116679-83-5

Basic information

• Product Name: P-FLUORO-HEXAHYDRO-SILA-DIFENIDOL
• Synonyms: P-FLUORO-HEXAHYDRO-SILA-DIFENIDOL;HEXAHYDRO-SILA-DIFENIDOL HYDROCHLORIDE P -FLUORO ANALOG (P-F-;p-fluorohexahydro-sila-difenidol hydrochloride;4-fluorohexahydrosiladifenidol;P-F-HHSiD hydrochloride, Cyclohexyl-(4-fluorophenyl)-(3-N-piperidinopropyl)silanol hydrochloride;Cyclohexyl(3-piperidinopropyl)(4-fluorophenyl)silanol;Cyclohexyl(4-fluorophenyl)(3-piperidinopropyl)silanol;p-FHHSiD
• CAS NO: 116679-83-5
• Molecular Formula: C₂₀H₃₂FNOSi
• Molecular Weight: 386.024
• Mol File: 116679-83-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 447.5°Cat760mmHg
• Flash Point: 224.4°C
• Appearance: white/solid
• Density: 1.07g/cm³
• Vapor Pressure: 8.59E-09mmHg at 25°C
• Refractive Index: 1.536
• Solubility: H2O: 1.5 mg/mL, slightly soluble
• PKA: 13.74±0.20(Predicted)
• CAS DataBase Reference: P-FLUORO-HEXAHYDRO-SILA-DIFENIDOL(CAS DataBase Reference)
• NIST Chemistry Reference: P-FLUORO-HEXAHYDRO-SILA-DIFENIDOL(116679-83-5)
• EPA Substance Registry System: P-FLUORO-HEXAHYDRO-SILA-DIFENIDOL(116679-83-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 116679-83-5(Hazardous Substances Data)

Usage

Uses

p-Fluorohexahydro-sila-difenidol is a high affinity M3 muscarinic acetylcholine receptor antagonist.

InChI:InChI=1/C20H32FNOSi/c21-18-10-12-20(13-11-18)24(23,19-8-3-1-4-9-19)17-7-16-22-14-5-2-6-15-22/h10-13,19,23H,1-9,14-17H2

Upstream product

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Relevant articles and documents

Cyclohexyl(4-fluorophenyl)(3-piperidinopropyl)silanol (p-fluoro-hexahydro-sila-difenidol, p-F-HHSiD) and derivatives: synthesis and antimuscarinic properties

Four different syntheses of the potent and selective muscarinic antagonist cyclohexyl(4-fluorophenyl)(3-piperidinopropyl)silanol (p-fluoro-hexahydro-sila-difenidol, p-F-HHSiD (2b); isolated as hydrochloride 2b * HCl) are described (starting materials: (CH3O)3SiCH2CH2CH2Cl and Si(OCH3)4).In addition, the synthesis of the corresponding carbon analogue p-fluoro-hexahydro-difenidol (p-F-HHD (2a); isolated as 2a * HCl) and the syntheses of three p-F-HHSiD derivatives (3-5), with a modified cyclic amino group, are reported (3: piperidino/pyrrolidino exchange, isolated as 3 * HCl; 4; piperidino/hexamethylenimino exchange, isolated as 4 * HCl; 5; quaternization of 2b with methyl iodide).The chiral compounds 2a, 2b, 3, 4 and 5 were prepared as racemates.In functional pharmacological studies, 3-5 behaved as simple competitive antagonists at muscarinic M1 receptors in rabbit vas deferens, M2 receptors in guinea-pig atria, and M3 receptors in guinea-pig ileal smooth muscle.The pyrrolidino (3) and hexamethylenimino (4) analogues of the parent drug p-F-HHSiD (2b) displayed the highest affinity for M1 and M3 receptors (pA2 values: 7.0-7.4) but exhibited lower affinity for cardiac M2 receptors (pA2: 5.9 and 6.0).Their affinity profile (M1 ca.M3 above M2) is different from that of p-F-HHSiD (2b) (M3 above M1 above M2), but qualitatively very similar to that of p-F-HHD (2a).The methiodide 5 exhibited the highest affinity for M1 receptors (pA2 : 8.5) but lower affinity for M2 and M3 receptors by factors of 5.6 and 3.6, respectively.