Retaspimycin

Base Information

• Chemical Name: Retaspimycin
• CAS No.: 857402-23-4
• Molecular Formula: C31H45 N3 O8
• Molecular Weight: 587.714
• Mol file: 857402-23-4.mol

Synonyms:Geldanamycin,18,21-didehydro-17-demethoxy-18,21-dideoxo-18,21-dihydroxy-17-(2-propenylamino)-(9CI); 17 AAGH2; Retaspimycin

Chemical Property of Retaspimycin

Chemical Property:

• Boiling Point: 800.9±65.0 °C(Predicted)
• PKA: 10.15±0.70(Predicted)
• PSA: 172.60000
• Density: 1.23
• LogP: 5.06750
• Solubility.: Soluble in DMSO

Purity/Quality:

99% ^*data from raw suppliers

Retaspimycin 98+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Retaspimycin is a small-molecule inhibitor of heat shock protein 90 (HSP90) with antiproliferative and antineoplastic activities. Retaspimycin binds to and inhibits the cytosolic chaperone functions of HSP90, which maintains the stability and functional shape of many oncogenic signaling proteins and may be overexpressed or overactive in tumor cells. Retaspimycin-mediated inhibition of HSP90 promotes the proteasomal degradation of oncogenic signaling proteins in susceptible tumor cell populations, which may result in the induction of apoptosis.
• Uses: Retaspimycin (IPI-504) was previously under development by manufacturer Infinity Pharmaceuticals in conjunction with MedImmune, a part of AstraZeneca. Retaspimycin is a small-molecule inhibitor of heat shock protein 90 (HSP90) with antiproliferative and antineoplastic activities. Retaspimycin binds to and inhibits the cytosolic chaperone functions of HSP90, which maintains the stability and functional shape of many oncogenic signaling proteins and may be overexpressed or overactive in tumor cells. Retaspimycin-mediated inhibition of HSP90 promotes the proteasomal degradation of oncogenic signaling proteins in susceptible tumor cell populations, which may result in the induction of apoptosis. Orphan drug designation was assigned to the compound by the FDA for the treatment of gastrointestinal stromal cancer (GIST). Infinity Pharmaceuticals has discontinued the development of retaspimycin (IPI-504) an inhibitor of the HSP-90) complex, for the treatment of cancer due to lack of efficacy in 1913.

Technology Process of Retaspimycin

There total 1 articles about Retaspimycin 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: 90.0%

17-allylamino-17-demethoxygeldanamycin (75747-14-7) → (4E,6Z,8S,9S,10E,12S,13R,14S,16R)‐19‐(allylamino)‐13,20,22‐trihydroxy‐8,14‐dimethoxy‐4,10,12,16‐tetramethyl‐3‐oxo‐2‐azabicyclo[1 6.3.1]docosa‐1(22),4,6,10,18,20‐hexaen‐9‐yl carbamate (857402-23-4)

Guidance literature:

With sodium dithionite; water; In ethyl acetate; for 0.5h;

Reference yield:

(4E,6Z,8S,9S,10E,12S,13R,14S,16R)‐19‐(allylamino)‐13,20,22‐trihydroxy‐8,14‐dimethoxy‐4,10,12,16‐tetramethyl‐3‐oxo‐2‐azabicyclo[1 6.3.1]docosa‐1(22),4,6,10,18,20‐hexaen‐9‐yl carbamate (857402-23-4) + 2-bromoacetyl chloride (22118-09-8) → C33H45N3O9

Guidance literature:

(4E,6Z,8S,9S,10E,12S,13R,14S,16R)‐19‐(allylamino)‐13,20,22‐trihydroxy‐8,14‐dimethoxy‐4,10,12,16‐tetramethyl‐3‐oxo‐2‐azabicyclo[1 6.3.1]docosa‐1(22),4,6,10,18,20‐hexaen‐9‐yl carbamate; 2-bromoacetyl chloride; In ethyl acetate; at 20 ℃; for 12h;

With sodium carbonate; In tetrahydrofuran; water; for 1h;

Reference yield:

(4E,6Z,8S,9S,10E,12S,13R,14S,16R)‐19‐(allylamino)‐13,20,22‐trihydroxy‐8,14‐dimethoxy‐4,10,12,16‐tetramethyl‐3‐oxo‐2‐azabicyclo[1 6.3.1]docosa‐1(22),4,6,10,18,20‐hexaen‐9‐yl carbamate (857402-23-4) + bis(trichloromethyl) carbonate (32315-10-9) → C32H43N3O9

Guidance literature:

In ethyl acetate; at 20 ℃; for 2h;

upstream raw materials:

17-allylamino-17-demethoxygeldanamycin

Refernces

• 1、 -. "ANSAMYCIN HYDROQUINONE COMPOSITIONS". Page/Page column 55-56. . Retrieved 2010/04/30.
• 2、 -. "Hsp90 inhibitors, methods of making and uses therefor". Figure 1. . Retrieved 2008/06/13.