204130-60-9

Usage

Uses

Used in Organic Synthesis:
2-(benzyloxy)-5-nitrobenzaldehyde is used as a versatile intermediate in organic synthesis for the production of a wide range of chemical compounds. Its functional groups facilitate various chemical reactions, making it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(benzyloxy)-5-nitrobenzaldehyde is used as a key intermediate for the synthesis of potential drug candidates. Its unique chemical structure allows for the development of new therapeutic agents with specific pharmacological properties.
Used in Perfumery and Flavorings:
2-(benzyloxy)-5-nitrobenzaldehyde is used as a flavoring agent in the food and beverage industry, capitalizing on its pleasant vanilla-like aroma. It enhances the flavor profile of various products, providing a rich and desirable taste.
Used in the Production of Fine Fragrances and Essential Oils:
2-(benzyloxy)-5-nitrobenzaldehyde is also utilized in the perfumery industry for the production of fine fragrances and essential oils. Its aromatic properties make it an ideal ingredient for creating unique and complex scents in perfumes and other fragranced products.

Upstream product

• 100-39-0 benzyl bromide 
• 97-51-8 5-Nitrosalicylaldehyde 
• 100-02-7 4-nitro-phenol 

Downstream Products

• 1101179-83-2 methyl 3-(2-benzyloxy-5-nitro)phenyl-3-hydoxy-2-methylenepropanoate 
• 168702-54-3 (2-(benzyloxy)-5-nitrophenyl)methanol 
• 1608150-42-0 C₃₅H₃₆BF₂N₅O₃ 
• 1608150-43-1 C₃₁H₂₈BF₂N₅O₃ 
• 134577-69-8 t-Butyl 3-(2-hydroxy-5-aminophenyl)propionate 

Relevant academic research and scientific papers

Synthesis, evaluation, and biological applications of visible-light-controllable nitric oxide releasers

Nitric oxide (NO) is biologically synthesized in human body and mediates various signal pathway. Because NO is too unstable to handle for biological assay, NO releasers had been developed for NO research. Among them, light-controllable NO releasers are quite useful tool because their NO release can be spatiotemporally controlled by light irradiation. This article shows how to synthesize visible-light controllable NO releasers based on N-nitrosoaminophenol structure, evaluate NO releasing efficiency in various methods, and apply them for biological experiments.

Design, synthesis, biological evaluation, and molecular modeling studies of rhodanine derivatives as pancreatic lipase inhibitors

A series of rhodanine-3-acetic acid derivatives were synthesized via Knoevenagel condensation of rhodanine-3-acetic acid with various substituted aromatic aldehydes. The synthesized derivatives were screened in vitro for understanding the inhibitory potential towards pancreatic lipase (PL), a key enzyme responsible for the digestion of dietary fats. Derivative 8f exhibited a potential inhibitory activity towards PL (IC50=5.16 μM), comparable to that of the standard drug, orlistat (0.99 μM). An increase in the density of the aromatic ring resulted in potential PL inhibition. The enzyme kinetics of 8f exhibited a reversible competitive-type inhibition, similar to that of orlistat. Derivative 8f exhibited a MolDock score of -125.19 kcal/mol in docking studies, and the results were in accordance with their PL inhibitory potential. Furthermore, the reactive carbonyl group of 8f existed at a distance adjacent to Ser152 (≈3 ?) similar to that of orlistat. Molecular dynamics simulation (10 ns) of the 8f-PL complex revealed a stable binding conformation of 8f in the active site of PL (maximum root mean square displacement of ≈2.25 ?). The present study identified novel rhodanine-3-acetic acid derivatives with promising PL inhibitory potential, and further lead optimization might result in potent PL inhibitors.

Synthesis and bioevaluation of 2-phenyl-5-methyl-2H-1,2,3-triazole-4-carboxylic acid/carbohydrazide derivatives as potent xanthine oxidase inhibitors

A series of 2-phenyl-5-methyl-2H-1,2,3-triazole-4-carboxylic acids/carbohydrazides as analogues of febuxostat were synthesized and evaluated for their in vitro xanthine oxidase (XO) inhibitory activity. Among these compounds, the carboxylic acid derivatives 7a-h and 8a-h exhibited high potency in the submicromolar/nanomolar range. Steady-state kinetics experiment revealed that 7f was a mixed-type inhibitor of xanthine oxidase. In addition, a molecular docking study of 7f was performed to determine its binding mode at the active site of xanthine oxidase.

N-NITROSOANILINE DERIVATIVE, NO GENERATOR USING THE SAME, AND GENERATION METHOD OF NO

PROBLEM TO BE SOLVED: To provide an N-nitrosoaniline derivative not containing a poisonous metal, capable of discharging nitrogen monoxide (NO) by irradiation of visible light, and to provide an NO generator using the same, and a generation method of NO. SOLUTION: An N-nitrosoaniline derivative has a pyrromethene boron complex structure shown by following formula 1 synthesized by combining together, for example, 2-(5-amino-2-hydroxyphenyl)-propionate ester, 2,4-dimethyl-3-cyanopyrrole and 4-formylbenzoic acid. COPYRIGHT: (C)2015,JPO&INPIT

Photomanipulation of vasodilation with a blue-light-controllable nitric oxide releaser

Spatiotemporally controllable nitric oxide (NO)-releasers allow us to analyze the physiological effects of NO, a gaseous mediator that modulates many biological signaling networks, and are also candidate chemotherapeutic agents. We designed and synthesized a blue-light-controllable NO releaser, named NOBL-1, which bears an N-nitrosoaminophenol moiety for NO release tethered to a BODIPY dye moiety for harvesting blue light. Photoinduced electron transfer from N-nitrosoaniline to the antenna moiety upon irradiation with relatively noncytotoxic blue light (470-500 nm) should result in NO release with formation of a stable quinone moiety. NO release from NOBL-1 was confirmed by ESR spin trapping and fluorescence detection. Spatially controlled NO release in cells was observed with DAR-4M AM, a fluorogenic NO probe. We also demonstrated temporally controlled vasodilation of rat aorta ex vivo by blue-light-induced NO release from NOBL-1. This compound should be useful for precise examination of the functions of NO with excellent spatiotemporal control.

A novel series of 6-substituted 3-(pyrrolidin-1-ylmethyl)chromen-2-ones as selective monoamine oxidase (MAO) A inhibitors

A series of 6-substituted 3-(pyrrolidin-1-ylmethyl)chromen-2-ones (coumarins) have been synthesized and their inhibitory activity to human monoamine oxidase A (MAO A) and B (MAO B) determined. Incorporation of a basic amino function in the C3 position together with substitution at the C6 position produced novel coumarin compounds with selectivity for the MAO A subtype. Substitution in the C6 position with small hydrophilic groups such as hydroxy (19, IC50 = 1.46 μM) or amino (18, IC50 = 3.77 μM) gave the most potent and selective compounds for MAO A. These compounds also showed excellent aqueous solubility properties. Compound 18 [6-amino-3- (pyrrolidin-1-ylmethyl)chromen-2-one] administrated in vivo induced in rat brain a neurotransmitter metabolite profile typical of MAO A inhibition: decreased 3,4-dihydroxyphenylacetic acid (DOPAC) and 5-hydroxyindoleacetic acid (5-HIAA) but increased 3-methoxytyramine (3-MT) levels.

Synthesis and biological evaluation of thiazolidine-2,4-dione and 2,4-thione derivatives as inhibitors of translation initiation

A series of 2′-benzyloxy-5′-substituted-5-benzylidene- thiazolidine-2,4-thione and -dione derivatives was synthesized and evaluated as inhibitors of translation initiation. In an effort to generate novel translation initiation inhibitors for cancer therapy, a series of 2′-benzyloxy- 5′-substituted-5-benzylidene-thiazolidine-2,4-thione and dione derivatives was synthesized and evaluated for activity in translation initiation specific assays. Several candidates of the 5-benzylidene-thiazolidine-2,4-diones (3c, 3d, and 3f) and -thiones (2b, 2e, and 2j), inhibit cell growth with low μM GI50 mediated by inhibition of translation initiation, which involves partial depletion of intracellular Ca2+ stores and strong phosphorylation of eIF2Iα.

Nitroarylhydroxymethylphosphonic acids as inhibitors of CD45

A series of nitroarylhydroxymethylphosphonic acids was synthesized and evaluated as inhibitors of CD45. It was discovered that both the alpha hydroxy and nitro groups are essential for activity. Potency is enhanced by the addition of a large lipophilic group on the aryl ring adjacent to the phosphonic acid moiety. Kinetics studies have shown that these compounds are competitive inhibitors and thus bind at the active site of this enzyme.