4147-36-8

Upstream product

• 58635-45-3 methyl 2-(1-H-indol-3-yl)ethylcarbamate 
• 61-49-4 [2-(1H-indol-3-yl)-ethyl]-methylamine 
• 444809-68-1 (3aS,8aS,3'aS,8'aS)-8-((S)-1-Phenyl-ethylcarbamoyl)-2,3,8,8a,2',3',8',8'a-octahydro-[3a,3'a]bi[pyrrolo[2,3-b]indolyl]-1,1'-dicarboxylic acid dimethyl ester 
• 444809-69-2 (3aR,8aR,3'aR,8'aR)-8-((S)-1-Phenyl-ethylcarbamoyl)-2,3,8,8a,2',3',8',8'a-octahydro-[3a,3'a]bi[pyrrolo[2,3-b]indolyl]-1,1'-dicarboxylic acid dimethyl ester 

Downstream Products

• 595-05-1 Calycanthin 
• 595-05-1 (4bR,5S,10bR,11S)-13,18-dimethyl-5,6,11,12-tetrahydro-5,10b:11,4b-bis(epiminoethano)dibenzo[c,h][2,6]naphthyridine 

Relevant academic research and scientific papers

Collective synthesis and biological evaluation of tryptophan-based dimeric diketopiperazine alkaloids

A 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. All in one: A concise synthesis of tryptophan-based dimeric diketopiperazine alkaloids (see scheme) is detailed based on a unique bioinspired dimerization reaction of tryptophan derivatives and a one-pot procedure for construction of diketopiperazine rings. Some of the synthetic alkaloids were discovered as new drug candidates for cancer or atherosclerosis therapy.

Dimerization of indole derivatives with hypervalent iodines(III): A new entry for the concise total synthesis of rac- and meso-chimonanthines

Hypervalent iodine(III)-induced dimerization of indole derivatives, mitragynine, tetrahydrocarbazole, and Nb-carbomethoxytryptamine, was investigated. By applying this procedure, the concise total synthesis of rac- and meso-chimonanthines was accomplished.

Synthesis and antinociceptive activity of chimonanthines and pyrrolidinoindoline-type alkaloids

Hodgkinsine, a trimeric pyrrolidinoindoline type alkaloid, present as a major constituent of Psychotria spp. (Rubiaceae), has shown to produce dose-dependent, naloxone reversible, analgesic effect in thermal models of nociception and in the capsaicin-induced pain. SAR studies have been initiated by synthesizing the three diastereomeric dimers (chimonanthines) (11-13) which were evaluated in vitro and in vivo along with the synthetic intermediates. Strong binding affinities for μ opioid receptors were found for (-)- and (+)-chimonanthine monourethanes (9 and 10), whereas (-)-, (+)- and (meso)-chimonanthine (11-13) and hodgkinsine displayed low affinity. In vivo data have shown that only (+)-chimonanthine (12) and calycosidine resemble the analgesic profile found for hodgkinsine.