(2R,3S)-N1-((S)-3,3-Dimethyl-1-(Methylamino)-1-Oxobutan-2-yl)-N4,3-Dihydroxy-2-Isobutylsuccinamide (2R,3S)-N1-((S)-3,3-二甲基-1-(甲基氨基)-1-氧代丁烷-2-基)-N4,3-二羟基-2-异丁基琥珀酰胺
CAS 154039-60-8 MFCD00866242
化学结构图
SMILES: CNC(=O)[C@@H](NC(=O)[C@H](CC(C)C)[C@H](O)C(=O)NO)C(C)(C)C
化学属性
| Mol. Formula | C15H29N3O5 |
|---|---|
| Mol. Weight | 331.41 |
| Appearance | White to off-white solid powder |
| Solubility | Soluble in DMSO, not soluble in water. |
别名和识别编码
| Chemical Name | (2R,3S)-N1-((S)-3,3-Dimethyl-1-(Methylamino)-1-Oxobutan-2-yl)-N4,3-Dihydroxy-2-Isobutylsuccinamide |
|---|---|
| Synonym | BB-2516; BB2516; BB 2516; TA-2516; TA2516; TA 2516; Marimastat. BB2516, (2S,3R)-N4-[(1S)-2,2-Dimethyl-1-[(methylamino)carbonyl] propyl]-N1,2-dihydroxy-3-(2-methylpropyl)butanediamide Marimastat |
| MDL Number | MFCD00866242 |
| PubChem Substance ID | 329817950 |
| CAS Number | 154039-60-8 |
| Formula | C15H29N3O5 |
| IUPAC Name | (2R,3S)-N1-((S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-N4,3-dihydroxy-2-isobutylsuccinamide |
| InChIKey | BSGICWROEOGEDW-UHFFFAOYSA-N |
| InChI | InChI=1S/C9H20Cl2N2O5PS2/c10-2-4-13(5-3-11)19(14)12-9(1-6-18-19)20-7-8-21(15,16)17/h9,12,19H,1-8H2,(H,15,16,17)/q-1 |
| Canonical SMILES | O=C(N[C@@H](C(C)(C)C)C(NC)=O)[C@H](CC(C)C)[C@H](O)C(NO)=O |
| Chemical Name Translation | (2R,3S)-N1-((S)-3,3-二甲基-1-(甲基氨基)-1-氧代丁烷-2-基)-N4,3-二羟基-2-异丁基琥珀酰胺 |
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分类
- {SNA} Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, Cytoskeleton and Extracellular Matrix, Extracellular Matrix, M, Metalloproteinase Inhibitors
- {SNA} Bioactive Small Molecule Alphabetical Index, Cytoskeleton and Extracellular Matrix, Extracellular Matrix, M, Metalloproteinase Inhibitors,
产品应用
- Marimastat, aslo known as BB-2516 and TA-2516, is an orally-active synthetic hydroxamate and inhibitor of matrix metalloproteinases with potential antineoplastic activity. Marimastat covalently binds to the zinc(II) ion in the active site of matrix metalloproteinases (MMPs), thereby inhibiting the action of MMPs, inducing extracellular matrix degradation, and inhibiting angiogenesis, tumor growth and invasion, and metastasis. This agent may also inhibit tumor necrosis factor-alpha converting enzyme (TACE), an enzyme involved in tumor necrosis factor alpha (TNF-alpha) production that may play a role in some malignancies as well as in the development of arthritis and sepsis.
相关文献及参考
- [2]. Yu M, et al. Incorporation of Bulky and Cationic Cyclam-Triazole Moieties into Marimastat Can Generate Potent MMP Inhibitory Activity without Inducing Cytotoxicity. ChemistryOpen. 2013 Jun;2(3):99-105.
- [3]. van Wijngaarden J, et al. An in vitro model that can distinguish between effects on angiogenesis and on established vasculature: actions of TNP-470, marimastat and the tubulin-binding agent Ang-510. Biochem Biophys Res Commun. 2010 Jan 8;391(2):1161-5.
- [4]. Skipper JB, et al. In vivo efficacy of marimastat and chemoradiation in head and neck cancer xenografts. ORL J Otorhinolaryngol Relat Spec. 2009;71(1):1-5.
- [1]. Rasmussen HS, et al. Matrix metalloproteinase inhibition as a novel anticancer strategy: a review with special focus on batimastat and mari
- [1]. Rasmussen HS, et al. Matrix metalloproteinase inhibition as a novel anticancer strategy: a review with special focus on batimastat and marimastat. Pharmacol Ther. 1997;75(1):69-75.
