144036-17-9

Basic information

• Product Name: 3-(CYCLOPENTYLOXY)-4-METHOXYBENZOIC ACID
• Synonyms: 3-(CYCLOPENTYLOXY)-4-METHOXYBENZOIC ACID;BUTTPARK 75\04-33;RARECHEM AL BO 1947;3-(Cyclopentyloxy)-4-methoxybezoic acid
• CAS NO: 144036-17-9
• Molecular Formula: C₁₃H₁₆O₄
• Molecular Weight: 236.26
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 144036-17-9.mol

Chemical Properties

• Melting Point: 160-164°C
• Boiling Point: 376.3°Cat760mmHg
• Flash Point: 142°C
• Appearance: /
• Density: 1.213±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 2.48E-06mmHg at 25°C
• Refractive Index: 1.559
• Storage Temp.: 2-8°C
• PKA: 4.22±0.10(Predicted)
• CAS DataBase Reference: 3-(CYCLOPENTYLOXY)-4-METHOXYBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(CYCLOPENTYLOXY)-4-METHOXYBENZOIC ACID(144036-17-9)
• EPA Substance Registry System: 3-(CYCLOPENTYLOXY)-4-METHOXYBENZOIC ACID(144036-17-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 144036-17-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
3-(Cyclopentyloxy)-4-methoxybenzoic acid is used as a building block in the synthesis of pharmaceuticals and agrochemicals for its unique chemical properties and structure, contributing to the development of new drugs and agrochemical products.
Used in Dye and Pigment Industries:
3-(CYCLOPENTYLOXY)-4-METHOXYBENZOIC ACID is utilized as a key component in the production of dyes and pigments, enhancing the color properties and performance of these materials in various applications.
Used in Functional Materials:
3-(Cyclopentyloxy)-4-methoxybenzoic acid is employed in the creation of functional materials, where its chemical structure imparts specific properties that are beneficial for various technical applications.
Used in Medical and Biological Research:
In the field of medical and biological research, 3-(Cyclopentyloxy)-4-methoxybenzoic acid is used as a starting material for the development of new drugs and therapeutic agents, potentially leading to advancements in healthcare and treatment options.

InChI:InChI=1/C13H16O4/c1-16-11-7-6-9(13(14)15)8-12(11)17-10-4-2-3-5-10/h6-8,10H,2-5H2,1H3,(H,14,15)

Upstream product

• 154464-24-1 methyl 3-(cyclopentyloxy)-4-methoxybenzoate 
• 6702-50-7 3-hydroxy-4-methoxybenzoate 
• 621-59-0 isovanillin 
• 5329-14-6 aminosulfonic acid 
• 67387-76-2 3-cyclopentyloxy-4-methoxybenzylaldehyde 
• 7758-19-2 sodium chlorite 
• 137-43-9 Cyclopentyl bromide 

Downstream Products

• 158429-30-2 3-cyclopentyloxy-4-methoxybenzthioamide 
• 141184-48-7 1-[3-(cyclopentyloxy)-4-methoxyphenyl]-ethanone 
• 158429-29-9 2-N[3-(cyclopentyloxy)-4-methoxyphenylcarbonyl]amino-3-hydroxypyridine 
• 144036-19-1 3-cyclopentyloxy-4-methoxy benzoic acid chloride 
• 159783-15-0 N-methoxy-N-methyl-3-cyclopentoxy-4-methoxybenzamide 

Relevant articles and documents

Comparison of the full-length and 152~528 truncate of human cyclic nucleotide phosphodiesterase 4b2 for the characterization of inhibitors

Aim and Objective: Human full-length cyclic nucleotide phosphodiesterase isozyme 4B2 (hPDE4B2) as the target for screening and characterizing inhibitors suffers from low activity yield and the coexistence of two conformational states bearing different aff

Catecholic amides as potential selective phosphodiesterase 4D inhibitors: Design, synthesis, pharmacological evaluation and structure-activity relationships

In this study, a series of catechol-based amides (8a-n) with different amide linkers linking the catecholic moiety to the terminal phenyl ring was designed and synthesized as potent phosphodiesterase (PDE) 4D inhibitors. The inhibitory activities of these compounds were evaluated against the core catalytic domains of human PDE4 (PDE4CAT), full-length PDE4B1 and PDE4D7 enzymes, and other PDE family members. The results indicated the majority of compounds 8a-n displayed moderate to good inhibitory activities against PDE4CAT. Among these compounds, compound 8j with a short amide linker (-CONHCH2-) displayed comparable PDE4CAT inhibitory activity (IC50 = 410 nM) with rolipram. More interestingly, compound 8g, a potent and selective PDE4D inhibitor (IC50 = 94 nM), exhibited a 10-fold selectivity over the PDE4B subtypes and an over 1000-fold selectivity against other PDE family members. Docking simulations suggested that 8g forms three extra H-bonds with the N-H of residue Asn487 and two water molecules.

Synthesis, biological evaluation, and molecular modeling of new 3-(cyclopentyloxy)-4-methoxybenzaldehyde O-(2-(2,6-dimethylmorpholino)-2- oxoethyl) oxime (GEBR-7b) related phosphodiesterase 4D (PDE4D) inhibitors

A new series of 3-(cyclopentyloxy)-4-methoxyphenyl derivatives, structurally related to our hit GEBR-4a (1) and GEBR-7b (2), has been designed by changing length and functionality of the chain linking the catecholic moiety to the terminal cycloamine portion. Among the numerous molecules synthesized, compounds 8, 10a, and 10b showed increased potency as PDE4D enzyme inhibitors with respect to 2 and a good selectivity against PDE4A4, PDE4B2, and PDE4C2 enzymes, without both cytotoxic and genotoxic effects. The ability to enhance cAMP level in neuronal cells was assessed for compound 8. SAR considerations, also confirmed by in silico docking simulations, evidenced that both chain and amino terminal function characterized by higher hydrophilicity are required for a good and selective inhibitor-catalytic pocket interaction.

INHIBITORS OF PHOSPHODIESTERASE TYPE-IV

The present invention relates to oxazine derivatives, which can be used as selective inhibitors of phosphodiesterase (PDE) type IV. Compounds disclosed herein can be useful in the treatment of CMS disorders, AIDS, asthma, arthritis, bronchitis, chronic ob

INHIBITORS OF PHOSPHODIESTERASE TYPE-IV

The present invention relates to oxazine derivatives, which can be used as selective inhibitors of phosphodiesterase (PDE) type IV. Compounds disclosed herein can be useful in the treatment of CMS disorders, AIDS, asthma, arthritis, bronchitis, chronic ob

AMIDE DERIVATIVES

The invention concerns amide derivatives of Formula (Ia) wherein X is -NHCO- or -CONH-; m is 0-3; R1 is a group such as hydroxy, halogeno, trifluoromethyl, cyano, mercapto, nitro, amino, carboxy and carbamoyl; n is 0-2; R2 is a group

NEW HETEROCYCLIC AMIDE COMPOUNDS USEFUL FOR THE TREATMENT OF INFLAMMATORY AND ALLERGIC DISORDERS: PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

The present invention relates to novel heterocyclic compounds that inhibit phosphodiesterase type 4 (PDE 4). The compounds are useful for treating inflammatory conditions, diseases of the central nervous systems and insulin resistant diabetes.

Phthalazine derivatives as phosphodiesterase 4 inhibitors

The present invention provides a compound selected from the group including: N-3-acetyl-1-(3,5-dichloropyridin-4-ylmethyl)-5-cyclopentyloxy-6-methoxy-4H-phthalazine; 6,7-dimethoxy-1-pyridin-4-ylmethyl-4-thiazol-2-yl-phthalazine; 1-(6,7-dimethoxy-4-pyridin-4-ylmethyl-1H-phthalazin-2-yl)ethanone; 2-methanesulphonyl-6,7-dimethoxy-4-pyridin-4-ylmethyl-1,2-dihydrophthalazine; 2-formyl-6,7-dimethoxy-4-pyridin-4-ylmethyl-1,2-dihydrophthalazine; 1-(6,7-dimethoxy-4-pyridin-4-ylmethyl-1H-phthalazin-2-yl)-1-imidazol-1-ylmethanone; 1-(3,5-dichloro-pyridin-4-ylmethyl)-3-methansulphonyl-6-difluoromethoxy-5-(tetrahydro-furan-2-yloxy)-4H-phthalazine; N→O derivatives thereof; and pharmaceutically acceptable salts thereof. The invention also provides a pharmaceutical composition, which contains a therapeutically effective amount of the above compound in admixture with a pharmaceutically acceptable carrier.

Cathecol derivatives and a method for the preparation thereof and a pharmaceutical composition containing the same

A phosphodiesterase IV inhibiting cathecol derivatives of the general formula I: or a pharmaceutically acceptable salt thereof in which R1 is C1-7 alkyl; C3-7 cycloalkane; phenyl optionally substituted with lower alkyl lower alkoxy, nitro or halogen; pyrimidine optionally substituted with lower alkyl, lower alkoxy, nitro or halogen; or pyridine optionally substituted with lower alkyl, lower alkoxy, nitro or halogen; X, Y and Z are each independently oxygen, nitrogen or sulfur optionally substituted with C1-7 alkyl, C3-7 cycloalkane or phenyl; W is oxygen or sulfur is disclosed. In addition, a process for producing the compound of the general formula I and a pharmaceutical composition containing pharmaceutically effective amount of the compound of the general formula I are disclosed.

COMPOUNDS CONTAINING PHENYL LINKED TO ARYL OR HETEROARYL BY AN ALIPHATIC- OR HETEROATOM-CONTAINING LINKING GROUP

This invention is directed to the pharmaceutical use of phenyl compounds, which are linked to an aryl moiety by various linkages, for inhibiting tumor necrosis factor. The invention is also directed to the compounds, their preparation and pharmaceutical compositions containing these compounds. Furthermore, this invention is directed to the pharmaceutical use of the compounds for inhibiting cyclic AMP phosphodiesterase