58115-31-4

Basic information

• Product Name: TMC-58B
• Synonyms: (S)-α-(Benzoylamino)-N-[(S)-1-(hydroxymethyl)-2-phenylethyl]benzenepropanamide;(S)-α-(Benzoylamino)-N-[(S)-α-(hydroxymethyl)phenethyl]benzenepropanamide;Aurantiamide;TMC-58B
• CAS NO: 58115-31-4
• Molecular Formula: C₂₅H₂₆N₂O₃
• Molecular Weight: 402.48554
• Mol File: 58115-31-4.mol

Chemical Properties

• Boiling Point: 723.6°Cat760mmHg
• Flash Point: 391.4°C
• Appearance: /
• Density: 1.191g/cm³
• Vapor Pressure: 5.61E-22mmHg at 25°C
• Refractive Index: 1.609
• PKA: 13.31±0.46(Predicted)
• CAS DataBase Reference: TMC-58B(CAS DataBase Reference)
• NIST Chemistry Reference: TMC-58B(58115-31-4)
• EPA Substance Registry System: TMC-58B(58115-31-4)

Safety Data

• Hazardous Substances Data: 58115-31-4(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
TMC-58B is used as a pharmaceutical compound for its potential therapeutic effects. TMC-58B's unique structure and properties make it a candidate for further research and development in the field of medicine.
2. Used in Chemical Research:
TMC-58B is used as a research compound for studying its chemical properties and potential applications in various fields. Its unique structure and properties make it an interesting subject for further investigation and experimentation.
3. Used in Drug Development:
TMC-58B is used as a potential drug candidate for the development of new medications. Its unique structure and properties may offer new opportunities for the treatment of various diseases and conditions.
4. Used in Natural Product Chemistry:
TMC-58B is used as a natural product for studying the chemical constituents of Piper aurantiacurn seeds. Its isolation and characterization contribute to the understanding of the chemical diversity and potential bioactive compounds present in this plant source.

References

Banerji, Das,Ind. 1. Chern., 13, 1234 (1975)

InChI:InChI=1/C25H26N2O3/c28-18-22(16-19-10-4-1-5-11-19)26-25(30)23(17-20-12-6-2-7-13-20)27-24(29)21-14-8-3-9-15-21/h1-15,22-23,28H,16-18H2,(H,26,30)(H,27,29)/t22-,23-/m0/s1

Upstream product

• 5267-64-1 (R)-2-amino-3-phenylpropanol 
• 37002-52-1 N-benzoyl-D-phenylalanine 
• 2566-22-5 N-benzoyl-L-phenylalanine 
• 3182-95-4 L-Phenylalaninol 
• 138772-65-3 tert-butyl ((2S)-1-(((2S)-1-hydroxy-3-phenylpropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 138772-70-0 (S)-2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-phenylpropyl acetate 
• 63-91-2 L-phenylalanine 
• 611-73-4 Benzoylformic acid 
• 98-88-4 benzoyl chloride 
• 17224-88-3 benzyl ((S)-1-(((S)-1-hydroxy-3-phenylpropan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate 
• 2578-84-9 N-benzyloxycarbonyl-L-phenylalanine p-nitrophenyl ester 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 5874-62-4 N-Benzoyl-phenyl-alanin-<4-nitro-phenylester> 

Downstream Products

• 2566-22-5 DL-N-benzoylphenylalanine 
• 80780-41-2 aurantiamide acetate 

Relevant articles and documents

Aurantiamide acetate and fluorinated derivatives thereof as well as preparation method and application thereof

The invention belongs to the technical field of medicines, and discloses aurantiamide acetate and fluorinated derivatives thereof, and a preparation method and application thereof. The general formulaof the aurantiamide acetate, the aurantiamide acetate fluorinated derivatives or pharmaceutically acceptable salts of the aurantiamide acetate and the aurantiamide acetate fluorinated derivatives isshown in the specification, wherein R1 represents OH, CH2OH or OCOCH3, and R2, R3 and R4 each independently represent H, an alkyl group or F. The aurantiamide acetate and the fluorinated derivatives or the pharmaceutically acceptable salts thereof have a good effect of preventing or treating influenza viruses, especially infection caused by influenza A viruses. The aurantiamide acetate is subjected to fluorination modification, so that the biological activity of the aurantiamide acetate is stronger. The aurantiamide acetate and the fluorinated derivative thereof act on a target to aim at viruses and also aim at host cells, so that drug resistance is not easy to generate.

A Hydroperoxide-Mediated Decarboxylation of α-Ketoacids Enables the Chemoselective Acylation of Amines

Strategies for the formation of amide bonds, that is, one of the most basic and important transformations in organic synthesis, have so far focused predominantly on dehydration reactions. Herein, we report and demonstrate the practical utility of a novel decarboxylative amidation of α-ketoacids by using inexpensive tert-butyl hydroperoxide (TBHP), which is characterized by high yields, a broad substrate scope, mild reaction conditions, and a unique chemoselectivity. These features enable the synthesis of peptides from amino acid derived α-ketoacids under preservation of the stereochemical information.

Efficient Synthesis of Glycosylated Matijin-Su Derivatives via Ultrasonic Irradiation

Matijin-Su (1) is a phenylalanine dipeptide compound with anti-hepatitis B virus (HBV) activity. Previous reports suggest that the synthesis of glycosylated Matijin-Su derivatives needs at least 10 steps. To simplify the synthetic procedure, we have developed a shorter and more efficient method for the preparation via ultrasound irradiation. Two galactopyranosylated (2) and two glucopyranosylated (3) derivatives were synthesized in 6 or 7 steps. The overall yields for the total synthesis of galactopyranosylated derivatives were markedly increased to 39% (2a) or 22% (2b). And the yields for glucopyranosylated derivatives also reached 29% (3a) or 16% (3b).

Synthesis and anti-hepatitis B virus activities of Matijing-Su derivatives

A series of derivatives of Matijing-Su (MTS, N-(N-benzoyl-l-phenylalanyl)-O-acetyl-l-phenylalanol) was synthesized and evaluated for their anti-hepatitis B virus (HBV) activities in 2.2.15 cells. The IC50 of compounds 9c (1.40 μM), 9g (2.33 μM) and 9n (2.36 μM), etc. and the selective index of 9n (45.93) of the inhibition on the replication of HBV DNA were higher than those of the positive control lamivudine [41.59, (IC50: 82.42 μM)]. Compounds 11d, 12a and 12e also exhibited significant anti-HBV activities.

PHENYLALANINE DIPEPTIDE DERIVATIVES, COMPOSITIONS AND USE THEREOF

Disclosed are a compound of formula I, stereoisomers, pharmaceutically acceptable salts or hydrates thereof, a pharmaceutical composition comprising the smae, a process for preparing the same and use thereof. The compound may also be used to prepare a medicament to treat viral infections, especially to prepare a medicament to treat hepatitis B virus and human immunodeficiency virus with little toxic side effects.

Isolation of aurantiamide acetate from Arisaema erubescens

Aurantiamide acetate (N-benzoyl-1-phenylalanyl-1-phenylalaninol acetate) has been isolated by chromatographic separation of a methanol extract of Arisaema erubescens and its structure confirmed by synthesis.

Components of the Chinese drug 'Ti-ku-'pi'. Isolation and establishment of structure of a new dipeptide, lyciumamide

A new dipeptide, lyciumamide (1), was isolated from the Chinese crude drug 'Ti-ku-'pi', root bark of Lycium chinense MILL. (Solanaceae), and was shown by spectroscopy, chemical degradation, and synthesis to be N-benzoyl-L-phenylalanyl-L-phenylalaninol O-acetate (1).

AURANTIAMIDES: A NEW CLASS OF MODIFIED DIPEPTIDES FROM PIPER AURANTIACUM

Two new amides, aurantiamide and aurantiamide acetate, were isolated from Piper aurantiacum.Their structures were determined as N-(N'-benzoyl-S-phenylalaninyl)-S-phenylalaninol and its acetate, respectively, from chemical and spectroscopic studies.The structures and stereochemistry were confirmed by synthesis.The corresponding diastereoisomers were also synthesized and their spectroscopic properties compared with those of the natural compounds.Key Word Index- Piper aurantiacum; Piperaceae; seeds; modified dipeptides; aurantiamide, dia-aurantiamide and their acetates.