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Relevant academic research and scientific papers

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.

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.

2-Aminothiophene derivatives in a novel synthesis of phthalimidines

New aminophthalides were synthesized from o-formylbenzoic acid and substituted 2-aminothiophenes. Two of these compounds underwent recyclization in boiling Ac2O to give the previously unknown 3-acetoxy-2-(3-cyano-4, 5-dimethylthiophen-2-yl)-1,3-dihydroisoindol-1-one and 3-acetoxy-2-(3-cyano-4,5- tetramethylenethiophen-2-yl)-1,3-dihydroisoindol-1-one. The possible reaction mechanism and factors preventing the recyclization, in particular, the formation of intramolecular hydrogen bonds in the starting phthalides, were discussed. Some reactions of the resulting compounds with C-nucleophiles in trifluoroacetic acid were investigated. Two derivatives containing 4-hydroxy-3,5-di-tert- butylphenyl substituents were studied by X-ray diffraction.