A new diketopiperazine dimer designated as SF5280-415 (1) was isolated from an EtOAc extract of the marine-derived fungus Aspergillus sp. SF-5280 by various chromatographic methods. The structure of 1 was mainly determined by analysis of the NMR spectroscopic data and MS data, along with Marfey's method. This compound is a new diastereoisomer of known bispyrrolidinoindoline diketopiperazine alkaloid WIN 64745, which possesses unique architecture biosynthetically derived from an indole oxidation reaction of tryptophan.

22 Jan 2016·Chemistry – A European JournalQ2 · CHEMISTRY

Collective Synthesis and Biological Evaluation of Tryptophan‐Based Dimeric Diketopiperazine Alkaloids

Q2 · CHEMISTRY

Article

Author: Sumimoto, Michinori ; Tadano, Shinji ; Tsukamoto, Sachiko ; Ishikawa, Hayato ; Sugimachi, Yukihiro

AbstractA concise two one‐pot synthesis of WIN 64821, eurocristatine, 15,15′‐bis‐epi‐eurocristatine, ditryptophenaline, ditryptoleucine A, WIN 64745, cristatumin C, asperdimin, naseseazine A, and naseseazine B is detailed, based on a unique bioinspired dimerization reaction of tryptophan derivatives in aqueous acidic solution and a one‐pot procedure for the construction of diketopiperazine rings. Total yields of these alkaloid syntheses were from 10 up to 27 %. In addition, 1′‐(2‐phenylethylene)‐ditryptophenaline was synthesized by using three one‐pot operations. The studies detailed herein provided synthesized natural products for inhibitory activities of ubiquitin‐specific protease 7 (USP7) and foam cell formation in macrophages. The newly listed biological evaluation for tryptophan‐based dimeric diketopiperazine alkaloids discovered 15,15′‐bis‐epi‐eurocristatine, 1′‐(2‐phenylethylene)‐ditryptophenaline, and WIN 64745 as new drug candidates.

28 Sep 2009·Chemistry – A European JournalQ2 · CHEMISTRY

Stereocontrolled and Versatile Total Synthesis of Bispyrrolidinoindoline Diketopiperazine Alkaloids: Structural Revision of the Fungal Isolate (+)‐Asperdimin

Q2 · CHEMISTRY

Article

Author: Paula Rodríguez-Graña ; Carlos Pérez-Balado ; Ángel R. de Lera

AbstractHomo‐ and heterodimeric bispyrrolidinoindoline diketopiperazine alkaloids have been synthesized following a concise, versatile, and stereoselective route. Highlights of the sequence are a diastereoselective construction of the C3a‐bromo‐hexahydropyrrolo[2,3‐b]indole nucleus, its CoI‐induced C3aC3a′ dimerization, and the twofold or sequential amide‐bond formation before cyclization to the diketopiperazine of the homo‐ or heterodimeric alkaloids, respectively. Stereochemical diversity is achieved through the choice of the appropriate amino acids combined with the base‐induced epimerization of the C2‐acyl‐hexahydropyrrolo[2,3‐b]indole at C2. According to this strategy, the natural products (+)‐WIN 64821 1, (+)‐WIN 64745 2 and (+)‐asperdimin 6 as well as analogues (5, 22, 32, 44) with different relative and absolute configuration have been efficiently synthesized. The flexibility of this synthetic methodology has facilitated the structural revision of the natural product (+)‐asperdimin, whose structure has been corrected to diastereomer 6.

100 Deals associated with WIN-64745

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Indication	Highest Phase	Country/Location	Organization	Date
Asthma	Discovery	US	Sterling Winthrop Products, Inc.	-
Inflammatory Bowel Diseases	Discovery	US	Sterling Winthrop Products, Inc.	-
Rheumatoid Arthritis	Discovery	US	Sterling Winthrop Products, Inc.	-

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