17-Aminogeldanamycin

Base Information

• Chemical Name: 17-Aminogeldanamycin
• CAS No.: 64202-81-9
• Deprecated CAS: 1174669-94-3,949449-23-4
• Molecular Formula: C₂₈H₃₉N₃O₈
• Molecular Weight: 545.633
• UNII: SLQ1AJG3VB
• Nikkaji Number: J696.835J
• Wikidata: Q27289269
• NCI Thesaurus Code: C78843
• Pharos Ligand ID: SZLAHZFLYQ1W
• Metabolomics Workbench ID: 153900
• ChEMBL ID: CHEMBL339231
• Mol file: 64202-81-9.mol

Synonyms:17-(allylamino)-17-demethoxy-geldanamycin;17-(allylamino)-17-demethoxygeldanamycin;17-AAG;17-allyl-aminogeldanamycin;17-allylamino-17-demethoxygeldanamycin;17-allylamino-17-demethoxygeldanamycin hydroquinone;17-allylamino-17-demethoxygeldanamycin hydroquinone salt;17-allylamino-geldanamycin;17-allylaminogeldanamycin;17-N-allylamino-17-demethoxygeldanamycin;17AAG;CNF1010;IPI 493;IPI 504;IPI-493;IPI-504;IPI493;IPI504;NSC 330507;NSC-330507;retaspimycin hydrochloride;tanespimycin

Chemical Property of 17-Aminogeldanamycin

Chemical Property:

• Vapor Pressure: 6.1E-28mmHg at 25°C
• Melting Point: 178-180°C
• Refractive Index: 1.574
• Boiling Point: 777.8 °C at 760 mmHg
• PKA: 8.59±0.70(Predicted)
• Flash Point: 424.2 °C
• PSA: 180.27000
• Density: 1.25 g/cm³
• LogP: 3.45010
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Methanol
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 545.27371521
• Heavy Atom Count: 39
• Complexity: 1130

Purity/Quality:

99.3% ^*data from raw suppliers

17-Amino geldanamycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(C(C(C=C(C(C(C=CC=C(C(=O)NC2=CC(=O)C(=C(C1)C2=O)N)C)OC)OC(=O)N)C)C)O)OC
• Isomeric SMILES: C[C@H]1C[C@@H]([C@@H]([C@H](/C=C(/[C@@H]([C@H](/C=C\C=C(\C(=O)NC2=CC(=O)C(=C(C1)C2=O)N)/C)OC)OC(=O)N)\C)C)O)OC
• Recent ClinicalTrials: A Phase 1 Dose Escalation Study of IPI-493
• Uses: The active metabolite of 17-(Allylamino)geldanamycin (17AAG).

Technology Process of 17-Aminogeldanamycin

There total 2 articles about 17-Aminogeldanamycin 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%

geldanmycin (30562-34-6) → 17-amino-17-demethoxygeldanamycin (64202-81-9)

Guidance literature:

With ammonia; In water; acetonitrile; at 20 ℃; for 5h;

Reference yield:

17-allylamino-17-demethoxygeldanamycin (75747-14-7) → 17-amino-17-demethoxygeldanamycin (64202-81-9)

Guidance literature:

With human liver microsomes; at 37 ℃; for 0.25h; Kinetics; aq. phosphate buffer;

DOI:10.1124/dmd.110.036418

Reference yield:

17-amino-17-demethoxygeldanamycin (64202-81-9) → Carbamic acid (4E,6Z,10E)-(8S,9S,12S,13R,14S,16R)-13,20,22-trihydroxy-8,14-dimethoxy-19-(3-methoxy-benzoylamino)-4,10,12,16-tetramethyl-3-oxo-2-aza-bicyclo[16.3.1]docosa-1(22),4,6,10,18,20-hexaen-9-yl ester

Guidance literature:

Multi-step reaction with 2 steps

1: aq. Na₂S₂O₄ / ethyl acetate / 2 h / 20 °C

2: tetrahydrofuran / 12 h / 20 °C

With sodium dithionite; In tetrahydrofuran; ethyl acetate;

DOI:10.1021/jm0306125

upstream raw materials:

geldanmycin

17-allylamino-17-demethoxygeldanamycin

Downstream raw materials:

17-amino-22-(4'-aminophenacyl)-17-demethoxygeldanamycin

Refernces

• 1、 Zheng, Nan,Zou, Peng,Wang, Shaomeng,Sun, Duxin. "In vitro metabolism of 17-(dimethylaminoethylamino)-17- demethoxygeldanamycin in human liver microsomes". experimental part. p. 627 - 635. Retrieved 2012/06/01.
• 2、 -. "Hydroquinone Ansamycin Formulations". Page/Page column 9. . Retrieved 2008/12/04.