256453-84-6

Usage

Methyl ester derivative

2-(3-hydroxy-4-nitrophenyl)acetic acid 2-(3-hydroxy-4-nitrophenyl)acetic acid methyl ester is derived from 2-(3-hydroxy-4-nitrophenyl)acetic acid by replacing the carboxyl group (-COOH) with a methyl ester group (-COOCH3).

Nitro group present

The compound contains a nitro group (-NO2) attached to the phenyl ring, which contributes to its reactivity and potential applications in various fields.

Hydroxyl group present

The compound also contains a hydroxyl group (-OH) on the phenyl ring, which can form hydrogen bonds and participate in various chemical reactions.

Applications in synthesis

Pharmaceutical and agrochemical industries 2-(3-hydroxy-4-nitrophenyl)acetic acid methyl ester is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals due to its unique structure and reactivity.

Potential applications

Organic chemistry and materials science The compound may have potential applications in organic chemistry and materials science, as its unique structure and functional groups can be utilized in the development of new compounds and materials.

Hazardous compound

Handling precautions 2-(3-hydroxy-4-nitrophenyl)acetic acid methyl ester is considered to be a potentially hazardous compound, and it should be handled with care in a laboratory setting to avoid accidents and ensure the safety of researchers.

Upstream product

• 42058-59-3 3-hydroxy-benzeneacetic acid, methyl ester 
• 152148-79-3 (3-hydroxy-4-nitro-phenyl)-acetic acid 
• 67-56-1 methanol 

Downstream Products

• 256453-85-7 methyl 2-phenylaminobenzoxazol-6-acetate 
• 353525-11-8 methyl (4-amino-3-hydroxyphenyl)acetate 

Relevant academic research and scientific papers

N-{[2-(PIPERIDIN-1-YL)PHENYL](PHENYL)METHYL}-2-(3-OXO-3,4-DIHYDRO-2H-1,4-BENZOXA ZIN-7-YL)ACETAMIDE DERIVATIVES AND RELATED COMPOUNDS AS ROR-GAMMA MODULATORS FOR TREATING AUTOIMMUNE DISEASES

The present invention provides e.g. N-{[2-(piperidin-1-yl)phenyl] (phenyl)methyl}-2-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl)acetamide derivatives and related compounds as ROR-gamma modulators for treating e.g. autoimmune diseases, autoimmune-related diseases, inflammatory diseases, metabolic diseases, fibrotic diseases or cholestatic diseases, such as e.g. arthitis and asthma.

A novel and potent VLA-4 antagonist based on trans-4-substituted cyclohexanecarboxylic acid

During the course of our study, it was revealed that the poor pharmacokinetic properties of a series of benzoic acid derivatives such as 1 should be attributed to the diphenylurea moiety. Thus, we replaced the diphenylurea moiety in 1 with a 2-(2-methylphenylamino)benzoxazole moiety which mimics the diphenylurea structure. However, this modification resulted in a significant decrease (3, IC50 = 19 nM) in VLA-4 inhibitory activity compared to 1 (IC50 = 1.6 nM). To address this discrepancy, we worked on optimization of the carboxylic acid moiety in compound 3. As a result, our efforts have led to the discovery of trans-4-substituted cyclohexanecarboxylic acid derivative 11b (IC50 = 2.8 nM) as a novel and potent VLA-4 antagonist. In addition, compound 11b exhibited favorable pharmacokinetic properties (CL = 3.3 ml/min/kg, F = 51%) in rats.

PHARMACEUTICALLY ACTIVE BENZOXAZOLE, BENZTHIAZOLE AND BENZIMIDAZOLE ACID DERIVATIVES

Compounds of formula (I): wherein R1, R2 and R3 are independently, hydrogen, halogen, CF3, OR6, NR7R8, NR8COR10, NR8SO2R10 or C1-6 alkyl optionally substituted by hydroxy, C1-6 alkoxy or NR7R8; R4 is NR8CONR8R9, NR8COR9, NR8SO2R9, or W-CONR8R9, where W is a bond, C1-6 alkylene, C2-6 alkenylene or C2-6 alkynylene; and R5 is Formula (A) methods for their synthesis, pharmaceutical compositions comprising them and their use in medicine, in particular for the treatment of cancer.

VLA-4 INHIBITORS

The present invention relates to a compound represented by the following formula (I): (wherein, W represents WA-A1 -WB - (in which, WA is substituted or unsubstituted aryl, etc., A1 is -NR1-, single bond, -C(O)-, etc., and WB is substituted or unsubstituted arylene, etc.), R is single bond, -NH-, -OCH2-, alkenylene, etc., X is -C(O) -CH2-, etc., and M is, for example, the following formula: (in which, R11, R12 and R13 each independently represents hydrogen, hydroxyl, amino, halogen, etc., R14 is hydrogen or lower alkyl, Y represents -CH2-O-, etc., Z is substituted or unsubstituted arylene, etc., A2 is single bond, etc, and R10 is hydroxyl or lower alkoxy)), or salt thereof; and a medicament containing the same. This compound or salt thereof selectively inhibits binding of cell adhesion molecules to VAL-4 and exhibits high bioavailability so that it is useful as a preventive and/or remedy for inflammatory diseases, autoimmune diseases, metastasis, bronchial asthma, rhinostenosis, diabetes, and the like.

Chemical compounds

Compound of formula (I) wherein: A is a bicyclic heteroaryl, optionally substituted with one or more substituents; B is linker group connecting group A to group D and comprising a 3 or 4 atom linker where each atom is independently selected from carbon, oxygen, nitrogen and sulphur and is optionally subsituted with one or more C1-6alkyl groups or two of such adjacent alkyl substituents may form a ring; C is aryl or a mono or bicyclic heteroaryl, each of which can be optionally substituted; D is an aryl or heteroaryl, both of which are optionally substituted R1is hydrogen, C1-5alkyl, C1-3alkanoyl or C1-3alkoxycarbonyl; R2to R5are each independently selected from hydrogen, C1-6alkyl, aryl and heteroaryl containing up to 2 heteroatoms chosen from oxygen, sulphur and nitrogen, the aryl and heteroaryl optionally substituted with C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C1-4alkoxy, C1-4alkanoyl, C1-6alkylamino, C1-4alkylC1-6alkyoxyl, C1-6alkylaminoC1-6alkyl, nitro, cyano, halogeno, trifluoromethyl, hydroxy, (CH2)pOH where p is 1 or 2, —CO2Ra, and —CONRaRb, where Raand Rbare independently selected from hydrogen and C1-6alkyl or two of R2to R5can be taken together to form a 3 to 7 membered ring; R6is an acidic functional group; r and s are each independently 0 or 1 with the proviso that r and s cannot both be 0; or a pharmaceutically acceptable salt or in vivo hydrolysable derivative thereof.