Obatoclax

Base Information

• Chemical Name: Obatoclax
• CAS No.: 803712-67-6
• Molecular Formula: C₂₀H₁₉N₃O
• Molecular Weight: 317.39
• UNII: QN4128B52A
• ChEMBL ID: CHEMBL408194,CHEMBL4802292,CHEMBL4525540
• Metabolomics Workbench ID: 153224
• NCI Thesaurus Code: C60770
• Pharos Ligand ID: XCLYS95UPJ79
• Wikidata: Q76421489
• Wikipedia: Obatoclax
• Mol file: 803712-67-6.mol

Synonyms:1H-indole, 2-(2-((3,5-dimethyl-1H-pyrrol-2-yl)methylene)-3-methoxy-2H-pyrrol-5-yl)-;2-((2Z)-2-((3,5-Dimethyl-1H-pyrrol-2-yl)methylene)-3-methoxy-2H-pyrrol-5-yl)-1H-indole methanesulfonate (1:1);2-(2-((3,5-dimethyl-1H-pyrrol-2-yl)methylene)-3-methoxy-2H-pyrrol-5-yl)-1H-indole;2-(2-((3,5-Dimethyl-1H-pyrrol-2-yl)methylene)-3-methoxy-2H-pyrrol-5-yl)-1H-indole methanesulfonate;GX 15-070;GX-15-070;GX015-070;GX15-070;obatoclax;obatoclax mesylate

Chemical Property of Obatoclax

Chemical Property:

• PSA: 53.17000
• LogP: 3.92250
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 317.152812238
• Heavy Atom Count: 24
• Complexity: 777

Purity/Quality:

99% ^*data from raw suppliers

Obatoclax ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=C(N1)C=C2C(=CC(=C3C=C4C=CC=CC4=N3)N2)OC)C
• Isomeric SMILES: CC1=CC(=C(N1)/C=C\2/C(=C/C(=C/3\C=C4C=CC=CC4=N3)/N2)OC)C
• Recent ClinicalTrials: A Phase I/II Study of Carboplatin and Etoposide With or Without Obatoclax in Extensive-stage Small Cell Lung Cancer (ES-SCLC)
• Uses: Obatoclax is a small molecule mimetic of the BH3 domain of BCL-2 family proteins.

Technology Process of Obatoclax

There total 16 articles about Obatoclax 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: 98.0%

2,4-dimethyl-1H-pyrrole (625-82-1) + 1-(N-methoxycarbonyl)indole-2-boronic acid (1001162-89-5) → obatoclax (803712-67-6)

Guidance literature:

2,4-dimethyl-1H-pyrrole; 1-(N-methoxycarbonyl)indole-2-boronic acid; With hydrogenchloride; In methanol; at 16 - 20 ℃;

In N,N-dimethyl-formamide; for 0.333333h;

DOI:10.1021/op7001613

Reference yield: 50.0%

2,4-dimethyl-1H-pyrrole (625-82-1) + tert-butyl 2-(5-formyl-4-methoxy-1H-pyrrol-2-yl)-1H-indole-1-carboxylate (803712-70-1) → obatoclax (803712-67-6)

Guidance literature:

With hydrogenchloride; In methanol; at 25 ℃; for 5h; Inert atmosphere;

DOI:10.1021/jm200543y

Reference yield:

2-[5-(3,5-dimethyl-1H-pyrrol-2-ylmethylene)-4-methoxy-5H-pyrrol-2-yl]-1H-indole hydrochloride → obatoclax (803712-67-6)

Guidance literature:

With sodium hydroxide; In water; ethyl acetate;

upstream raw materials:

tert-butyl 2-(5-formyl-4-methoxy-1H-pyrrol-2-yl)-1H-indole-1-carboxylate

4-methoxy-3-pyrrolin-2-one

2,4-dimethyl-1H-pyrrole

N-((5-bromo-3-methoxy-2H-pyrrol-2-ylidene)-methyl)-N-ethylethanamine

Refernces

• 1、 Papireddy, Kancharla,Smilkstein, Martin,Kelly, Jane Xu,Shweta,Salem, Shaimaa M.,Alhamadsheh, Mamoun,Haynes, Stuart W.,Challis, Gregory L.,Reynolds, Kevin A.. "Antimalarial activity of natural and synthetic prodiginines". supporting information; experimental part. p. 5296 - 5306. Retrieved 2011/10/02.
• 2、 -. "METHODS FOR TREATING ARTHRITIS USING TRIHETEROCYCLIC COMPOUNDS". Page/Page column 103-104. . Retrieved 2008/06/13.