Cephalostatin Analogues — Synthesis and Biological Activity

Flessner, Timo; Jautelat, Rolf; Scholz, Ulrich; Winterfeldt, Ekkehard

doi:10.1007/978-3-7091-0581-8_1

Progress in the Chemistry of Organic Natural Products 2004

DOI: 10.1007/978-3-7091-0581-8_1

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Cephalostatin Analogues — Synthesis and Biological Activity

Timo Flessner

Rolf Jautelat²,

Ulrich Scholz

et al.

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Cited by 12 publications

References 86 publications

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Ritterostatin G_N1_N, a Cephalostatin–Ritterazine Bis‐steroidal Pyrazine Hybrid, Selectively Targets GRP78

et al. 2017

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Natural products discovered using agnostic approaches, unlike rationally designed or HTS obtained leads, offer the ability to reveal new biological pathways, and hence, serve as an important vehicle to unveil new avenues in drug discovery. The ritterazine-cephalostatin family of natural products displays robust and potent anti-tumor activities, with sub-nanomolar growth inhibition against multiple cell lines and potent activity in xenograft models. Herein, we use comparative cellular and molecular biological methods to uncover the ritterazine/cephalostatin mode of cytotoxic action (MOA) in human tumor cells. Our findings indicate that while ritterostatin GN1N, a cephalostatin-ritterazine hybrid, binds to multiple HSP70s, its cellular trafficking confines activity to the endoplasmic reticulum (ER) based HSP70 isoform, GRP78. This targeting results in activation of the unfolding protein response (UPR) and subsequent apoptotic cell death.

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Ritterostatin G_N1_N, a Cephalostatin–Ritterazine Bis‐steroidal Pyrazine Hybrid, Selectively Targets GRP78

et al. 2017

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Cephalostatin Analogues — Synthesis and Biological Activity

et al. 2005

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Palladium-catalyzed diaminocarbonylation: synthesis of androstene dimers containing 3,3′- or 17,17′-dicarboxamide spacers

et al. 2014

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Novel androstene-based dimers linked through A-and D-ring with 3,3 0 -and 17,17 0 -dicarboxamide spacers, were synthesized via palladium-catalyzed aminocarbonylation. Androstane derivatives possessing either 3-iodo-3,5-diene or 17-iodo-16-ene functionality were used as substrates in the presence of palladium-phosphine in situ catalysts and aliphatic and aromatic diamines as N-nucleophiles. Since androst-4-ene-3,17-dione was used as starting material, a multistep synthesis including protection/deprotection of one of the keto functionalities (3-one or 17-one) as ethylene ketals, transformation of the other keto group to iodoalkene functionality via its hydrazone, and palladium-catalyzed aminocarbonylation of the iodoalkene functionality was used. In this way, new dimeric compounds possessing a keto functionality were obtained in moderate-to-good isolated yields, via highly chemoselective reactions, under relatively mild conditions.

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Cephalostatin Analogues — Synthesis and Biological Activity

Cited by 12 publications

References 86 publications

Ritterostatin G_N1_N, a Cephalostatin–Ritterazine Bis‐steroidal Pyrazine Hybrid, Selectively Targets GRP78

Ritterostatin G_N1_N, a Cephalostatin–Ritterazine Bis‐steroidal Pyrazine Hybrid, Selectively Targets GRP78

Cephalostatin Analogues — Synthesis and Biological Activity

Palladium-catalyzed diaminocarbonylation: synthesis of androstene dimers containing 3,3′- or 17,17′-dicarboxamide spacers

Contact Info

Product

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About

Cephalostatin Analogues — Synthesis and Biological Activity

Cited by 12 publications

References 86 publications

Ritterostatin GN1N, a Cephalostatin–Ritterazine Bis‐steroidal Pyrazine Hybrid, Selectively Targets GRP78

Ritterostatin GN1N, a Cephalostatin–Ritterazine Bis‐steroidal Pyrazine Hybrid, Selectively Targets GRP78

Cephalostatin Analogues — Synthesis and Biological Activity

Palladium-catalyzed diaminocarbonylation: synthesis of androstene dimers containing 3,3′- or 17,17′-dicarboxamide spacers

Contact Info

Product

Resources

About

Ritterostatin G_N1_N, a Cephalostatin–Ritterazine Bis‐steroidal Pyrazine Hybrid, Selectively Targets GRP78

Ritterostatin G_N1_N, a Cephalostatin–Ritterazine Bis‐steroidal Pyrazine Hybrid, Selectively Targets GRP78