362476-85-5

Upstream product

• 362477-53-0 (4-methoxyphenyl)chlorophosphonic acid ethyl ester 
• 404001-44-1 (3R)-N-benzyloxy-1,2,3,4-tetrahydroisoquinoline-3-hydroxamide 
• 362477-34-7 (3R)-N-benzyloxy-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinoline-3-carboxamide 
• 41220-48-8 (3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride 
• 3762-33-2 diethyl (p-methoxyphenyl)phosphonate 
• 37632-18-1 4-methoxyphenylphosphonic dichloride 
• 64-17-5 ethanol 
• 78879-20-6 D-N-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinolinoline-3-carboxylic acid 
• 63818-65-5 4-methoxylphenyl phosphonic acid monoethyl ester 
• 622-33-3 N-benzyloxyamine 

Relevant academic research and scientific papers

New type of metalloproteinase inhibitor: Design and synthesis of new phosphonamide-based hydroxamic acids

A series of phosphonamide-based hydroxamate derivatives were synthesized, and the inhibitory activities were evaluated against various metalloproteinases in order to clarify its selectivity profile. Among the four diastereomeric isomers resulting from the

New strategy for antedrug application: Development of metalloproteinase inhibitors as antipsoriatic drugs

Phosphonamide-based inhibitors were synthesized and evaluated for the inhibitory activities against the shedding of epidermal growth factors, amphiregulin and heparin-binding EGF-like growth factor, that would participate in the development of psoriasis. All compounds exhibited excellent inhibitory activities for these EGF sheddings; however, they also inhibited matrix metalloproteinases (MMPs). To avoid adverse effects reported by the clinical development of MMP inhibitors, the antedrug concept was introduced. Among the phosphonamide inhibitors, the 2,2,2-trifluoroethyl ester 8d and 2,2-difluoroethyl ester 8c showed rapid decomposition in human plasma, which is an essential property for the antedrug. Topical applications of these compounds significantly suppressed TPA-induced epidermal hyperplasia in murin skin, a model of psoriasis. These results suggested that the phosphonamide-based inhibitors have a therapeutic potential for the treatment of psoriasis as an antedrug application.

Encounter with unexpected collagenase-1 selective inhibitor: Switchover of inhibitor binding pocket induced by fluorine atom

Phosphonamide-based inhibitors having trifluoromethyl moiety showed highly selective inhibition against MMP-1. A possible mechanism of the selectivity of MMP-1 inhibitors through the switchover of the binding pocket was speculated by computational calculations. As a consequence of the unexpected selectivity, the specific interaction of CF3 group of the inhibitor and Arg214 in the S1′ pocket of MMP-1 conducted a low binding energy.