1044759-00-3

Basic information

• Product Name: (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-((1-benzylpiperidin-4-yl)amino)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1⁽²¹⁾,4,6,10,18-pentaen-9-yl carbamate
• Synonyms: (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-((1-benzylpiperidin-4-yl)amino)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1⁽²¹⁾,4,6,10,18-pentaen-9-yl carbamate
• CAS NO: 1044759-00-3
• Molecular Weight: 718.891
• Mol File: 1044759-00-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-((1-benzylpiperidin-4-yl)amino)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1⁽²¹⁾,4,6,10,18-pentaen-9-yl carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-((1-benzylpiperidin-4-yl)amino)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1⁽²¹⁾,4,6,10,18-pentaen-9-yl carbamate(1044759-00-3)
• EPA Substance Registry System: (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-((1-benzylpiperidin-4-yl)amino)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1⁽²¹⁾,4,6,10,18-pentaen-9-yl carbamate(1044759-00-3)

Safety Data

• Hazardous Substances Data: 1044759-00-3(Hazardous Substances Data)

Upstream product

• 50541-93-0 4-amino-1-benzylpiperidine 
• 30562-34-6 geldanmycin 

Relevant articles and documents

Synthesis, structure and anticancer activity of new geldanamycin amine analogs containing C(17)- or C(20)- flexible and rigid arms as well as closed or open ansa-bridges

The nucleophilic attack of amines at C(17) or C(17)/C(20) positions of geldanamycin's (GDM) benzoquinone, via initial 1,4-Michael conjugate addition mechanism, yield new analogs with closed or open ansa-bridges (1–31), respectively. X-ray structures of analogs 22 and 24 reveals an unexpected arrangement of the ansa-bridge in solid (conformer B), that is located between those of conformers A, prevailing in solution (trans-lactam), and C, crucial at binding to Hsp90 (cis-lactam). The structure of a new-type conformer B allows to better understand the molecular recognition mechanism between the GDM analogs and the target Hsp90. Combined analysis of: anticancer test results (SKBR-3, SKOV-3, PC-3, U-87, A-549) and those performed in normal cells (HDF), KD values and docking modes at Hsp90 as well as clogP parameters, reveals that the rigid C(17)-arm (piperidyl, cyclohexyl) with a H-bond acceptor as carbonyl group together with a lipophilicity clogP～3 favor high potency of analogs, even up to IC50 ～0.08 μM, at improved selectivity (SIHDF > 30), when compared to GDM. The most active 25 show higher anticancer potency than 17-AAG (in SKOV-3 and A-549) as well as reblastatin (in SKBR-3 and SKOV-3). Opening of the ansa-bridge within GDM analogs, at the best case, decreases activity (IC50～2 μM) and toxicity in HDF cells (SIHDF～2–3), relative to GDM.

A SET OF GELDANAMYCIN DERIVATIVES AND THEIR PREPARATION METHODS

A set of geldanamycin derivatives and their preparation methods. Pharmaceutical compositions comprising the said compounds as an active ingredient which are used as antivirus and antitumor agents. The said derivatives are used in the manufacture of heat shock protein 90(Hsp 90) inhibiting agents which have the utility as antivirus and antitumor agents.