Fenretinide

Base Information

• Chemical Name: Fenretinide
• CAS No.: 65646-68-6
• Molecular Formula: C26H33NO2
• Molecular Weight: 391.554
• Hs Code.: 2924297099
• European Community (EC) Number: 636-255-5
• NSC Number: 760419,374551
• UNII: 187EJ7QEXL
• DSSTox Substance ID: DTXSID2032005
• Nikkaji Number: J2.845.877K,J23.263G
• Wikipedia: Fenretinide
• Wikidata: Q5443576
• NCI Thesaurus Code: C1098
• Pharos Ligand ID: NMY5THLZ9P6V
• Metabolomics Workbench ID: 56466
• ChEMBL ID: CHEMBL7301
• Mol file: 65646-68-6.mol

Synonyms:13-cis-Isomer Fenretinide;4 Hydroxyphenylretinamide;4-HPR;4-Hydroxyphenylretinamide;Fenretinide;Fenretinide, 13 cis Isomer;Fenretinide, 13-cis-Isomer;Fenretinimide;MCN R 1967;MCN-R-1967;MCNR1967;N-(4-Hydroxyphenyl)-trans-Retinamide;N-(4-Hydroxyphenyl)retinamide

Chemical Property of Fenretinide

Chemical Property:

• Appearance/Colour: Yellow Powder
• Vapor Pressure: 7.07E-15mmHg at 25°C
• Melting Point: 162-163°C
• Refractive Index: 1.607
• Boiling Point: 597.6 ºC at 760 mmHg
• PKA: 9.98±0.26(Predicted)
• Flash Point: 315.2 ºC
• PSA: 49.33000
• Density: 1.081 g/cm³
• LogP: 6.93530
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 7.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 391.251129295
• Heavy Atom Count: 29
• Complexity: 726

Purity/Quality:

99% ^*data from raw suppliers

HPR ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 60-61-20/21/22-36/37/38
• Safety Statements: 53-26-36/37/39-45-52

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)NC2=CC=C(C=C2)O)C)C
• Isomeric SMILES: CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C(=O)NC2=CC=C(C=C2)O)/C)/C
• Recent ClinicalTrials: N2004-03: Intravenous Fenretinide in Treating Young Patients With Recurrent or Resistant Neuroblastoma
• Recent EU Clinical Trials: A randomized double blind placebo controlled study on the effects of fenretinide Lym-X-Sorb on insulin sensitivity in obese insulin resistant subjects
• General Description: 4-HYDROXYPHENYLRETINAMIDE (4-HPR), also known as Fenretinide, is a synthetic retinoid derivative with demonstrated antiproliferative activity against cancer cells, particularly in promyelocytic leukemia (HL60). While glycosyl conjugates of 4-HPR were synthesized to explore reduced toxicity and retained efficacy, the parent compound itself remains more potent in inhibiting tumor cell growth. However, certain glycosylated analogs, such as the mannosyl derivative, exhibit significantly lower toxicity, suggesting potential for improved therapeutic selectivity. This highlights 4-HPR's role as a promising chemotherapeutic agent with scope for structural optimization to enhance safety profiles.

Technology Process of Fenretinide

There total 6 articles about Fenretinide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

all-trans-retinoic-acid (302-79-4) + 4-amino-phenol (123-30-8) → N-(4-hydroxyphenyl)-all-trans-retinamide (65646-68-6)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; for 1h; Ambient temperature;

DOI:10.1080/00397919808004874

Reference yield:

retinoic acid, t-butyl mixed anhydride + 4-amino-phenol (123-30-8) → N-(4-hydroxyphenyl)-all-trans-retinamide (65646-68-6)

Guidance literature:

With pyridine; In ethyl acetate; at 3 - 5 ℃; for 2.5h; Product distribution / selectivity;

Reference yield:

retinoic acid, isobutyl mixed carbonate + 4-amino-phenol (123-30-8) → N-(4-hydroxyphenyl)-all-trans-retinamide (65646-68-6)

Guidance literature:

retinoic acid, isobutyl mixed carbonate; 4-amino-phenol; In tert-butyl methyl ether; N,N-dimethyl-formamide; at 10 ℃; for 2.16667h;

With hydrogenchloride; In tert-butyl methyl ether; water; N,N-dimethyl-formamide; at 10 ℃; Product distribution / selectivity;

upstream raw materials:

retinoyl chloride

4-amino-phenol

all-trans-retinoic-acid

Downstream raw materials:

all-trans-N-<4-(Pivaloyloxy)phenyl>retinamide

4-{(2E,4E,6E,8E)-[3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoylamino]}-phenyl propionate

4-Methoxyfenretinide

4'-hydroxy 4-HPR

Refernces

Synthesis and biological activity of glycosyl conjugates of N-(4-hydroxyphenyl)retinamide

10.1016/S0014-827X(01)01074-6

The research aimed to synthesize and test the biological activity of glycosyl conjugates of N-(4-hydroxyphenyl)retinamide (4-HPR), a synthetic derivative of retinoic acid, on various tumor cell lines. The purpose was to investigate the potential antiproliferative effects and reduced toxicity of these conjugates compared to the parent compound, 4-HPR. The study focused on glucosyl, galactosyl, and mannosyl conjugates, which were synthesized through a five-step process involving the use of peracetylated monosaccharides, bismuth bromide as a catalyst, p-nitrophenol, Pearlman’s catalyst for nitro group reduction, and EDC/DMAP for coupling with RA. The synthesized compounds were then tested for their antiproliferative potential in vitro using four human cancer cell lines and their toxicity on normal cells. The results showed that all three conjugates were active on promyelocytic leukemia cell lines HL60 but were less potent than 4-HPR. Notably, the mannosyl analog (5c) demonstrated significantly lower toxicity than 4-HPR, with a selectivity index close to 15 on HL60 cells, indicating its potential as a less toxic and effective antiproliferative agent.