optimized experimental conditions, i.e. 60 °C, hexane, phenylboronic acid-PBA (15 mol%), boric acid-BA (15 mol%) or without catalyst-WC, using a hot-plate for 24 h, amides were obtained in excellent isolated yields (WC, 77-94% to S-Aa-Ad; PBA, 11-94% to S-Ae-Aj; and BA, 28-90% to S-Ae-Aj). The reaction employing CAL-B also permitted a moderate conversion for the production of amides S-Ae-Aj (3-42%). However, in our efforts to reduce the amide synthesis time (24 h), the reactions were performed in the presence of microwave-MW radiation using a free-solvent system [60 °C, PBA (15 mol%) or WC], which reduced the time of the reaction by 32-fold (45 min) and afforded nine amides (S-Aa-Ah and S-Aj) in 80-99% isolated yield and S-Ai in 23% yield. A cytotoxicity assay demonstrated that the amide S-Ag was capable of inhibiting four human tumor cell lines (MCF-7, HCT116, HepG2, and HL-60) with an IC50 ranging from 8.68 to 17.57 μg mL-1. In this study, MW radiation provided an attractive way for faster reactions, improved yields, and cleaner reactions, as well as the synthesis of amide S-Ag with cytotoxic activity.

Palladium and copper complexes with oxygen-nitrogen mixed donors as efficient catalysts for the Heck reaction

A simple bidentate ligand, 2-(2′-hydroxyphenyl)-5,6-dihydro-1,3- oxazine, was readily prepared with a two-step synthesis. Two novel complexes of Pd(II) and Cu(II) with this (N,O) oxazine ligand have been prepared and the molecular structures of these complexes have been confirmed by X-ray structure analysis, NMR, IR and UV-Vis spectroscopy. These complexes efficiently catalyze the Heck reaction of aryl halides with olefins at 120 °C in 8 h. The reaction conditions for the Heck coupling of iodobenzene with styrene was optimized by varying the amount of the catalyst, reaction temperature, solvent and exogenous base.

Effects of mixed CH3CN - H2O solvents on rate of intramolecular general base-catalyzed cleavage of ionized phenyl salicylate in the presence of 3-aminopropan-1 -ol, 1,2-diaminoethane, and glycine

The effects of mixed CH3CN - H2O solvents on rates of aminolysis of ionized phenyl salicylate, PS-, reveal a nonlinear decrease in the nucleophilic second-order rate constants, knms. (for aminolysis) with increase in the content of CH3CN until it becomes ≈ 50%. v/v. The values of knms remain almost unchanged with change in the CH3CN content within 50 to 70 or 80%, v/v. The effects of mixed CH3CN - H2O solvents on pKa of leaving group, phenol, and protonated amine nucleophile have been concluded to be the major source for the ob- served mixed solvent effects on knms.

New Antianginal Nitro Esters with Reduced Hypotensive Activity. Synthesis and Pharmacological Evaluation of 3--2H-1,3-benzoxazin-4(3H)-ones

New nitro ester 3--2H-1,3-benzoxazin-4(3H)-ones show marked inhibitory activity against ischemia-induced electrocardiographic changes, with only limited systemic hemodynamic effects, and are reported in the present study.These new nitro vasodilators are potent inhibitors of the electrocardiographic T-wave and S-T segment elevation induced by intravenous or intracoronary administration of Arg-vasopressin or methacholine in the anesthetized rat.The most active compounds are up to 300- and 600- fold more potent than glyceryl trinitrate or Nicorandil, respectively.These nitro esters relax in a concentration-dependent manner the isolated rabbit aorta, at higher concentrations (2 - 40-fold) than glyceryl trinitrate, and reduce the mean arterial blood pressure at doses 7 - 300-fold higher than those required by glyceryl trinitrate to exert a similar hypotensive effect.Remarkably, these compounds retain their anti-ischemic and hemodynamic profile after oral (po) administration.These new nitro ester derivatives, endowed with a marked antianginal activity, which is not associated with concurrent and pronounced falls in systemic blood pressure, represent the leads of a new class of selective nitrovasodilators having a preferential action on large coronary vessels, which could be clinically relevant in the treatment of coronary artery diseases.

Solvent effect on intramolecular general base-catalysed aminolysis of ionized phenyl salicylate

The nucleophilic second-order rate constants (k1) for the reactions of ionized phenyl salicylate (PS-) with primary and secondary amines in 70percent (v/v) ethanol-water reveal Bronsted plots of slopes βnuc1 = 0.32 +/- 0.10 and βnuc2 = 0.22 +/- 0.02, respectively.Different Bronsted slopes obtained for the reactions of PS- with primary and secondary amines suggest the occurrence of different locations of the transition state in the critical rate-determining step.The change in water content from 99.2 to 70percent (v/v) in EtOH-H2O causes reduction in k1 by ca. 3-fold for all the amines studied.Ionization constants of all the protonated amines turn out to be larger in 70percent (v/v) EtOH-H2O than in pure water.

Intramolecular General Base Catalysis and the Rate-determining Step in the Nucleophilic Cleavage of Ionized Phenyl Salicylate with Primary and Secondary Amines

The nucleophilic second-order rate constants for the reactions of ionized phenyl salicylate (PS-) with primary and secondary amines have revealed Broensted plots of slopes βnuc1 = 0.52+/-0.06 and βnuc2 = 0.27+/-0.05, respectively.The suggested stepwise reaction mechanism involves the intramolecular proton transfer from cationic nitrogen to the anionic phenolic oxygen to form the monoanionic tetrahedral addition intermediate as the rate-determining step.The low value of βnuc2 is attributed to the extensive of proton transfer in the late transition state while the large value of βnuc1 is ascribed to the proton transfer in the early transition state of the rate-determining step.However, these low and high values of βnuc2 and βnuc1, respectively, are also compatible with the occurence of respective early and late transition states in the rate-determining step involving concerted intramolecular general base-catalysed nucleophilic attack at the carbonyl carbon of PS-.Significantly large positive deviations from Broensted plots have been observed for the reactivities of α-nucleophiles toward PS-.Monoprotonated ethane-1,2-diamine is ca. 20-fold more reactive than would be expected from its basicity, and this is attributed to the occurence of the intramolecular general acid catalysis.The reactions of PS- with hydroxylamine and N-methylhydroxylamine involve ca. >/=70 percent aminolysis and -.