288580-52-9

Usage

Uses

Used in Pharmaceutical Synthesis:
Ethyl 2-(3-hydroxy-4-nitrophenyl)acetate is used as a starting material for the synthesis of pharmaceuticals due to its unique structural properties. Its phenolic hydroxyl and nitro groups can be utilized in various chemical reactions to produce a range of pharmaceutical compounds.
Used in Agrochemical Synthesis:
Ethyl 2-(3-hydroxy-4-nitrophenyl)acetate is also used as a starting material in the synthesis of agrochemicals. Its reactivity and structural properties make it suitable for the development of new agrochemical compounds.
Used in Organic Chemistry:
Ethyl 2-(3-hydroxy-4-nitrophenyl)acetate is used as a versatile building block in organic chemistry. Its aromatic nature and potential reactivity allow it to be employed in a wide range of chemical reactions, contributing to the synthesis of various organic compounds.

Upstream product

• 152148-79-3 (3-hydroxy-4-nitro-phenyl)-acetic acid 
• 22446-38-4 ethyl 3-hydroxyphenylacetate 
• 621-37-4 m-hydroxyphenylacetic acid 

Downstream Products

• 1258845-94-1 (3-methoxy-4-nitrophenyl)acetic acid ethyl ester 
• 1402585-26-5 ethyl 2-(3-methoxy-4-nitrophenyl)propanoate 

Relevant academic research and scientific papers

Discovery of 2-(3,5-difluoro-4-methylsulfonaminophenyl)propanamides as potent TRPV1 antagonists

A series of A-region analogues of 2-(3-fluoro-4-methylsufonamidophenyl) propanamide 1 were investigated as TRPV1 antagonists. The analysis of structure-activity relationship indicated that a fluoro group at the 3- (or/and) 5-position and a methylsulfonamido group at the 4-position were optimal for antagonism of TRPV1 activation by capsaicin. The most potent antagonist 6 not only exhibited potent antagonism of activation of hTRPV1 by capsaicin, low pH and elevated temperature but also displayed highly potent antagonism of activation of rTRPV1 by capsaicin. Further studies demonstrated that antagonist 6 blocked the hypothermic effect of capsaicin in vivo, consistent with its in vitro mechanism, and it showed promising analgesic activity in the formalin animal model.

Receptor activity and conformational analysis of 5′-halogenated resiniferatoxin analogs as TRPV1 ligands

A series of 5′-halogenated resiniferatoxin analogs have been investigated in order to examine the effect of halogenation in the A-region on their binding and the functional pattern of agonism/antagonism for rat TRPV1 heterologously expressed in Chinese hamster ovary cells. Halogenation at the 5-position in the A-region of RTX and of 4-amino RTX shifted the agonism of parent compounds toward antagonism. The extent of antagonism was greater as the size of the halogen increased (I > Br > Cl > F) while the binding affinities were similar, as previously observed for our potent agonists. In this series, 5-bromo-4-amino RTX (39) showed very potent antagonism with K i (ant) = 2.81 nM, which was thus 4.5-fold more potent than 5′-iodo RTX, previously reported as a potent TRPV1 antagonist. Molecular modeling analyses with selected agonists and the corresponding halogenated antagonists revealed a striking conformational difference. The 3-methoxy of the A-region in the agonists remained free to interact with the receptor whereas in the case of the antagonists, the compounds assumed a bent conformation, permitting the 3-methoxy to instead form an internal hydrogen bond with the C4-hydroxyl of the diterpene.

Halogenation of 4-hydroxy/amino-3-methoxyphenyl acetamide TRPV1 agonists showed enhanced antagonism to capsaicin

As an extension of our analysis of the effect of halogenation on thiourea TRPV1 agonists, we have now modified selected 4-hydroxy(or 4-amino)-3- methoxyphenyl acetamide TRPV1 agonists by 5- or 6-halogenation on the aromatic A-region and evaluated them for potency for TRPV1 binding and regulation and for their pattern of agonism/antagonism (efficacy). Halogenation shifted the functional activity at TRPV1 toward antagonism with a greater extent of antagonism as the size of the halogen increased (I > Br > Cl), as previously observed for the thiourea series. The extent of antagonism was greater for halogenation at the 5-position than at the 6-position, in contrast to SAR for the thiourea series. In this series, compounds 55 and 75 showed the most potent antagonism, with Ki (ant) = 2.77 and 2.19 nM, respectively, on rTRPV1 expressed in Chinese hamster ovary cells. The compounds were thus ca. 40-60-fold more potent than 6′-iodononivamide.

Indane derivatives

The invention is directed to physiologically active compounds of general formula (I): wherein: R1 represents aryl, heteroaryl or a group R3-L2-Ar1-L3-; R2 represents hydrogen or lower alkyl

Substituted bicyclic heteroaryl compounds and their use as integrin antagonists

The invention is directed to physiologically active compounds of general formula (I): R1Z1—Het—L1—Ar1—L2—Y??(I) wherein Het is an optionally substituted, saturated, partially saturated or fully unsaturated 8 to 10 membered bicyclic ring containing at least one heteroatom selected from O, S or N; R1 is optionally substituted aryl, heteroaryl, alkyl, alkenyl, alkynyl, cycloalkyl or heterocycloalkyl; Z1 represents a direct bond, an alkylene chain, NR4, O or S(O)n; L1 is an a —R5—R6— linkage where R5 is alkylene, alkenylene or alkynylene and R6 is a direct bond, cycloalkylene, heterocycloalkylene, arylene, heteroaryldiyl, —C(═Z3)—NR4—, —NR4—C(═Z3)—, —Z3—, —C(═O)—, —C(═NOR4)—, —NR4—, —NR4—C(═Z3)—NR4—, —SO2—NR4—, —NR4—SO2—, —O—C(═O)—, —C(═O)—O—, —NR4—C(═O)—O— or —O—C(═O)—NR4—; L2 is a direct bond; an optionally substituted alkylene, alkenylene, alkynylene, cycloalkenylene, cycloalkylene, heteroaryldiyl, heterocycloalkylene or arylene linkage; a —[C(═O)—N(R9)—C(R4)(R10)]p— linkage; a —Z4—R11— linkage; a —C(═O)—CH2—C(═O)— linkage; a —R11—Z4—R11— linkage; or a —L3—L4—L5— linkage; and Y is carboxy or an acid bioisostere; and the corresponding N-oxides, and their prodrugs; and pharmaceutically acceptable salts and solvates (e.g. hydrates) of such compounds and their N-oxides and prodrugs. Such compounds have valuable pharmaceutical properties, in particular the ability to regulate the interaction of VCAM-1 and fibronectin with the integrin VLA-4 (α4β1).

Substituted bicyclic compounds

The invention is directed to physiologically active compounds of formula (Ia): wherein R1 is optionally substituted aryl or optionally substituted heteroaryl; R2 is hydrogen, halogen, lower alkyl or lower alkoxy; R3 is alk

Substituted bicyclic compounds

The invention is directed to physiologically active compounds of general formula (I): wherein Het is an optionally substituted, saturated, partially saturated or fully unsaturated 8 to 10 membered bicyclic ring system containing at least one heteroatom se