82689-19-8

Basic information

• Product Name: N-alpha-Boc-L-tryptophanol
• Synonyms: BOC-TRP-OL;BOC-TRYPTOPHANOL;BOC-(S)-2-AMINO-3-(3-INDOLYL)-1-PROPANOL;BOC-L-TRYPTOPHANOL;BOC-L-TRP-OL;Boc-L-tryptophanol≥ 98% (NMR);N-α-Boc-L-tryptophanol,99%e.e.;BOC-(R)-2-AMINO-3-(3-INDOLYL)-1-PROPANOL
• CAS NO: 82689-19-8
• Molecular Formula: C₁₆H₂₂N₂O₃
• Molecular Weight: 290.36
• Product Categories: Amino Acids;Tryptophan [Trp, W];Amino Alcohols;Boc-Amino acid series;Amino Acid Derivatives;Peptide Synthesis;Tryptophan
• Mol File: 82689-19-8.mol

Chemical Properties

• Melting Point: 118-122 °C(lit.)
• Boiling Point: 518.1 °C at 760 mmHg
• Flash Point: 267.1 °C
• Appearance: White to off-white/Powder
• Density: 1.19 g/cm³
• Vapor Pressure: 1.47E-11mmHg at 25°C
• Refractive Index: 1.593
• Storage Temp.: Store at 0°C
• Solubility: soluble in Methanol
• PKA: 12.06±0.46(Predicted)
• CAS DataBase Reference: N-alpha-Boc-L-tryptophanol(CAS DataBase Reference)
• NIST Chemistry Reference: N-alpha-Boc-L-tryptophanol(82689-19-8)
• EPA Substance Registry System: N-alpha-Boc-L-tryptophanol(82689-19-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 82689-19-8(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

InChI:InChI=1/C16H22N2O3/c1-16(2,3)21-15(20)18-12(10-19)8-11-9-17-14-7-5-4-6-13(11)14/h4-7,9,12,17,19H,8,10H2,1-3H3,(H,18,20)/t12-/m0/s1

Upstream product

• 13139-14-5 Boc-Trp-OH 
• 127476-51-1 C₂₁H₂₈N₂O₆ 
• 141215-69-2 methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 73-22-3 L-Tryptophan 
• 154-09-6 L-tryptophanol 
• 3392-11-8 2,5-dioxopyrrolidin-1-yl N-(tert-butoxycarbonyl)-L-tryptophanate 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 4299-70-1 L-tryptophan methyl ester 
• 219497-33-3 3-(1-benzyl-1H-indol-3-yl)-2-tert-butoxycarbonylamino-propionic acid methyl ester 

Downstream Products

• 82689-14-3 N-tert-butyloxycarbonyl-tryptophanal 
• 882169-91-7 (S)-[2-(5-bromopyridin-3-yloxy)-1-(1H-indol-3-ylmethyl)ethyl]carbamic acid tert-butyl ester 
• 882170-23-2 [1-(3-bromo-phenoxymethyl)-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester 
• 882170-21-0 [2-(1H-indol-3-yl)-1-(5-styryl-pyridin-3-yloxymethyl)-ethyl]-carbamic acid tert-butyl ester 
• 882170-28-7 {2-(1H-indol-3-yl)-1-[3-(2-pyridin-4-yl-vinyl)-phenoxymethyl]-ethyl}-carbamic acid tert-butyl ester 
• 940310-05-4 2S-N₂-[[2-(t-Butoxycarbonyl)amino-3-(1H-indol-3-yl)]propoxycarbonyl]-N₄-(2,2-dimethyl-3-oxo-4H-5-pyrido[1,4]oxazin-6-yl)-5-fluoro-N₂-(3,4,5-trimethoxyphenyl)-2,4-pyrimidinediamine 
• 1403949-81-4 (S,E)-methyl 3-(4-(2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propoxy)-3-methoxyphenyl)acrylate 
• 1403949-80-3 (S)-methyl 3-(4-(2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propoxy)-3-methoxyphenyl)propanoate 
• 1403949-55-2 C₂₆H₃₃N₃O₆ 
• 1403949-54-1 C₂₆H₃₁N₃O₆ 
• 1403949-56-3 C₂₁H₂₃N₃O₄*ClH 

Relevant articles and documents

Total syntheses of Hexahydropyrrolo[2,3-b]indole Alkaloids, (+)-pseudophrynamine 270 and (+)-pseudophrynamine 272A

A general strategy for asymmetric approach to the hexahydropyrrolo[2,3-b]indole alkaloids sharing a vicinal quaternary-tertiary centers has been disclosed via Pd(0)-catalyzed N-deacylative allylations (N-DaA) (dr > 20:1). Utilizing this strategy, asymmetric total syntheses of pseudophrynamines 270 (3c) and 272A (3b) have been achieved from a 3-substituted N-acyl indole 8 (pro-nucleophile) with allyl alcohol (pro-electrophile).

Preparation method of chiral alpha-methyl arylethylamine

The invention provides a preparation method of chiral alpha-methyl arylethylamine, and relates to the technical field of organic synthesis medicines. Boc-amino acid methyl ester is used as an initial raw material, Boc-amino alcohol is obtained through reduction, Boc-amino alcohol reacts with thionyl chloride and is oxidized through sodium periodate to obtain a sulfonamide compound, and then the sulfonamide compound is reduced through sodium borohydride promoted by lewis acid and a protecting group is removed under the acidic condition to obtain a target compound. According to the method, raw materials are cheap and easy to obtain, a single optical isomer product is obtained by using chiral raw materials, the problem of column chromatography resolution is solved, generation of a large amount of solid wastes and isomers is avoided, atom economy is improved, the product purity is high, the yield is high, and the production cost is effectively reduced. In addition, the mild reduction system is used for replacing the original high-pressure hydrogenation reaction, the process operation is relatively simple, and the method is more suitable for large-scale industrial production.

ANTIBODY DRUG CONJUGATES COMPRISING ECTEINASCIDIN DERIVATIVES

Drug conjugates having formula [D-(X) b -(AA) w -(T) g -(L)-] n -Ab wherein: D is a drug moiety having the following formula (I) or a pharmaceutically acceptable salt, ester, solvate, tautomer or stereoisomer th

A catalytic N-deacylative alkylation approach to hexahydropyrrolo[2,3-b]indole alkaloids

A versatile unprecedented strategy to diversely functionalized hexahydropyrrolo[2,3-b]indole alkaloids is described in high chemical yields. The synthesis features a key Pd(0)-catalyzed deacylative alkylation of N-acyl 3-substituted indoles using only 1 mol% of Pd(PPh3)4. The scope of this methodology is further defined in the asymmetric synthesis of pyrroloindolines using a diastereoselective approach.

Synthesis, biological evaluation, and molecular modeling studies of chiral chloroquine analogues as antimalarial agents

In a focused exploration, we designed, synthesized, and biologically evaluated chiral conjugated new chloroquine (CQ) analogues with substituted piperazines as antimalarial agents. In vitro as well as in vivo studies revealed that compound 7c showed potent activity (in vitro 50% inhibitory concentration, 56.98 nM for strain 3D7 and 97.76 nM for strain K1; selectivity index in vivo [up to at a dose of 12.5 mg/kg of body weight], 3,510) as a new lead antimalarial agent. Other compounds (compounds 6b, 6d, 7d, 7h, 8c, 8d, 9a, and 9c) also showed moderate activity against a CQ-sensitive strain (3D7) and superior activity against a CQ-resistant strain (K1) of Plasmodium falciparum. Furthermore, we carried out docking and three-dimensional quantitative structure-activity relationship (3D-QSAR) studies of all in-house data sets (168 molecules) of chiral CQ analogues to explain the structure-activity relationships (SAR). Our new findings specify the significance of the H-bond interaction with the side chain of heme for biological activity. In addition, the 3D-QSAR study against the 3D7 strain indicated the favorable and unfavorable sites of CQ analogues for incorporating steric, hydrophobic, and electropositive groups to improve the antimalarial activity.

Design, synthesis, and evaluation of novel Akt1 inhibitors based on an indole scaffold

A new series of potential Akt1 inhibitors with indole scaffold were designed and synthesized. The antiproliferative activity against PC-3 cell line and enzyme inhibitory activity against Akt1 were evaluated. Among them, some compounds showed much more potent antiproliferative activity and stronger Akt1 inhibitory activity compared to the positive control of GSK690693. In particular, compound 19b exhibited the most potent inhibitory activity against Akt1 with inhibition rate of 70.3% at a concentration of 10?nm. Furthermore, compound 19b could dose dependently reduce the phosphorylation of the downstream GSK3β protein in the PC-3 cell line and displayed fivefold higher antiproliferative activity against PC-3 cell line with IC50 value of 3.1?±?0.1?μm than positive control (15.5?±?0.4?μm). Herein, compound 19b may serve as a promising lead for further optimization and development of novel Akt1 inhibitors based on an indole scaffold.

Synthesis and evaluation of chirally defined side chain variants of 7-chloro-4-aminoquinoline to overcome drug resistance in malaria chemotherapy

A novel 4-aminoquinoline derivative [(S)-7-chloro-N-(4-methyl-1-(4-methyl-piperazin-1-yl)pentan-2-yl)-quinolin-4-amine triphosphate] exhibiting curative activity against chloroquine-resistant malaria parasites has been identified for preclinical development as a blood schizonticidal agent. The lead molecule selected after detailed structure-activity relationship (SAR) studies has good solid-state properties and promising activity against in vitro and in vivo experimental malaria models. The in vitro absorption, distribution, metabolism, and excretion (ADME) parameters indicate a favorable drug-like profile.

Synthesis of fully protected, reverse N-prenylated (2S,3R)-3-hydroxytryptophan, a unique building block of the cyclomarins

Reverse N-prenylated 3-hydroxytryptophan, the rather exotic amino acid of the cyclomarins, is obtained in enantio- and diastereomerically pure and fully protected form by a combination of a highly stereoselective addition of a zincated indole toward protected serinal and subsequent palladium-catalyzed N-prenylation.

Design, synthesis and evaluation of novel indole derivatives as AKT inhibitors

Herein, we describe the discovery and synthesis of a new series of 1,2,4,7-tetra-substituted indole derivatives as novel AKT inhibitors by optimization of a weak hit methyl 4-(2-aminoethoxy)-1H-indole-2-carboxylate (1). Both representative compounds 6a and 6o exhibited the most potent inhibitory activities against AKT1, with inhibition rates of 72.5% and 78.6%, respectively, at concentrations of 10 nM. In addition, compounds 6a and 6o also potently inhibited the phosphorylation of the downstream GSK3 protein and displayed slightly better anti-proliferative activities in a prostate cancer cell line.

Discovery of the first N -hydroxycinnamamide-based histone deacetylase 1/3 dual inhibitors with potent oral antitumor activity

In our previous study, we designed and synthesized a novel series of N-hydroxycinnamamide-based HDAC inhibitors (HDACIs), among which the representative compound 14a exhibited promising HDACs inhibition and antitumor activity. In this current study, we report the development of a more potent class of N-hydroxycinnamamide-based HDACIs, using 14a as lead, among which, compound 11r gave IC50 values of 11.8, 498.1, 3.9, 2000.8, 5700.4, 308.2, and 900.4 nM for the inhibition of HDAC1, HDAC2, HDAC3, HDAC8, HDAC4, HDAC6, and HDAC11, exhibiting dual HDAC1/3 selectivity. Compounds 11e, 11r, 11w, and 11y showed excellent growth inhibition in multiple tumor cell lines. In vivo antitumor assay in U937 xenograft model identified compound 11r as a potent, orally active HDACI. To the best of our knowledge, this work constitutes the first report of oral active N-hydroxycinnamamide-based HDACIs with dual HDAC1/3 selectivity.