Amebacilin;NSC9168

Base Information

• Chemical Name: Amebacilin;NSC9168
• CAS No.: 23110-15-8
• Molecular Formula: C26H34O7
• Molecular Weight: 458.552
• Hs Code.: 29419090
• European Community (EC) Number: 245-433-8
• Metabolomics Workbench ID: 28238
• NCI Thesaurus Code: C75963
• Pharos Ligand ID: ZQ67LNMMJS8Q
• Wikipedia: Fumagillin
• Mol file: 23110-15-8.mol

Synonyms:fumagillin;fumidil B

Chemical Property of Amebacilin;NSC9168

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 2.7E-16mmHg at 25°C
• Melting Point: >190oC-192oC
• Refractive Index: 1.562
• Boiling Point: 608.772 °C at 760 mmHg
• PKA: 4.27±0.10(Predicted)
• Flash Point: 198.793 °C
• PSA: 97.89000
• Density: 1.199 g/cm³
• LogP: 3.91540
• Storage Temp.: −20°C
• Sensitive.: Air Sensitive
• Solubility.: ethanol: 1 mg/mL
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 11
• Exact Mass: 458.23045342
• Heavy Atom Count: 33
• Complexity: 879

Purity/Quality:

99% ^*data from raw suppliers

H3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,F
• Statements: 22-36-20/21/22-11
• Safety Statements: 36-36/37-16-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1C(O1)(C)C2C(C(CCC23CO3)OC(=O)C=CC=CC=CC=CC(=O)O)OC)C
• Isomeric SMILES: CC(=CC[C@@H]1[C@@](O1)(C)[C@@H]2[C@@H]([C@@H](CC[C@]23CO3)OC(=O)/C=C/C=C/C=C/C=C/C(=O)O)OC)C
• Description: Fumagillin is a fungal metabolite that has been found in A. fumigatus and has diverse biological activities. It inhibits methionyl aminopeptidase 2 (METAP2; IC50 = 10 nM). Fumagillin (10 ng/ml) inhibits tube formation in a rat blood vessel organ culture assay. It inhibits E. cuniculi replication in isolated rabbit kidney cells and canine embryo cells when used at a concentration of 5 μg/ml. In vivo, fumagillin (30 mg/kg per day) decreases tumor growth and the number of metastases in a mouse model of diethylnitrosamine-induced hepatocellular carcinoma. It also reduces subcutaneous and gonadal fat mass in a mouse model of high-fat diet-induced obesity. Formulations containing fumagillin have been used to treat conjunctival and intestinal microsporidial infections in immunocompromised patients.
• Uses: Methionine aminopeptidase 2 inhibitor Fumagillin is a compound isolated from the fungus Aspergillus fumigatus. Fumagillin is an antimicrobial agent used in the treatment of microsporidiosis. Fumagillin shows promise as both an an anti-inf ective and antiangiogenic agent. Fumagillin is a polyene mycotoxin isolated from Aspergillus fumigatus in 1951 as a potent antiprotozoan for the treatment of amoebiasis. More recently, fumagillin has been shown to inhibit endothelial cell proliferation and angiogenesis by inhibiting methionine aminopeptidase-2 (MetAP-2).
• Therapeutic Function: Antibiotic

Technology Process of Amebacilin;NSC9168

There total 2 articles about Amebacilin;NSC9168 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: 75.0%

fumagillol (35903-52-7,128656-25-7,132746-73-7,108102-51-8) + (2E,4E,6E,8E)-Deca-2,4,6,8-tetraenedioyl dichloride → fumagillin (23110-15-8,297-95-0)

Guidance literature:

DOI:10.1021/ja990784k

Reference yield:

→ (3R,4S)-6t-(9t-carboxy-nona-2t,4t,6t,8-tetraenoyloxy)-4r-((1S,2Ξ)-1,2-epoxy-1,5-dimethyl-hex-4-enyl)-5t-methoxy-1-oxa-spiro[2.5]octane (23110-15-8,35903-50-5,297-95-0)

Guidance literature:

durch Synthese des Racemats;

DOI:10.1021/ja00762a080

Reference yield: 90.0%

fumagillin (23110-15-8,297-95-0) → fumagillol (35903-52-7,128656-25-7,132746-73-7,108102-51-8)

Guidance literature:

With water; sodium hydroxide; In methanol; at 0 - 40 ℃;

DOI:10.1021/ol4035269

upstream raw materials:

fumagillol

Downstream raw materials:

fumagillol

C₂₆H₃₃O₇^(1-)*Na⁽¹⁺⁾

ligerin

1-chloromethyl-3-methoxy-2-[2-methyl-3-(3-methylbut-2-enyl)oxiranyl]cyclohexane-1,4-diol

Refernces

• 1、 Corey,Snider. "A total synthesis of ( )-fumagillin.". . p. 2549 - 2550. Retrieved 2007/12/02.