33125-69-8

Upstream product

• 16824-02-5 3-ethoxy-3H-isobenzofuran-1-one 
• 62-53-3 aniline 
• 142-04-1 aniline hydrochloride 
• 119-67-5 o-carboxybenzaldehyde 
• 87-41-2 2-benzofuran-1(3H)-one 
• 6940-49-4 3-Bromophthalide 

Downstream Products

• 64692-99-5 Sodium salt of 2-carboxybenzaldehyde 
• 89313-76-8 2-phenylisoindoline-1-thione 
• 18167-15-2 3-hydroxy-2-phenylisoindolin-1-one 
• 1258424-54-2 3-propargyloxy-2-phenylisoindolin-1-one 
• 1258424-82-6 3-(benzoxazol-2-yl-sulfanyl)-2-phenylisoindolin-1-one 
• 1258424-78-0 3-morpholino-2-phenylisoindolin-1-one 
• 1258424-84-8 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-phenylisoindolin-1-one 
• 55740-87-9 3-acetoxy-2-phenylisoindol-1(3H)-one 
• 1258424-76-8 3-propionyloxy-2-phenylisoindolin-1-one 
• 5388-42-1 N-phenylphthalimidine 
• 119-67-5 o-carboxybenzaldehyde 

Relevant academic research and scientific papers

Metal-Free Cascade Formation of Intermolecular C-N Bonds Accessing Substituted Isoindolinones under Cathodic Reduction

An electrochemical protocol for the construction of substituted isoindolinones via reduction/amidation of 2-carboxybenzaldehydes and amines has been realized. Under metal-free and external-reductant-free electrolytic conditions, the reaction achieves the cascade formation of intermolecular C-N bonds and provides a series of isoindolinones in moderate to good yields. The deuterium-labeling experiment proves that the hydrogen in the methylene of the product is mainly provided by H2O in the system.

Synthesis of new 3-arylaminophthalides and 3-indolyl-phthalides using ammonium chloride, evaluation of their anti-mycobacterial potential and docking study

Objective: The study aims at the derivatization of “Phthalides” and synthesizes 3-arylaminophthalides & 3-indolyl-phthalides compounds, and evaluates their anti-tubercular and antioxidant activities. The study has also intended to employ the in silico methods for the identification of possible drug targets in Mycobacterium and evaluate the binding affinities of synthesized compounds. Methods: This report briefly explains the synthesis of phthalide derivatives using ammonium chloride. The synthesized compounds were characterized using spectral analysis. Resazurin Microtiter Assay (REMA) plate method was used to demonstrate the anti-mycobacterial activity of the synthesized compounds. An in-silico pharmacophore probing approach was used for target identification in Mycobacterium. The structural level interaction between the identified putative drug target and synthesized phthalides was studied using Lamarckian genetic algorithm-based software. Results and Discussion: In the present study, we report an effective, environmentally benign scheme for the synthesis of phthalide derivatives. Compounds 5c and 5d from the current series appear to possess good anti-mycobacterial activity. dCTP: deaminasedUTPase was identified as a putative drug target in Mycobacterium. The docking results clearly showed the interactive involvement of conserved residues of dCTP with the synthesized phthalide compounds. Conclusion: On the eve of evolving anti-TB drug resistance, the data on anti-tubercular and allied activities of the compounds in the present study demonstrates the enormous significance of these newly synthesized derivatives as possible candidate leads in the development of novel anti-tubercular agents. The docking results from the current report provide a structural rationale for the promising anti-tubercular activity demonstrated by 3-arylaminophthalides and 3-indolyl-phthalides compounds.

Hantzsch ester triggered metal-free cascade approach to isoindolinones

Disclosed herein is an expedient synthesis of biologically important isoindolinone derivatives from reactions of 2-formylbenzoic acids with various amines. This method operates via a deliberately designed catalyst-free tandem reductive amination/cyclization cascade event triggered by a transfer hydrogenation process with easily available Hantzsch ester as the organic hydride source. The ease of operation, mild reaction conditions, facile accessibility of the starting materials, and easy scalability of the current method distinguish it from the other precedent protocols, thus enable it a practical approach to the syntheses of valuable isoindolinone-incorporated drugs.

Catalyst-Free Synthesis of 3-(2-Quinolinemethylene)-Substituted Isoindolinones in Water

A facile and environmentally benign approach toward the synthesis of novel 3-alkyl-substituted isoindolinones by three-component reactions of 2-formylbenzoic acids, primary amines and 2-methylazaarenes in water under catalyst- and additive-free conditions is described. This protocol features the direct construction of multiple C-N and C-C bonds via a tandem Mannich-type reaction and intramolecular cyclization in a one-pot fashion, affording the desired 3-(2-quinolinemethylene)-substituted isoindolinones in high to excellent yields.

Triphenylstannyl((arylimino)methyl)benzoates with selective potency that induce G1 and G2/M cell cycle arrest and trigger apoptosis: Via ROS in human cervical cancer cells

Metal complexes with organelle specificity and potent but selective cytotoxicity are highly desirable. A novel series of triphenylstannyl 4-((arylimino)methyl)benzoates (2-8) were obtained by the reactions of triphenylstannyl 4-formylbenzoate [Ph3Sn(L1)] 1 with primary aromatic amines. Two representative compounds (10, 11) were also synthesized by reacting aqua-triphenylstannyl 2-formylbenzoate [Ph3Sn(L9)(H2O)] (9) with aniline and p-fluoroaniline, respectively. These compounds were characterized by elemental analysis, IR and 1H, 13C and 119Sn NMR spectroscopy, as well as single-crystal X-ray diffraction for compounds 5, 7-11 and three pro-ligands. The in vitro cytotoxic activities of 1-11 were assessed using the MTT tetrazolium dye assay against HeLa (human cervical) and MDA-MB-231 (breast) cancer cells, with IC50 values revealing high activity. Compared to cisplatin, compounds 1-11 exhibited enhanced cytotoxic efficacy, indicating their potential as potent anticancer agents. Among these, 1 and 5 demonstrated maximum inhibition in HeLa cells, with negligible effect on normal human embryonic kidney (HEK) cells. The combined results of the DCFH-DA dye and Hoechst 33342/PI nuclear staining assays, along with flow cytometry analysis, show that they possess a dual mode of action: They induced apoptotic cell death, attributable to the tin-assisted generation of reactive oxygen species. Cell cycle analyses indicated that compounds 1 and 5 exhibit cell growth inhibition and may cause turbulences in the G1 and G2/M phases.

Experimental and theoretical study on solvent and substituent effects on the intramolecular charge transfer in 3-[(4-substituted)phenylamino]isobenzofuran-1(3H)-ones

The substituent and solvent effects on solvatochromism in 3-[(4-sub-stituted)phenylamino]isobenzofuran-1(3H)-ones were studied using experimental and theoretical methodologies. The effect of specific and non-specific solvent–solute interactions on the shi

Chiral 3-substituted isoindolinone compounds, and preparation method and application thereof

The invention discloses chiral 3-substituted isoindolinone compounds, and a preparation method and application thereof. The compounds are as shown in a formula I which is described in the specification. The preparation method comprises a step of subjecting a compound as shown in a formula II and a compound as shown in a formula III to a Ugi two-component four-center reaction or subjecting a compound as shown in a formula IV, a compound as shown in a formula V and the compound as shown in the formula III to a Ugi three-component four-center reaction in the presence of a chiral phosphoric acid catalyst so as to obtain the compounds as shown in the formula I after completion of the reactions. According to the invention, extensively available raw materials and the cheap and easily available chiral catalyst are used; the raw materials are subjected to the Ugi two-component four-center reaction or the Ugi three-component four-center reaction so as to efficiently prepare the chiral 3-substituted isoindolinone compounds in one step; reaction conditions are mild; and the prepared compounds are stable in the air, high in yield, good in enantioselectivity and easy to separate and purify, and have good application prospects.

Chiral Phosphoric Acid Catalyzed Asymmetric Ugi Reaction by Dynamic Kinetic Resolution of the Primary Multicomponent Adduct

Reaction of isonitriles with 3-(arylamino)isobenzofuran-1(3H)-ones in the presence of a catalytic amount of an octahydro (R)-binol-derived chiral phosphoric acid afforded 3-oxo-2-arylisoindoline-1-carboxamides in high yields with good to high enantioselec

Efficient syntheses of substituted (±)-3-oxoisoindoline-1-carbonitriles and carboxamides using OSU-6

An efficient synthesis of 3-oxoisoindolines is described from 2-carboxybenzaldehyde, TMSCN and benzylic or aliphatic amines using a Strecker approach with OSU-6 as the catalyst. The reaction can be tuned to generate two different products: a substituted (

A new synthesis of phthalimidines

A new synthesis of phthalimidines is described. 3-Acyloxy-2-aryl- and 2-acylamino-3-acyloxyphthalimidines were prepared by the reaction of 3-arylaminophthalides or o-formylbenzoic acid acylhydrazones with acetic or propionic anhydrides. Their reactions wi