31329-57-4

Basic information

• Product Name: NAFRONYL
• Synonyms: 2-(Diethylamino)ethyl 3-(1-naphthyl)-2-(tetrahydro-2-furanylmethyl)propanoate;2-(Diethylamino)ethyl ester tetrahydro-alpha-(1-naphthalenylmethyl)-2-furanpropanic acid;2-(Diethylamino)ethyl tetrahydro-alpha-(1-naphthylmethyl)-2-furanpropionate;2-(diethylamino)ethyltetrahydro-alpha-(1-naphthylmethyl)-2-furanpropionate;2-Furanpropanoic acid, tetrahydro-alpha-(1-naphthalenylmethyl)-, 2-(diethylamino)ethyl ester;2-Furanpropionic acid, tetrahydro-alpha-(1-naphthylmethyl)-, 2-(diethylamino)ethyl ester;3-(1-Naphthyl)-2-tetrahydrofurfurylpropionic acid 2-(diethylamino)ethyl ester;3-(1-naphthyl)-2-tetrahydrofurfurylpropionicacid2-(diethylamino)ethylester
• CAS NO: 31329-57-4
• Molecular Formula: C₂₄H₃₃NO₃
• Molecular Weight: 383.52
• EINECS: 250-572-2
• Product Categories: Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 31329-57-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: bp0.5 190°
• Flash Point: 267.3°C
• Appearance: /
• Density: d431 1.0465
• Vapor Pressure: 7.57E-11mmHg at 25°C
• Refractive Index: nD29 1.5513
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 9.21±0.25(Predicted)
• CAS DataBase Reference: NAFRONYL(CAS DataBase Reference)
• NIST Chemistry Reference: NAFRONYL(31329-57-4)
• EPA Substance Registry System: NAFRONYL(31329-57-4)

Safety Data

• Hazardous Substances Data: 31329-57-4(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 31329-57-4 differently. You can refer to the following data:
1. Nafronyl is a selective inhibitor of serotonin receptors. Nafronyl is a vasodilator used in the treatment of intermittent claudication.
2. Vasodilator.
3. Nafronyl is a selective inhibitor of serotonin receptors

Therapeutic Function

Vasodilator

World Health Organization (WHO)

Naftidrofuryl is a vasoactive spasmolytic used to treat peripheral vascular disease. It also improves the oxygen utilization in tissues.

InChI:InChI=1/C24H33NO3.C2H2O4/c1-3-25(4-2)14-16-28-24(26)21(18-22-12-8-15-27-22)17-20-11-7-10-19-9-5-6-13-23(19)20;3-1(4)2(5)6/h5-7,9-11,13,21-22H,3-4,8,12,14-18H2,1-2H3;(H,3,4)(H,5,6)

Upstream product

• 31329-57-4 (2RS,2'SR)-2-(diethylamino)ethyl 2-<(naphth-1-yl)methyl>-3-(tetrahydrofuran-2-yl)propanoate 
• 71862-15-2 ethyl (2'R)-2-carboethoxy-3-(tetrahydro-2'-furyl)propanoate 
• 86-52-2 1-Chloromethylnaphthalene 
• 869-24-9 2-chloro-N,N-diethylethylamine hydrochloride 
• 25379-26-4 (2S,2'R)-acide 2-<(naphth-1-yl)methyl>-3-(tetrahydrofur-2-yl)propanoique 
• 1392400-79-1 2-[(naphthalen-1-yl)methyl]-3-[(R)-tetrahydrofuran-2-yl]propanoic acid 
• 1376220-54-0 (R)-diethyl 2-[(naphthalen-1-yl)methyl]-3-(tetrahydrofuran-2-yl)malonate 
• 1376220-55-1 C₁₉H₂₀O₅ 
• 22415-60-7 [(2R)-tetrahydrofuran-2-yl]methyl 4-methylbenzenesulfonate 
• 97-99-4 (R)-(tetrahydrofuran-2-yl)methanol 
• 139157-67-8 2-<(naphth-1-yl)methyl>-2-<(tetrahydrofur-2-yl)methyl>propanedioate de dimethyle 
• 139157-65-6 2-<(tetrahydrofur-2-yl)methyl>propanedionate de dimethyle 
• 100-35-6 2-(diethylamino)ethyl chloride 
• 71862-16-3 ethyl (2'S)-2-carboethoxy-3-(tetrahydro-2'-furyl)propanoate 

Downstream Products

• 31329-57-4 (2R,2'S)-2-(diethylamino)ethyl-2-<(naphth-1-yl)methyl>-3-(tetrahydro-2-yl)propanoate 
• 31329-57-4 (2S,2'R)-2-(diethylamino)ethyl-2-<(naphth-1-yl)methyl>-3-(tetrahydro-2-yl)propanoate 
• 31329-57-4 (2R,2'R)-2-(diethylamino)ethyl-2-<(naphth-1-yl)methyl>-3-(tetrahydro-2-yl)propanoate 
• 31329-57-4 (2S,2'S)-2-(diethylamino)ethyl-2-<(naphth-1-yl)methyl>-3-(tetrahydro-2-yl)propanoate 
• 3200-06-4 (R)-3-Naphthalen-1-yl-2-[(S)-1-(tetrahydro-furan-2-yl)methyl]-propionic acid 2-diethylamino-ethyl ester; compound with oxalic acid 
• 3200-06-4 (R)-3-Naphthalen-1-yl-2-[(R)-1-(tetrahydro-furan-2-yl)methyl]-propionic acid 2-diethylamino-ethyl ester; compound with oxalic acid 
• 3200-06-4 (S)-3-Naphthalen-1-yl-2-[(S)-1-(tetrahydro-furan-2-yl)methyl]-propionic acid 2-diethylamino-ethyl ester; compound with oxalic acid 
• 3200-06-4 (S)-3-Naphthalen-1-yl-2-[(R)-1-(tetrahydro-furan-2-yl)methyl]-propionic acid 2-diethylamino-ethyl ester; compound with oxalic acid 
• 3200-06-4 Gevatran 
• 25379-26-4 (2RS,2'RS)-acide 2-<(naphth-1-yl)methyl>-3-(tetrahydrofur-2-yl)propanoique 
• 25379-26-4 (2R,2'R)-acide 2-<(naphth-1-yl)methyl>-3-(tetrahydrofur-2-yl)propanoique 
• 25379-26-4 (2S,2'S)-acide 2-<(naphth-1-yl)methyl>-3-(tetrahydrofur-2-yl)propanoique 
• 25379-26-4 (2RS,2'SR)-acide 2-<(naphth-1-yl)methyl>-3-(tetrahydrofur-2-yl)propanoique 
• 25379-26-4 (2R,2'S)-acide 2-<(naphth-1-yl)methyl>-3-(tetrahydrofur-2-yl)propanoique 

Relevant articles and documents

Separation of Stereoisomeric Mixtures of Nafronyl as a Representative of Compounds Possessing Two Stereogenic Centers by Coupling Crystallization, Diastereoisomeric Conversion and Chromatography

A procedure for the isolation of the most biologically active component of a stereoisomeric mixture of nafronyl-2-(diethylamino)ethyl 3-(naphthalen-1-yl)-2-((tetrahydrofuran-2-yl)methyl)propanoate has been proposed. The molecule of nafronyl is a representative of compounds possessing two stereogenic centers, which may be produced in the form of a quaternary mixture that contains two pairs of racemates being diastereoisomers of one another. The components of such stereoisomeric mixtures usually differ in pharmacological activity; therefore, there is an interest in developing efficient methods for their resolution. The method suggested in this study comprised two sequential separation processes, including multistage cross-current crystallization and chiral chromatography. Crystallization was employed to enrich the raw material mixture with the target racemate, which contained the stereoisomer exhibiting the highest biological activity. To intensify the process, the mother liquors depleted with the target racemate were subjected to fast base-catalyzed diastereoisomeric conversion in the melt, which provided equimolar mixtures of all four stereoisomers. The coupling of cross-current crystallization and diastereoisomeric conversion could improve yield of crystallization from 29% up to 84%. The purified racemate was further processed by chromatography to isolate finally the most active stereoisomer with 99% purity and total yield of 84%, at a relatively high throughput.

Optical isomers of naftidrofuryl (=2-(diethylamino)ethyl 2-[(naphth-1-yl)methyl]-3-(tetrahydrofur-2-yl)propanoate)

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Some new naphthalenic structures with antispasmodic activity

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