MMP-8 INHIBITOR I

Base Information

• Chemical Name: MMP-8 INHIBITOR I
• CAS No.: 236403-25-1
• Molecular Formula: C17H18N2O5S
• Molecular Weight: 362.4
• Mol file: 236403-25-1.mol

Synonyms:

Chemical Property of MMP-8 INHIBITOR I

Chemical Property:

• Storage Temp.: -20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

MMP8-I ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: MMP-8 Inhibitor I is a selective inhibitor of the neutrophil collagenase matrix metalloproteinase-8 (MMP-8) with an IC50 value of 4 nM. This inhibitor does not target the activities of other MMPs in vitro. MMP-8 cleaves interstitial collagens and has exhibited activity in atherosclerotic plaques, angiogenesis, and stem cell mobilization. Additionally, MMP-8 expression is observed in normal mammary epithelial cells, whereas a loss of expression is observed in human ductal carcinoma in situ and the deletion of MMP-8 accelerates tumor onset in a mouse model of aggressive breast cancer.
• Uses: MMP 8-I is a matrix metalloproteinase 8 inhibitor. Matrix metalloproteinases are involved with tight junction protein degradation in endothelial cells.

Technology Process of MMP-8 INHIBITOR I

There total 9 articles about MMP-8 INHIBITOR I which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 51.0%

(3R)-2-(4-Methoxybenzenesulfonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid → (3R)-N-hydroxy-2-((4-methoxyphenyl)sulfonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide (236403-25-1)

Guidance literature:

(3R)-2-(4-Methoxybenzenesulfonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid; With 4-methyl-morpholine; chloroformic acid ethyl ester; In tetrahydrofuran; at 20 ℃; for 0.5h; Cooling with ice;

With hydroxylamine hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 1.16667h;

DOI:10.1039/c4md00172a

Reference yield:

C18H18NO5PolS → 2-(4-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid hydroxyamide (236403-25-1)

Guidance literature:

With hydroxylamine; potassium cyanide; In tetrahydrofuran; methanol; water; at 20 ℃; for 0.5 - 1h; HMBA-AM resine Product distribution / selectivity;

Reference yield:

(S)-2-(4-Methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid → (S)-2-(4-Methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid hydroxyamide (236403-25-1)

Guidance literature:

(S)-2-(4-Methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid; With N-Ethylmaleimide; chloroformic acid ethyl ester; In tetrahydrofuran;

With O-Trimethylsilylhydroxylamine;

Acid hydrolysis;

DOI:10.1016/S0968-0896(02)00215-8

upstream raw materials:

L-Tic-OH

4-methoxy-phenyl-sulphonyl chloride

(3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

D-(R)-phenylalanine

Refernces

• 1、 -. "Preparation of hydroxamic acids from esters in solution and on the solid phase". Page/Page column 5-6. . Retrieved 2010/02/15.
• 2、 Matter, Hans,Schudok, Manfred,Schwab, Wilfried,Thorwart, Werner,Barbier, Denis,Billen, Guenter,Haase, Burkhard,Neises, Bernhard,Weithmann, Klaus-Ulrich,Wollmann, Theo. "Tetrahydroisoquinoline-3-carboxylate based matrix-metalloproteinase inhibitors: Design, synthesis and structure-activity relationship". . p. 3529 - 3544. Retrieved 2007/10/03.