A novel total synthesis of isocryptolepine based on a microwave-assisted tandem Curtius rearrangement and aza-electrocyclic reaction

Kaori, Hayashi; Choshi, Tominari; Chikaraishi, Kyoko; Oda, Aimi; Yoshinaga, Rikako; Hatae, Noriyuki; Ishikura, Minoru; Hibino, Satoshi

doi:10.1016/j.tet.2012.03.055

Cited by 55 publications

(34 citation statements)

References 47 publications

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“…16 Hibino and co-workers prepared isoindoloindolone by employing Suzuki-Miyaura reaction of N-Boc-indole-boronic acid 5 and methyl-o-iodobenzoate 6 to give N-Boc-indole esters 7 followed by deprotection to give prominent precursor 8 and finally base mediated cyclisation to isoindoloindolones (Scheme 2). 19 The method was further modified to complete the total synthesis of indoloquinoline alkaloid isocryptolepine. Bao's group 20 reported a synthesis of isoindoloindolones through one-pot sequential Cu catalyzed C-N coupling and Pd catalyzed C-H activation reaction (Scheme 3).…”

Section: Palladium Catalyzed Coupling Reactionsmentioning

confidence: 99%

Isoindoloindolones - biological activities and syntheses

Kadam¹,

Tilve

2015

Arkivoc

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Section: Palladium Catalyzed Coupling Reactionsmentioning

confidence: 99%

Isoindoloindolones - biological activities and syntheses

Kadam¹,

Tilve

2015

Arkivoc

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“…A similar approach was later reported by Kumar in 2009 55 using 1-methyl-1,2,3,4-tetrahydroquinolin-4-one and phenylhydrazine. Furthermore, a multistep method was described by Choshi, Hibino et al 56 for isocryptolepine using the methyl 2-(indol-2-yl)benzoate, in which the microwave-assisted tandem Curtius rearrangement and electrocyclic ring closure of an aza 6π-electron system was employed as the key operation.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis, β-haematin inhibition, and in vitro antimalarial testing of isocryptolepine analogues: SAR study of indolo[3,2-c]quinolines with various substituents at C2, C6, and N11

Wang

Wicht

Imai

et al. 2014

Bioorganic & Medicinal Chemistry

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A series of indolo[3,2-c]quinolines were synthesized by modifying the side chains of the ω-aminoalkylamines at the C6 position and introducing substituents at the C2 position, such as F, Cl, Br, Me, MeO and NO2, and a methyl group at the N11 position for an SAR study. The in vitro antiplasmodial activities of the derivative agents against two different strains (CQS: NF54 and CQR: K1) and the cytotoxic activity against normal L6 cells were evaluated. The test results showed that compounds 6k and 6l containing the branched methyl groups of 3-aminopropylamino at C6 with a Cl atom at C2 exhibited a very low cytotoxicity with IC50 values above 4000 nM, high antimalarial activities with IC50 values of about 11 nM for CQS (NF54), IC50 values of about 17 nM for CQR (K1), and RI resistance indices of 1.6. Furthermore, the compounds were tested for β-haematic inhibition, and QSAR revealed an interesting linear correlation between the biological activity of CQS (NF54) and three contributing factors, namely solubility, hydrophilic surface area, and β-haematin inhibition for this series. In vivo testing of 6l showed a reduction in parasitaemia on day 4 with an activity of 38%.

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“…[70][71][72][73] They can also be used in cycloaddition or electrocyclization. [74][75][76][77][78][79] Introduced in 1972 by Yamada, the use of diphenylphosphoryl azide (DPPA) allows ester activation, azidation and Curtius rearrangement to be easily done in one-pot, facilitating the access towards isocyanates. 80,81 However, its use for the desymmetrization of bis-carboxylic acid carbocycles has been scarcely reported.…”

Section: Introductionmentioning

confidence: 99%