99592-32-2

Basic information

• Product Name: Sertaconazole nitrate
• Synonyms: 1-(2-((7-chlorobenzo(b)thien-3-yl)methoxy)-2-(2,4-dichlorophenyl)ethyl)-1h-i;1h-imidazole,1-(2-((7-chlorobenzo(b)thien-3-yl)methoxy)-2-(2,4-dichlorophenyl);7-chloro-3-(1-(2,4-dichlorophenyl)-2-(1h-imidazol-1-yl)ethoxy-methyl)benzo(b;7-cloro-3-(1-(2,4-diclorofenil)-2-(1h-imidazol-1-il)etoxi-metil)benzo(b)tiof;eno;fi-7045;SERTACONAZOLE;7-CHLORO-3-[1-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YL)ETHOXY-METHYL] BENZO[B]THIOPHENE NITRATE
• CAS NO: 99592-32-2
• Molecular Formula: C₂₀H₁₅Cl₃N₂OS
• Molecular Weight: 437.77
• EINECS: 1312995-182-4
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 99592-32-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 146-147°
• Boiling Point: 614.1 °C at 760 mmHg
• Flash Point: 325.2 °C
• Appearance: /
• Density: 1.43 g/cm³
• Vapor Pressure: 2.35E-14mmHg at 25°C
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 6.68±0.12(Predicted)
• CAS DataBase Reference: Sertaconazole nitrate(CAS DataBase Reference)
• NIST Chemistry Reference: Sertaconazole nitrate(99592-32-2)
• EPA Substance Registry System: Sertaconazole nitrate(99592-32-2)

Safety Data

• Hazardous Substances Data: 99592-32-2(Hazardous Substances Data)

Usage

Description

Sertaconazole has been developed and launched for the treatment of dermatological fungal infections by Ferrer Internacional S. A. Mylan received FDA approval for sertaconazole nitrate cream for the treatment of athlete's foot (tinea pedis) at the end of 2003.

Uses

An imidazole antifungal agent, inhibits the synthesis of ergosterol, an essential cell wall component of fungi.

Synthesis

2,4-Dichloro acetophenone 169 was brominated at low temperature to give bromide intermediate 170, which was used without isolation. To the same pot, five-fold excess of imidazole was added to give imidazolylacetophenone 171 in 71% yield from 169. Sodium borohydride was employed to reduce ketone 171 to alcohol 172 in 78% yield. Racemic alcohol 172 was resolved with (-)-DIP-chloride to give its corresponding chiral R-alcohol 173 in 80% yield. Compound 173 was then alkylated with 3-bromomethyl-7-chlorobenzo[b]thiophene (174) in dry DMF in the presence of potassium t-butoxide to give the alkylation product in 68% yield. Finally, 60% nitric acid was used to make sertaconazole mononitrate (XXI) in 89% yield.

InChI:InChI=1/C20H15Cl3N2OS.HNO3/c21-14-4-5-16(18(23)8-14)19(9-25-7-6-24-12-25)26-10-13-11-27-20-15(13)2-1-3-17(20)22;2-1(3)4/h1-8,11-12,19H,9-10H2;(H,2,3,4)

Upstream product

• 24155-42-8 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol 
• 142181-53-1 (7-chlorobenzo[b]thiophen-3-yl)methanol 
• 84483-28-3 2-chloro-6-iodoaniline 
• 17512-61-7 3-Bromomethyl-7-chlorobenzothiophene 

Downstream Products

• 583057-51-6 Arasertaconazole GRUPO FERRER 
• 583057-51-6 sertaconazole 

Relevant articles and documents

Visible-Light-Induced Radical Carbo-Cyclization/ gem-Diborylation through Triplet Energy Transfer between a Gold Catalyst and Aryl Iodides

Geminal diboronates have attracted significant attention because of their unique structures and reactivity. However, benzofuran-, indole-, and benzothiophene-based benzylic gem-diboronates, building blocks for biologically relevant compounds, are unknown. A promising protocol using visible light and aryl iodides for constructing valuable building blocks, including benzofuran-, indole-, and benzothiophene-based benzylic gem-diboronates, via radical carbo-cyclization/gem-diborylation of alkynes with a high functional group tolerance is presented. The utility of these gem-diboronates has been demonstrated by a 10 g scale conversion, by versatile transformations, by including the synthesis of approved drug scaffolds and two approved drugs, and even by polymer synthesis. The mechanistic investigation indicates that the merging of the dinuclear gold catalyst (photoexcitation by 315-400 nm UVA light) with Na2CO3 is directly responsible for photosensitization of aryl iodides (photoexcitation by 254 nm UV light) with blue LED light (410-490 nm, λmax = 465 nm) through an energy transfer (EnT) process, followed by homolytic cleavage of the C-I bond in the aryl iodide substrates.

Synthesis and antimycotic activity of (benzo[b]thienyl)methyl ethers of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-ethanol and of (Z)-1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanone oxime

A new series of (benzo[b]thienyl)methyl ethers of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol and of (Z)-1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanone oxime were synthesized and tested for antifungal activity. Series design, synthesis, preliminary antimycotic data and structure-activity relationships are reported. 7-Chloro-3-[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxymethyl] benzo[b]thiophene (8i, Sertaconazole, FI-7045, CAS 99592-32-2) and its nitrate were selected for further research.