5545-89-1

Basic information

• Product Name: chimonanthine
• Synonyms: chimonanthine;(3aS,3'aS,8aS,8'aS)-3a,3'a-Bi[1-methyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole];1-Demethylcalycanthidine;3a,3'a-Bi[(3aS,8aS)-1-methyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole];Chimonanthin;l-Chimonanthine
• CAS NO: 5545-89-1
• Molecular Formula: C₂₂H₂₆N₄
• Molecular Weight: 346.46864
• Mol File: 5545-89-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 188-189°
• Boiling Point: 490.9°Cat760mmHg
• Flash Point: 272.5°C
• Appearance: /
• Density: 1.224g/cm³
• CAS DataBase Reference: chimonanthine(CAS DataBase Reference)
• NIST Chemistry Reference: chimonanthine(5545-89-1)
• EPA Substance Registry System: chimonanthine(5545-89-1)

Safety Data

• Hazardous Substances Data: 5545-89-1(Hazardous Substances Data)

Usage

Definition

ChEBI: The (3aS,3a'S,8aS,8a'S)-stereoisomer of chimonanthine.

Upstream product

• 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 
• 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 
• 58635-45-3 methyl 2-(1-H-indol-3-yl)ethylcarbamate 
• 61-49-4 [2-(1H-indol-3-yl)-ethyl]-methylamine 

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 articles and documents

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.

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.