306935-74-0

Basic information

• Product Name: 4-(4-CHLOROANILINO)-4-OXOBUT-2-ENOIC ACID
• Synonyms: TIMTEC-BB SBB000655;4-OXO-4-(4-CHLOROPHENYLAMINO)-2-BUTENOIC ACID;4-(4-CHLOROANILINO)-4-OXOBUT-2-ENOIC ACID
• CAS NO: 306935-74-0
• Molecular Formula: C₁₀H₈ClNO₃
• Molecular Weight: 225.63
• Mol File: 306935-74-0.mol
• Article Data: 10

Chemical Properties

• Melting Point: 200 °C
• Boiling Point: 466.2°Cat760mmHg
• Flash Point: 235.7°C
• Appearance: /
• Density: 1.448g/cm³
• Vapor Pressure: 1.72E-09mmHg at 25°C
• Refractive Index: 1.642
• PKA: 3.44±0.10(Predicted)
• CAS DataBase Reference: 4-(4-CHLOROANILINO)-4-OXOBUT-2-ENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-CHLOROANILINO)-4-OXOBUT-2-ENOIC ACID(306935-74-0)
• EPA Substance Registry System: 4-(4-CHLOROANILINO)-4-OXOBUT-2-ENOIC ACID(306935-74-0)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S37/39:Wear suitable g
• Hazardous Substances Data: 306935-74-0(Hazardous Substances Data)

Usage

Description

4-(4-CHLOROANILINO)-4-OXOBUT-2-ENOIC ACID, with the systematic name 4-(4-chlorophenylamino)-3-oxo-2-butenoic acid, is a chemical compound characterized by the molecular formula C10H9ClNO3. It is a derivative of 4-aminobenzoic acid and is classified within the aromatic amide category. 4-(4-CHLOROANILINO)-4-OXOBUT-2-ENOIC ACID is recognized for its chlorine atom and amino group, which are key features that may contribute to its potential applications in medicinal chemistry and drug development. Its chemical properties and functional groups render it a valuable intermediate for the synthesis of new compounds with diverse biological activities.

Uses

Used in Pharmaceutical Research:
4-(4-CHLOROANILINO)-4-OXOBUT-2-ENOIC ACID is used as a building block in pharmaceutical research for its potential to contribute to the development of new drugs. Its unique structure, including the chlorine atom and amino group, makes it a promising candidate for the synthesis of compounds with therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, 4-(4-CHLOROANILINO)-4-OXOBUT-2-ENOIC ACID is utilized as an intermediate. Its functional groups and chemical properties allow for the creation of a variety of new compounds, expanding the scope of chemical reactions and products that can be achieved.
Used in Medicinal Chemistry:
4-(4-CHLOROANILINO)-4-OXOBUT-2-ENOIC ACID is employed in medicinal chemistry to explore its potential in the development of pharmaceuticals. The presence of a chlorine atom can influence the compound's reactivity and lipophilicity, which are important factors in drug design and optimization.
Used in Drug Development:
As part of drug development processes, 4-(4-CHLOROANILINO)-4-OXOBUT-2-ENOIC ACID is used to create new chemical entities with potential biological activities. Its versatility as an intermediate allows researchers to modify its structure to enhance or discover new pharmacological properties, which could lead to the creation of innovative treatments for various diseases.

InChI:InChI=1/C10H8ClNO3/c11-7-1-3-8(4-2-7)12-9(13)5-6-10(14)15/h1-6H,(H,12,13)(H,14,15)/b6-5+

Upstream product

• 108-31-6 maleic anhydride 
• 106-47-8 4-chloro-aniline 

Downstream Products

• 1631-29-4 N-(4-chlorophenyl)maleimide 
• 485826-47-9 C₂₆H₁₆ClNO₅ 

Relevant articles and documents

Identification of two arylimides as cholinesterase inhibitors and testing of propranolol addition on impaired rat memory

Alzheimer's disease (AD) is clearly linked to the decline of acetylcholine (ACh) effects in the brain. These effects are regulated by the hydrolytic action of acetylcholinesterase (AChE). Therefore, a central palliative treatment of AD is the administration of AChE inhibitors although additional mechanisms are currently described and tested for generating advantageous therapeutic strategies. In this work, we tested new arylamides and arylimides as potential inhibitors of AChE using in silico tools. Then, these compounds were tested in vitro, and two selected compounds, C7 and C8, as well as propranolol showed inhibition of AChE. In addition, they demonstrated an advantageous acute toxicity profile compared to that of galantamine as a reference AChE inhibitor. in vivo evaluation of memory performance enhancement was performed in an animal model of cognitive disturbance with each of these compounds and propranolol individually as well as each compound combined with propranolol. Memory improvement was observed in each case, but without a significant additive effect with the combinations.

The discovery, design and synthesis of potent agonists of adenylyl cyclase type 2 by virtual screening combining biological evaluation

Adenylate cyclases (ACs), play a critical role in the conversion of adenosine triphosphate (ATP) into the second messenger cyclic adenosine monophosphate (cAMP). Studies have indicated that adenylyl cyclase type 2 (AC2) is potential drug target for many diseases, however, up to now, there is no AC2-selective agonist reported. In this research, docking-based virtual screening with the combination of cell-based biological assays have been performed for discovering novel potent and selective AC2 agonists. Virtual screening disclosed a novel hit compound 8 as an AC2 agonist with EC50 value of 8.10 μM on recombinant human hAC2 + HEK293 cells. The SAR (structure activity relationship) based on the derivatives of compound 8 was further explored on recombinant AC2 cells and compound 73 was found to be the most active agonist with the EC50 of 90 nM, which is 160-fold more potent than the reported agonist Forskolin and could selectively activate AC2 to inhibit the expression of Interleukin-6. The discovery of a new class of AC2-selective agonists would provide a novel chemical probe to study the physiological function of AC2.

Alizarin red S-TiO2-catalyzed cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions toward tetrahydroquinoline derivatives under visible light irradiation

A very low amount of organic dye (Alizarin red S) sensitized TiO2 and it was successfully used to catalyze cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions under visible light irradiation. The modified TiO2 photocatalyst efficiently, for the first time, advanced [4+2] cyclization of N,N-dimethylanilines and maleimides to the corresponding tetrahydroquinolines in air atmosphere. The reaction proceeds through α-amino radicals without additional oxidant at ambient temperature to afford products in good to excellent yields.