Monorderne

Base Information

• Chemical Name: Monorderne
• CAS No.: 12772-57-5
• Molecular Formula: C18H17ClO6
• Molecular Weight: 364.78
• Hs Code.: 29322090
• European Community (EC) Number: 642-889-3
• DSSTox Substance ID: DTXSID20860103
• Wikipedia: Radicicol
• Wikidata: Q27166962,Q105322846,Q105322876,Q104667570
• NCI Thesaurus Code: C1462
• ChEMBL ID: CHEMBL3972342
• Mol file: 12772-57-5.mol

Synonyms:5-chloro-6-(7,8-epoxy-10-hydroxy-2-oxo-3,5-undecadienyl)-beta-resorcylic acid mu-lactone;KF58332;KF9-A;monorden;monordene;radicicol

Chemical Property of Monorderne

Chemical Property:

• Appearance/Colour: White/yellow powder
• Vapor Pressure: 7.97E-18mmHg at 25°C
• Melting Point: 193.5°
• Refractive Index: 1.583
• Boiling Point: 656.2 °C at 760 mmHg
• PKA: 6.29±0.40(Predicted)
• Flash Point: 350.7 °C
• PSA: 96.36000
• Density: 1.364 g/cm³
• LogP: 2.69160
• Storage Temp.: −20°C
• Solubility.: ethanol: 10 mg/mL
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 364.0713660
• Heavy Atom Count: 25
• Complexity: 588

Purity/Quality:

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

Radicicol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T
• Statements: 22-36/37/38-46-45
• Safety Statements: 26-45-53

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2C(O2)C=CC=CC(=O)CC3=C(C(=CC(=C3Cl)O)O)C(=O)O1
• Description: Radicicol (12772-57-5) inhibits heat shock protein 90 (HSP90) activity by binding to the ATP-binding pocket.1?In cells HSP90 client proteins such as Raf kinase2, HIF-1α3?and estrogen receptor4?are destabilized and proteolytically degraded. Radicicol inhibits expression of COX-2 without affecting COX-1 expression in LPS-stimulated macrophages (IC50=27 nM).5?Inhibits angiogenesis.6
• Uses: Radicicol is a resorcylic acid lactone, produced by several fungal species, that exhibits broad spectrum antifungal and antitumour activity. Radicicol has been the subject of extensive investigation and inhibits protein tyrosine kinase, induces the differentiation of HL-60 cells into macrophages, blocks cell cycle at G1 and G2, suppresses NIH 3T3 cell transformation by diverse oncogenes such as src, ras and mos, and also suppresses the expression of mitogen-inducible cyclooxygenase-2. As a cell differentiation modulator, radicicol has anti-angiogenic activity in vivo, inhibiting the proliferation of plasminogen activator production by vascular endothelial cells. Radicicol is an antitumor antibiotic, which inhibits the Hsp90 molecular chaperone. Radicicol from Diheterospora chlamydosporia has been used as an inhibitor of heat shock protein 90 (Hsp90):to study its effects on lifespan extension and health in Caenorhabditis elegansto study its effects on protein aggregation in yeast to study its effects on xanthone sensitized cancer cells

Technology Process of Monorderne

There total 58 articles about Monorderne 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: 86.0%

KF 23541 (184537-19-7) → (9Z,11E)-(4R,6R,8R)-16-Chloro-17,19-dihydroxy-4-methyl-3,7-dioxa-tricyclo[13.4.0.06,8]nonadeca-1(15),9,11,16,18-pentaene-2,13-dione (12772-57-5)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 23 ℃; for 1h;

DOI:10.1002/anie.200454108 DOI:10.1002/chem.200500160

Reference yield: 58.0%

Monocillin I (75207-13-5) → (9Z,11E)-(4R,6R,8R)-16-Chloro-17,19-dihydroxy-4-methyl-3,7-dioxa-tricyclo[13.4.0.06,8]nonadeca-1(15),9,11,16,18-pentaene-2,13-dione (12772-57-5)

Guidance literature:

With sulfuryl dichloride; In diethyl ether; at 0 ℃;

DOI:10.1021/ja011364+

Reference yield:

(3R,4R,6S)-6-(hydroxy)-3,4-(oxiranyl)hept-1-ene (378749-88-3) → (9Z,11E)-(4R,6R,8R)-16-Chloro-17,19-dihydroxy-4-methyl-3,7-dioxa-tricyclo[13.4.0.06,8]nonadeca-1(15),9,11,16,18-pentaene-2,13-dione (12772-57-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 84 percent / tris(3-chlorophenyl)phosphine; DIAD / toluene / 3 h / 23 °C

2.1: 91 percent / iPr₂NEt; tetrabutylammonium iodide / dimethylformamide / 4 h / 80 °C

3.1: LDA / tetrahydrofuran / 0.08 h / -78 °C

3.2: 81 percent / tetrahydrofuran / 0.08 h / -78 °C

4.1: 94 percent / PhCH=Ru{[(MeS)NCH₂CH₂N(MeS)]}(PCy₃)Cl₂ / toluene / 0.17 h / 120 °C

5.1: aq. H₂O₂ / toluene / 3 h

6.1: toluene / 1 h / 80 °C

7.1: 68 percent / SO₂Cl₂ / diethyl ether / 1.5 h / 0 °C

8.1: 74 percent / aq. HCl / dioxane / 1 h / 0 - 23 °C

9.1: 86 percent / K₂CO₃ / dimethylformamide / 1 h / 23 °C

With hydrogenchloride; sulfuryl dichloride; di-isopropyl azodicarboxylate; tri(m-chlorophenyl)-phosphine; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; potassium carbonate; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; 1,4-dioxane; diethyl ether; N,N-dimethyl-formamide; toluene; 1.1: Mitsunobu esterification;

DOI:10.1002/chem.200500160

upstream raw materials:

(9Z,11E)-(4R,6R,8R)-17,19-Bis-(tert-butyl-dimethyl-silanyloxy)-16-chloro-4-methyl-3,7-dioxa-tricyclo[13.4.0.0^6,8]nonadeca-1⁽¹⁵⁾,9,11,16,18-pentaene-2,13-dione

Monocillin I

KF 23541

(3R,4R,6S)-6-(tert-Butyl-diphenyl-silanyloxy)-3-chloro-hept-1-en-4-ol

Downstream raw materials:

radicicol 10-(E)-O-benzyloxime

radicicol 10-(Z)-O-benzyloxime

C₂₄H₂₃ClO₆S

C₂₄H₂₃ClO₆S

Refernces

• 1、 Agatsuma, Tsutomu,Ogawa, Harumi,Akasaka, Kazuhito,Asai, Akira,Yamashita, Yoshinori,Mizukami, Tamio,Akinaga, Shiro,Saitoh, Yutaka. "Halohydrin and oxime derivatives of radicicol: Synthesis and antitumor activities". . p. 3445 - 3454. Retrieved 2002.
• 2、 Barluenga, Sofia,Moulin, Emilie,Lopez, Pilar,Winssinger, Nicolas. "Solution- and solid-phase synthesis of radicicol (monorden) and pochonin C". . p. 4935 - 4952. Retrieved 2007/10/03.