164520-98-3

Basic information

• Product Name: 4-CYCLOPENTYLOXY-BENZALDEHYDE
• Synonyms: 4-CYCLOPENTYLOXY-BENZALDEHYDE;AKOS B029049;AKOS BC-2524;CHEMBRDG-BB 4004192;ASINEX-REAG BAS 05882196;Albb-005345;4-(cyclopentyloxy)benzaldehyde(SALTDATA: FREE)
• CAS NO: 164520-98-3
• Molecular Formula: C₁₂H₁₄O₂
• Molecular Weight: 190.24
• Mol File: 164520-98-3.mol

Chemical Properties

• Boiling Point: 322.1°C at 760 mmHg
• Flash Point: 146.6°C
• Appearance: /
• Density: 1.119g/cm³
• Vapor Pressure: 0.000286mmHg at 25°C
• Refractive Index: 1.574
• CAS DataBase Reference: 4-CYCLOPENTYLOXY-BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CYCLOPENTYLOXY-BENZALDEHYDE(164520-98-3)
• EPA Substance Registry System: 4-CYCLOPENTYLOXY-BENZALDEHYDE(164520-98-3)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 164520-98-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Cyclopentyloxy-benzaldehyde is used as a key intermediate in the synthesis of rhodanine derivatives, which are known to act as inhibitors of phosphodiesterase 4 (PDE4). PDE4 inhibitors are of significant interest in the pharmaceutical industry due to their potential therapeutic applications in treating various inflammatory and autoimmune diseases, such as rheumatoid arthritis, psoriasis, and inflammatory bowel disease.
In the synthesis process, 4-cyclopentyloxy-benzaldehyde serves as a crucial building block, enabling the formation of rhodanine-based compounds with improved potency, selectivity, and pharmacokinetic properties. The development of these inhibitors can lead to the discovery of novel therapeutic agents that modulate the activity of PDE4, offering new treatment options for patients suffering from inflammatory and autoimmune disorders.

InChI:InChI=1/C12H14O2/c13-9-10-5-7-12(8-6-10)14-11-3-1-2-4-11/h5-9,11H,1-4H2

Upstream product

• 96-41-3 Cyclopentanol 
• 459-57-4 4-fluorobenzaldehyde 
• 137-43-9 Cyclopentyl bromide 
• 123-08-0 4-hydroxy-benzaldehyde 

Downstream Products

• 1515856-38-8 C₁₉H₁₉N₃OS 
• 1508310-39-1 N-(4-{[{[4-(cyclopentyloxy)phenyl]methyl}(propyl)amino]methyl}phenyl)-2-[4-(ethylsulfonyl)phenyl]acetamide 
• 936343-74-7 1-cyclopentyloxy-4-((E)-2-nitro-vinyl)-benzene 

Relevant articles and documents

Synthesis, antitumour and antioxidant activities of novel α,β-unsaturated ketones and related heterocyclic analogues: EGFR inhibition and molecular modelling study

New α,β-unsaturated ketones 4a,b; 5a–c; and 6a,b; as well as 4-H pyran 7; pyrazoline 8a,b; isoxazoline 9; pyridine 10–11; and quinoline-4-carboxylic acid 12a,b derivatives were synthesized and evaluated for in vitro antitumour activity against HepG2, MCF-

Synthesis of coumaperine derivatives: Their NF-κB inhibitory effect, inhibition of cell migration and their cytotoxic activity

Coumaperine (an amide alkaloid, present in white piper) and its derivatives were synthesized and investigated for their cytotoxicity against L428 and A549 cells and their NF-κB inhibitory activity. It was found that the coumaperine derivatives CP-9 and CP-38 suppress NF-κB subunits p50 and p65 in nuclear fractions by western blot and by NF-κB luciferase reporter gene assay in a dose dependent manner. Confirmation of these results was obtained by confocal microscopy. CP-9, CP-32 and CP-38 also exhibited dose dependent cell cytotoxicity in a L428?cells expressing constitutively active NF-κB and in A549?cells, with an IC50 value of 43.25?μg/ml, 0.39?μg/ml and 16.85?μg/ml respectively against L428?cells and 57.15?μg/ml, 69.1?μg/ml and 63.2?μg/ml respectively against A549?cells. In addition, the coumaperine derivatives show remarkable inhibitory activity on the cancer cell migration assay against A549 lung adenocarcinoma cells at the concentrations of 5?μg/ml, 10?μg/ml, and 5?μg/ml of CP-9, CP-32 and CP-38 respectively. Aromatic substituents and number of olefinic double bond in coumaperine derivatives found to influence the inhibitory activity. In luciferase reporter gene assay, di-olefin conjugated coumaperine derivatives, CP-38, CP-32 and PIP exhibited higher inhibitory activity than their corresponding tri-olefin conjugated coumaperine derivatives, CP-102, CP-146 and PIP-155 respectively. CP-32 with a stronger electron donating group (-N(CH3)2) showed better inhibitory activity in luciferase reporter gene assay and in cell proliferation of L428?cells. Simple coumaperine derivative (CP-9, with no substituent) effectively inhibited A549?cells proliferation and migration than the other coumaperine derivatives. CP-9 and CP-38 diminish significantly the NF-κB subunits (p50 and p65) of L428?cells in nuclear fractions at the dosage of 10?μg/ml and 30?μg/ml respectively. Which clearly shows that CP-9 and CP-38 inactivate the NF-κB pathway in?vitro.

DIAMINOGUANIDINE DERIVATIVES AND APPLICATION THEREOF IN PREPARATION OF ANIMAL GROWTH PROMOTERS USED IN FEED

Diaminoguanidine derivatives in preparation of animal growth promoters used in feed. The diaminoguanidine derivatives have a structural formula as shown in formula (I), wherein R1 is methyl, ethyl, isopropyl, n-butyl, n-propyl, n-pentyl, n-octyl, n-tetradecyl, sec-butyl, 3-pentyl, cyclopentyl or benzyl. The diaminoguanidine compounds significantly improve the productivity of ducks if they are fed with the diaminoguanidine compounds. Productivity of pigs or chickens is also improved with such diaminoguanidine compounds.

Novel 8-(p-substituted-phenyl/benzyl)xanthines with selectivity for the A2A adenosine receptor possess bronchospasmolytic activity

A new series of 8-(p-substituted-phenyl/benzyl)xanthines has been synthesized and evaluated in vitro for adenosine receptor binding affinity and in vivo for bronchospasmolytic effects. It was observed that the nature of substituent at para-position of 8-phenyl/benzyl group on the xanthine scaffold remarkably affects the binding affinity and selectivity of xanthine derivatives for various adenosine receptor subtypes and also their bronchospasmolytic effects. Newly synthesized 8-phenylxanthines displayed potent binding affinity and significant selectivity for A2A receptors and also produced potent bronchospasmolytic effects. Replacement of phenyl ring with benzyl moiety at C8 of xanthine skeleton resulted in notable reduction in adenosine receptor affinity and broncholytic effects.

Novel 2-(2-benzylidenehydrazinyl)benzo[d]thiazole as potential antitubercular agents

Molecular hybridization approach was used to synthesize substituted 2-(2-(4-aryl oxy benzylidene) hydrazinyl)benzo thiazole derivatives with 2-hydrazinobenzothiazole and 4-(alicycli/aryl/biaryl/heteroaryl oxy)benzaldehyde as new anti-TB agents. The synthesized compounds, when tested against H37Rv strains of Mtb using Resazurin Microtitre Assay (REMA) method, showed promising activity (MIC 1.35-36.50μg/mL). 6-chloro-2-(2-(4- (pyridin-4-yloxy) benzylidene) hydrazinyl) benzo[d]thiazole (10v) gave MIC of 1.35 μg/mL. Thus making it, a potential lead could be developed for further antitubercular studies.

SUBSTITUTED HETEROCYCLIC COMPOUNDS

The present invention relates to substituted heterocyclic compounds of Formula I or XI: or pharmaceutically acceptable salts or N-oxides or quaternary ammonium salts thereof wherein constituent members are provided hereinwith, as well as their compositions and methods of use, which are histamine II4 receptor inhibitors useful in the treatment of histamine II4 receptor-associated conditions or diseases or disorders including, for example, inflammatory diseases or disorders, pruritus, and pain.

PYRIDINE DERIVATIVES SUBSTITUTED BY HETEROCYCLIC RING AND PHOSPHONOAMINO GROUP, AND ANTI-FUNGAL AGENT CONTAINING SAME

Anti-fungal agent having excellent anti-fungal action physicochemical properties including safety and water solubility. Compound represented by formula (I), or salt thereof: wherein R1 represents hydrogen, halogen, amino, R11-NH- wherein R11 represents C1-6 alkyl, hydroxy C1-6 alkyl, C1-6 alkoxy C1-6 alkyl, or C1-6alkoxycarbonyl C1-6 alkyl, R12-(CO)-NH- wherein R12 represents C1-6 alkyl group or C1-6 alkoxy C1-6 alkyl, C1-6 alkyl, hydroxy C1-6 alkyl, cyano C1-6 alkyl, C1-6 alkoxy, or C1-6 alkoxy C1-6 alkyl or a phosphonoamino group; R2 represents hydrogen, C1-6 alkyl, amino, or a di C1-6 alkylamino group or a phosphonoamino group; one of X and Y is nitrogen while the other is nitrogen or oxygen; ring A represents a 5- or 6-member heteroaryl ring or a benzene ring which may have a halogen atom or 1 or 2 C1-6 alkyl groups; Z represents a single bond, a methylene group, an ethylene group, oxygen, sulfur, -CH2O-, -OCH2-, -NH-, -CH2NH-, -NHCH2-, -CH2S-, or -SCH2-; R3 represents hydrogen or halogen or C1-6 alkyl, C3-8 cycloalkyl, C6-10 aryl, a 5- or 6-member heteroaryl group or a 5- or 6-member nonaromatic heterocyclic group which may have 1 or 2 substituents; and R4 represents hydrogen or halogen; provided that either R1 or R2 represents a phosphonoamino group.

Heterocycles substituted pyridine derivatives and antifungal agent containing thereof

An object of the present invention is to provide an antifungal agent which has excellent antifungal effects and is superior in terms of its physical properties, safety and metabolic stability. According to the present invention, there is disclosed a compound represented by the following formula (I), or a salt thereof: wherein R1 represents a hydrogen atom, a halogen atom, an amino group, a C1-6 alkyl group, a C1-6 alkoxy group or a C1-6 alkoxy C1-6 alkyl group; R2 represents a hydrogen atom, a C1-6 alkyl group, an amino group or a di C1-6 alkylamino group; one of X and Y is a nitrogen atom while the other is a nitrogen atom or an oxygen atom; ring A represents a 5- or 6-member heteroaryl ring or a benzene ring which may have a halogen atom, or 1 or 2 C1-6 alkyl groups; Z represents a single bond, a methylene group, an ethylene group, an oxygen atom, a sulfur atom, —CH2O—, —OCH2—, —NH—, —CH2NH—, —NHCH2—, —CH2S—, or —SCH2—; R3 represents a hydrogen atom, a halogen atom, a C1-6 alkyl group, a C3-8 cycloalkyl group, a C6-10 aryl group, a 5- or 6-member heteroaryl group, or 5- or 6-member non-aromatic heterocyclic group which may have 1 or 2 substituents; and R4 represents a hydrogen atom or a halogen atom.