22780-32-1

Usage

Molecular structure

2-[(2E)-3-(4-METHOXYPHENYL)PROP-2-ENOYL]AMINOBENZOIC ACID consists of a benzoic acid group, an amino group, a prop-2-enoic acid group, and a 4-methoxyphenyl group.

Functional groups

The compound contains a carboxylic acid group (benzoic acid), an amino group, and a prop-2-enoic acid group with a double bond.

Aromatic rings

The compound has two aromatic rings one in the benzoic acid group and the other in the 4-methoxyphenyl group.

Substitution pattern

The 4-methoxyphenyl group is attached to the prop-2-enoic acid group, which is connected to the amino group, which in turn is attached to the benzoic acid group.

Potential applications

This chemical compound may have potential uses in pharmaceuticals, dyes, and organic synthesis due to its unique structure and properties.

Research and analysis

Further research and analysis are needed to fully understand the potential uses and safety considerations of 2-[(2E)-3-(4-METHOXYPHENYL)PROP-2-ENOYL]AMINOBENZOIC ACID.

InChI:InChI=1/C17H15NO4/c1-22-13-9-6-12(7-10-13)8-11-16(19)18-15-5-3-2-4-14(15)17(20)21/h2-11H,1H3,(H,18,19)(H,20,21)/p-1/b11-8+

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 89-52-1 o-acetylamino-benzoic acid 
• 118-92-3 anthranilic acid 
• 53947-84-5 2-[(2-carboxyacetyl)amino]benzoic acid 

Downstream Products

• 639466-04-9 2-[5-(4-methoxy-phenyl)-4,5-dihydro-isoxazol-3-ylamino]-benzoic acid 
• 1187616-50-7 C₁₇H₁₇N₃O₃ 
• 1187616-77-8 C₁₈H₁₇N₃O₃S 
• 1187616-62-1 C₂₃H₂₁N₃O₃ 
• 1187616-71-2 C₁₈H₁₇N₃O₄ 

Relevant academic research and scientific papers

N-Cinnamoylanthranilates as human TRPA1 modulators: Structure-activity relationships and channel binding sites

The transient receptor potential ankyrin 1 (TRPA1) channel is a non-selective cation channel, which detects noxious stimuli leading to pain, itch and cough. However, the mechanism(s) of channel modulation by many of the known, non-reactive modulators has not been fully elucidated. N-Cinnamoylanthranilic acid derivatives (CADs) contain structural elements from the TRPA1 modulators cinnamaldehyde and flufenamic acid, so it was hypothesized that specific modulators could be found amongst them and more could be learnt about modulation of TRPA1 with these compounds. A series of CADs was therefore screened for agonism and antagonism in HEK293 cells stably transfected with WT-human (h)TRPA1, or C621A, F909A or F944A mutant hTRPA1. Derivatives with electron-withdrawing and/or electron-donating substituents were found to possess different activities. CADs with inductive electron-withdrawing groups were agonists with desensitising effects, and CADs with electron-donating groups were either partial agonists or antagonists. Site-directed mutagenesis revealed that the CADs do not undergo conjugate addition reaction with TRPA1, and that F944 is a key residue involved in the non-covalent modulation of TRPA1 by CADs, as well as many other structurally distinct non-reactive TRPA1 ligands already reported.

Synthesis and biological evaluation of some anthranilic acid and 2-phenylquinazoline-4(3H)-one analogues

In the present investigation a novel series of N-(phenyl) chalconyl anthranilic acids containing pyrazolines (4a-j), tetra- hydropyrimidines (4k-o), tetrahydrothiopyrimidines (4p-t) and 2-phenylquinazolin-4(3iJ)-ones containing pyrazolines (8a-f), isoxazolines (8g-l), tetrahydropyrimidines (8m-r) and tetrahydrothiopyrimidines (8s-x) were synthesized and characterized by elemental analysis, FT-IR, 1H NMR and mass spectroscopy. The title compounds (4a-t) and (8a-x) were investigated for their analgesic, anti-inflammatory, antimicrobial and in vitro protein denaturation activities. Compounds 4j and 8x were identified as lead compounds with optimum analgesic, anti-inflammatory and antimicrobial activities.

Isoxazolinyl derivatives of anthranilic acid as antiinflammatory agents

A number of 5-substituted-N-[4′-(substitutedphenyl) aminomethyl-5′-(substitutedphenyl)isoxazolin-2′-yl]anthranilic acids have been synthesized by the Mannich reaction of 5-substituted-N-[5′-(substitutedphenyl)isoxazolin-2′-yl]anthranilic acids, which in turn is synthesized by the reaction of 5-substituted-N-chalconylanthranilic acids. In this series, compounds 9, 11, 15 and 18 show significant protection against carrageenan induced rat's paw oedema with lower ulcerogenic liability than phenylbutazone. The most active compound of this series is N-[5′-(m-methoxy, p-hydroxyphenyl)isoxazolin-2′-yl]anthranilic acid which has shown higher antiinflammatory activity and lower ulcerogenic property than phenylbutazone.