Hypothemycin

Base Information

• Chemical Name: Hypothemycin
• CAS No.: 76958-67-3
• Molecular Formula: C₁₉H₂₂O₈
• Molecular Weight: 378.379
• Hs Code.: 29419000
• DSSTox Substance ID: DTXSID301017784
• Nikkaji Number: J1.252.055G,J1.740.057F
• Wikidata: Q27097139
• ChEMBL ID: CHEMBL471474
• Mol file: 76958-67-3.mol

Synonyms:hypothemycin

Chemical Property of Hypothemycin

Chemical Property:

• Vapor Pressure: 4.92E-19mmHg at 25°C
• Melting Point: 170-172℃
• Boiling Point: 673.1°C at 760 mmHg
• Flash Point: 242.7°C
• PSA: 125.82000
• Density: 1.343g/cm³
• LogP: 1.02690
• Storage Temp.: ?20°C
• Solubility.: DMSO: soluble
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 1
• Exact Mass: 378.13146766
• Heavy Atom Count: 27
• Complexity: 590

Purity/Quality:

98% ^*data from raw suppliers

Hypothemycin ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CC=CC(=O)C(C(CC2C(O2)C3=C(C(=CC(=C3)OC)O)C(=O)O1)O)O
• Isomeric SMILES: C[C@H]1C/C=C\C(=O)[C@H]([C@H](C[C@@H]2[C@H](O2)C3=C(C(=CC(=C3)OC)O)C(=O)O1)O)O
• Description: Hypothemycin (76958-67-3) is a potent and selective inhibitor of MEK.1-3?Acts via covalent binding to Cys residue.2?In cells, hypothemycin inhibits the MEK-ERK axis with sufficient selectivity to normalize transformed phenotypes3. Inhibits TNFα production in LPS-stimulated macrophages.4
• Uses: Hypothemycin is a potent and selective inhibitor of threonine/tyrosine-specific kinase, MEK, and other protein kinases that contain a conserved cysteine residue in the ATP-binding site in in vitro studies.

Technology Process of Hypothemycin

There total 8 articles about Hypothemycin 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: 25.0%

(5Z)-7-oxozeaenol → Hypothemycin (76958-67-3)

Guidance literature:

With 3,3-dimethyldioxirane; In acetone; acetonitrile; for 1h; Inert atmosphere;

DOI:10.1002/chem.200901373

Reference yield: 17.0%

LL-Z1640-2 (253863-19-3) → Hypothemycin (76958-67-3)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; at -20 - 0 ℃; for 4h;

DOI:10.1016/S0040-4039(02)00871-7

Reference yield:

(2E,11Z)-(5S,9R,14S)-10,18-Dihydroxy-20-methoxy-7,7,14-trimethyl-6,8,15-trioxa-tricyclo[15.4.0.05,9]henicosa-1(21),2,11,17,19-pentaen-16-one (460358-69-4) → Hypothemycin (76958-67-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / Jones' reagent / acetone / 0.17 h / 0 °C

2: 76 percent / pTsOH / CH₂Cl₂; methanol / 0.5 h / 20 °C

3: 17 percent / MCPBA; NaHCO₃ / 4 h / -20 - 0 °C

With jones' reagent; sodium hydrogencarbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; acetone;

DOI:10.1016/S0040-4039(02)00871-7

upstream raw materials:

LL-Z₁₆₄₀-2

(2E,11Z)-(5S,9R,14S)-10,18-Dihydroxy-20-methoxy-7,7,14-trimethyl-6,8,15-trioxa-tricyclo[15.4.0.0^5,9]henicosa-1⁽²¹⁾,2,11,17,19-pentaen-16-one

FR₂₆₄₇₄₄

(2E,11Z)-(5S,9R,10R,14S)-10,18-Dihydroxy-20-methoxy-7,7,14-trimethyl-6,8,15-trioxa-tricyclo[15.4.0.0^5,9]henicosa-1⁽²¹⁾,2,11,17,19-pentaen-16-one

Refernces

• 1、 Sellès, Patrice,Lett, Robert. "Convergent stereospecific synthesis of LL-Z1640-2 (or C292), hypothemycin and related macrolides. Part 2". . p. 4627 - 4631. Retrieved 2007/10/03.