cas 286844-91-5, 1-(4-(TRIFLUOROMETHOXY)PHENOXY)-4-(METHYLSULFONYL)BENZENE | Articles data ｜lookchem

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286844-91-5

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The development of a large-scale synthesis of matrix metalloproteinase inhibitor, ABT-518
A process for the preparation of matrix metalloproteinase inhibitor ABT-518 has been developed. Significant improvements have been made to the first generation synthesis and are described here. The new process is very robust and efficient; multikilogram quantities of the title compound have been synthesized for clinical trials. ABT-518 was prepared by this six-step synthetic sequence in 51% overall yield with >99% ee.
Chang, Sou-Jen,Fernando, Dilinie,Fickes, Michael,Gupta, Ashok K.,Hill, David R.,McDermott, Todd,Parekh, Shyamal,Tian, Zhenping,Wittenberger, Steven J.
p. 329 - 335
(2002)
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Process for the preparation of matrix metalloproteinase inhibitors
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(2008/06/13)

Phenoxyphenyl sulfone N-formylhydroxylamines (Retrohydroxamates) as potent, selective, orally bioavailable matrix metalloproteinase inhibitors
A novel series of sulfone N-formylhydroxylamines (retrohydroxamates) have been investigated as matrix metalloproteinases (MMP) inhibitors. The substitution of the ether linkage of ABT-770 (5) with a sulfone group 13a led to a substantial increase in activity against MMP-9 but was accompanied by a loss of selectivity for inhibition of MMP-2 and -9 over MMP-1 and diminished oral exposure. Replacement of the biphenyl P1′ substituent with a phenoxyphenyl group provided compounds that are highly selective for inhibition of MMP-2 and -9 over MMP-1. Optimization of the substituent adjacent to the retrohydroxamate center in this series led to the clinical candidate ABT-518 (6), a.highly potent, selective, orally bioavailable MMP inhibitor that has been shown to significantly inhibit tumor growth in animal cancer models.
Wada,Holms,Curtin,Dai,Florjancic,Garland,Guo,Heyman,Stacey,Steinman,Albert,Bouska,Elmore,Goodfellow,Marcotte,Tapang,Morgan,Michaelides,Davidsen
p. 219 - 232
(2007/10/03)

Process for the selective N-formylation of N-hydroxylamines
The instant invention provides a process for the selective N-formylation of N-hydroxylamines.
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Example 4

(2010/01/30)

Process for the selective N-formylation of N-hydroxylamines
The instant invention provides a process for the selective N-formylation of N-hydroxylamines.
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(2008/06/13)

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Chemical Properties

Boiling Point: 405.543oC at 760 mmHg
Flash Point:199.066oC
Density: 1.372g/cm3
Vapor Pressure: 0mmHg at 25°C
PSA: 60.98000
LogP: 4.86180

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