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TMI-1

Names

[ CAS No. ]:
287403-39-8

[ Name ]:
TMI-1

[Synonym ]:
3-Thiomorpholinecarboxamide, 4-[[4-(2-butyn-1-yloxy)phenyl]sulfonyl]-N-hydroxy-2,2-dimethyl-, (3S)-
TMI 1
4-[[4-(2-Butynyloxy)phenyl]sulfonyl]-N-hydroxy-2,2-dimethyl-(3S)thiomorpholinecarboxamide
TMI-1
(3S)-4-{[4-(2-Butyn-1-yloxy)phenyl]sulfonyl}-N-hydroxy-2,2-dimethyl-3-thiomorpholinecarboxamide
(3S)-4-{[4-(BUT-2-YNYLOXY)PHENYL]SULFONYL}-N-HYDROXY-2,2-DIMETHYLTHIOMORPHOLINE-3-CARBOXAMIDE
WAY-171318

Biological Activity

[Description]:

TMI-1 is a potent inhibitor of disintegrin metalloenzyme 17 (ADAM17) and other MMPs. TMI-1 inhibits LPS-induced TNF-α secretion in human primary monocytes, and human whole blood[1]. TMI-1 selectively induces caspase-dependent apoptosis in triple negative (TN) and ERBB2-overexpressing breast tumor cell lines[2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cancer
Research Areas >> Inflammation/Immunology
Signaling Pathways >> Metabolic Enzyme/Protease >> MMP

[Target]

ADAM17:8.4 nM (IC50)


[References]

[1]. Zhang Y, et al. Identification and characterization of 4-[[4-(2-butynyloxy)phenyl]sulfonyl]-N-hydroxy-2,2-dimethyl-(3S)thiomorpholinecarboxamide (TMI-1), a novel dual tumor necrosis factor-alpha-converting enzyme/matrix metalloprotease inhibitor for the treatment of rheumatoid arthritis. J Pharmacol Exp Ther. 2004 Apr;309(1):348-55.

[2]. Mezil L, et al. Tumor selective cytotoxic action of a thiomorpholin hydroxamate inhibitor (TMI-1) in breast cancer. PLoS One. 2012;7(9):e43409.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Molecular Formula ]:
C17H22N2O5S2

[ Molecular Weight ]:
398.497

[ Exact Mass ]:
398.097015

[ LogP ]:
2.56

[ Index of Refraction ]:
1.590

Related Compounds