Marimastat

Base Information

• Chemical Name: Marimastat
• CAS No.: 154039-60-8
• Molecular Formula: C₁₅H₂₉N₃O₅
• Molecular Weight: 331.412
• Hs Code.: 29241990
• NSC Number: 719333,689451
• UNII: D5EQV23TDS
• DSSTox Substance ID: DTXSID20165524
• Nikkaji Number: J930.059G
• Wikipedia: Marimastat
• Wikidata: Q6763659
• NCI Thesaurus Code: C1652
• Pharos Ligand ID: 4Q1RUA16HTLF
• Metabolomics Workbench ID: 43079
• ChEMBL ID: CHEMBL279785
• Mol file: 154039-60-8.mol

Synonyms:BB-2516;marimastat

Chemical Property of Marimastat

Chemical Property:

• Melting Point: 148℃
• Refractive Index: 1.498
• PKA: 9.44±0.40(Predicted)
• PSA: 127.76000
• Density: 1.14 g/cm³
• LogP: 0.96460
• Storage Temp.: Store at -20°C
• Solubility.: DMSO: ≥20mg/mL
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 331.21072103
• Heavy Atom Count: 23
• Complexity: 431

Purity/Quality:

99% ^*data from raw suppliers

Marimastat ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CC(C(C(=O)NO)O)C(=O)NC(C(=O)NC)C(C)(C)C
• Isomeric SMILES: CC(C)C[C@H]([C@@H](C(=O)NO)O)C(=O)N[C@H](C(=O)NC)C(C)(C)C
• Recent ClinicalTrials: Marimastat Following Chemotherapy in Treating Patients With Small Cell Lung Cancer
• Uses: Antineoplastic (matrix metalloproteinase inhibitor). Marimastat acts as a matrix metalloproteinase inhibitor in the treatment of various cancers, and pathological occurrences such as arthritis and atherosclerosis. Marimastat has been used as an inhibitor of:metalloproteinase 2/9 (MMP2/9), to study its effects on exercise-mediated interleukin-6 (IL-6) release in micemetalloproteinase, to determine protease activity in Pseudomonas aeruginosa culturesmetalloproteinase 10 (MMP10), to study its effect on monoclonal antibody H3 binding to MMP10

Technology Process of Marimastat

There total 8 articles about Marimastat 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: 93.0%

(R)-2-((S)-2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-yl)-4-methyl-pentanoic acid ((S)-2,2-dimethyl-1-methylcarbamoyl-propyl)-amide → marimastat (154039-60-8)

Guidance literature:

With hydroxylamine; In tetrahydrofuran; water; for 1h; Heating;

DOI:10.1016/S0040-4039(00)01376-9

Reference yield: 55.0%

(2S,3R)-3-((S)-2,2-Dimethyl-1-methylcarbamoyl-propylcarbamoyl)-2-hydroxy-5-methyl-hexanoic acid methyl ester (200866-75-7) → marimastat (154039-60-8)

Guidance literature:

With potassium hydroxide; hydroxylamine hydrochloride; In methanol; Ambient temperature;

DOI:10.1021/jm970494j

Reference yield:

(2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-4-methylpentanoic acid (157518-70-2) → marimastat (154039-60-8)

Guidance literature:

Multi-step reaction with 5 steps

1: HOBT, NMM / CH₂Cl₂ / 0.25 h / Ambient temperature

2: CH₂Cl₂ / 2 h / Ambient temperature

3: 100 percent / 2 N aq. HCl / tetrahydrofuran / 4.5 h / Ambient temperature

4: 93 percent / methanol; diethyl ether

5: 55 percent / KOH, HONH₂*HCl / methanol / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; potassium hydroxide; hydroxylamine hydrochloride; benzotriazol-1-ol; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1021/jm970494j

upstream raw materials:

(2S,3R)-3-((S)-2,2-Dimethyl-1-methylcarbamoyl-propylcarbamoyl)-2-hydroxy-5-methyl-hexanoic acid methyl ester

(S)-2-amino-N,3,3-trimethylbutanamide

(2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-4-methylpentanoic acid

3R-(2,2-Dimethyl-1S-methylcarbamoyl-propylcarbamoyl)-2S-hydroxy-5-methyl-hexanoic acid

Refernces

• 1、 Levy, Daniel E.,Lapierre, France,Liang, Weisheng,Ye, Wenqing,Lange, Christopher W.,Li, Xiaoyuan,Grobelny, Damian,Casabonne, Marie,Tyrrell, David,Holme, Kevin,Nadzan, Alex,Galardy, Richard E.. "Matrix metalloproteinase inhibitors: A structure-activity study". . p. 199 - 223. Retrieved 2007/10/03.