Oxindole as starting material in organic synthesis

Ziarani, Ghodsi Mohammadi; Gholamzadeh, Parisa; Lashgari, Negar; Hajiabbasi, Parvin

doi:10.3998/ark.5550190.p008.074

Cited by 68 publications

(24 citation statements)

References 37 publications

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“…Benzolactams, which feature a lactam ring fused to a benzene ring as a fundamental chemical structure, are an important motif in medicinal [1][2][3][4] and synthetic chemistry. [5][6][7] Thus, a method that could give rapid access to the benzolactam skeleton is highly desirable.…”

Section: Introductionmentioning

confidence: 99%

μ-Oxo-Hypervalent-Iodine-Catalyzed Oxidative C–H Amination for Synthesis of Benzolactam Derivatives

Sasa

Kikushima

Kita

et al. 2022

CHEMICAL & PHARMACEUTICAL BULLETIN

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Benzolactams have unique biological activity and high utility in the synthesis of valuable compounds with direct applicability to oxindole alkaloids and antibacterial agents. Despite recent advances in organic chemistry and the growing number of reported methods for synthesizing benzolactams, their preparation still requires a multistep process. C-H amination reactions can convert aromatic C(sp 2 )-H bonds directly to C(sp 2 )-N bonds, and this direct approach to C-N bond formation offers effective access to benzolactams. Hypervalent iodine reagents are promising tools for achieving oxidative C-H amination. Motivated by our ongoing research efforts toward the development of useful hypervalent-iodine-mediated oxidative transformations, we herein describe an effective intramolecular oxidative C-H amination reaction based on -oxo hypervalent iodine catalysis for the synthesis of benzolactams bearing various functional groups.

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Section: Introductionmentioning

confidence: 99%

μ-Oxo-Hypervalent-Iodine-Catalyzed Oxidative C–H Amination for Synthesis of Benzolactam Derivatives

Sasa

Kikushima

Kita

et al. 2022

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Therefore, synthetic strategies involving MCRs are valuable and powerful tools for the efficient and rapid synthesis of a wide variety of organic compounds. 20,21 In continuous of our previous studies on the synthesis of heterocyclic compounds and in MCRs, [22][23][24][25][26][27][28][29][30][31][32][33][34][35] it was decided to study the application of phthalhydrazide as a starting material in the MCRs based on different heterocyclic compounds.…”

Section: Introductionmentioning

confidence: 99%

Recent Achievements in the Synthesis of Heterocyclic Compounds by Phthalhydrazide-Based Multicomponent Reactions

Ziarani¹,

Jamasbi²,

Mohajer³

2021

HETEROCYCLES

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Phthalhydrazide is one of the useful starting material toward the synthesis of heterocyclic compounds, and considered as a valuable structural unit in organic synthesis due to its significant pharmacological and biological activities.There are many multicomponent reactions using phthalhydrazide under different conditions. This review article aims to give an overview of recent applications of phthalhydrazide in the multicomponent reactions during the period of 2006 to 2021.

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“…The vast majority of reactions of the C-3 carbonyl group of isatins are nucleophilic additions or spiroannulation, which transform it into 2-oxindole derivatives [9]. To this end, 2-Oxindoles, particularly those that are spiro-fused to other cyclic frames, have attracted significant research interest in the disciplines of synthetic organic chemistry and medicinal chemistry [10][11][12][13][14]. They represent the core structures in a variety of natural products and drugs, such as isomitraphylline, isocorynoxine, isorhnchophlline, mitraphylline and uncarine [10][11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Bioactivity Assessment of Novel Spiro Pyrazole-Oxindole Congeners Exhibiting Potent and Selective in vitro Anticancer Effects

et al. 2020

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The present work aims to design and synthesize novel series of spiro pyrazole-3,3'-oxindoles analogues and investigate their bioactivity as antioxidant and antimicrobial agents, as well as antiproliferative potency against selected human cancerous cell lines (i.e., breast, MCF-7; colon, HCT-116 and liver, HepG-2) relative to healthy noncancerous control skin fibroblast cells (BJ-1). The mechanism of their cytotoxic activity has been also examined by immunoassaying the levels of key anti-and proapoptotic protein markers. The analytical and spectral data of the all synthesized target congeners were compatible with their structures. Synthesized compounds showed diverse moderate to powerful antimicrobial and antioxidant activities. Results of MTT assay revealed that seven synthesized compounds (i.e., 11a, 11b, 12a, 12b, 13b, 13c and 13h) particularly exhibited significant cytotoxicity against the three cancerous cell lines under investigation. Ranges of IC 50 values obtained were 5.7-21.3 and 5.8-37.4 µg/mL against HCT-116 and MCF-7, respectively; which is 3.8 and 6.5-fold (based on the least IC 50 values) more significant relative to the reference chemotherapeutic drug doxorubicin. In HepG-2 cells, the analogue 13h exhibited the highest cytotoxicity with IC 50 value of 19.2µg/mL relative to doxorubicin (IC 50 = 21.6µg/mL). The observed cytotoxicity was specific to cancerous cells, as evidenced by the minimal toxicity in the noncancerous control skin-fibroblast cells. ELISA results indicated that the observed antiproliferative effect against examined cancer cell lines is mediated via engaging the activation of apoptosis as illustrated by the significant increase in proapoptotic protein markers (p53, bax and caspase-3) and reduction in the antiapoptotic marker bcl-2. Taken together, results of the present study emphasize the potential of spiro pyrazole-oxindole analogues as valuable candidate anticancer agents against human cancer cells.

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Oxindole as starting material in organic synthesis

Cited by 68 publications

References 37 publications

μ-Oxo-Hypervalent-Iodine-Catalyzed Oxidative C–H Amination for Synthesis of Benzolactam Derivatives

μ-Oxo-Hypervalent-Iodine-Catalyzed Oxidative C–H Amination for Synthesis of Benzolactam Derivatives

Recent Achievements in the Synthesis of Heterocyclic Compounds by Phthalhydrazide-Based Multicomponent Reactions

Synthesis and Bioactivity Assessment of Novel Spiro Pyrazole-Oxindole Congeners Exhibiting Potent and Selective in vitro Anticancer Effects

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