(4Z,12E)-19-benzyl-15-hydroxy-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo[12.7.0.01,18]henicosa-4,12-diene-3,6,21-trione

Base Information

• Chemical Name: (4Z,12E)-19-benzyl-15-hydroxy-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo[12.7.0.01,18]henicosa-4,12-diene-3,6,21-trione
• CAS No.: 14110-64-6
• Molecular Formula: C29H35 N O5
• Molecular Weight: 477.601
• Hs Code.: 29349990
• European Community (EC) Number: 237-964-9
• Mol file: 14110-64-6.mol

Synonyms:cytochalasin A

Chemical Property of (4Z,12E)-19-benzyl-15-hydroxy-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo[12.7.0.01,18]henicosa-4,12-diene-3,6,21-trione

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 147 to 148'c
• Boiling Point: 725.1 °C at 760 mmHg
• PKA: 13.54±0.70(Predicted)
• Flash Point: 392.3 °C
• PSA: 92.70000
• Density: 1.2 g/cm³
• LogP: 4.02910
• Storage Temp.: −20°C
• Sensitive.: Light Sensitive
• Solubility.: ethanol: 20 mg/mL, clear, colorless
• Water Solubility.: Soluble in DMF, DMSO, ethanol and acetone. Insoluble in water.
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 477.25152322
• Heavy Atom Count: 35
• Complexity: 901

Purity/Quality:

98%,99%, ^*data from raw suppliers

Cytochalasin A ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+T
• Hazard Codes: T+,T
• Statements: 26/27/28-63
• Safety Statements: 28-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCCC(=O)C=CC(=O)OC23C(C=CC1)C(C(=C)C(C2C(NC3=O)CC4=CC=CC=C4)C)O
• Isomeric SMILES: CC1CCCC(=O)/C=C\C(=O)OC23C(/C=C/C1)C(C(=C)C(C2C(NC3=O)CC4=CC=CC=C4)C)O
• Description: The cytochalasins are cell-permeable fungal metabolites which inhibit actin polymerization. This interferes with such diverse processes as cell movement, growth, phagocytosis, degranulation, and secretion. Cytochalasin A is an oxidized analog of cytochalasin B which uniquely inhibits HIV-1 protease (IC50 = 3 μM). Cytochalasins A and B differ from other cytochalasins in being able to rapidly and reversibly inhibit glucose transport by competitively binding glucose transporters (Ki = 4.0 and 0.6 μM, respectively). Cytochalasin A also induces the phosphorylation of the tyrosine phosphatase PTP3 of Dictyostelium, activating STATc.
• Uses: Cytochalasin A is one of a family of potent mycotoxins produced by several species of fungi. All members of the class exhibit profound effects on cytoskeletal proteins, giving rise to pronounced morphogenic activity in animals and plants. Like most cytochalsins, cytochalasin A exhibits potent inhibition of actin filament function leading to cell death by apoptosis, and displays a broad range of resultant cellular actions. Despite the common mode of action, there is evidence that individual members of the class display diverse selectivity. Specifically, cytochalasin A is one of the few cytochalasins exhibiting activity against HIV-1 protease. Cytochalasin A binds to the glucose transporter and inhibit monosaccharide transport across the plasma membrane. Preventing growth and sugar uptake in a Saccharomyces strain.

Technology Process of (4Z,12E)-19-benzyl-15-hydroxy-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo[12.7.0.01,18]henicosa-4,12-diene-3,6,21-trione

There total 8 articles about (4Z,12E)-19-benzyl-15-hydroxy-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo[12.7.0.01,18]henicosa-4,12-diene-3,6,21-trione 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:

Phomin (14930-96-2) → 7β-hydroxy-16α-methyl-10-phenyl-24-oxa-[14]cytochalasa-6(12),13t,21t-triene-1,20,23-trione (14110-64-6)

Guidance literature:

With manganese(IV) oxide; In chloroform;

DOI:10.1039/j39670001667

Reference yield:

(16R,20R)-7β,20-diacetoxy-9-hydroxy-16-methyl-1-oxo-10-phenyl-9,23-seco-[13]cytochalasa-6(12),13t,21t-triene-23-thioic acid S-phenyl ester (64760-39-0) → cytochalasin A (14110-64-6)

Guidance literature:

Multi-step reaction with 3 steps

1: Na₂HPO₄, CF₃CO₂Ag / benzene

2: (alkaline hydrolysis)

3: MnO₂

With manganese(IV) oxide; disodium hydrogenphosphate; silver trifluoroacetate; In benzene;

DOI:10.1021/ja00462a049

Reference yield:

cytochalasin B (14930-96-2) → cytochalasin A (14110-64-6)

Guidance literature:

With pyridine; chromium(VI) oxide; at 22 ℃; for 12h;

DOI:10.1002/hlca.19700530404

upstream raw materials:

Phomin

cytochalasin B

7,20-O,O'-di-acetyl-cytochalasin B

(16R,20R)-7β,20-diacetoxy-9-hydroxy-16-methyl-1-oxo-10-phenyl-9,23-seco-[13]cytochalasa-6(12),13t,21t-triene-23-thioic acid S-phenyl ester

Downstream raw materials:

21,22-dihydro-cytochalasin B

7β,20α-dihydroxy-16α-methyl-10-phenyl-24-oxa-[14]cytochalasa-6(12),13t-diene-1,23-dione

7β,20β-dimethoxy-2,16α-dimethyl-10-phenyl-24-oxa-[14]cytochalasa-6(12),13t-diene-1,23-dione

7β,20β-dimethoxy-16α-methyl-10-phenyl-24-oxa-[14]cytochalasa-6(12),13t-diene-1,23-dione

Refernces

• 1、 Rothweiler,Tamm. "Isolation and structure of the antibiotics Phomin and 5-dehydrophomin". . p. 696 - 724. Retrieved 2007/10/10.