63631-36-7

Usage

Uses

Used in Anticancer Applications:
Asperphenamate is used as an anticancer agent for its ability to inhibit the growth of breast and leukemia cancer cell lines. It has shown significant inhibitory effects on the proliferation of T47D, MDA-MB-231, and HL-60 cells, with IC50s of 92.3, 96.5, and 97.9 μM, respectively.
Used in Pharmaceutical Synthesis:
Asperphenamate is used as a key component in the synthesis of N-Benzoyl-O-(N''-(1-benzyloxycarbonyl-4-piperidiylcarbonyl)-D-phenylalanyl)-D-phenylalaninol (BBP), an asperphenamate derivative that specifically targets and inhibits the growth of human breast carcinoma MCF-7 cells.
Used in Enzyme Inhibition:
Asperphenamate is used as an inhibitor of yeast α-glucosidase activity, with an IC50 of 8.3 μM. This application highlights its potential in the development of therapeutic agents targeting enzyme-related diseases and conditions.

InChI:InChI=1/C32H30N2O4/c35-30(26-17-9-3-10-18-26)33-28(21-24-13-5-1-6-14-24)23-38-32(37)29(22-25-15-7-2-8-16-25)34-31(36)27-19-11-4-12-20-27/h1-20,28-29H,21-23H2,(H,33,35)(H,34,36)/t28-,29-/m0/s1

Upstream product

• 1042715-33-2 C₂₅H₂₆N₂O₃ 
• 98-88-4 benzoyl chloride 
• 5267-65-2 (S)-N-(1-hydroxy-3-phenylpropan-2-yl)benzamide 
• 2566-22-5 N-benzoyl-L-phenylalanine 
• 67736-12-3 (S)-2-Amino-3-phenyl-propionic acid (S)-2-benzoylamino-3-phenyl-propyl ester 
• 65-85-0 benzoic acid 
• 63-91-2 L-phenylalanine 
• 3182-95-4 L-Phenylalaninol 
• 849123-63-3 (S)-(S)-2-benzamido-3-phenylpropyl 2-(tert-butoxycarbonylamino)-3-phenylpropanoate 
• 1042715-31-0 (R)-(S)-2-benzamido-3-phenylpropyl 2-(tert-butoxycarbonylamino)-3-phenylpropanoate 

Relevant academic research and scientific papers

Asperphenamate biosynthesis reveals a novel two-module NRPS system to synthesize amino acid esters in fungi

Amino acid esters are a group of structurally diverse natural products with distinct activities. Some are synthesized through an inter-molecular esterification step catalysed by nonribosomal peptide synthetase (NRPS). In bacteria, the formation of the intra-molecular ester bond is usually catalysed by a thioesterase domain of NRPS. However, the mechanism by which fungal NRPSs perform this process remains unclear. Herein, by targeted gene disruption in Penicillium brevicompactum and heterologous expression in Aspergillus nidulans, we show that two NRPSs, ApmA and ApmB, are sufficient for the synthesis of an amino acid ester, asperphenamate. Using the heterologous expression system, we identified that ApmA, with a reductase domain, rarely generates dipeptidyl alcohol. In contrast, ApmB was determined to not only catalyse inter-molecular ester bond formation but also accept the linear dipeptidyl precursor into the NRPS chain. The mechanism described here provides an approach for the synthesis of new small molecules with NRPS as the catalyst. Our study reveals for the first time a two-module NRPS system for the formation of amino acid esters in nature.

Synthesis and in vitro antitumor activity of asperphenamate derivatives as autophagy inducer

In an effort to improve the aqueous solubility and the antitumor activity of natural product asperphenamate, we have designed and synthesized three series of asperphenamate derivatives, including series I (simplifying molecular skeleton series), series II (introducing a hydroxyl group to A-phenyl ring series) and series III (disrupting molecular planarity series). All derivatives have displayed a significantly increased solubility compared with asperphenamate. Their growth inhibitory activities in vitro were screened by the standard MTT method in MCF-7, HeLa, and BEL-7402 cell lines. With the exception of the derivatives in series I, most of derivatives in series II and series III showed growth inhibitory activity. Among all derivatives, IM23b in series III showed the greatest potency in human breast cancer MCF-7 cells. The cellular potency of IM23b was approximately 1.5-fold more potent than that of cisplatin. The mechanism of cell death induced by IM23b in human breast cancer MCF-7 cells was further investigated. We concluded that the cell death was induced by autophagy instead of apoptosis or cell cycle arrest.

Total synthesis and anticancer activity studies of the stereoisomers of asperphenamate and patriscabratine

All stereoisomers of asperphenamate 1a and patriscabratine 2a were achieved with a high yield, and total synthesis of 2a is firstly described here. The absolute configuration of patriscabratine was determined as (S,S). The compounds 1a-d and 2a-d have been tested by MTT assay in T47D, MDA-MB231, HL60, Hela and SGC-7901 cell lines in vitro. Among them, the (R,S) stereoisomer shows the strongest anticancer effects, while the (S,R) shows the weakest one.

Auranamide, a New Phenylalanine Derivative Isolated from Piper aurantiacum Wall

A new amide, designated auranamide, has been isolated from the seed of Piper aurantiacum Wall.Its structure and stereochemistry as VIII have been settled from spectroscopic and synthetic evidences.