18852-53-4

Usage

Class

Coumarins

Biological activities

Anti-inflammatory, antimicrobial, and anticancer properties

Applications

a. Drug discovery and development
b. Starting material in the synthesis of pharmaceuticals and agrochemicals

Structure

A derivative of coumarin with a chlorine atom at the 3-position and a phenyl group also at the 3-position

Pharmacological and biological effects

Studied for its potential effects on various biological processes and diseases

Natural occurrence

Part of the class of coumarins, which includes both natural and synthetic compounds

Stability

Relatively stable under normal conditions

Solubility

Soluble in organic solvents such as ethanol, methanol, and acetone

Reactivity

Can undergo various chemical reactions, such as substitution and condensation, to form new compounds

Safety and handling

Handle with care, as it may have potential toxic effects and should be stored in a well-ventilated area, away from heat and moisture.

Upstream product

• 85-52-9 2-Benzoylbenzoic acid 
• 7719-09-7 thionyl chloride 

Downstream Products

• 31802-10-5 (2-benzoylphenyl)(morpholino)methanone 
• 84538-58-9 3-Phenyl-3-(1-imidazolyl)-1(3H)-isobenzofuranone 
• 157951-81-0 dimethyl 2-benzoylbenzoylphosphonate 
• 27687-35-0 3-hydroxy-3-phenyl-2-propyl-2,3-dihydroisoindol-1-one 
• 13369-57-8 3-(2-benzoyl-benzoyloxy)-3-phenyl-phthalide 
• 40825-12-5 Phenyl 2-benzoylbenzoate 
• 92868-11-6 3-Carbamoyl-4-phenyl-isochinolin-1(2H)-on 
• 78945-99-0 1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid 
• 137537-27-0 2-methyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbonitrile 
• 137537-65-6 3-Aminomethyl-2-isopropyl-4-phenyl-isochinolin-1(2H)-on 
• 137537-51-0 2-Methyl-1-oxo-4-phenyl-1,2-dihydro-isoquinoline-3-carboxylic acid amide 
• 134563-33-0 2-Isopropyl-1-oxo-4-phenyl-1,2-dihydro-isoquinoline-3-carbonitrile 
• 137537-28-1 2-Butyl-1-oxo-4-phenyl-1,2-dihydro-isoquinoline-3-carbonitrile 
• 134563-30-7 2-Isopropyl-1-oxo-4-phenyl-1,2-dihydro-isoquinoline-3-carboxylic acid amide 

Relevant academic research and scientific papers

A facile synthesis of novel cyclic esters of γ-keto acid derivatives by heck coupling reaction

γ-Keto acids and esters are highly useful compounds in organic synthesis, because a number of five-membered carbocycles and various other heterocycles can be readily obtained from them. A number of γ-keto acids derivatives have been synthesized with high

Relay catalysis using a rhodium complex/chiral Bronsted acid binary system: Enantioselective reduction of a carbonyl ylide as the reactive intermediate

Pass the baton: A one-pot relay catalysis for a carbonyl ylide formation/enantioselective reduction sequence using a dirhodium(II) tetracarboxylate and chiral phosphoric acid catalyst system is described. The four-step transformation involves a rhodium ca

Ni(0)-Catalyzed Dimerization of o-Keto Carboxylic Acid Pseudochlorides

A new protocol of the synthesis of 3,3′-diaryl-3,3′-diphthalides by dehalogenation of o-keto carboxylic acid pseudochlorides is implemented. The feature of the new protocol is that the reaction is carried out in the presence of a zero-valent nickel comple

High-purity 2 - (benzoyl) benzoyl chloride synthesis method

The invention discloses a method for synthesizing 2 - (benzoyl) benzoyl chloride method, comprises the following steps: (1) under the action of a catalyst, the O benzoyl benzoic acid and thionyl chloride takes acylation reaction, the preparation of 3 - ch

Isoindolinone inhibitors of the murine double minute 2 (MFM2)-p53 protein-protein interaction: Structure-activity studies leading to improved potency

Inhibition of the MDM2-p53 interaction has been shown to produce an antitumor effect, especially in MDM2 amplified tumors. The isoindolinone scaffold has proved to be versatile for the discovery of MDM2-p53 antagonists. Optimization of previously reported inhibitors, for example, NU8231 (7) and NU8165 (49), was guided by MDM2 NMR titrations, which indicated key areas of the binding interaction to be explored. Variation of the 2-N-benzyl and 3-alkoxy substituents resulted in the identification of 3-(4-chlorophenyl)-3-((1- (hydroxymethyl)cyclopropyl)methoxy)-2-(4-nitrobenzyl)isoindolin-1-one (74) as a potent MDM2-p53 inhibitor (IC50 = 0.23 A± 0.01 μM). Resolution of the enantiomers of 74 showed that potent MDM2-p53 activity primarily resided with the (+)-R-enantiomer (74a; IC50 = 0.17 A± 0.02 μM). The cellular activity of key compounds has been examined in cell lines with defined p53 and MDM2 status. Compound 74a activates p53, MDM2, and p21 transcription in MDM2 amplified cells and shows moderate selectivity for wild-type p53 cell lines in growth inhibition assays.

ISOINDOLIN-1-ONE DERIVATIVES

A compound of formula (1) or a prodrug and/or pharmaceutically acceptable salt thereof, wherein X is selected from O, N or S; R1 is selected from hydrogen, halo, hydroxy, substituted or unsubstituted alkyl, substituted or unsubstituted hydroxyalkyl, substituted or unsubstituted alkylamine, alkoxy, substituted or unsubstituted aryl or heteroaryl, and substituted or unsubstituted aralkyl or heteroaralkyl; R2 is selected from hydrogen, halo, hydroxy, substituted or unsubstituted alkyl, substituted or unsubstituted hydroxyalkyl substituted or unsubstituted alkylamine, alkoxy, substituted or unsubstituted aryl or heteroaryl, and substituted or unsubstituted aralkyl or heteroalkyl; R3 is selected from hydrogen, halo, hydroxy, substituted or unsubstituted alloy substituted or unsubstituted hydroxyalkyl, substituted or unsubstituted alkylamine alkoxy, substituted or unsubstituted aryl or heteroaryl, and substituted or unsubstituted aralkyl or heteroalkyl; and R4-R7, is used to represent groups R4, R5, R6 and R7 which are independently selected from H, OH, alkyl, alkoxy, alkylamine, hydroxyalkyl, halo, CF3, NH2, NO2, COOH, C=0.

Small-molecule inhibitors of the MDM2-p53 protein-protein interaction based on an isoindolinone scaffold

From a set of weakly potent lead compounds, using in silico screening and small library synthesis, a series of 2-alkyl-3-aryl-3-alkoxyisoindolinones has been identified as inhibitors of the MDM2-p53 interaction. Two of the most potent compounds, 2-benzyl-3-(4-chlorophenyl)-3-(3-hydroxypropoxy)-2,3- dihydroisoindol-1-one (76; IC50 = 15.9 ± 0.8 μM) and 3-(4-chlorophenyl)-3-(4-hydroxy-3,5-dimethoxybenzyloxy)-2-propyl-2, 3-dihydroisoindol-1-one (79; IC50 = 5.3 ± 0.9 μM), induced p53-dependent gene transcription, in a dose-dependent manner, in the MDM2 amplified, SJSA human sarcoma cell line.

Isoindolinone-based inhibitors of the MDM2-p53 protein-protein interaction

A series of 2-N-alkyl-3-aryl-3-alkoxyisoindolinones has been synthesised and evaluated as inhibitors of the MDM2-p53 interaction. The most potent compound, 3-(4-chlorophenyl)-3-(4-hydroxy-3,5-dimethoxybenzyloxy)-2-propyl-2,3- dihydroisoindol-1-one (NU8231), exhibited an IC50 of 5.3 ± 0.9 μM in an ELISA assay, and induced p53-dependent gene transcription in a dose-dependent manner, in the SJSA human sarcoma cell line.

Synthesis of 3-alkoxy- and 3-alkylamino-2-alkyl-3-arylisoindolinones

Solvent-controlled regioselectivity in the reactions of 3- chloroisoindolinones with primary amines allows the rational synthesis of isoindolinones by a route suitable for parallel combinatorial chemistry.

Pseudoacids. II. 2-Acylbenzoic Acid Derivatives

Structures of derivatives of cyclic o-acylbenzoic acids, including the chloride, endo- and exocyclic amides, esters and anhydrides, are examined. 3-Chloro-1(3H)-isobenzofuranone (1), orthorhombic, Pbca, a = 11.616 (5), b = 8.120 (3), c = 15.640 (9) A; 3-methoxy-3-phenyl-1(3H)-isobenzofuranone (3), orthorhombic, P212121, a = 6.923 (2), b = 8.291 (4), c = 21.551 (8) A; 3-hydroxy-3-phenyl-N-propyl-1(3H)-isoindolone (4), orthorhombic, P212121, a = 8.662 (4), b = 9.551 (7), c = 17.649 (14) A; 3-(N-morpholino)-1(3H)-isobenzofuranone (5), triclinic, P1, a = 6.172 (4), b = 11.163 (7), c = 17.33 (2) A, α = 105.91 (6), β = 99.85 (6), γ = 97.57 (5)°; 3-(2′-benzoylbenzoyloxy)-3-phenyl-1(3H)-isobenzofuranone (7), triclinic, P1, a = 9.694 (3), b = 10.505 (4), c = 11.163 (4) A°, α = 80.58 (3), β = 80.41 (3), γ = 76.49 (3)°; bis[1(3H)-isobenzofuranone-3-yl]ether (8), monoclinic, I2/a, a = 15.31 (2), b = 6.111 (12), c = 28.30 (5) A, β = 101.61 (12)°. An open oxoacid tertiary amide is also described: N-morpholino 2′-benzoylbenzamide (6): monoclinic, P21/c, a = 6.844 (4), b = 15.696 (8), c = 14.154 (7) A, β = 99.43 (4)°. Pseudoacid derivatives form planar isobenzofuran and isoindole rings, and the former aldehyde/ketone carbon-heteroatom endocyclic and exocyclic bond distances show bond length variations which correlate with the relative basicities of the attached groups. Structures of both endocyclic and exocyclic nitrogen pseudoamides are reported as well as examples of the normal-pseudoanhydride and the dipseudoanhydride.