MPC3100

Base Information

• Chemical Name: MPC3100
• CAS No.: 958025-66-6
• Molecular Formula: C22H25BrN6O4S
• Molecular Weight: 549.448
• Mol file: 958025-66-6.mol

Synonyms:CS-215;MPC3100;(2S)-1-[4-[2-[6-amino-8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]purin-9-yl]ethyl]piperidin-1-yl]-2-hydroxypropan-1-one;(2S)-1-[4-[2-[6-Amino-8-[(6-bromo-1,3-benzodioxol-5-yl)thio]-9H-purin-9-yl]ethyl]-1-piperidinyl]-2-hydroxy-1-propanone

Chemical Property of MPC3100

Chemical Property:

• PSA: 153.92000
• LogP: 3.57950
• Solubility.: Soluble in DMSO

Purity/Quality:

98% min ^*data from raw suppliers

MPC-3100 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: MPC-3100 is a recently discovered fully synthetic purine-based Hsp90 Inhibitor exhibiting anticancer properties

Technology Process of MPC3100

There total 20 articles about MPC3100 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: 74.0%

8-((6-bromobenzo[d][1,3]dioxol-5-yl)thio)-9-(2-(piperidin-4-yl)ethyl)-9H-purin-6-amine + L-Lactic acid (79-33-4,106989-11-1,26811-96-1,31587-11-8,26100-51-6) → MPC-3100 (958025-66-6)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 - 25 ℃; for 18h;

DOI:10.1016/j.bmcl.2015.09.053

Reference yield:

8-((6-bromobenzo[d][1,3]dioxol-5-yl)thio)-9-(2-(piperidin-4-yl)ethyl)-9H-purin-6-amine + (S)-2-acetoxypropanoyl chloride (36394-75-9) → MPC-3100 (958025-66-6)

Guidance literature:

8-((6-bromobenzo[d][1,3]dioxol-5-yl)thio)-9-(2-(piperidin-4-yl)ethyl)-9H-purin-6-amine; (S)-2-acetoxypropanoyl chloride; With triethylamine; In tetrahydrofuran; dichloromethane; at 20 ℃;

With silver carbonate; In methanol; dichloromethane; for 6h;

Reference yield:

tert-butyl 4-[2-(6-amino-8-bromo-9H-purin-9-yl)ethyl]piperidine-1-carboxylate (1156468-58-4) → MPC-3100 (958025-66-6)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / 10 h / 70 °C

2: trifluoroacetic acid / dichloromethane / 2 h / 10 - 20 °C

3: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran; N,N-dimethyl-formamide / 10 h / 20 °C

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm3004619

upstream raw materials:

L-Lactic acid

3,4-methylenedioxybenzenethiol

tert-butyl 4-{2-[6-amino-8-(1,3-benzodioxol-5-ylthio)-9H-purin-9-yl]ethyl}piperidine-1-carboxylate

8-(7-bromo-2,3-dihydro-benzo[1,4]dioxin-6-ylsulfanyl)adenine

Downstream raw materials:

C₃₃H₃₈BrN₆O₉PS

(2S)-1-[4-(2-{6-amino-8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9H-purin-9-yl}ethyl)piperidin-1-yl]-1-oxopropan-2-yl 3-(phosphonooxy)benzoate

(2S)-1-[4-(2-{6-amino-8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9H-purin-9-yl}ethyl)piperidin-1-yl]-1-oxopropan-2-yl hydrogen sulfate sodium salt

Refernces

• 1、 Kim, Se-Ho,Bajji, Ashok,Tangallapally, Rajendra,Markovitz, Benjamin,Trovato, Richard,Shenderovich, Mark,Baichwal, Vijay,Bartel, Paul,Cimbora, Daniel,McKinnon, Rena,Robinson, Rosann,Papac, Damon,Wettstein, Daniel,Carlson, Robert,Yager, Kraig M.. "Discovery of (2 S)-1-[4-(2-{6-amino-8-[(6-bromo-1,3-benzodioxol-5-yl) sulfanyl]-9 H-purin-9-yl}ethyl)piperidin-1-yl]-2-hydroxypropan-1-one (MPC-3100), a purine-based Hsp90 inhibitor". . p. 7480 - 7501. Retrieved 2012/11/06.