Kibdelone C

Base Information

• Chemical Name: Kibdelone C
• CAS No.: 934464-79-6
• Molecular Formula: C₂₉H₂₈ClNO₁₀
• Molecular Weight: 585.995
• DSSTox Substance ID: DTXSID501043886
• Metabolomics Workbench ID: 117760
• Nikkaji Number: J2.447.739H
• Mol file: 934464-79-6.mol

Synonyms:kibdelone C

Chemical Property of Kibdelone C

Chemical Property:

• XLogP3: 2.4
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 3
• Exact Mass: 585.1401738
• Heavy Atom Count: 41
• Complexity: 1170

Purity/Quality:

>95% by HPLC ^*data from raw suppliers

KibdeloneC ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCC1=C(C2=C(C3=C(C4=C(CC3)C(=C5C(=C4O)C(=O)C6=C(O5)C(CC(C6O)O)O)OC)C(=C2C(=O)N1C)O)O)Cl
• Isomeric SMILES: CCCC1=C(C2=C(C3=C(C4=C(CC3)C(=C5C(=C4O)C(=O)C6=C(O5)[C@H](C[C@@H]([C@@H]6O)O)O)OC)C(=C2C(=O)N1C)O)O)Cl
• Description: Kibdelone C is a member of a family of natural heterocyclic polyketides first isolated from a soil actinomycete, Kibdelosporangium. Kibdelones have been described as having potent and selective cytotoxicity against a panel of human tumor cell lines, and kibdelone C has low nanomolar effectiveness in these assays. Kibdelone C disrupts the actin cytoskeleton without directly binding actin or affecting its polymerization in vitro.
• Uses: Kibdelone C is the major analogue of a potent antitumour complex isolated from Kibdelosporangium sp.. Structurally, kibdelone C is related to lysolipin and albofungin, however no comparative investigation of this class has been reported. The mode of action and pharmacology of the kibdelones has received little attention. Kibdelone C is the major analogue of a potent antitumor complex isolated from Kibdelosporangium sp.. Structurally, kibdelone C is related to lysolipin and albofungin, however no comparative investigation of this class has been reported. The mode of action and pharmacology of the kibdelones has received little attention. Kibdelone C is the major analogue of a potent antitumor complex.

Technology Process of Kibdelone C

There total 51 articles about Kibdelone C 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: 62.0%

kibdelone C methyl ether (1311379-39-1) → kibdelone C (934464-79-6) + C28H26ClNO10

Guidance literature:

kibdelone C methyl ether; With ammonium cerium (IV) nitrate; water; acetic acid; In water; acetonitrile; for 0.0333333h; Inert atmosphere;

With sodium dithionite; water; for 0.333333h; Inert atmosphere;

DOI:10.1021/ja203642n

Reference yield:

C41H49NO13 → kibdelone C (934464-79-6)

Guidance literature:

C₄₁H₄₉NO₁₃; With 2,2,3,4,5,6-hexachloro-cyclohexa-2,4-dien-1-one; In dichloromethane; N,N-dimethyl-formamide; at 0 ℃; for 1h; Inert atmosphere;

With perchloric acid; In tetrahydrofuran; tert-butyl alcohol; at 0 - 20 ℃; for 12h; Further stages; Inert atmosphere;

DOI:10.1021/jacs.6b05484

Reference yield:

C17H20O4 → kibdelone C (934464-79-6) + C28H26ClNO10

Guidance literature:

Multi-step reaction with 13 steps

1.1: sodium chlorite; sodium phosphate monobasic monohydrate / 2-methyl-but-2-ene; water; tert-butyl alcohol / 0 °C

2.1: sulfuric acid / 0 - 20 °C / Inert atmosphere

3.1: toluene-4-sulfonic acid / tetrahydrofuran / 80 °C / Inert atmosphere

4.1: chloro-trimethyl-silane; sodium cyanoborohydride / acetonitrile / 0 °C / Inert atmosphere; Heating

5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / 80 °C / Inert atmosphere

6.1: magnesium iodide / dichloromethane / -78 - -20 °C / Inert atmosphere

7.1: boron trichloride / dichloromethane / 1 h / -78 °C / Inert atmosphere

8.1: 10-camphorsufonic acid / dichloromethane / 1 h / 40 °C / Inert atmosphere; Sonication

9.1: potassium phosphate / dimethyl sulfoxide / 50 °C / Inert atmosphere

10.1: lithium hydroxide monohydrate; water / 1,4-dioxane / 75 °C / Inert atmosphere

11.1: pyridine; 1,3,5-trichloro-2,4,6-triazine / 1,2-dichloro-ethane / 1.08 h / 20 - 75 °C / Inert atmosphere

12.1: hydrogenchloride; water / tetrahydrofuran / 4 h / 40 °C / Inert atmosphere

13.1: ammonium cerium (IV) nitrate; water; acetic acid / water; acetonitrile / 0.03 h / Inert atmosphere

13.2: 0.33 h / Inert atmosphere

With pyridine; hydrogenchloride; sodium chlorite; potassium phosphate; chloro-trimethyl-silane; 1,3,5-trichloro-2,4,6-triazine; ammonium cerium (IV) nitrate; sodium phosphate monobasic monohydrate; lithium hydroxide monohydrate; sulfuric acid; 10-camphorsufonic acid; water; boron trichloride; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; magnesium iodide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; 2-methyl-but-2-ene; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; 1,2-dichloro-ethane; acetonitrile; tert-butyl alcohol; 1.1: Pinnick oxidation / 6.1: intramolecular halo-Michael aldol reaction;

DOI:10.1021/ja203642n

upstream raw materials:

C₁₅H₁₈O₅

C₂₂H₂₂O₅

C₂₂H₂₄O₅

C₂₂H₂₂O₅

Refernces

Enantioselective total synthesis of ( - )-kibdelone C

10.1021/ja204040k

The research focuses on the enantioselective total synthesis of (-)-Kibdelone C, a naturally occurring compound with significant anticancer activity. The synthesis strategy involves the assembly of the AB-DEF-ring system from an isoquinolinone and a tetrahydroxanthone fragment, which are derived from simpler precursors through a series of chemical reactions. Key steps include a Shi epoxidation to establish stereochemistry, an acid-catalyzed cyclization to form the tetrahydroxanthone, and a C-H arylation to complete the hexacyclic skeleton. Reactants used in the synthesis include amino alcohol, benzoic acid, and various other organic compounds and reagents such as TEMPO, BCl3, and Sonogashira coupling partners. The synthesis process also involves the use of Swern oxidation, Dess-Martin oxidation, and other protective group manipulations. Analytical techniques employed to characterize the intermediates and final product include 1H and 13C NMR spectroscopy, HPLC/MS, and molecular weight determination, confirming the successful replication of (-)-Kibdelone C with optical rotation and spectroscopic data matching those of the natural product.

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