54135-60-3

Usage

Uses

Used in Pharmaceutical Applications:
2,2'-METHYLENEBIS(1,3-CYCLOHEXANEDIONE) is used as a cell-permeable inhibitor for the induction of apoptosis. It functions by inhibiting caspase-3 activation, a key enzyme involved in the execution of apoptosis. However, it does not directly inhibit caspase-3 even at high concentrations such as 1 mg/ml.
Used in Research and Development:
In the field of research and development, 2,2'-METHYLENEBIS(1,3-CYCLOHEXANEDIONE) serves as a valuable tool for studying the mechanisms of apoptosis and the role of caspase-3 in this process. Its ability to inhibit caspase-3 activation without directly targeting the enzyme provides researchers with a unique opportunity to explore the intricate relationships between various cellular components and pathways involved in apoptosis.
Used in Drug Discovery:
2,2'-METHYLENEBIS(1,3-CYCLOHEXANEDIONE) may also be utilized in the drug discovery process, particularly in the development of novel therapeutic agents targeting apoptosis-related diseases. Its unique mechanism of action could potentially be harnessed to create new drugs that can modulate apoptosis in a controlled manner, offering new treatment options for conditions where apoptosis dysregulation is a contributing factor.
Used in Chemical Synthesis:
Furthermore, 2,2'-METHYLENEBIS(1,3-CYCLOHEXANEDIONE) may find applications in the field of chemical synthesis, where it could be used as a building block or intermediate in the production of more complex molecules with potential applications in various industries, such as pharmaceuticals, materials science, and agrochemicals.

Biological Activity

m50054, 2,2'-methylenebis (1,3-cyclohexanedione), is a novel inhibitor of apoptosis. [1]in human fas-expressing wc8 cells, m50054 inhibited apoptosis by soluble human fas ligand in vitro cell death assay. m50054 inhibited the apoptotic u937 cell death which is a human monocytic leukemic cell line, induced by anticancer agents such as etoposide. m50054 inhibited apoptotic characters such as dna phosphatidylserine and fragmentation exposure in these cells. these anti-apoptotic effects were dependent on inhibition of caspase-3 activation. additionally, m50054 significantly inhibited anti-fas-antibody-induced elevation of plasma aspartate aminotransferase and alanine aminotransferase. alopecia (hair loss) symptoms were also significantly improved with topical treatment with m50054. m50054 inhibits apoptosis induced by a variety of stimuli via inhibition of caspase-3 activation, and may thus be effective for hepatitis and chemotherapy-induced alopecia. [1]

references

tsuda t, ohmori y, muramatsu h et al. inhibitory effect of m50054, a novel inhibitor of apoptosis, on anti-fas-antibody-induced hepatitis and chemotherapy-induced alopecia.eur j pharmacol. 2001 dec 14;433(1):37-45.

Upstream product

• 5146-68-9 N-(Hydroxymethyl)succinimide 
• 504-02-9 1,3-cylohexanedione 
• 50-00-0 formaldehyd 
• 30038-67-6 1,8-dioxo-1,2,3,4,5,6,7,8-octahydroxanthene 
• 7732-18-5 water 

Downstream Products

• 15581-39-2 Bis-<2-benzolsulfonylhydrazino-6-oxo-cyclohexen-(1)-yl>-methan 
• 817624-74-1 10-(2-methoxyphenyl)-3,4,6,7,9,10-hexahydro-1,8(2H,5H)acridinedione 
• 1040735-65-6 ethyl 2-(2-ethoxycarbonylethyl)-3-oxocyclohexenebutyrate 
• 55998-74-8 3-(methylamino)-2-cyclohexen-1-one 
• 21081-45-8 2.2'-Methylen-bis-<1-phenylhydrazino-cyclohexen-(1)-on-(3)> 
• 128229-77-6 N-phenyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione 
• 61137-12-0 3,4,6,7,9,10-hexahydro-1,8(2H,5H)acridinedione 
• 505-52-2 brassylic acid 

Relevant academic research and scientific papers

The crystal structure and conformational studies of acridinedione derivatives

Two crystal structures of acridinediones namely, TMHAD and MPHAD were studied by X-ray crystallographic method in view of their occurrence in numerous commercial products including pharmaceuticals, fragrances and dyes. Crystal data of TMHAD are: C17H23NO2, orthorhombic, Fdd2, with cell parameters a = 40.417(6) A, b = 5.744(1) A, c = 12.979(2) A, V = 3013.1(7) A3, Z = 8, Dcal = 1.205 Mg/m3, μ = 0.078 mm-1. Crystal data of MPHAD are: C20H18NO3; monoclinic, P21/c with cell parameters a = 10.182(9) A, b = 17.105(14) A, c = 10.895(9) A, β = 117.857(1)°, V = 1678(2) A3, Z = 4, Dcal = 1.268 Mg/m3, μ = 0.085 mm-1. Both data were collected using λ (MoKα) = 0.71073 A. The central ring in the acridinedione moieties tends to be planar while the outer two rings adopt sofa conformations. Intermolecular interactions of C-H...O type of hydrogen bond help the molecules to stabilize into the crystal packing. Interestingly, a week forces of C-H...π interactions also helps the molecules for stabilization. Graphical Abstract: Two crystal structures of acridinediones namely, TMHAD and MPHAD have been synthesized and its structural chemistry has been proved by crystallographic study.

Synthesis of tetraketones in water and under catalyst-free conditions

A simple, environmentally friendly, tandem Knoevenagel condensation and Michael addition procedure is reported. The reactions between cyclic-13-diketones and a variety of aldehydes were carried out in water to afford tetraketones (64-99%). In this green synthetic protocol, the solvent water itself catalysed the reaction by hydrogen bonding, thus avoiding the use of any other catalysts to make the work up procedure easier.

Thermal and microwave assisted synthesis of N-aroylamino acridinediones

A series of N-aroylamino acridinediones (3a-3d and 6a-6e) have been synthesized from tetraketones (1 and 4) and benzoic hydrazides (2a-2d and 5a-5e) under thermal and microwave irradiation conditions with solid supports.

APOPTOSIS INHIBITORS

Apoptosis inhibitors containing as the active ingredient compounds represented by general formula (I) or salts thereof, wherein W1 represents -O-, -CH2-, etc.; W2 represents -CH2-, etc.; W3 represents -O-, -CH2-, etc.; X represent CH, C-, etc.; and A represents formula (α) wherein W4 represents -O-, -CH2-, etc.; W5 represents -CH2 -, etc.; and W6 represents -O-, CH2 -, etc. These apoptosis inhibitors inhibit apoptosis of WC8 cells induced by Fas ligand. In animal models, they potently inhibit the progress of fulminant hepatitis and relieve alopecia caused by anticancer agents. Because of being highly safe, these apoptosis inhibitors are usable as beneficial drugs.

A New Class of Laser Dyes from Acridinedione Derivatives

Synthesis of 10-aryl-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione as a new class of laser dyes is reported.These dyes lase around 475-495 nm and are compared to the standard dye coumarin 102.