133347-36-1

Basic information

• Product Name: 1-Piperazineethanol, 4-(2-hydroxyphenyl)-α-[(1-naphthalenyloxy)Methyl]-
• Synonyms: 1-Piperazineethanol, 4-(2-hydroxyphenyl)-α-[(1-naphthalenyloxy)Methyl]-
• CAS NO: 133347-36-1
• Molecular Formula: C₂₃H₂₆N₂O₃
• Molecular Weight: 378.46414
• EINECS: -0
• Mol File: 133347-36-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 613.6±55.0 °C(Predicted)
• Appearance: /
• Density: 1.238±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 11.25±0.35(Predicted)
• CAS DataBase Reference: 1-Piperazineethanol, 4-(2-hydroxyphenyl)-α-[(1-naphthalenyloxy)Methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Piperazineethanol, 4-(2-hydroxyphenyl)-α-[(1-naphthalenyloxy)Methyl]-(133347-36-1)
• EPA Substance Registry System: 1-Piperazineethanol, 4-(2-hydroxyphenyl)-α-[(1-naphthalenyloxy)Methyl]-(133347-36-1)

Safety Data

• Hazardous Substances Data: 133347-36-1(Hazardous Substances Data)

Usage

Uses

2-(4-(2-Hydroxy-3-(naphthalen-1-yloxy)propyl)piperazin-1-yl)phenol?is an impurity of Naftopidil (N213501), an α-1-adrenergic receptor antagonist and an antihypertensive agent.

Upstream product

• 1011-17-2 2-hydroxyphenylpiperazine 
• 2461-42-9 3-(1-naphthyloxy)-1,2-epoxypropane 
• 57149-07-2 naftopidil 
• 90-15-3 α-naphthol 

Relevant articles and documents

Identification of HUHS190, a human naftopidil metabolite, as a novel anti-bladder cancer drug

We carried out structure-activity relationship study on anti-cancer effects of naftopidil (1) and its metabolites, resulted in identification of 1-(4-hydroxy-2-methoxyphenyl)piperazin-1-yl)-3-(naphthalen-1-yloxy) propan-2-ol (2, HUHS190), a major human metabolite of 1, which exhibited the most selective toxicities between against normal and cancer cells (Table 1). 2 was more hydrophilic compared to 1, was enough to be prepared in high concentration solution of more than 100 μM in saline for an intravesical instillation drug. Moreover, serum concentration of 2 was comparable to that of 1, an oral preparation drug, after oral administration at 32 mg/kg (Fig. 3). Both of 1 and 2 showed broad-spectrum anti-cancer activities in vitro, for example, 1 and 2 showed inhibitory activity IC50 = 21.1 μM and 17.2 μM for DU145, human prostate cancer cells, respectively, and IC50 = 18.5 μM and 10.5 μM for T24 cells, human bladder cancer cells. In this study, we estimated anticancer effects of 2 in a bladder cancer model after intravesical administration similar to clinical cases. A single intravesical administration of 2 exhibited the most potent inhibitory activities among the clinical drugs for bladder cancers, BCG and Pirarubicin, without obvious side effects and toxicity (Fig. 4). Thus, HUHS190 (2) can be effective for patients after post-TURBT therapy of bladder cancer without side effects, unlike the currently available clinical drugs.

Metabolic fate of the novel antihypertensive drug naftopidil

The metabolism of 14C-naftopidil ((R,S)-1-(2-methoxyphenyl)-1-piperazinyl-3-(1-naphthyl-oxy)-2-propanol , CAS 57149-07-2) and the pharmacodynamic action of the metabolites was investigated. The metabolic pathway in rat, dog, mouse and man was qualitatively similar, with preference for the hydroxylation of the phenyl or naphthyl moiety of naftopidil ((phenyl)hydroxy-metabolite, (naphthyl)hydroxy-metabolite). Cleavage of the parent compound and production of the propylene glycol metabolite was a further important reaction especially for rat and man. In all species investigated, demethylation of naftopidil occurs to a minor extent. O-desmethyl-naftopidil, (phenyl)hydroxy-naftopidil and (naphthyl)hydroxy-naftopidil were found to have similar affinities for the α1-adrenoceptors as the parent compound (IC50(nmol/l): 433.0; 585.0; 52.7; respectively; naftopidil: 235.0). The naftopidil metabolites, like the parent compound showed no α2- or β-adrenoceptor affinity.