144036-19-1

Basic information

• Product Name: 3-(CYCLOPENTYLOXY)-4-METHOXYBENZOYL CHLORIDE
• Synonyms: BUTTPARK 95\04-44;3-(CYCLOPENTYLOXY)-4-METHOXYBENZOYL CHLORIDE
• CAS NO: 144036-19-1
• Molecular Formula: C₁₃H₁₅ClO₃
• Molecular Weight: 254.71
• Mol File: 144036-19-1.mol

Chemical Properties

• Boiling Point: 372.8°Cat760mmHg
• Flash Point: 151.5°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 9.39E-06mmHg at 25°C
• Refractive Index: 1.548
• CAS DataBase Reference: 3-(CYCLOPENTYLOXY)-4-METHOXYBENZOYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(CYCLOPENTYLOXY)-4-METHOXYBENZOYL CHLORIDE(144036-19-1)
• EPA Substance Registry System: 3-(CYCLOPENTYLOXY)-4-METHOXYBENZOYL CHLORIDE(144036-19-1)

Safety Data

• Hazardous Substances Data: 144036-19-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-(Cyclopentyloxy)-4-methoxybenzoyl chloride is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the creation of new drug molecules that can target specific biological pathways, potentially leading to the development of novel treatments for a variety of diseases and conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 3-(Cyclopentyloxy)-4-methoxybenzoyl chloride serves as a crucial component in the development of new pesticides and herbicides. Its ability to react with other molecules enables the production of compounds that can effectively control pests and weeds, thereby enhancing crop protection and yield.
Used in Organic Synthesis:
3-(Cyclopentyloxy)-4-methoxybenzoyl chloride is utilized as a versatile building block in organic synthesis for creating complex organic molecules. Its presence in the molecular structure can influence the reactivity and properties of the final product, making it an essential component in the synthesis of specialty chemicals and materials for various applications.

InChI:InChI=1/C13H15ClO3/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

Upstream product

• 144036-17-9 3-cyclopentyloxy-4-methoxy benzoic acid 
• 621-59-0 isovanillin 
• 137-43-9 Cyclopentyl bromide 
• 67387-76-2 3-cyclopentyloxy-4-methoxybenzylaldehyde 
• 14989-32-3 thioyl chloride 
• 6702-50-7 3-hydroxy-4-methoxybenzoate 
• 154464-24-1 methyl 3-(cyclopentyloxy)-4-methoxybenzoate 

Downstream Products

• 144035-83-6 piclamilast 
• 144035-58-5 N-(2-methylthiophenyl)-3-cyclopentyloxy-4-methoxybenzamide 

Relevant articles and documents

Discovery of N-Alkyl Catecholamides as Selective Phosphodiesterase-4 Inhibitors with Anti-neuroinflammation Potential Exhibiting Antidepressant-like Effects at Non-emetic Doses

Depression involving neuroinflammation is one of the most common disabling and life-threatening psychiatric disorders. Phosphodiesterase 4 (PDE4) inhibitors produce potent antidepressant-like and cognition-enhancing effects. However, their clinical utilit

Development of highly potent phosphodiesterase 4 inhibitors with anti-neuroinflammation potential: Design, synthesis, and structure-activity relationship study of catecholamides bearing aromatic rings

In this study, catecholamides (7a–l) bearing different aromatic rings (such as pyridine-2-yl, pyridine-3-yl, phenyl, and 2-chlorophenyl groups) were synthesized as potent phosphodiesterase (PDE) 4 inhibitors. The inhibitory activities of these compounds w

Synthesis and evaluation of clioquinol-rolipram/roflumilast hybrids as multitarget-directed ligands for the treatment of Alzheimer's disease

Considering the importance of PDE4D inhibition and the modulation of biometals in Alzheimer's disease (AD) therapeutics, we have designed, synthesized and evaluated a series of new clioquinol-rolipram/roflumilast hybrids as multitarget-directed ligands fo

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.

Catechol pyrazolinones as trypanocidals: Fragment-based design, synthesis, and pharmacological evaluation of nanomolar inhibitors of trypanosomal phosphodiesterase B1

Trypanosomal phosphodiesterases B1 and B2 (TbrPDEB1 and TbrPDEB2) play an important role in the life cycle of Trypanosoma brucei, the causative parasite of human African trypanosomiasis (HAT), also known as African sleeping sickness. We used homology modeling and docking studies to guide fragment growing into the parasite-specific P-pocket in the enzyme binding site. The resulting catechol pyrazolinones act as potent TbrPDEB1 inhibitors with IC50 values down to 49 nM. The compounds also block parasite proliferation (e.g., VUF13525 (20b): T. brucei rhodesiense IC50 = 60 nM, T. brucei brucei IC50 = 520 nM, T. cruzi = 7.6 μM), inducing a typical multiple nuclei and kinetoplast phenotype without being generally cytotoxic. The mode of action of 20b was investigated with recombinantly engineered trypanosomes expressing a cAMP-sensitive FRET sensor, confirming a dose-response related increase of intracellular cAMP levels in trypanosomes. Our findings further validate the TbrPDEB family as antitrypanosomal target.

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.

Synthesis and biological evaluation of neutrophilic inflammation inhibitors

In several non-infectious human diseases, such as ulcerous colitis, rheumatoid arthritis, chronic obstructive pulmonary disease (COPD), the extravasal recruitment of neutrophils plays a crucial role in the development of tissue damage, which, when persist

Phthalazine derivatives as phosphodiesterase 4 inhibitors

Compounds of formula (I) wherein B is alkylene, amino, CONH or a bond; Cy is optionally substituted phenyl or heteroaryl; R is H, phenyl or (C1-4)alkyl optionally substituted; R1is (C1-6)alkyl or polyfluoro(C1-6)-alkyl; R2is (C4-7)cycloalkyl optionally containing an oxygen atom and optionally substituted; and the N→O derivatives and pharmaceutically acceptable salt thereof are PDE 4 and TNFα inhibitors.

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.