20772-56-9Relevant articles and documents
Total synthesis of (-)-spirotryprostatin B: Synthesis and related studies
Marti, Christiane,Carreira, Erick M.
, p. 11505 - 11515 (2005)
The total synthesis of spirotryprostatin B, a cytostatic spiro[pyrrolidine-3,3′-oxindole] alkaloid, is described. The key step of the synthetic approach consists of the application of the Mgl 2-mediated ring-expansion reaction of a spiro[cyclopropane-1, 3′-oxindole] with an aldimine, leading to rapid assembly of the spirotryprostatin core. The route documents the installation of the prenyl side chain by Julia-Kocienski olefination of a key aldehyde precursor, a transformation that ultimately allows for facile synthesis of analogues and facilitates structure-activity relationships studies.
A method for preparing [...] (by machine translation)
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Paragraph 0023-0026; 0031; 0033-0034; 0039; 0041-0042, (2019/05/29)
The invention relates to a method for preparing [...], comprising the following steps: S1. The nucleophilic substitution reaction: to propylene glycol and thionyl chloride as the starting material, chloroform as solvent, the nucleophilic substitution reaction, by the sulfurous acid propylene chloroform solution; S2. Oxidation reaction: high iodic acid as the oxidizing agent, the ruthenium trichloride hydrate catalyst, to S1 to obtain solution in the oxidation process is performed on the sulfurous acid propylene shall [...]; S3. The refined purification: sulfuric acid propylene crude soluble in chloroform, under the protection of nitrogen, heating to reflux is fully dissolved, then lower the temperature crystallization, filtering, filters the cake to pass through reduced-pressure drying, to obtain. The mild reaction conditions of the present invention, the synthetic process is simple, easy to operate, high safety, preparation cycle is short, the raw materials used are simple and easy to obtain, the cost is low, few by-products, the preparation of the product has high purity, low water content, low acid value of the product, the product yield is high, and is suitable for industrial production. (by machine translation)
Potent ketoamide inhibitors of HCV NS3 protease derived from quaternized P1 groups
Venkatraman, Srikanth,Velazquez, Francisco,Wu, Wanli,Blackman, Melissa,Madison, Vincent,Njoroge, F. George
scheme or table, p. 2151 - 2155 (2010/06/19)
Blood borne hepatitis C infections are the primary cause for liver cirrhosis and hepatocellular carcinoma. HCV NS3 protease, a pivotal enzyme in the replication cycle of HCV virus has been the primary target for development of new drug candidates. Boceprevir and telaprevir are two novel ketoamide derived inhibitors that are currently undergoing phase-III clinical trials. These inhibitors include ketoamide functionality as serine trap and have an acidic alpha-ketoamide center that undergoes epimerization under physiological conditions. Our initial attempts to arrest this epimerization by introducing quaternary amino acids at P1 had resulted in significantly diminished activity. In this manuscript we describe alpha quaternized P1 group that result in potent inhibitors in the enzyme assay and demonstrate cellular activity comparable to boceprevir.
