Anisomycin

Base Information

• Chemical Name: Anisomycin
• CAS No.: 22862-76-6
• Deprecated CAS: 2322-08-9,11023-48-6,11023-48-6
• Molecular Formula: C14H19NO4
• Molecular Weight: 265.309
• Hs Code.: 29419090
• European Community (EC) Number: 245-269-7
• NSC Number: 76712
• UNII: 6C74YM2NGI
• DSSTox Substance ID: DTXSID5040966
• Nikkaji Number: J60.442I
• Wikipedia: Anisomycin
• Wikidata: Q378498
• NCI Thesaurus Code: C95312
• Pharos Ligand ID: R9BNSB2MGVBV
• Metabolomics Workbench ID: 52749
• ChEMBL ID: CHEMBL423192
• Mol file: 22862-76-6.mol

Synonyms:Anisomycin;Flagecidin

Chemical Property of Anisomycin

Chemical Property:

• Appearance/Colour: White crystalline solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 140-141 °C
• Refractive Index: 1.5230 (estimate)
• Boiling Point: 398.7 °C at 760 mmHg
• PKA: 7.9(at 25℃)
• Flash Point: 194.9 °C
• PSA: 67.79000
• Density: 1.21 g/cm³
• LogP: 0.83090
• Storage Temp.: 2-8°C
• Solubility.: methanol: 20 mg/mL, clear, colorless to faintly yellow
• Water Solubility.: Soluble in water at 2 mg/ml, in DMSO at 20mg/ml, and in methanol at 20mg/ml
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 265.13140809
• Heavy Atom Count: 19
• Complexity: 302

Purity/Quality:

≥98% ^*data from raw suppliers

Anisomycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, Xn
• Hazard Codes: T,Xn
• Statements: 25-36/37/38-20/21/22
• Safety Statements: 45-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OC1C(CNC1CC2=CC=C(C=C2)OC)O
• Isomeric SMILES: CC(=O)O[C@@H]1[C@H](CN[C@@H]1CC2=CC=C(C=C2)OC)O
• Description: Anisomycin (22862-76-6) activates JNK/SAPKs and reduces c-fos and c-jun. Protein synthesis inhibitor. Anisomycin induces apoptosis and sensitizes cells to anoikis. Cell permeable.
• Uses: Anisomycin is a phenylmethylenepyrrolidine first isolated from Streptomyces griseolus in 1954 as an antiprotozoan with antifungal activity. Anisomycin is an inhibitor of protein synthesis by binding to the 60S ribosomal subunit. Interestingly, anisomycin has found use for the induction of amnesia in animal models. More recently, anisomycin has been demonstrated to induce apoptosis, to be a selective signalling agonist, to activate mitogen-activated protein (MAP) kinases and to be immunomodulatory via its action on T cells. It is applied as an antiparasitic agent and antineoplastic agent. It acts as a protein synthesis inhibitor (blocks translation), potent activator of stress-activated protein kinases (JNK/SAPK) and p38 MAP kinase. It also scts as a potent signaling agonist to selectively elicit homologous desensitization of immediate early gene induction (c-fos, fosB, c-jun, junB and junD). Activates mitogen-activated protein (MAP) kinases (JNK/SAPK and p38/RK).

Technology Process of Anisomycin

There total 57 articles about Anisomycin 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: 95.0%

(2R,3S,4S)-3-acetoxy-N-(benzyloxycarbonyl)-4-hydroxy-2-(4-methoxybenzyl)pyrrolidine (27958-08-3) → (-)-anisomycin (22862-76-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 0.25h; under 760 Torr;

DOI:10.1021/jo00357a023

Reference yield: 88.0%

(2R,3S,4S)-3-Acetoxy-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyl)pyrrolidine (180081-83-8) → (-)-anisomycin (22862-76-6)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃;

DOI:10.1039/CC9960001521

Reference yield: 78.0%

C19H27NO6 (1262850-97-4) → (-)-anisomycin (22862-76-6)

Guidance literature:

With hydrogenchloride; In methanol;

DOI:10.1016/j.cclet.2012.03.029

upstream raw materials:

(2R,3S,4S)-3-acetoxy-1-benzyl-4-hydroxy-2-(4-methoxybenzyl)-pyrrolidine

(2R,3S,4S)-3-acetoxy-4-allyloxy-1-benzyl-2-(p-methoxybenzyl)pyrrolidine

(2R,3S,4S)-3-acetoxy-N-(benzyloxycarbonyl)-4-hydroxy-2-(4-methoxybenzyl)pyrrolidine

Acetic acid (1S,2R)-2-azido-1-((R)-2-bromo-1-hydroxy-ethyl)-3-(4-methoxy-phenyl)-propyl ester

Downstream raw materials:

C₁₉H₂₇NO₆

(2R,3S,4S)-3-acetoxy-1-benzyl-4-hydroxy-2-(4-methoxybenzyl)-pyrrolidine

Refernces

• 1、 Joo, Jae-Eun,Lee, Kee-Young,Pham, Van-Thoai,Tian, Yong-Shou,Ham, Won-Hun. "Application of Pd(0)-catalyzed intramolecular oxazine formation to the efficient total synthesis of ( - )-anisomycin". . p. 3627 - 3630. Retrieved 2008/02/12.
• 2、 Shi, Zhi-cai,Lin, Guo-qiang. "Enantioselective Syntheses of (-)-Anisomycin and Its Propionate Derivative (3097-B1)". . p. 2907 - 2910. Retrieved 2007/10/03.