A new synthesis of α‐substituted δ‐carbolines

Arzel, Erwan; Rocca, Patrick; Marsais, Francis; Godard, Alain; Quéguiner, G.

doi:10.1002/jhet.5570340418

Cited by 20 publications

(7 citation statements)

References 16 publications

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“…72 Essentially the same kind of approach to the general synthesis of a-substituted d-carbolines proceeds via palladiumcatalysed cross-coupling of a boronic acid and a fluoroiodopyridine. 73 A new synthesis of isocryptolepine 52 by Joule and coworkers 74 utilizes palladium(0) coupling and intramolecular Vilsmeier reaction as key steps. Choosing an appropriate protecting group, 2-(trimethylsilyl)ethoxymethyl (SEM), for the indole nitrogen was crucial for the ring closing Vilsmeier step (Scheme 5).…”

Section: Indoloquinolines Several Indoloquinoline-type Alkaloids Have...mentioning

confidence: 99%

Simple indole alkaloids and those with a nonrearranged monoterpenoid unit (July 1997 to December 1998)

Lounasmaa¹,

Tolvanen²

2000

Nat. Prod. Rep.

229

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Introduction 2 Simple indole alkaloids 2.1 Non-tryptamines 2.1.1 Indole auxins and phytoalexins 2.1.2 Mitomycin C and related compounds 2.1.3 Carbazoles 2.1.4 Indoloquinolines 2.2 Non-isoprenoid tryptamines 2.2.1 Piperazinediones 2.2.2 Physostigmine and related compounds 2.2.3 Indoloiminoquinones 2.2.4 b-Carbolines 2.2.5 Canthinones and indolopyridoquinazolines 3 Isoprenoid tryptamines 3.1 Ergot alkaloids 4 Bisindoles 4.1 Indolocarbazoles 4.2 Duocarmycins 4.3 Dimeric b-carbolines 5 Peptide alkaloids containing a tryptophan residue 6 Indole alkaloids with a nonrearranged monoterpenoid unit 7 References

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Section: Indoloquinolines Several Indoloquinoline-type Alkaloids Have...mentioning

confidence: 99%

Simple indole alkaloids and those with a nonrearranged monoterpenoid unit (July 1997 to December 1998)

Lounasmaa¹,

Tolvanen²

2000

Nat. Prod. Rep.

229

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“…20 Moreover, some quindoline derivatives have been described as potent antitumor-active compounds. 21 Recently, we described 22,23 a new synthesis of R-substituted, β-substituted, and R,β-disubstituted δ-carbolines (Table 1). This synthesis was based on metalation and cross-coupling reactions, starting with simple benzene and pyridine blocks.…”

Section: Introductionmentioning

confidence: 99%

New Synthesis of Benzo-δ-carbolines, Cryptolepines, and Their Salts: In Vitro Cytotoxic, Antiplasmodial, and Antitrypanosomal Activities of δ-Carbolines, Benzo-δ-carbolines, and Cryptolepines

et al. 2001

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The paper describes, in its first part, a new synthesis of benzo-delta-carbolines, cryptolepines, and their salts. The strategy is based on the association between halogen-dance and hetero-ring cross-coupling. It is fully convergent and regioselective with interesting overall yields from 27% to 70%. A halogen-dance mechanism in quinoline series is also proposed. The formal synthesis of potential antimalarial compounds and the first total synthesis of 11-isopropylcryptolepine are also described. In the second part, cytotoxic activity against mammalian cells and activities against Plasmodium falciparum and Trypanosoma cruzi of benzo-delta-carbolines and delta-carbolines were evaluated in vitro to study the structure-activity relationships. For benzo-delta-carbolines, methylation at N-5 increases the cytotoxic and antiparasitic activities. A further alkylation on C-11 generally increases the cytotoxic activity but not the antiparasitic activity, cryptolepine and 11-methylcryptolepine being the most active on both parasites. Taking advantage of the fluorescence of the indoloquinoline chromophore, cryptolepine was localized by fluorescence microscopy in parasite DNA-containing structures suggesting that these compounds act through interaction with parasite DNA as proposed for cryptolepine on melanoma cells. For delta-carbolines, methylation at N-1 is essential for the antimalarial activity. 1-Methyl-delta-carboline specifically accumulates in the intracellular parasite. It has weak cytotoxic activity and can be considered as a potential antimalarial compound.

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“…The classical Fischer and Graebe–Ullmann reactions have been used for single examples of the synthesis of only unsubstituted δ‐carbolines, which is due to the inaccessibility of other starting materials for these reactions . A majority of substituted δ‐carbolines has been synthesized using six reactions such as the Rh II 2 ‐catalyzed thermolysis reaction of 1‐methyl‐2‐(2‐azidoaryl)pyridinium triflate obtained by Suzuki cross coupling‐azidation‐methylation scheme; the arylation of 3‐aminopyridines (Buchwald–Hartwig reaction) and subsequent intramolecular closure of the pyrrole ring using palladium acetate to form a C–C bond; the intramolecular reaction of nucleophilic substitution of the fluorine atom in the position 3 of the pyridine core with the o ‐amino and pivaloylamino group of the phenyl substituent; the Pd‐catalyzed reaction of 2‐iodoanilines with N ‐tosylenynamines and the Ni‐catalyzed [2+2+2] cycloaddition of internal alkynes to o ‐ N ‐(tosyl)alkynylbenzonitriles; the three‐component reaction of 1‐acetylindolin‐3‐ones, β,γ‐unsaturated α‐ketoesters and amines under aerobic conditions; the reductive Cadogan cyclization of 2‐aryl‐3‐nitropyridines obtained by the five steps from a minor product in the nitration of 2‐aminopyridine …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Optical Properties of Alkaloid Quindoline, Its Structural Analogues and Substituted δ‐Carbolines

et al. 2019

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Alkaloid quindoline, its structural analogues and δ-carbolines were obtained through the Cadogan reaction using DPPE under solvent-free conditions as a key stage of the synthesis.Various o-nitroarylpyridines prepared by one-pot synthesis from nitroacetophenones, methyl orthoformate and acetoacetic ester enamine were used as starting materials for the preparation of δ-carbolines. 2-Aryl-3-nitro-5,6,7,8-tetrahydroquinolines obtained by reacting 2-hydroxymethylenecyclohexanone with nitroacetophenones enamines were used for the synthesis of quindoline and its structural analogs. A relationship between the structure and optical properties of the synthesized compounds was found.

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A new synthesis of α‐substituted δ‐carbolines

Abstract: The paper describes a new general synthesis of α‐substituted δ‐carbolines based on key steps such as metalation, cross‐coupling and cyclization.

Cited by 20 publications

References 16 publications

Simple indole alkaloids and those with a nonrearranged monoterpenoid unit (July 1997 to December 1998)

Simple indole alkaloids and those with a nonrearranged monoterpenoid unit (July 1997 to December 1998)

New Synthesis of Benzo-δ-carbolines, Cryptolepines, and Their Salts: In Vitro Cytotoxic, Antiplasmodial, and Antitrypanosomal Activities of δ-Carbolines, Benzo-δ-carbolines, and Cryptolepines

Synthesis and Optical Properties of Alkaloid Quindoline, Its Structural Analogues and Substituted δ‐Carbolines

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