Pseurotin A

Base Information

• Chemical Name: Pseurotin A
• CAS No.: 58523-30-1
• Molecular Formula: C22H25 N O8
• Molecular Weight: 431.442
• UNII: H73C5W8FNE
• DSSTox Substance ID: DTXSID901017601
• Wikipedia: Pseurotin_A
• Wikidata: Q15424789
• Metabolomics Workbench ID: 63428
• ChEMBL ID: CHEMBL253179
• Mol file: 58523-30-1.mol

Synonyms:pseurotin;pseurotin A

Chemical Property of Pseurotin A

Chemical Property:

• Vapor Pressure: 1E-23mmHg at 25°C
• Melting Point: 126.0-126.9℃
• Boiling Point: 751.5°C at 760 mmHg
• PKA: 14.76±0.20(Predicted)
• Flash Point: 408.3°C
• PSA: 142.39000
• Density: 1.41g/cm³
• LogP: 0.33160
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (10 mg/ml)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 431.15801676
• Heavy Atom Count: 31
• Complexity: 814

Purity/Quality:

99% ^*data from raw suppliers

PB1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CC(C(C1=C(C(=O)C2(O1)C(C(NC2=O)(C(=O)C3=CC=CC=C3)OC)O)C)O)O
• Isomeric SMILES: CC/C=C\[C@@H]([C@@H](C1=C(C(=O)[C@@]2(O1)[C@H]([C@@](NC2=O)(C(=O)C3=CC=CC=C3)OC)O)C)O)O
• Description: Pseurotin A (58523-30-1) is a fungal metabolite with novel structure. Displays potent neuritogenic activity in PC12 cells. Induces multipolar and branching neurites comparable to that produced by β-NGF.1 Displays immunosuppressive activity via inhibition of immunoglobulin E production in vitro.2 Displays antiproliferative effects on four glioma cell lines by regulating tumor metabolic enzymes.3 Inhibits osteoclastogenesis and prevents ovariectomized-induced bone loss by suppression of ROS.4
• Uses: Pseurotin A shows antiparasitic and anticancer activity. It exhibits inhibition towards IgE (immunoglobin E) production. Pseurotin A is a fungal metabolite with an unusual hetero-spirocyclic ring system. It has potent neuritogenic activity in PC12 phaechromocytoma cells, a useful model for adrenergic neuronal differentiation. Pseurotin A induces multipolar and branching neurites comparable to β-NGF, an endogenous neurotrophic factor. Pseurotin A also exhibits chitinase inhibition and acts synergistically with azole antifungal agents.

Technology Process of Pseurotin A

There total 42 articles about Pseurotin A 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: 67.0%

methanol (67-56-1) + (5S,8S,9R)-8-benzoyl-2-((2S,4S,5S)-(Z)-5-(but-1-enyl)-2-methyl-[1,3]dioxolan-4-yl)-8,9-dihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione (562858-39-3) → pseurotin A (58523-30-1) + (5S,8S,9R)-8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexenyl]-8,9-dihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione (149883-42-1)

Guidance literature:

With acetyl chloride; In methanol; at 20 ℃; for 11h;

DOI:10.1021/ol034630s

Reference yield: 54.0%

(+)-synerazol (127941-81-5) → pseurotin A (58523-30-1)

Guidance literature:

With water; toluene-4-sulfonic acid; In tetrahydrofuran; at 30 ℃; for 24h;

DOI:10.7164/antibiotics.57.537

Reference yield: 41.0%

methanol (67-56-1) + (5S,8S,9R)-8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexenyl]-8,9-dihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione (149883-42-1) → pseurotin A (58523-30-1)

Guidance literature:

With camphor-10-sulfonic acid; In methanol; at 40 ℃;

DOI:10.3987/com-03-s(p)25

upstream raw materials:

(12S,13S)-12,13-dibromo-12,13-dihydropseurotin A

methanol

(5S,8S,9R)-8-benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxy-3-hexenyl]-8,9-dihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

(5S,8S,9R)-8-benzoyl-2-((2S,4S,5S)-(Z)-5-(but-1-enyl)-2-methyl-[1,3]dioxolan-4-yl)-8,9-dihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione

Downstream raw materials:

trans-2-pentenal

6-O-methylpseurotin A

7-N-methylpseurotin A

C₂₉H₂₉NO₉S

Refernces

• 1、 Aoki, Shin-Ya,Oi, Takahiro,Shimizu, Kazuya,Shiraki, Ryota,Takao, Ken-Ichi,Tadano, Kin-Ichi. "Total syntheses of natural pseurotins A and F2 and azaspirene". . p. 161 - 166. Retrieved 2007/10/03.
• 2、 Igarashi, Yasuhiro,Yabuta, Yukihiro,Furumai, Tamotsu. "Determination of the absolute configuration of synerazol". . p. 537 - 540. Retrieved 2007/10/03.