Naftifine

Base Information

• Chemical Name: Naftifine
• CAS No.: 65472-88-0
• Molecular Formula: C21H21N
• Molecular Weight: 287.404
• Hs Code.: 29214990
• UNII: 4FB1TON47A
• DSSTox Substance ID: DTXSID6048545
• Nikkaji Number: J19.990G,J3.124.773J
• Wikipedia: Naftifine
• Wikidata: Q413586
• NCI Thesaurus Code: C66217
• RXCUI: 31476
• Pharos Ligand ID: V9QDZMKNX1TU
• ChEMBL ID: CHEMBL626
• Mol file: 65472-88-0.mol

Synonyms:N-cinnamyl-N-methyl-1-naphthalenemethylamine hydrochloride;naftifin;naftifine;naftifine hydrochloride;naftifine hydrochloride, (E)-isomer

Chemical Property of Naftifine

Chemical Property:

• Vapor Pressure: 6.07E-08mmHg at 25°C
• Melting Point: 177 °C
• Boiling Point: 440.1 °C at 760 mmHg
• PKA: 7.99±0.50(Predicted)
• Flash Point: 194.4 °C
• PSA: 3.24000
• Density: 1.082 g/cm³
• LogP: 5.78700
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 287.167399674
• Heavy Atom Count: 22
• Complexity: 342

Purity/Quality:

99% ^*data from raw suppliers

(E)-Naftifine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(CC=CC1=CC=CC=C1)CC2=CC=CC3=CC=CC=C32
• Isomeric SMILES: CN(C/C=C/C1=CC=CC=C1)CC2=CC=CC3=CC=CC=C32
• Recent ClinicalTrials: Multicenter Study of the Safety and Efficacy of NAFT-500 in Tinea Pedis
• Uses: Naftifine (Naftin) is a synthetic allylamine derivative topical antifungal agent that works by blocking squalene 2,3-epoxidase, resulting in increased cell membrane permeability and cell death. It is structurally and pharmacologically related to terbinafine. It also has some antiinflammatory properties that may be due to its ability to alter chemotaxis by polymorphonucleocytes. It is most effective against dermatophytes, moderately active against molds, and less active against yeasts, including C. albicans. Naftifine is only permitted to be used externally and only superficially as a drug with a broad spectrum of action against dermatophytes and candida infections. According to the initial data, it exceeds the activity of econazole. Moreover, it does not have a locally irritating effect. It is believed that the fungicide activity of this drug is based on its ability to inhibit the fungal enzyme squalene epoxidase, thus lowering the concentration of ergosterol. The corresponding enzyme in mammals is inhibited significantly less. Synonyms of this drug are exoderil, naftin, and others. (E)-Naftifine is an intermediate in synthesizing Naftifine N-Oxide (N213110), which is an impurity or metabolite of Naftifine Hydrochloride (N213100), an allylamine antifungal agent.
• Indications: Naftifine (Naftin) is a synthetic allylamine derivative topical antifungal agent that works by blocking squalene 2,3-epoxidase, resulting in increased cell membrane permeability and cell death. It is structurally and pharmacologically related to terbinafine. It also has some antiinflammatory properties that may be due to its ability to alter chemotaxis by polymorphonucleocytes. It is most effective against dermatophytes, moderately active against molds, and less active against yeasts, including C. albicans.
• Therapeutic Function: Antifungal
• Clinical Use: Naftifine was the first allyl amine to be discovered and marketed. It is subject to extensive first-pass metabolism to be orally active and, consequently, is only available in topical preparations. The widest use of naftifine is against various tinea infections of the skin.

Technology Process of Naftifine

There total 40 articles about Naftifine 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: 100.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (E)-N-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine (92610-10-1) → naftifine (65472-88-0)

Guidance literature:

With sodium dihydrogen phosphate; In 1,4-dioxane; water; at 60 ℃; for 0.166667h;

DOI:10.1016/S0040-4039(01)81224-7

Reference yield: 98.0%

N-methyl-1-naphthalenemethylamine (14489-75-9) + (2E)-3-phenyl-2-propen-1-ol (4407-36-7) → naftifine (65472-88-0)

Guidance literature:

Pt(COD)Cl₂; bis[2-(diphenylphosphino)phenyl] ether; In 1,4-dioxane; for 12h; Heating;

DOI:10.1021/ol071365s

Reference yield: 98.0%

(E)-cinnamyl phenyl ether (16519-25-8) + N-methyl-1-naphthalenemethylamine (14489-75-9) → naftifine (65472-88-0)

Guidance literature:

With bis(η3-allyl-μ-chloropalladium(II)); Methyl formate; potassium carbonate; bis[2-(diphenylphosphino)phenyl] ether; In water; at 20 ℃; for 0.333333h; chemoselective reaction;

DOI:10.1039/b914982a

upstream raw materials:

formaldehyd

trans-2-phenylvinylboronic acid

N-methyl-1-naphthalenemethylamine

(E)-N-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine

Downstream raw materials:

N-methyl-N-(3-phenylpropyl)-1-naphthalenemethanamine

Refernces

• 1、 -. "Preparation method for synthesizing amine compound through co-catalysis and hydrosilylation of amide by iridium and boron reagents". Paragraph 0035-0038. . Retrieved 2022/04/03.
• 2、 Kaldas, Sherif J.,Tien, Chieh-Hung,Gomes, Gabriel Dos Passos,Meyer, Stephanie,Sirvinskas, Martynas,Foy, Hayden,Dudding, Travis,Yudin, Andrei K.. "Oxidative Rearrangement of MIDA (N-Methyliminodiacetic Acid) Boronates: Mechanistic Insights and Synthetic Applications". supporting information. p. 324 - 328. Retrieved 2021/01/26.