Synthetic Approaches to Ellipticines and Other Derivatives and Analogues of 6<i>H</i>-Pyrido[4,3-<i>b</i>]carbazole

Hewlins, M. J. E.; Oliveira-Campos, Ana-M.; Shannon, P. V. R.

doi:10.1055/s-1984-30816

Cited by 64 publications

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“…Synthetic strategies leading to ellipticine are usually classified according to the construction of the last ring as B, C, D, and B þ C types [7][8][9][10]. One of the most versatile ''D-type'' routes to ellipticine starting from appropriately substituted indoles or carbazoles is due to Cranwell and Saxton [11], and subsequently, a number of important modifications have increased the utility of this route further [12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Modifications to the Vilsmeier‐Haack formylation of 1,4‐dimethylcarbazole and its application to the synthesis of ellipticines

Deane

Miller

Maguire

et al. 2011

Journal of Heterocyclic Chem

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An improved method for the preparation of 3‐formyl‐1,4‐dimethylcarbazole, a key intermediate in the synthesis of ellipticine, is presented. Conditions of the Vilsmeier‐Haack reaction have been modified to facilitate the production of 3‐formyl‐1,4‐dimethylcarbazole as a major product leading to an overall improvement in yield of ellipticine from 3% to 14%. This approach was also applied to the synthesis of 6‐methylellipticine and 9‐methoxyellipticine. J. Heterocyclic Chem., (2011).

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Section: Introductionmentioning

confidence: 99%

Modifications to the Vilsmeier‐Haack formylation of 1,4‐dimethylcarbazole and its application to the synthesis of ellipticines

Deane

Miller

Maguire

et al. 2011

Journal of Heterocyclic Chem

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“…In recent times 2,3-disubstituted indoles have been used as bidentate synthons for the synthesis of various medicinally important carbazole alkaloids. In carbazole derivatives, the preliminary study showed that the presence of oxygenated substituents on the carbazole ring increases their biological activity [3]. The structures of these derivatives are analogous to that of ellipticine, a plant alkaloid having pronounced anti-tumour activity [4] and are found to have DNA intercalating properties [5][6][7].…”

Section: Introductionmentioning

confidence: 99%

Crystal structure of 3‐hydroxy methyl 4,6‐dimethoxy‐9‐phenylsulfonyl‐carbazole

Govindasamy¹,

Rajakannan²,

Velmurugan³

et al. 2003

Cryst. Res. Technol.

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“…Construction of the tetracyclic structure was achieved by a new route and two important precursor compounds (4a and 4b) for the synthesis of pyridocarbazole alkaloids and also many new tetrahydrocarbazole derivatives (7,8,9,10,11,12,13) were synthesized.J. Heterocyclic Chem., 40, 1005Chem., 40, (2003.…”

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confidence: 99%

“…Especially 1-substituted ellipticines with dialkylamino-alkylamino side chain such as compound 3 have higher antitumor activity on L1210 leukaemia in mice with lower cardiovascular effect compared with the parent ellipticines [5][6][7]. Therefore, many chemists have paid great attention to the synthesis of 6H-pyrido [4,3-b]carbazole alkaloids [8][9][10][11][12]. The 6H-pyrido [4,3-b]carbazole alkaloids are tetracyclic.…”

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A novel synthetic approach for the synthesis of pyridocarbazole alkaloids

Ergün

Okaya

Patir

2003

Journal of Heterocyclic Chem

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The synthesis of 11-methyl-6H-pyrido [4,3-b]carbazole-1(2H)-one (5), which can be important for the synthesis of other pyridocarbazole alkaloids and especially 1-substituted ellipticines, is described. Construction of the tetracyclic structure was achieved by a new route and two important precursor compounds (4a and 4b) for the synthesis of pyridocarbazole alkaloids and also many new tetrahydrocarbazole derivatives (7,8,9,10,11,12,13) were synthesized.J. Heterocyclic Chem., 40, 1005Chem., 40, (2003.The 6H-pyrido [4,3-b]carbazole alkaloids, ellipticine (1a), olivacine (1b) and their derivatives such as janetine (2a) and guatambuine (2b), occur in the genera Ochrasia, Aspidosperma, Tabernaemontana which are members of the family Apocynnaceae [1]. These alkaloids display pronounced antitumor activity in several animal and human tumor systems [2][3][4]. Especially 1-substituted ellipticines with dialkylamino-alkylamino side chain such as compound 3 have higher antitumor activity on L1210 leukaemia in mice with lower cardiovascular effect compared with the parent ellipticines [5][6][7]. Therefore, many chemists have paid great attention to the synthesis of 6H-pyrido [4,3-b]carbazole alkaloids [8][9][10][11][12]. The 6H-pyrido [4,3-b]carbazole alkaloids are tetracyclic. The synthetic strategies for the preparation of the tetracyclic 6H-pyrido [4,3-b]carbazole alkaloids are classified in four main groups, such as B type, C type, B+C type and D type, based upon the last ring to be constructed [13,14].The B type synthesis includes Goldberg's coupling of substituted nitro anilines with a bromo isoquinoline derivative. The B ring is constructed with the subsequent reactions [15]. In the C type of synthesis, Diels-Alder reaction plays a role between pyrano[3,4-b]indol-3-one and arynes [16]. The B+C type of synthesis covers an intramolecular Diels-Alder cycloaddition of an acetylenic vinylketeneimine as a key step in constructing the B+C ring of the ellipticine or its derivatives simultaneously [17]. In the D type of synthesis, ellipticine and its derivatives are synthesized by the intramolecular aromatic electrophilic substitution reaction with suitable carbazole derivatives [18,19].In this work, we used a D type of synthetic strategy and developed a novel approach. All of the previous studies on D type of synthesis construct the D ring in the final step using the intramolecular aromatic electrophilic substitution reaction. In the present work we first achieved the construction of the D ring both with an intramolecular condensation reaction between an ester and a ketone group on the tetrahydrocarbazole derivative (Scheme 1) and with intramolecular aldol condensation reaction between an aldehyde and ketone group on the tetrahydrocarbazole derivative (Scheme 2). Thus we synthesized two new precursor compounds 4a and 4b which can be a useful key intermediate for the synthesis of 6H-pyrido [4,3-b]carbazole alkaloids using a new synthetic approach. Finally we accomplished the synthesis of 11-methyl-6H-pyrido [4,3-b]carbazole-1(...

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Synthetic Approaches to Ellipticines and Other Derivatives and Analogues of 6H-Pyrido[4,3-b]carbazole

Cited by 64 publications

References 0 publications

Modifications to the Vilsmeier‐Haack formylation of 1,4‐dimethylcarbazole and its application to the synthesis of ellipticines

Modifications to the Vilsmeier‐Haack formylation of 1,4‐dimethylcarbazole and its application to the synthesis of ellipticines

Crystal structure of 3‐hydroxy methyl 4,6‐dimethoxy‐9‐phenylsulfonyl‐carbazole

A novel synthetic approach for the synthesis of pyridocarbazole alkaloids

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