Chaetominine

Base Information

• Chemical Name: Chaetominine
• CAS No.: 918659-56-0
• Molecular Formula: C₂₂H₁₈N₄O₄
• Molecular Weight: 402.409
• DSSTox Substance ID: DTXSID80582495
• Metabolomics Workbench ID: 64019
• Nikkaji Number: J2.407.479J
• NSC Number: 746369
• Wikidata: Q27134076
• Mol file: 918659-56-0.mol

Synonyms:chaetominine

Chemical Property of Chaetominine

Chemical Property:

• Melting Point: 164℃
• PSA: 95.74000
• Density: 1.63
• LogP: 1.13540
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 402.13280507
• Heavy Atom Count: 30
• Complexity: 845

Purity/Quality:

99% ^*data from raw suppliers

Chaetominine >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(=O)N2C3N1C(=O)C(CC3(C4=CC=CC=C42)O)N5C=NC6=CC=CC=C6C5=O
• Isomeric SMILES: C[C@H]1C(=O)N2[C@@H]3N1C(=O)[C@@H](C[C@@]3(C4=CC=CC=C42)O)N5C=NC6=CC=CC=C6C5=O
• Description: (–)-Chaetominine is a cytotoxic alkaloid originally isolated from Chaetomium sp. IFB-E015. It inhibits the growth of K562 leukemia and SW1116 colon cancer cells (IC50s = 20 and 28 nM, respectively). (–)-Chaetominine induces apoptosis of K562 cells via upregulation of the Bax/Bcl-2 ratio, decreasing mitochondrial membrane potential, inducing mitochondrial cytochrome C release, and activation of caspase-3 and caspase-9. It also decreases doxorubicin efflux mediated by multidrug resistance-associated protein 1 (MRP1) and restores sensitivity to doxorubicin in resistant K562 cells.

Technology Process of Chaetominine

There total 60 articles about Chaetominine 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: 94.0%

(2R,4R,5aS,9cS)-4,5,5a,9c-tetrahydro-2-methyl-4-(4-oxo-3(4H)-quinazolinyl)-5a-[(2,2,6,6-tetramethyl-1-piperidinyl)oxy]-3H-2a,9b-diazacyclopenta[jk]fluorene-1,3(2H)-dione → chaetominine (1173180-39-6,918659-56-0)

Guidance literature:

With acetic acid; zinc; In tetrahydrofuran; at 50 ℃;

DOI:10.1016/j.tet.2014.09.029

Reference yield: 94.0%

(2S,4R,5aS,9cS)-4,5,5a,9c-tetrahydro-2-methyl-4-(4-oxo-3(4H)-quinazolinyl)-5a-[(triethylsilyl)oxy]-3H-2a,9b-diazacyclopenta[jk]fluorene-1,3(2H)-dione → chaetominine (918659-56-0)

Guidance literature:

With hydrogen fluoride; In water; acetonitrile; at 20 - 30 ℃; Inert atmosphere;

DOI:10.1021/ol802155n

Reference yield: 90.0%

(2S,4S,5aR,9cR)-4,5,5a,9c-tetrahydro-2-methyl-4-(4-oxo-3(4H)-quinazolinyl)-5a-[(2,2,6,6-tetramethyl-1-piperidinyl)oxy]-3H-2a,9b-diazacyclopenta[jk]fluorene-1,3(2H)-dione → (+)-2,3,14-triepi-chaetominine (1558046-43-7,918659-56-0)

Guidance literature:

With acetic acid; zinc; In tetrahydrofuran; at 50 ℃;

DOI:10.1016/j.tet.2014.09.029

upstream raw materials:

(R)-3-(1H-indol-3-yl)-2-(2-nitrobenzamido)propanoic acid

(S)-3-(1H-indol-3-yl)-2-(2-nitrobenzamido)propanoic acid

ortho-nitrobenzoic acid

2-nitrobenzyl chloride

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