903575-58-6

Upstream product

• 14907-27-8 (R)-(+)-tryptophan methyl ester hydrochloride 
• 100-52-7 benzaldehyde 
• 153-94-6 D-tryptophan 
• 1453864-01-1 (1S,3S)-methyl 1-phenyl-2-(naphthalen-1-ylmethyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate 
• 91200-21-4 (1S,3S)-methyl 1-phenyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-3-carboxylate 
• 4299-70-1 D-Tryptophan methyl ester 
• 31771-33-2 2-phenyl-4,4,6-trimethyltetrahydro-(2H)-1,3-oxazine 
• 4299-70-1 L-tryptophan methyl ester 

Relevant academic research and scientific papers

Discovery of novel phosphatidylcholine-specific phospholipase C drug-like inhibitors as potential anticancer agents

Phosphatidylcholine–specific phospholipase C (PC-PLC) is a promising target for new anticancer treatment. Herein, we report our work in the discovery of novel drug-like PC-PLC inhibitors. Virtual screening led to the identification of promising hits from

Aryl substituted 1 H - pyrido [3, 4 - b] indole -3 - carboxylic acid methyl ester chiral separation of (by machine translation)

The invention discloses a toS- 1 - (2 - Tert-butyl phenyl) ethylamine is chiral resolving agent, one category of containing two chiral centers 1 - aryl - 1 H - pyrido [3, 4 - b] indole - 3 - carboxylic acid methyl ester non-enantiomers on chiral separation method. The method mainly through hydrolysis, split, dissociation, esterification and main experimental steps. The method has the high split yield, chiral resolving agent is easy to obtain, chiral reagent is easy to recycle, splitting effect is good and the like. (by machine translation)

Design, synthesis and biological evaluation of a novel library of antimitotic C2-aroyl/arylimino tryptamine derivatives that are also potent inhibitors of indoleamine-2, 3-dioxygenase (IDO)

A novel library of C2-substituted tryptamines (based on diverse C2-aroyl/arylimino indoles and indole-diketopiperazine hybrids) possessing antimitotic properties were designed, synthesized and screened for their inhibitory activity against tubulin polymerization, and against proliferation of A549 lung cancer, HeLa cervical cancer, MCF7 breast cancer and HePG2 liver cancer cell lines. The design of molecules were inspired from known antimitotic compounds and natural products. The molecular docking of the designed compounds indicated that they bind to the colchicin binding site of tubulin. They were synthesized by a unique iodine catalysed oxidative ring opening reaction of 1-aryltetrahydro-β-carbolines. Among the compounds synthesized quite a few compounds induced cytotoxicity on the cancer cells by disrupting the tubulin polymerization. They were found to be non-toxic for healthy cells. Immuno Fluorescence study for the most active molecules (between ~6 μM concentration) against A549 and HeLa cells demonstrated complete disruption and shrinkage of the microtubule structures. These compounds also inhibited indoleamine-2, 3-dioxygenase with low micromolar IC50.

Asymmetric synthesis of 1-aryl-1H-pyridine[3,4-b]indole-3-carboxylic acid methyl ester derivatives

The invention discloses an asymmetric synthesis method for synthesizing 1-aryl-1H-pyridine[3,4-4]indole-3-carboxylic acid methyl ester derivatives containing two chiral centers from (R)methyl-2-amino-3-(1H-indol-3-yl)propanoate and aldehyde as main starting materials under catalysis of a catalyst, namely, chiral Lewis acid formed by a chiral tridentate ligand compound L and Ti(O-iPr)4. Compared with the prior art, the method has the advantages that the reaction yield is increased and the reaction non-correspondence selectivity is remarkably improved.

Non-correspondence selective synthesis of 1-aryl-1H-pyridine[3,4-b]indole derivative

The invention discloses an asymmetric synthesis method for synthesizing 1-aryl-1H-pyridine[3,4-b]indole-3-carboxylic acid methyl ester derivatives containing two chiral centers by taking (R)-tryptophan methyl ester and aldehyde as main starting raw materials, taking chiral Lewis acid Salen-Mn as a catalyst and taking (R)-alpha-methyl-4-nitrophenylacetic acid as a chiral additive. Compared with the prior art, the reaction yield is improved and the non-correspondence selectivity of the reaction is remarkably improved.

Chiral separation of 1-aryl-1H-pyridyl[3,4-b]indole-3-carboxylic acid methyl ester

The invention discloses a method for carrying out chiral separation on 1-aryl-1H-pyridyl[3,4-b]indole-3-carboxylic acid methyl ester non-corresponding isomers, which respectively contain two chiral centers, by using (R)-3-(2-chloracetyl)-2-thioketone-thia

Highly stereoselective transformation of (1S,3S)-cis-1,3-disubstituted tetrahydro-β-carbolines into (1S,3R)-trans-1,3-disubstituted tetrahydro-β-carbolines: An improved asymmetric synthesis of tadalafil from l-tryptophan

An efficient and general method for the highly stereoselective transformation of (1S,3S)-cis-1,3-disubstituted 1,2,3,4-tetrahydro-β- carbolines (THBCs) into (1S,3R)-trans-1,3-disubstituted THBCs is described. The method contains the following three steps: the enantiomerically pure (1S,3S)-cis-1,3-disubstituted THBCs 1 were first converted into (1S,3S)-cis-1,2,3-trisubstituted THBCs 2 by N-1-naphthylmethylation/benzylation; (1S,3S)-cis-1,2,3-trisubstituted THBCs2 were then converted into (1S,3R)-trans-1,2,3-trisubstituted THBCs 3 in high yields and with high stereoselectivities via a base-catalyzed epimerization at C-3; (1S,3R)-trans-1,2,3-trisubstituted THBCs 3 were subsequently converted into (1S,3R)-trans-1,3-disubstituted THBCs 4 after reductive removal of the 1-naphthylmethyl/benzyl group. In addition, as an application of this method, an improved and highly stereoselective synthesis of the PDE5 inhibitor tadalafil (Cialis) starting from natural and less expensive l-tryptophan was developed.

Synthesis and cytotoxicity evaluation of (tetrahydro-β-carboline)-1,3,5-triazine hybrids as anticancer agents

A series of tetrahydro-β-carbolines and 1,3,5-triazine hybrids have been synthesized and evaluated for their cytotoxicity against a panel of eight human cancer cell lines and normal human fibroblasts (NIH3T3). It led us to discovery of racemic compounds 69, 71 and 75, which are selectively cytotoxic towards KB (oral cancer) cell line with IC50 values of 105.8, 664.7 and 122.2?nM, respectively; while their enantiopure forms are less active and not selective. Enantiopure compound 42 showed 2.5 times more selectivity towards MCF7 cells over normal fibroblast NIH3T3 cells with an IC50 value of 740?nM, also arrests cell cycle in G1 phase and induces apoptosis in MCF7 and MDA MB231cell lines.

Pictet-Spengler cyclization in room temperature ionic liquid: A convenient access to tetrahydro β-carbolines

1,2,3,4-Tetrahydro-β-carbolines have been synthesized in moderate to good yields in short reaction time using the ionic liquid [bbim] BF4 as reaction medium and promoter. There was no need for the use of an additional catalyst normally employed

Modified Pictet-Spengler reaction. A highly diastereoselective approach to 1,2,3-trisubstituted-1,2,3,4-tetrahydro-β-carbolines using perhydro-1,3-heterocycles

A flexible variant of the Pictet-Spengler reaction employing oxazinanes as synthetic equivalents of several carbonyl compounds has been developed. Using acid catalyzed one pot condensation of perhydro-1,3-heterocycles various 1,3-disubstituted and 1,2,3-trisubstituted-1,2,3,4-tetrahydro-β-carbolines (THBCs) have been synthesized diastereoselectively.