Cytochalasin

Base Information

• Chemical Name: Cytochalasin
• CAS No.: 36084-18-1
• Molecular Formula: C29H37 N O5
• Molecular Weight: 479.613
• Mol file: 36084-18-1.mol

Synonyms:24-Oxa[14]cytochalasa-13,21-diene-1,23-dione,6,7-epoxy-20-hydroxy-16-methyl-10-phenyl-, (7S,13E,16R,20R,21E)-;3H-Oxacyclotetradecino[2,3-d]oxireno[f]isoindole,24-oxa[14]cytochalasa-13,21-diene-1,23-dione deriv.;3H-Oxacyclotetradecino[2,3-d]oxireno[f]isoindole-11,13(4H,14H)-dione,5,6,7,8,15,15a,16,16a,17a,17b-decahydro-8-hydroxy-4,16,16a-trimethyl-15-(phenylmethyl)-,[4R-(1E,4R*,8R*,9E,12aS*,15S*,15aS*,16S*,16aR*,17aS*,17bS*)]-; Cytochalasin F;Cytochalasin F6

Chemical Property of Cytochalasin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 709.9°Cat760mmHg
• Flash Point: 383.1°C
• PSA: 91.65000
• Density: 1.22g/cm³
• LogP: 4.00840

Purity/Quality:

98%Min ^*data from raw suppliers

CYTOCHALASIN F 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Cytochalasin

There total 7 articles about Cytochalasin 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: 75.0%

C35H51NO5Si → cytochalasin F (36084-18-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1021/ja00354a072

Reference yield:

C37H53NO6Si (86542-46-3) → cytochalasin F (36084-18-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / K₂CO₃ / methanol

2: 75 percent / tetrabutylammonium fluoride / tetrahydrofuran

With tetrabutyl ammonium fluoride; potassium carbonate; In tetrahydrofuran; methanol;

DOI:10.1021/ja00354a072

Reference yield:

(E)-(1R,6R,10S,14S,17S,18S,19S)-19-Benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10,16,17-trimethyl-4-phenylselanyl-2-oxa-20-aza-tricyclo[12.7.0.01,18]henicosa-12,15-diene-3,21-dione → cytochalasin F (36084-18-1)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂O₂ / pyridine; CH₂Cl₂

2: 88 percent / DMAP / triethylamine

3: 89 percent Turnov_. / t-BuOOH/Mo(CO)6 / benzene / 1.5 h / 75 °C

4: 86 percent / K₂CO₃ / methanol

5: 75 percent / tetrabutylammonium fluoride / tetrahydrofuran

With tert.-butylhydroperoxide; dmap; hexacarbonyl molybdenum; tetrabutyl ammonium fluoride; dihydrogen peroxide; potassium carbonate; In tetrahydrofuran; pyridine; methanol; dichloromethane; triethylamine; benzene;

DOI:10.1021/ja00354a072

upstream raw materials:

(4E,12E)-(1R,6R,10S,14S,17S,18S,19S)-19-Benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10,16,17-trimethyl-2-oxa-20-aza-tricyclo[12.7.0.0^1,18]henicosa-4,12,15-triene-3,21-dione

(4E,12E)-(1R,6R,10S,14S,17S,18S,19S)-20-Acetyl-19-benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10,16,17-trimethyl-2-oxa-20-aza-tricyclo[12.7.0.0^1,18]henicosa-4,12,15-triene-3,21-dione

C₃₇H₅₃NO₆Si

(E)-(1R,6R,10S,14S,17S,18S,19S)-19-Benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10,16,17-trimethyl-2-oxa-20-aza-tricyclo[12.7.0.0^1,18]henicosa-12,15-diene-3,21-dione

Refernces

Deoxy-cytochalasins from a marine-derived fungus Spicaria elegans

10.1139/V09-006

This research aimed to discover new bioactive secondary metabolites from marine fungi, specifically focusing on the marine-derived fungus Spicaria elegans. The study sought to isolate cytochalasins, which are known for their cytotoxic properties against cancer cell lines. To achieve this, the researchers treated Spicaria elegans with the cytochrome P-450 inhibitor metyrapone, leading to the discovery of two new deoxy-cytochalasins, 7-deoxy-cytochalasin Z7 (1) and 7-deoxy-cytochalasin Z9 (2), which were identified as plausible precursors of cytochalasins Z7 and Z9, respectively. The structures of these compounds were elucidated using spectroscopic methods, and the absolute configuration of compound 1 was determined by the conventional Mosher ester method. The cytotoxicities of the compounds were evaluated against two cancer cell lines, A-549 and P-388. Key chemicals used in the process included metyrapone as the P-450 inhibitor, (S)- and (R)-α-methoxy-α-trifluoromethyl-α-phenylacetic acid (MTPA) for the determination of absolute configuration, and the MTT assay for cytotoxicity evaluation. The results indicated that the biosynthetic oxidation at the 7 position of cytochalasins was due to cytochrome P-450, and that the double bond at C-6,7 in compounds 1 and 2 resulted in significantly weaker cytotoxicity compared to cytochalasins Z7 and Z9.

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