15386-78-4

Basic information

• Product Name: 3-(4-CHLOROANILINO)-3-OXOPROPANOIC ACID
• Synonyms: RARECHEM AL BO 1299;3-(4-CHLOROANILINO)-3-OXOPROPANOIC ACID
• CAS NO: 15386-78-4
• Molecular Formula: C₉H₈ClNO₃
• Molecular Weight: 213.62
• Mol File: 15386-78-4.mol

Chemical Properties

• Melting Point: 168 °C (decomp)
• Boiling Point: 479.3±30.0 °C(Predicted)
• Appearance: /
• Density: 1.467±0.06 g/cm3(Predicted)
• PKA: -0.45±0.32(Predicted)
• CAS DataBase Reference: 3-(4-CHLOROANILINO)-3-OXOPROPANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-CHLOROANILINO)-3-OXOPROPANOIC ACID(15386-78-4)
• EPA Substance Registry System: 3-(4-CHLOROANILINO)-3-OXOPROPANOIC ACID(15386-78-4)

Safety Data

• Hazardous Substances Data: 15386-78-4(Hazardous Substances Data)

Usage

General Description

3-(4-Chloroanilino)-3-oxopropionic acid is a chemical compound with the molecular formula C10H8ClNO3. It is a derivative of 3-oxopropanoic acid and contains a 4-chloroanilino group. 3-(4-CHLOROANILINO)-3-OXOPROPANOIC ACID is often used as an intermediate in the synthesis of pharmaceuticals and research chemicals. It is primarily utilized in the production of drugs with potential biological activity. Additionally, it is also used in the development of new compounds for various applications in the pharmaceutical and agrochemical industries. Overall, 3-(4-Chloroanilino)-3-oxopropionic acid has significant importance in the field of medicinal chemistry and drug discovery.

Upstream product

• 2033-24-1 cycl-isopropylidene malonate 
• 106-47-8 4-chloro-aniline 
• 106109-63-1 C₁₀H₁₀ClNO₃ 
• 141-82-2 malonic acid 
• 15386-84-2 ethyl 3-(4-chloroanilino)-3-oxopropionate 

Downstream Products

• 131239-59-3 2-methoxy-trans-cinnamic acid-(4-chloro-anilide) 
• 109309-52-6 N-(4-chloro-phenyl)-2-(2-methoxy-benzylidene)-malonamic acid 
• 1677-36-7 6-chloro-4-hydroxyquinolin-2(1H)-one 
• 133131-30-3 2-benzylidene-N-(4-chloro-phenyl)-malonamic acid 
• 101681-91-8 (2E)-N-(4-chlorophenyl)cinnamamide 
• 539-03-7 N-(4-chlorophenyl)acetamide 

Relevant articles and documents

A convenient one-pot synthesis of N-arylmalonamic acid via in-situ generation of malonyl monoacyl chloride

A convenient one-pot synthesis of N-arylmalonamic acid has been demonstrated based on the in-situ generation of malonyl monoacyl chloride, followed by reaction with aniline.

Mild, efficient, and solvent-free synthesis of 4-hydroxy-2-quinolinones

Malonic acid monoanilides were obtained in excellent yield from the reaction of anilines with Meldrum's acid under solvent-free conditions. The malonic acid monoanilide intermediates were then treated with methanesulfonic acid anhydride (MSAA) to produce 4-hydroxy-2-quinolinones in excellent yield. It should be noted that both reactions had to be run under mild conditions to avoid the decarboxylation of the malonic acid monoanilide intermediate.

Discovery of 8-cyclopentyl-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-7- oxo-7,8-dihydro-pyrido[2,3- d ]pyrimidine-6-carbonitrile (7x) as a potent inhibitor of cyclin-dependent kinase 4 (CDK4) and AMPK-related kinase 5 (ARK5)

The success of imatinib, a BCR-ABL inhibitor for the treatment of chronic myelogenous leukemia, has created a great impetus for the development of additional kinase inhibitors as therapeutic agents. However, the complexity of cancer has led to recent interest in polypharmacological approaches for developing multikinase inhibitors with low toxicity profiles. With this goal in mind, we analyzed more than 150 novel cyano pyridopyrimidine compounds and identified structure-activity relationship trends that can be exploited in the design of potent kinase inhibitors. One compound, 8-cyclopentyl-2-[4-(4-methyl- piperazin-1-yl)-phenylamino]-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidine-6- carbonitrile (7x), was found to be the most active, inducing apoptosis of tumor cells at a concentration of approximately 30-100 nM. In vitro kinase profiling revealed that 7x is a multikinase inhibitor with potent inhibitory activity against the CDK4/CYCLIN D1 and ARK5 kinases. Here, we report the synthesis, structure-activity relationship, kinase inhibitory profile, in vitro cytotoxicity, and in vivo tumor regression studies by this lead compound.

Diamine derivatives

A compound represented by the general formula (1): Q1-Q2-T0-N(R1)-Q3-N(R2)-T1-Q4??(1) wherein R1 and R2 are hydrogen atoms or the like; Q1 is a saturated or unsaturated, 5- or 6-membered cyclic hydrocarbon group which may be substituted, or the like; Q2 is a single bond or the like; Q3 is a group in which Q5 is an alkylene group having 1 to 8 carbon atoms, or the like; and T0 and T1 are carbonyl groups or the like; a salt thereof, a solvate thereof, or an N-oxide thereof. The compound is useful as an agent for preventing and/or treating cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger's disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after valve or joint replacement, thrombus formation and reocclusion after angioplasty, systemic inflammatory response syndrome (SIRS), multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing.

DIAMINE DERIVATIVES

A compound represented by the general formula (1):Q1-Q2-T0-N(R1)-Q3-N(R2)-T1-Q4 wherein R1 and R2 are hydrogen atoms or the like; Q1 is a saturated or unsaturated, 5- or 6- membered cyclic hydrocarbon group which may be substituted, or the like; Q2 is a single bond or the like; Q3 is a group in which Q5 is an alkylene group having 1 to 8 carbon atoms, or the like; and T0 and T1 are carbonyl groups or the like; a salt thereof, a solvate thereof, or an N-oxide thereof. The compound is useful as an agent for preventing and/or treating cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger's disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after valve or joint replacement, thrombus formation and reocclusion after angioplasty, systemic inflammatory response syndrome (SIRS), multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing.