Dtxcid603638

Base Information

• Chemical Name: Dtxcid603638
• CAS No.: 29767-20-2
• Molecular Formula: C32H32O13S
• Molecular Weight: 656.664
• Hs Code.: 29349990
• European Community (EC) Number: 249-831-2
• ChEMBL ID: CHEMBL2355508
• NCI Thesaurus Code: C857
• Wikipedia: Teniposide
• Mol file: 29767-20-2.mol

Synonyms:Demethyl Epipodophyllotoxin Thenylidine Glucoside;NSC 122819;NSC-122819;NSC122819;Teniposide;Teniposide, (5a alpha,9 alpha(S*))-Isomer;VM 26;VM-26;VM26;Vumon

Chemical Property of Dtxcid603638

Chemical Property:

• Appearance/Colour: white or off-white crystalline powder
• Melting Point: 274 - 277oC
• Refractive Index: 1.5530 (estimate)
• Boiling Point: 864.3 °C at 760 mmHg
• PKA: 10.13(at 25℃)
• Flash Point: 476.5 °C
• PSA: 189.07000
• Density: 1.59 g/cm³
• LogP: 2.75290
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: soluble10mg/mL, clear
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 6
• Exact Mass: 656.15636224
• Heavy Atom Count: 46
• Complexity: 1090

Purity/Quality:

98%min ^*data from raw suppliers

Teniposide ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1O)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)OC6C(C(C7C(O6)COC(O7)C8=CC=CS8)O)O
• Isomeric SMILES: COC1=CC(=CC(=C1O)OC)[C@H]2[C@@H]3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)O[C@H]6[C@@H]([C@H]([C@H]7[C@H](O6)COC(O7)C8=CC=CS8)O)O
• Recent ClinicalTrials: Teniposide Incorporating Bu/Cy Conditioning Regimen for HLH With Central Nervous System Involvemen
• Recent EU Clinical Trials: HEMOS ALL 0105 Intensification therapy of mature B-ALL, Burkitt and Burkitt like and other HIgh Grade Non-Hodgkin?s Lymphoma in Adults
• Uses: A labelled semi-synthetic derivative of Podophyllotoxin. Antineoplastic. A semi-synthetic derivative of Podophyllotoxin. Antineoplastic. Teniposide is a podophyllotoxin derivative that causes dose-dependent single- and double-stranded breaks in DNA by inhibiting topoisomerase II. Its cytostatic effects are related to its ability to stabilize the DNA-topoisomerase II complex during DNA replication, inducing DNA damage and cellular apoptosis. Teniposide has been widely used in the treatment of various cancers including, small cell lung cancer, malignant lymphoma, breast cancer, oral squamous cell carcinoma, and acute lymphoblastic leukemia.
• Indications: Teniposide (VM-26, Vumon) is closely related to etoposide in structure, mechanisms of action and resistance, and adverse effects. It is more lipophilic and approximately threefold more potent than etoposide. Its major uses have been in pediatric cancers, particularly in acute lymphoblastic leukemias.
• Therapeutic Function: Antineoplastic
• Clinical Use: Teniposide is used in combination with other agents for the treatment of refractory childhood acute lymphoblastic leukemia.

Technology Process of Dtxcid603638

There total 3 articles about Dtxcid603638 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: 82.9%

→ teniposide (29767-20-2,35317-60-3,53956-10-8,89301-94-0,132880-84-3)

Guidance literature:

With palladium 10% on activated carbon; In 1,4-dioxane; methanol; at 30 ℃; for 4h; Inert atmosphere; Green chemistry;

Reference yield:

9-[(4,6-O-(thien-2-ylmethylidene-Β-D-glucopyranosyl)oxy)-5,8,9a,9-tetrahydro-5-(4-(5-nitrothien-2-yl)methoxy)3,5-dimethoxyphenyl]furo[3',4':6,7]naphtha[2,3-d]-1,3-dioxol-6(5aH)-one → teniposide (29767-20-2)

Guidance literature:

G-values;

Reference yield:

→ (5R,5aR,8aR,9R)-9-((4aR,6S,7R,8R,8aS)-7,8-Dihydroxy-2-thiophen-2-yl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-5-(4-hydroxy-3,5-dimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one (29767-20-2,35317-60-3,53956-10-8,89301-94-0,132880-84-3)

Guidance literature:

4'-Demethylpodophyllotoxinglucosid, Thiophen-2-aldehyd, ZnCl2;

Refernces

• 1、 -. "BIOREDUCTIVELY-ACTIVATED PRODRUGS". Page/Page column 20-21. . Retrieved 2008/06/13.