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Literature DB >> 10091695

On the relationship of OSW-1 to the cephalostatins.

Abstract

Antineoplastic bis-steroidal (cephalostatin-type) analogues of the saponin OSW-1 were produced from a dihydroaglycone of OSW-1. The key aglycone 6H was obtained from 5alpha-androstan-3beta-ol-17-one in 8 steps (38% yield). The SAR of the aglycones, intermediates, and hybrid analogues provide insights regarding the proposed common role of C22-oxocarbenium ions in the bioactivity of both OSW-1 and cephalostatins.

Entities: Chemical Disease

Mesh：

Substances：

Year: 1999 PMID： 10091695 DOI： 10.1016/s0960-894x(98)00743-4

Source DB: PubMed Journal: Bioorg Med Chem Lett ISSN： 0960-894X Impact factor: 2.823

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Cited

8 in total

1. A total synthesis of OSW-1.

Authors: Jie Xue; Peng Liu; Yanbin Pan; Zhongwu Guo
Journal: J Org Chem Date: 2007-12-08 Impact factor: 4.354

Review 2. Chemistry of trisdecacyclic pyrazine antineoplastics: the cephalostatins and ritterazines.

Authors: Seongmin Lee; Thomas G LaCour; Philip L Fuchs
Journal: Chem Rev Date: 2009-06 Impact factor: 60.622

3. Synthesis and evaluation of a fluorescent ritterazine-cephalostatin hybrid.

Authors: Kanduluru Ananda Kumar; James J La Clair; Philip L Fuchs
Journal: Org Lett Date: 2011-09-14 Impact factor: 6.005

4. Ritterostatin G_N 1_N , a Cephalostatin-Ritterazine Bis-steroidal Pyrazine Hybrid, Selectively Targets GRP78.

Authors: Andrew J Ambrose; Evelyne A Santos; Paula C Jimenez; Danilo D Rocha; Diego V Wilke; Paolo Beuzer; Josh Axelrod; Ananda Kumar Kanduluru; Philip L Fuchs; Hu Cang; Letícia V Costa-Lotufo; Eli Chapman; James J La Clair
Journal: Chembiochem Date: 2017-02-02 Impact factor: 3.164

On the relationship of OSW-1 to the cephalostatins.

1. A total synthesis of OSW-1.

Review 2. Chemistry of trisdecacyclic pyrazine antineoplastics: the cephalostatins and ritterazines.

3. Synthesis and evaluation of a fluorescent ritterazine-cephalostatin hybrid.

4. Ritterostatin G_N 1_N , a Cephalostatin-Ritterazine Bis-steroidal Pyrazine Hybrid, Selectively Targets GRP78.

5. The cephalostatins. 22. synthesis of bis-steroidal pyrazine pyrones (1).

Review 6. Preferential killing of cancer cells with mitochondrial dysfunction by natural compounds.

7. The cephalostatins. 21. Synthesis of bis-steroidal pyrazine rhamnosides (1).

8. Synthesis of biotinylated OSW-1.

On the relationship of OSW-1 to the cephalostatins.

1. A total synthesis of OSW-1.

Review 2. Chemistry of trisdecacyclic pyrazine antineoplastics: the cephalostatins and ritterazines.

3. Synthesis and evaluation of a fluorescent ritterazine-cephalostatin hybrid.

4. Ritterostatin GN 1N , a Cephalostatin-Ritterazine Bis-steroidal Pyrazine Hybrid, Selectively Targets GRP78.

5. The cephalostatins. 22. synthesis of bis-steroidal pyrazine pyrones (1).

Review 6. Preferential killing of cancer cells with mitochondrial dysfunction by natural compounds.

7. The cephalostatins. 21. Synthesis of bis-steroidal pyrazine rhamnosides (1).

8. Synthesis of biotinylated OSW-1.

4. Ritterostatin G_N 1_N , a Cephalostatin-Ritterazine Bis-steroidal Pyrazine Hybrid, Selectively Targets GRP78.