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Home > Imidazoles > 4311-88-0
4311-88-0 | 5-(1H-INDOL-3-YLMETHYL)-3-METHYL-2-THIOXO-4-IMIDAZOLIDINONE
CAS No: 4311-88-0 Catalog No: AG00D9QV MDL No:MFCD00056916
Product Description
Catalog Number:
AG00D9QV
Chemical Name:
5-(1H-INDOL-3-YLMETHYL)-3-METHYL-2-THIOXO-4-IMIDAZOLIDINONE
CAS Number:
4311-88-0
Molecular Formula:
C13H13N3OS
Molecular Weight:
259.3268
MDL Number:
MFCD00056916
IUPAC Name:
5-(1H-indol-3-ylmethyl)-3-methyl-2-sulfanylideneimidazolidin-4-one
InChI:
InChI=1S/C13H13N3OS/c1-16-12(17)11(15-13(16)18)6-8-7-14-10-5-3-2-4-9(8)10/h2-5,7,11,14H,6H2,1H3,(H,15,18)
InChI Key:
TXUWMXQFNYDOEZ-UHFFFAOYSA-N
SMILES:
S=C1NC(C(=O)N1C)Cc1c[nH]c2c1cccc2
Properties
Complexity:
373
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
259.078g/mol
Formal Charge:
0
Heavy Atom Count:
18
Hydrogen Bond Acceptor Count:
2
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
259.327g/mol
Monoisotopic Mass:
259.078g/mol
Rotatable Bond Count:
2
Topological Polar Surface Area:
80.2A^2
Undefined Atom Stereocenter Count:
1
Undefined Bond Stereocenter Count:
0
XLogP3:
1.9
Literature
| Title | Journal |
|---|---|
| Mechanical force-mediated pathological cartilage thinning is regulated by necroptosis and apoptosis. | Osteoarthritis and cartilage 20170801 |
| Necroptosis contributes to methamphetamine-induced cytotoxicity in rat cortical neurons. | Toxicology in vitro : an international journal published in association with BIBRA 20160901 |
| FTY720 induces autophagy-related apoptosis and necroptosis in human glioblastoma cells. | Toxicology letters 20150702 |
| The role of RIP3 mediated necroptosis in ouabain-induced spiral ganglion neurons injuries. | Neuroscience letters 20140822 |
| Role of receptor interacting protein (RIP)1 on apoptosis-inducing factor-mediated necroptosis during acetaminophen-evoked acute liver failure in mice. | Toxicology letters 20140321 |
| Akt and mTOR mediate programmed necrosis in neurons. | Cell death & disease 20140201 |
| The molecular mechanisms and gene expression profiling for shikonin-induced apoptotic and necroptotic cell death in U937 cells. | Chemico-biological interactions 20130925 |
| Cobalt triggers necrotic cell death and atrophy in skeletal C2C12 myotubes. | Toxicology and applied pharmacology 20130901 |
| Identification of potent Yes1 kinase inhibitors using a library screening approach. | Bioorganic & medicinal chemistry letters 20130801 |
| Necrostatin-1 blocks both RIPK1 and IDO: consequences for the study of cell death in experimental disease models. | Cell death and differentiation 20130201 |
| The targeted inhibition of mitochondrial Hsp90 overcomes the apoptosis resistance conferred by Bcl-2 in Hep3B cells via necroptosis. | Toxicology and applied pharmacology 20130101 |
| RIP1-mediated mitochondrial dysfunction and ROS production contributed to tumor necrosis factor alpha-induced L929 cell necroptosis and autophagy. | International immunopharmacology 20121201 |
| Necrostatin-1 protects photoreceptors from cell death and improves functional outcome after experimental retinal detachment. | The American journal of pathology 20121101 |
| Necrostatin-1 analogues: critical issues on the specificity, activity and in vivo use in experimental disease models. | Cell death & disease 20121101 |
| Staurosporine induces apoptosis and necroptosis in cultured rat astrocytes. | Drug and chemical toxicology 20121001 |
| Necrostatin-1 attenuates mitochondrial dysfunction in neurons and astrocytes following neonatal hypoxia-ischemia. | Neuroscience 20120906 |
| Fluorescence polarization assay for inhibitors of the kinase domain of receptor interacting protein 1. | Analytical biochemistry 20120815 |
| Necroptosis contributes to the cyclosporin A-induced cytotoxicity in NRK-52E cells. | Die Pharmazie 20120801 |
| Inhibition of RIP1-dependent necrosis prevents adverse cardiac remodeling after myocardial ischemia-reperfusion in vivo. | Basic research in cardiology 20120701 |
| Necroptosis modulated by autophagy is a predominant form of melanoma cell death induced by sanguilutine. | Biological chemistry 20120701 |
| Fas ligand-Fas signaling participates in light-induced apoptotic death in photoreceptor cells. | Investigative ophthalmology & visual science 20120601 |
| PI3K inhibitor D-116883 is effective in in vitro models of ovarian cancer. | Anticancer research 20120501 |
| Intermediate domain of receptor-interacting protein kinase 1 (RIPK1) determines switch between necroptosis and RIPK1 kinase-dependent apoptosis. | The Journal of biological chemistry 20120427 |
| Rip1 (receptor-interacting protein kinase 1) mediates necroptosis and contributes to renal ischemia/reperfusion injury. | Kidney international 20120401 |
| Heme induces programmed necrosis on macrophages through autocrine TNF and ROS production. | Blood 20120308 |
| Glutamate oxidative injury to RGC-5 cells in culture is necrostatin sensitive and blunted by a hydrogen sulfide (H2S)-releasing derivative of aspirin (ACS14). | Neurochemistry international 20120301 |
| Nec-1 enhances shikonin-induced apoptosis in leukemia cells by inhibition of RIP-1 and ERK1/2. | International journal of molecular sciences 20120101 |
| RIP kinase-dependent necrosis drives lethal systemic inflammatory response syndrome. | Immunity 20111223 |
| Water-soluble germanium nanoparticles cause necrotic cell death and the damage can be attenuated by blocking the transduction of necrotic signaling pathway. | Toxicology letters 20111215 |
| Necroptosis is a novel mechanism of radiation-induced cell death in anaplastic thyroid and adrenocortical cancers. | Surgery 20111201 |
| NO donor induces Nec-1-inhibitable, but RIP1-independent, necrotic cell death in pancreatic β-cells. | FEBS letters 20111003 |
| Discrimination between primary necrosis and apoptosis by necrostatin-1 in Annexin V-positive/propidium iodide-negative cells. | Biochemical and biophysical research communications 20110805 |
| 24(S)-hydroxycholesterol induces neuronal cell death through necroptosis, a form of programmed necrosis. | The Journal of biological chemistry 20110715 |
| MicroRNA-155 prevents necrotic cell death in human cardiomyocyte progenitor cells via targeting RIP1. | Journal of cellular and molecular medicine 20110701 |
| The dual functions of receptor interacting protein 1 in fas-induced hepatocyte death during sepsis. | Shock (Augusta, Ga.) 20110501 |
| Light- and sodium azide-induced death of RGC-5 cells in culture occurs via different mechanisms. | Apoptosis : an international journal on programmed cell death 20110401 |
| Necrostatin decreases oxidative damage, inflammation, and injury after neonatal HI. | Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism 20110101 |
| RIP1-dependent and independent effects of necrostatin-1 in necrosis and T cell activation. | PloS one 20110101 |
| Cyclophilin A release as a biomarker of necrotic cell death. | Cell death and differentiation 20101201 |
| Synergistic protective effects of humanin and necrostatin-1 on hypoxia and ischemia/reperfusion injury. | Brain research 20101008 |
| The role of PARP activation in glutamate-induced necroptosis in HT-22 cells. | Brain research 20100709 |
| Necroptosis, a novel form of caspase-independent cell death, contributes to neuronal damage in a retinal ischemia-reperfusion injury model. | Journal of neuroscience research 20100515 |
| Nitration of the mitochondrial complex I subunit NDUFB8 elicits RIP1- and RIP3-mediated necrosis. | Free radical biology & medicine 20100115 |
| Novel interventions targeting on apoptosis and necrosis induced by aluminum chloride in neuroblastoma cells. | Journal of biological regulators and homeostatic agents 20100101 |
| Enhanced tissue integration during cartilage repair in vitro can be achieved by inhibiting chondrocyte death at the wound edge. | Tissue engineering. Part A 20090701 |
| Attenuation of cadmium-induced necrotic cell death by necrostatin-1: potential necrostatin-1 acting sites. | Toxicology and applied pharmacology 20090301 |
| 3-Nitrofluoranthene (3-NF) but not 3-aminofluoranthene (3-AF) elicits apoptosis as well as programmed necrosis in Hepa1c1c7 cells. | Toxicology 20090131 |
| Necroptosis contributes to the NMDA-induced excitotoxicity in rat's cultured cortical neurons. | Neuroscience letters 20081212 |
| Structure-activity relationship and liver microsome stability studies of pyrrole necroptosis inhibitors. | Bioorganic & medicinal chemistry letters 20080601 |
| Identification of RIP1 kinase as a specific cellular target of necrostatins. | Nature chemical biology 20080501 |
| Acute myeloid leukemia-targeted toxin activates both apoptotic and necroptotic death mechanisms. | PloS one 20080101 |
| Necrostatin-1 protects against glutamate-induced glutathione depletion and caspase-independent cell death in HT-22 cells. | Journal of neurochemistry 20071201 |
| The cardioprotective effect of necrostatin requires the cyclophilin-D component of the mitochondrial permeability transition pore. | Cardiovascular drugs and therapy 20071201 |
| Necrostatin: a potentially novel cardioprotective agent? | Cardiovascular drugs and therapy 20070801 |
| Sitosterol-containing lipoproteins trigger free sterol-induced caspase-independent death in ACAT-competent macrophages. | The Journal of biological chemistry 20061103 |
| Structure-activity relationship study of novel necroptosis inhibitors. | Bioorganic & medicinal chemistry letters 20051115 |
| Chemical inhibitor of nonapoptotic cell death with therapeutic potential for ischemic brain injury. | Nature chemical biology 20050701 |
| Inhibition of indoleamine 2,3-dioxygenase, an immunoregulatory target of the cancer suppression gene Bin1, potentiates cancer chemotherapy. | Nature medicine 20050301 |
| Structural requirements for hydantoins and 2-thiohydantoins to induce lymphoproliferative popliteal lymph node reactions in the mouse. | International journal of immunopharmacology 19880101 |
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