176957-55-4

Basic information

• Product Name: Cyclopentanone, 2,5-bis(2-thienylMethylene)-, (E,E)-
• Synonyms: Cyclopentanone, 2,5-bis(2-thienylMethylene)-, (E,E)-;CCT007093;(2E,5E)-2,5-Bis(2-thienylmethylene)cyclopentanone;(2E,5E)-2,5-Bis(2-thienylmethylene)cyclopentanone CCT007093;2,5-bis(2-thienylMethylene)-, (E,E)-Cyclopentanone;(2E,5E)-2,5-Bis(thiophen-2-ylmethylene)cyclopentanone;CCTOO7093
• CAS NO: 176957-55-4
• Molecular Formula: C₁₅H₁₂OS₂
• Molecular Weight: 272.38518
• Product Categories: Inhibitors
• Mol File: 176957-55-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 222-223℃
• Appearance: /
• Storage Temp.: 2-8°C
• Solubility: DMSO: >3mg/mL
• Sensitive: Light Sensitive
• CAS DataBase Reference: Cyclopentanone, 2,5-bis(2-thienylMethylene)-, (E,E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopentanone, 2,5-bis(2-thienylMethylene)-, (E,E)-(176957-55-4)
• EPA Substance Registry System: Cyclopentanone, 2,5-bis(2-thienylMethylene)-, (E,E)-(176957-55-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 176957-55-4(Hazardous Substances Data)

Usage

Uses

Acts as a PPM1D inhibitor

Biological Activity

cct007093 is a small-molecule chemical inhibitor of ppm1d with ic50 value of 8.4μm [1].cct007093 is a thienylidene cyclopentanone and shows a potent inhibition of ppm1d in the in vitro assay when using the recombinant phospho-p38 as a substrate. in cellular assay, cct007093 shows specificity for mcf-7 cells over hela cells. it reduces 40% viability of the cells after 2 days. it is found that the cell death induced by cct007093 is dependent on p38 kinase activity. cct007093 mimics the effect of ppm1d rnai in activating p38 kinase. it induces p38 phosphorylation at 4 h post-exposure in mcf-7 cells and the loss of viability can be rescued by sb203580, the specific p38 inhibitor [1].

references

[1] rayter s, elliott r, travers j, rowlands mg, richardson tb, boxall k, jones k, linardopoulos s, workman p, aherne w, lord cj, ashworth a. a chemical inhibitor of ppm1d that selectively kills cells overexpressing ppm1d. oncogene. 2008 feb 14;27(8):1036-44.

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 120-92-3 cyclopentanone 

Relevant articles and documents

Potent and Selective Inhibitors of Trypanosoma cruzi Triosephosphate Isomerase with Concomitant Inhibition of Cruzipain: Inhibition of Parasite Growth through Multitarget Activity

Triosephosphate isomerase (TIM) is an essential Trypanosoma cruzi enzyme and one of the few validated drug targets for Chagas disease. The known inhibitors of this enzyme behave poorly or have low activity in the parasite. In this work, we used symmetrical diarylideneketones derived from structures with trypanosomicidal activity. We obtained an enzymatic inhibitor with an IC50value of 86 nm without inhibition effects on the mammalian enzyme. These molecules also affected cruzipain, another essential proteolytic enzyme of the parasite. This dual activity is important to avoid resistance problems. The compounds were studied in vitro against the epimastigote form of the parasite, and nonspecific toxicity to mammalian cells was also evaluated. As a proof of concept, three of the best derivatives were also assayed in vivo. Some of these derivatives showed higher in vitro trypanosomicidal activity than the reference drugs and were effective in protecting infected mice. In addition, these molecules could be obtained by a simple and economic green synthetic route, which is an important feature in the research and development of future drugs for neglected diseases.

Synthesis and anti-inflammatory activities of mono-carbonyl analogues of curcumin

Curcumin has been extensively studied for its anti-inflammatory activities. However, its potential beneficial effects on various disease preventions and treatments are limited by its unstable structure. The β-diketone moiety renders curcumin to be rapidly metabolized by aldo-keto reductase in liver. In the present study, a series of curcumin analogues with more stable chemical structures were synthesized and several compounds showed an enhanced ability to inhibit lipopolysaccharide (LPS)-induced TNF-α and IL-6 synthesis in macrophages.

Iodotrimethylsilane-Mediated Cross-Aldol Condensation: A Facile Synthesis of α,α′-Bis(substituted benzylidene)cycloalkanones

A facile and efficient method for the preparation of α, α′-bis(substituted benzylidene)cycloalkanones is described for the first time using iodotrimethylsilane generated in situ from chlorotrimethylsilane and sodium iodide in acetonitrile. The reaction proceeds rapidly at room temperature, giving high yields of products.