Picropodophyllin

Base Information

• Chemical Name: Picropodophyllin
• CAS No.: 477-47-4
• Deprecated CAS: 17434-18-3
• Molecular Formula: C22H22O8
• Molecular Weight: 414.412
• European Community (EC) Number: 637-166-4
• NSC Number: 36407
• UNII: 0F35AOI227
• DSSTox Substance ID: DTXSID80197245
• Nikkaji Number: J112.698I
• Wikidata: Q27088385
• NCI Thesaurus Code: C87736
• Pharos Ligand ID: TC4Y6GHF2DDK
• Metabolomics Workbench ID: 130025
• ChEMBL ID: CHEMBL283120
• Mol file: 477-47-4.mol

Synonyms:AXL-1717;AXL1717;cyclolignan PPP;picro-podophyllin;picropodophyllin;picropodophyllin (PPP)

Chemical Property of Picropodophyllin

Chemical Property:

• Melting Point: 225-227℃
• Refractive Index: 1.4480 (estimate)
• Boiling Point: 597.9°Cat760mmHg
• PKA: 13.26±0.40(Predicted)
• Flash Point: 210.2°C
• PSA: 92.68000
• Density: 1.37g/cm³
• LogP: 2.40920
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: H2O: soluble
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 414.13146766
• Heavy Atom Count: 30
• Complexity: 629

Purity/Quality:

99% ^*data from raw suppliers

IGF-1R Inhibitor, PPP ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A poison.
• Hazard Codes: Xi,T
• Statements: 36/37/38-68-25-21
• Safety Statements: 26-36-45-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1OC)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)O
• Isomeric SMILES: COC1=CC(=CC(=C1OC)OC)[C@H]2[C@H]3[C@H](COC3=O)[C@H](C4=CC5=C(C=C24)OCO5)O
• Recent ClinicalTrials: Phase I/II Trial of AXL1717 in the Treatment of Recurrent Malignant Astrocytomas
• Recent EU Clinical Trials: Phase II, randomized, open-label study of the IGF-1R inhibitor AXL1717 compared to docetaxel in patients with previously treated, locally advanced, or metastatic squamous cell carcinoma or adenocarcinoma of the lung
• Description: Picropodophyllotoxin (477-47-4) is a potent and selective inhibitor of insulin-like growth factor 1 receptor (IGF1R) which is non-competitive with ATP.1?Displays no activity at IR, EGFR, FGFR or PDGFR. Inhibits IGF1R autophosphorylation IC50 ~ 1 nM.1?Displays antiproliferative activity in numerous tumor cell lines, IC50 = 0.05 – 15 μM.2 Exhibits antiangiogenic activity.3?Picropodophyllotoxin attenuates intimal hyperplasia after vascular injury.4?Active in vivo.
• Uses: Insulin growth factor 1 receptor inhibitor, antineoplastic Picropodophyllotoxin is an insulin-like growth factor-I (IGF-I) receptor kinase inhibitor

Technology Process of Picropodophyllin

There total 147 articles about Picropodophyllin 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: 98.0%

podophyllotoxone (477-48-5,477-49-6,55515-07-6,60660-51-7,64550-42-1,64937-82-2,86594-36-7,130322-38-2) → picropodophyllotoxin (477-47-4)

Guidance literature:

With sodium tetrahydroborate; at 0 ℃;

DOI:10.1016/S0960-894X(97)00101-7

Reference yield: 96.0%

(+/-)-methyl epipodophyllate (1256-91-3,55515-12-3,75171-58-3,78216-03-2,86334-69-2,116180-67-7,122871-76-5,127126-86-7) → (+/-)-epi-picropodophyllin (477-47-4,518-28-5,4354-76-1,4375-06-8,4375-07-9,26540-82-9,55568-79-1,55568-80-4,60660-50-6,62319-21-5,77519-37-0,77519-38-1,79355-67-2,86334-73-8,118627-04-6,122871-77-6,122871-79-8,122871-81-2)

Guidance literature:

With sodium methylate; In methanol; at 25 ℃; for 3h;

DOI:10.1021/jo00279a011

Reference yield: 94.0%

(5aR,8aS,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione (477-48-5) → picropodophyllotoxin (477-47-4)

Guidance literature:

With lithium tri(t-butoxy)aluminum hydride; In tetrahydrofuran; for 3.5h; Ambient temperature;

DOI:10.1021/ja00231a041

upstream raw materials:

ethanol

8-hydroxy-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid

diazomethane

4'-O-demethylpicropodophyllotoxin

Downstream raw materials:

O-(3-Carboxy-propionyl)-picropodophyllin

(5R,5aR,8aS,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl acetate

benzoylpicropodophyllin

(5aS)-5c-(2-bromo-3,4,5-trimethoxy-phenyl)-9c-hydroxy-(5ar,8ac)-5,8,8a,9-tetrahydro-5aH-furo[3',4';6,7]naphtho[2,3-d][1,3]dioxol-6-one

Refernces

• 1、 Wang, Rong,Zhi, Xiaoyan,Li, Jie,Xu, Hui. "Synthesis of Novel Oxime Sulfonate Derivatives of 2′(2′,6′)-(Di)chloropicropodophyllotoxins as Insecticidal Agents". . p. 6668 - 6674. Retrieved 2015/08/18.
• 2、 Wang, Yi,Shao, Yonghua,Wang, Yangyang,Fan, Lingling,Yu, Xiang,Zhi, Xiaoyan,Yang, Chun,Qu, Huan,Yao, Xiaojun,Xu, Hui. "Synthesis and quantitative structure-activity relationship (QSAR) study of novel isoxazoline and oxime derivatives of podophyllotoxin as insecticidal agents". . p. 8435 - 8443. Retrieved 2012/10/29.