2899-29-8

Basic information

• Product Name: L-Tryptophanol
• Synonyms: L-Trp-ol;L-Tryptosol;L-TRYTOPHANOL;1H-INDOLE-3-PROPANOL, .BETA.-AMINO-, (.BETA.S)-;L-Tryptophanol ,97%;(2S)-2-Amino-3-(1H-indole-3-yl)-1-propanol;(βS)-β-Amino-1H-indole-3-(1-propanol);[S,(-)]-β-Amino-1H-indole-3-propane-1-ol
• CAS NO: 2899-29-8
• Molecular Formula: C₁₁H₁₄N₂O
• Molecular Weight: 190.24
• EINECS: 208-392-7
• Product Categories: Tryptophan [Trp, W];Amino Alcohols;Amino Alcohols (Chiral);Chiral Building Blocks;Indoles;Simple Indoles;Synthetic Organic Chemistry;Amino alcohols;Amino Acid Derivatives;Peptide Synthesis
• Mol File: 2899-29-8.mol

Chemical Properties

• Melting Point: 73-77 °C(lit.)
• Boiling Point: 444.2 °C at 760 mmHg
• Flash Point: 222.5 °C
• Appearance: Brown/Viscous Liquid
• Density: 1.245 g/cm³
• Vapor Pressure: 1.13E-08mmHg at 25°C
• Refractive Index: -21 ° (C=1, MeOH)
• Storage Temp.: Store at 0-5°C
• PKA: 12.85±0.10(Predicted)
• Water Solubility: Soluble in water 11.4 g/L (25°C).
• CAS DataBase Reference: L-Tryptophanol(CAS DataBase Reference)
• NIST Chemistry Reference: L-Tryptophanol(2899-29-8)
• EPA Substance Registry System: L-Tryptophanol(2899-29-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-41-37/38-22
• Safety Statements: 26-36-36/37/39-24/25
• WGK Germany: 3
• Hazardous Substances Data: 2899-29-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
L-Tryptophanol is used as a building block for the synthesis of peptides and proteins, which are vital for the development of new drugs and therapeutic agents. Its incorporation into these biomolecules can enhance their stability, bioavailability, and overall effectiveness.
Used in Research and Development:
L-Tryptophanol is utilized as a key component in the research and development of novel bioactive compounds. Its unique chemical properties allow scientists to explore its potential applications in various fields, such as drug discovery, protein engineering, and the study of molecular interactions.
Used in Nutritional Supplements:
L-Tryptophanol can be found in nutritional supplements, where it serves as a precursor to essential amino acids, particularly L-tryptophan. This helps support the body's protein synthesis and overall health.
Used in Cosmetics Industry:
In the cosmetics industry, L-Tryptophanol may be used as an ingredient in skincare and beauty products due to its potential role in promoting skin health and maintaining the integrity of the skin's natural barrier.

InChI:InChI=1/C11H14N2O/c12-9(7-14)5-8-6-13-11-4-2-1-3-10(8)11/h1-4,6,9,13-14H,5,7,12H2/t9-/m0/s1

Upstream product

• 54-12-6 Trp 
• 4299-70-1 L-tryptophan methyl ester 
• 7303-49-3 DL-tryptophan methyl ester 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 14907-27-8 (R)-(+)-tryptophan methyl ester hydrochloride 
• 73-22-3 L-Tryptophan 
• 61535-47-5 benzyl (S)-(1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate 
• 153-94-6 D-tryptophan 
• 152153-01-0 (S)-4-[(1H-indol-3-yl)methyl]oxazolidin-2-one 
• 4299-70-1 D-Tryptophan methyl ester 
• 154-09-6 2-amino-3-(1H-indol-3-yl)propan-1-ol 
• 110659-38-6 N-t-butoxycarbonyl-tryptophanol 
• 395063-37-3 (4S)-(1H-indol-3-ylmethyl)-3-[(1S)-phenylethyl]-oxazolidin-2-one 

Downstream Products

• 152153-01-0 (S)-4-[(1H-indol-3-yl)methyl]oxazolidin-2-one 
• 131423-66-0 (S,S)-((((2-(indol-3-yl)-1-(hydroxymethyl)ethyl)amino)carbonyl)-2-methylpropyl)(methyl)carbamic acid, phenylmethyl ester 
• 61535-47-5 benzyl (S)-(1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate 
• 66087-97-6 (2S)-3-(2-Indolyl)-2-(tosylamino)propyl toluene-p-sulfonate 
• 157636-81-2 4-(1H,indol-3-ylmethyl)-2-oxazolidinone 
• 161709-03-1 {(S)-1-[(S)-1-Hydroxymethyl-2-(1H-indol-3-yl)-ethylcarbamoyl]-3-methyl-butyl}-carbamic acid benzyl ester 
• 161709-02-0 {(S)-1-[(S)-1-Hydroxymethyl-2-(1H-indol-3-yl)-ethylcarbamoyl]-ethyl}-carbamic acid benzyl ester 
• 161708-94-7 {(S)-1-[(S)-1-Hydroxymethyl-2-(1H-indol-3-yl)-ethylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester 
• 161708-61-8 N-benzyloxycarbonyl-(L)-phenylalanyl-(L)-tryptophanol 
• 161708-67-4 {(1S,2S)-1-[(S)-1-Hydroxymethyl-2-(1H-indol-3-yl)-ethylcarbamoyl]-2-methyl-butyl}-carbamic acid benzyl ester 
• 161708-82-3 {[(S)-1-Hydroxymethyl-2-(1H-indol-3-yl)-ethylcarbamoyl]-methyl}-carbamic acid benzyl ester 
• 161709-35-9 Cyclohexanecarboxylic acid [(S)-1-hydroxymethyl-2-(1H-indol-3-yl)-ethyl]-amide 
• 190275-56-0 N-(4-chlorophenylsulfonyl)-L-valyl-L-tryptophanol 
• 502545-84-8 N-(4-fluorophenylsulfonyl)-L-valyl-L-tryptophanol 

Relevant articles and documents

Illuminating a Dark Kinase: Structure-Guided Design, Synthesis, and Evaluation of a Potent Nek1 Inhibitor and Its Effects on the Embryonic Zebrafish Pronephros

NIMA-related kinase 1 (Nek1) has lately garnered attention for its widespread function in ciliogenesis, apoptosis, and the DNA-damage response. Despite its involvement in various diseases and its potential as a cancer drug target, no directed medicinal chemistry efforts toward inhibitors against this dark kinase are published. Here, we report the structure-guided design of a potent small-molecule Nek1 inhibitor, starting from a scaffold identified by kinase cross-screening analysis. Seven lead compounds were identified in silico and evaluated for their inhibitory activity. The top compound, 10f, was further profiled for efficacy, toxicity, and bioavailability in a zebrafish polycystic kidney disease model. Administration of 10f caused the expansion of fluorescence-labeled proximal convoluted tubules, supporting our hypothesis that Nek1-inhibition causes cystic kidneys in zebrafish embryos. Compound 10f displayed insignificant inhibition in 48 of 50 kinases in a selectivity test panel. The findings provide a powerful tool to further elucidate the function and pharmacology of this neglected kinase.

Bisindole alkaloid compound as well as synthesis method and application thereof

The invention discloses a bisindole alkaloid compound as well as a synthesis method and application thereof. The compound has a structure as shown in formula I. In the formula I, R1 is independently selected from C1-C4 alkoxy or hydrogen; if R1 is alkoxy, n is 1 or 2; R2 is independently selected from C1-C4 alkyl groups or hydrogen; R3 is independently selected from a group consisting of C1-C4 alkoxy carbonyl groups or hydrogen; R4 is hydrogen; R5 is independently selected from a C1-C4 alkyl group or a C1-C4 hydroxyalkyl group; and R6 is independently selected from carbonyl, hydroxyl or hydrogen. The bisindole alkaloid compound can selectively relax pulmonary artery, inhibit proliferation of pulmonary artery endothelial cells and vascular smooth muscle cells, reduce right ventricular diastolic pressure of mice with pulmonary arterial hypertension and inhibit right ventricular hypertrophy. The bisindole alkaloid compound can resist drug addiction in a dose-dependent manner, has a chemical structure type different from that of an existing anti-addiction drug, and is expected to be developed into a novel anti-addiction drug.

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).

Tryptophanol‐derived oxazolopyrrolidone lactams as potential anticancer agents against gastric adenocarcinoma

Gastric cancer is one of the deadliest cancers in modern societies, so there is a high level of interest in discovering new drugs for this malignancy. Previously, we demonstrated the ability of tryptophanol‐derived polycyclic compounds to activate the tumor suppressor protein p53, a relevant therapeutic target in cancer. In this work, we developed a novel series of enantiomerically pure tryptophanol‐derived small molecules to target human gastric adenocarcinoma (AGS) cells. From an initial screening of fourteen compounds in AGS cell line, a hit compound was selected for optimization, leading to two derivatives selective for AGS gastric cells over other types of cancer cells (MDA‐MB‐231, A‐549, DU‐145, and MG‐63). More importantly, the compounds were non‐toxic in normal cells (HEK 293T). Additionally, we show that the growth inhibition of AGS cells induced by these compounds is mediated by apoptosis. Stability studies in human plasma and human liver microsomes indicate that the compounds are stable, and that the major metabolic transformations of these molecules are mono‐ and di‐hydroxylation of the indole ring.

An increase in side-group hydrophobicity largely improves the potency of ritonavir-like inhibitors of CYP3A4

Identification of structural determinants required for potent inhibition of drug-metabolizing cytochrome P450 3A4 (CYP3A4) could help develop safer drugs and more effective pharmacoenhancers. We utilize a rational inhibitor design to decipher structure-activity relationships in analogues of ritonavir, a highly potent CYP3A4 inhibitor marketed as pharmacoenhancer. Analysis of compounds with the R1 side-group as phenyl or naphthalene and R2 as indole or naphthalene in different stereo configuration showed that (i) analogues with the R2-naphthalene tend to bind tighter and inhibit CYP3A4 more potently than the R2-phenyl/indole containing counterparts; (ii) stereochemistry becomes a more important contributing factor, as the bulky side-groups limit the ability to optimize protein-ligand interactions; (iii) the relationship between the R1/R2 configuration and preferential binding to CYP3A4 is complex and depends on the side-group functionality/interplay and backbone spacing; and (iv) three inhibitors, 5a-b and 7d, were superior to ritonavir (IC50 of 0.055–0.085 μM vs. 0.130 μM, respectively).

Design and synthesis of novel monoterpenoid indole alkaloid-like analogues and their antitumour activities: In vitro

A biomimetic synthetic strategy and combinatorial chemistry were used to synthesize 34 novel monoterpenoid indole alkaloid (MIA) analogues, and their cytotoxic activities against five cancer cell lines (SW-480, A-549, HL-60, SMMC-7721, and MCF-7) were determined using the 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium (MTS) assay. Fourteen of these analogues (7, 16-18, and 23-32) showed significantly greater inhibition of tumour cell proliferation than cisplatin. Compounds 17 and 18 showed the highest cytotoxic activity against the HL-60 cell line with IC50 values of 0.90 μM and 0.43 μM, respectively. Compound 18 slightly induced apoptosis and arrested the cell cycle in SW-480, A-549, HL-60, SMMC-7721, and MCF-7 cells. Analysis of the primary structure-activity relationships reveals that the introduction of different substituent groups at the C-3, C-5, and C-6 positions of the indole moiety and the C-10 position of the genipin moiety might have an effect on the antitumour activity of the resulting compounds.

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.

Palladium-Catalyzed Amide-Directed Enantioselective Hydrocarbofunctionalization of Unactivated Alkenes Using a Chiral Monodentate Oxazoline Ligand

A Pd-catalyzed amide-directed enantioselective hydrocarbofunctionalization of unactivated alkenes with C-H nucleophiles has been developed using a chiral monodentate oxazoline (MOXin) ligand. Various indoles react at C3 position with aminoquinoline-coupled 3-alkenamides to give γ addition products in good to excellent yield and enantioselectivity. This study represents an important advance of the development of chiral monodentate oxazoline ligands, which have been underexplored for asymmetric catalysis.

ESTROGEN RECEPTOR MODULATORS

Compounds of Formula (I) are estrogen receptor alpha modulators, where the variables in Formula (I) are described in the disclosure. Such compounds, as well as pharmaceutically acceptable salts and compositions thereof, are useful for treating diseases or conditions that are estrogen receptor alpha dependent and/or estrogen receptor alpha mediated, including conditions characterized by excessive cellular proliferation, such as breast cancer.

Enantiopure indolo[2,3-a]quinolizidines: Synthesis and evaluation as NMDA receptor antagonists

Enantiopure tryptophanol is easily obtained from the reduction of its parent natural amino acid trypthophan (available from the chiral pool), and can be used as chiral auxiliary/inductor to control the stereochemical course of a diastereoselective reaction. Furthermore, enantiopure tryptophanol is useful for the syntheses of natural products or biological active molecules containing the aminoalcohol functionality. In this communication, we report the development of a small library of indolo[2,3-a]quinolizidines and evaluation of their activity as N-Methyl D-Aspartate (NMDA) receptor antagonists. The indolo[2,3-a]quinolizidine scaffold was obtained using the following key steps: (i) a stereoselective cyclocondensation of (S)- or (R)-tryptophanol with appropriate racemic δ-oxoesters; (ii) a stereocontrolled cyclization on the indole nucleus. The synthesized enantiopure indolo[2,3-a]quinolizidines were evaluated as NMDA receptor antagonists and one compound was identified to be 2.9-fold more potent as NMDA receptor blocker than amantadine (used in the clinic for Parkinson's disease). This compound represents a hit compound for the development of novel NMDA receptor antagonists with potential applications in neurodegenerative disorders associated with overactivation of NMDA receptors.