141595-98-4

Basic information

• Product Name: D-TRYPTOPHAN BENZYL ESTER 98
• Synonyms: D-TRYPTOPHAN BENZYL ESTER 98
• CAS NO: 141595-98-4
• Molecular Formula: C₁₈H₁₈N₂O₂
• Molecular Weight: 294.352
• Product Categories: Amino Acid Derivatives;Peptide Synthesis;Tryptophan
• Mol File: 141595-98-4.mol

Chemical Properties

• Melting Point: 77-80 °C(lit.)
• Boiling Point: 489.9oC at 760 mmHg
• Flash Point: 250.1oC
• Appearance: /
• Density: 1.247g/cm3
• Vapor Pressure: 9.59E-10mmHg at 25°C
• Refractive Index: 1.659
• CAS DataBase Reference: D-TRYPTOPHAN BENZYL ESTER 98(CAS DataBase Reference)
• NIST Chemistry Reference: D-TRYPTOPHAN BENZYL ESTER 98(141595-98-4)
• EPA Substance Registry System: D-TRYPTOPHAN BENZYL ESTER 98(141595-98-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 141595-98-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H18N2O2/c19-16(18(21)22-12-13-6-2-1-3-7-13)10-14-11-20-17-9-5-4-8-15(14)17/h1-9,11,16,20H,10,12,19H2/t16-/m1/s1

Upstream product

• 82333-00-4 C₂₅H₂₄N₂O₄S 
• 100-44-7 benzyl chloride 
• 153-94-6 D-tryptophan 
• 774485-83-5 tryptophan benzyl ester 
• 100-51-6 benzyl alcohol 
• 5241-64-5 Boc-D-Trp-OH 
• 765229-74-1 (R)-2-Amino-3-(1H-indol-3-yl)-propionyl chloride 
• 126090-33-3 (R)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid benzyl ester 
• 73-22-3 L-Tryptophan 
• 22839-16-3 L-tryptophan benzyl ester hydrochloride 
• 100-39-0 benzyl bromide 
• 13139-14-5 Boc-Trp-OH 
• 57229-67-1 (S)-benzyl 2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propanoate 

Downstream Products

• 4289-01-4 L-tryptophan benzyl ester p-toluenesulfonic acid salt 
• 1185198-44-0 N-[2-chloro-9-(tetrahydropyran-2-yl)-9H-purin-6-yl]-N-cyclopropylglycyl-L-trypthophane benzyl ester 
• 73-22-3 L-Tryptophan 
• 85612-32-4 (S)-3-{1-[2-Methyl-2-(2,2,2-trichloro-ethoxycarbonylamino)-propionyl]-1H-indol-3-yl}-2-(4-oxo-4H-quinazolin-3-yl)-propionic acid benzyl ester 
• 94141-26-1 (R)-2-(2-Amino-benzoylamino)-3-(1H-indol-3-yl)-propionic acid benzyl ester 

Relevant articles and documents

Indole-quinolizine-6-formyl-glucuronyl-ethylenediamine, preparation, activity and application thereof

The invention provides N-(6S)-3-acetyl base-4-oxo-4,6,7,12-tetraindole-[2,3-alpha]quinolizine-6-formyl-N'-glucuronyl-ethylenediamine, provides a preparation method thereof, discloses the anti-tumor activity thereof in a mice S180 transplanted sarcoma model, discloses the anti-tumor metastasis activity thereof in a mice Lewis lung cancer metastasis model, discloses an anti-inflammation role thereofin a mice ear swelling model, and further discloses an anti-thrombus role thereof in a rat common carotid artery-external jugular vein circulation bypath thread method anti-thrombus model. The invention discloses application of N-(6S)-3-acetyl base-4-oxo-4,6,7,12-tetraindole-[2,3-alpha]quinolizine-6-formyl-N'-glucuronyl-ethylenediamine in preparation of anti-tumor drugs, anti-lung cancer metastasis drugs, anti-inflammation drugs and anti-thrombus drugs.

Indole and quinolizine - 6 - formyl - 3 - amino-glucose, its preparation, active and application (by machine translation)

The present invention provides (6 S) - 3 - acetyl - 4 - oxo - 4, 6, 7, 12 - tetrahydro indolo [2, 3 - α] quinolizine - 6 - formyl - (3 - amino-glucose), provides the preparation method, discloses it in mouse S180 portability sarcoma on the model of the anti-tumor activity, discloses it in the mouse Lewis lung cancer transfer on the model of the anti-tumor activity, discloses it in the mouse ear swelling model on the anti-inflammatory effect, in the big mouse neck further discloses the total artery - outside neck vein circulation bypass wire france anti- thrombus model on the role of the anti-thrombus. The present invention thus discloses (6 S) - 3 - acetyl - 4 - oxo - 4, 6, 7, 12 - tetrahydro indolo [2, 3 - α] quinolizine - 6 - formyl - (3 - amino-glucose) in the preparation of anti-tumor drug, anti-tumor lung cancer metastasis drug, anti-inflammatory drugs and antithrombotic drug in the application. (by machine translation)

Synthesis and evaluation of oxindoles as promising inhibitors of the immunosuppressive enzyme indoleamine 2,3-dioxygenase 1

Indoleamine 2,3-dioxygenase 1 (IDO1) is considered as an important therapeutic target for the treatment of cancer, chronic infections and other diseases that are associated with immune suppression. Recent developments in understanding the catalytic mechanism of the IDO1 enzyme revealed that conversion of l-tryptophan (l-Trp) to N-formylkynurenine proceeded through an epoxide intermediate state. Accordingly, we synthesized a series of 3-substituted oxindoles from l-Trp, tryptamine and isatin. Compounds with C3-substituted oxindole moieties showed moderate inhibitory activity against the purified human IDO1 enzyme. Their optimization led to the identification of potent compounds, 6, 22, 23 and 25 (IC50 = 0.19 to 0.62 μM), which are competitive inhibitors of IDO1 with respect to l-Trp. These potent compounds also showed IDO1 inhibition potencies in the low-micromolar range (IC50 = 0.33-0.49 μM) in MDA-MB-231 cells. The cytotoxicity of these potent compounds was trivial in different model cancer (MDA-MB-231, A549 and HeLa) cells and macrophage (J774A.1) cells. Stronger selectivity for the IDO1 enzyme (124 to 210-fold) over the tryptophan 2,3-dioxygenase (TDO) enzyme was also observed for these compounds. These results suggest that the oxindole moiety of the compounds could mimic the epoxide intermediate state of l-Trp. Therefore, the structural simplicity and low-micromolar inhibition potencies of these 3-substituted oxindoles make them quite attractive for further investigation of IDO1 function and immunotherapeutic applications.

Enantiospecific C-H Activation Using Ruthenium Nanocatalysts

The activation of C-H bonds has revolutionized modern synthetic chemistry. However, no general strategy for enantiospecific C-H activation has been developed to date. We herein report an enantiospecific C-H activation reaction followed by deuterium incorporation at stereogenic centers. Mechanistic studies suggest that the selectivity for the α-position of the directing heteroatom results from a four-membered dimetallacycle as the key intermediate. This work paves the way to novel molecular chemistry on nanoparticles.

A general and enantioselective approach to pentoses: A rapid synthesis of PSI-6130, the nucleoside core of sofosbuvir

An efficient route towards biologically relevant pentose derivatives is described. The de novo synthetic strategy features an enantioselective α-oxidation reaction enabled by a chiral amine in conjunction with copper(II) catalysis. A subsequent Mukaiyama aldol coupling allows for the incorporation of a wide array of modular two-carbon fragments. Lactone intermediates accessed via this route provide a useful platform for elaboration, as demonstrated by the preparation of a variety of C-nucleosides and fluorinated pentoses. Finally, this work has facilitated expedient syntheses of pharmaceutically active compounds currently in clinical use.

COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS

The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.

A class of novel conjugates of substituted purine and Gly-AA-OBzl: Synthesis and evaluation of orally analgesic activity

Aimed at the chemotherapy of chronic pain two kinds of analgesic pharmacophores, substituted purine and Gly-AA-OBzl, were coupled via a five-step-reaction procedure and 19 novel conjugates N-[2-chloro-9- (tetrahydropyran-2-yl)-9H-purin-6-yl]-N-cyclopropylglycylamino acid benzylesters were provided. On mouse-tail flick model their in vivo analgesic activities were assayed. The results indicate that introducing Gly-OC2H 5 into the 6-position of the substituted purine leads to ambiguous increase of the analgesic activity, while introducing Gly-AA-OBzl into this position leads to significant increase of the analgesic activity.

Esterification of unprotected a-Amino acids in ionic liquids as the reaction media

Ionic liquid 1,3-dimethylimidazolium methanesulfonate was used to prepare a-amino acids benzylic esters from unprotected amino acids and benzyl chloride. Esterification of several amino acids was achieved with satisfactory yields: by-products can be removed by a simple work-up procedure to afford the pure product. The described method is simple, mild, rapid and save.

Unexpected cis selectivity in the Pictet-Spengler reaction

Whilst cis:trans selectivity of about 4:1 can be obtained from Pictet-Spengler reactions between tryptophan methyl esters and aldehydes using conditions of kinetic control, much higher cis selectivity (>95:5) can be obtained when both the tryptophan deriv

Solution-phase automated synthesis of tripeptide derivatives

An improved general method for automated synthesis of tripeptides was developed, in which methanesulfonic acid (MSA) was used in place of trifluoroacetic acid (TFA), thus making it possible to avoid, 1) corrosion of the apparatus by strong acid vapor, 2) formation of emulsions, and 3) use of the restricted solvent, dichloromethane. As an application of the automated synthesis apparatus, 216 fragment tripeptide derivatives were synthesized systematically using the MSA method, in excellent yield and with increased efficiency.