180005-03-2

Basic information

• Product Name: 4-(2-CHLORO-PHENYL)-CYCLOHEXANONE
• Synonyms: 4-(2-CHLORO-PHENYL)-CYCLOHEXANONE
• CAS NO: 180005-03-2
• Molecular Formula: C₁₂H₁₃ClO
• Molecular Weight: 208.687
• Mol File: 180005-03-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-(2-CHLORO-PHENYL)-CYCLOHEXANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-CHLORO-PHENYL)-CYCLOHEXANONE(180005-03-2)
• EPA Substance Registry System: 4-(2-CHLORO-PHENYL)-CYCLOHEXANONE(180005-03-2)

Safety Data

• Hazardous Substances Data: 180005-03-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(2-Chlorophenyl)-cyclohexanone is used as a synthetic intermediate for the preparation of cyclohexyl pyridylpiperazines. These compounds serve as Δ8-Δ7 sterol isomerase ligands, which possess antiproliferative activity. This makes them potential candidates for the development of drugs targeting the inhibition of cell proliferation, a key factor in various diseases including cancer and other proliferative disorders.
The specific application of 4-(2-Chlorophenyl)-cyclohexanone in the synthesis of these bioactive compounds highlights its importance in medicinal chemistry and drug discovery. Its role in creating molecules with potential therapeutic effects underscores the value of 4-(2-CHLORO-PHENYL)-CYCLOHEXANONE in advancing treatments for various health conditions.

Upstream product

• 694-80-4 2-bromo-1-chlorobenzene 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 615-41-8 2-iodochlorobenzene 
• 680596-79-6 4,4,5,5-tetramethyl-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1,3,2-dioxaborolane 
• 180005-02-1 2'-chloro-2,5-dihydro-[1,1'-biphenyl]-4(3H)-one 

Downstream Products

• 37416-32-3 2-[4-(2-Chloro-phenyl)-cyclohex-1-enyl]-propionic acid 
• 1247885-42-2 (4-(2-chlorophenyl)cyclohex-1-enyloxy)trimethylsilane 
• 37416-33-4 2-[4-(2-Chloro-phenyl)-cyclohex-1-enyl]-propionic acid ethyl ester 

Relevant articles and documents

Cobalt-Catalyzed Desymmetric Isomerization of Exocyclic Olefins

Chiral cyclic olefins, 1-methylcyclohexenes, are versatile building blocks for the synthesis of pharmaceuticals and natural products. Despite the prevalence of these structural motifs, the development of efficient synthetic methods remains an unmet challenge. Herein we report a novel desymmetric isomerization of exocyclic olefins using a series of newly designed chiral cobalt catalysts, which enables a straightforward construction of chiral 1-methylcyclohexenes with diversified functionalities. The synthetic utility of this methodology is highlighted by a concise and enantioselective synthesis of a natural product, β-bisabolene. The versatility of the reaction products is further demonstrated by multifarious derivatizations.

NOVEL 5 or 8-SUBSTITUTED IMIDAZO [1, 5-a] PYRIDINES AS SELECTIVE INHIBITORS OF INDOLEAMINE AND/OR TRYPTOPHANE 2, 3-DIOXYGENASES

Disclosed herein are 5 or 8-substituted imidazo [1, 5-a] pyridines and pharmaceutical compositions comprising at least one such 5 or 8-substituted imidazo [1, 5-a] pyridines, processes for the preparation thereof, and the use thereof in therapy. Disclosed herein are certain 5 or 8-substituted imidazo [1, 5-a] pyridines that can be useful for inhibiting indoleamine 2, 3-dioxygenase and/or tryptophane 2, 3-dioxygenase and for treating diseases or disorders mediated thereby.

Optimization of TRPV6 calcium channel inhibitors using a 3D ligand-based virtual screening method

Herein, we report the discovery of the first potent and selective inhibitor of TRPV6, a calcium channel overexpressed in breast and prostate cancer, and its use to test the effect of blocking TRPV6-mediated Ca2+-influx on cell growth. The inhib

1-Cyclohexyl-4-(4-arylcyclohexyl)piperazines: Mixed σ and Human Δ8-Δ7 Sterol Isomerase Ligands with Antiproliferative and P-Glycoprotein Inhibitory Activity

Many new chemotherapeutic agents are under preclinical investigation and, despite efforts to more selectively target cancer cells, limitations such as toxicity and inherent resistance are often encountered. Therefore, alternative strategies are needed to treat cancer and overcome such limitations. We describe novel cyclohexylpiperazine derivatives, designed as mixed affinity ligands for sigma (σ) receptors and human Δ8-Δ7 sterol isomerase (HSI) ligands, which also exhibit P-glycoprotein (P-gp) inhibitory activity, with the aim of exploiting the antiproliferative effects mediated by σ and HSI sites while overcoming P-gp-mediated resistance. All of the compounds displayed high affinities for σ receptors and HSI sites, P-gp inhibitory activity, and σ2 receptor agonist antiproliferative activity. Antiproliferative activity was also tested in PC-3 cells to establish σ1 and HSI contribution. Compound cis-11, which displayed the best antiproliferative and P-gp inhibitory activities, was co-administered with 0.1 μM doxorubicin in MDCK-MDR1 cells. Compound cis-11 caused 70 % and 90 % cell death when co-administered at 30 μM and 50 μm, respectively. When administered alone, cis-11 resulted in 50 % cell death, demonstrating its single agent antitumor properties in a tumor cell line overexpressing P-gp.Synergistic mixed activity: A series of cyclohexylpiperazines with mixed σ and HSI affinities and P-gp inhibitory activity were synthesized. Their antiproliferative activity, combined with P-gp inhibitory activity, shows the potential of these compounds to be used as antitumor agents devoid of P-gp-mediated resistance, or in association with classic antitumor agents susceptible to P-gp activity.

Novel 4-(4-aryl)cyclohexyl-1-(2-pyridyl)piperazines as Δ8- Δ7 sterol isomerase (emopamil binding protein) selective ligands with antiproliferative activity

To find Δ8-Δ7 sterol isomerase (EBP) selective ligands, various arylpiperazines previously studied and structurally related to some σ receptors ligands were preliminarily screened. Consequently, a novel series of 2- or 2,6-disubstitu

Insecticidal substituted-2,4-diamino-5,6,7,8-tetrahydroquinazolines

There is provided an insecticidal composition comprising, in admixture with an agriculturally acceptable carrier, an insecticidally effective amount of a tetrahydroquinazoline compound of the formula STR1 wherein R, R1, R2, R3, R5, R6, R7, R8, and R9 are as defined herein, and methods of using the same. Certain novel substituted-phenyl tetrahydroquinazoline compounds per se are also identified.