Thymectacin

Base Information

• Chemical Name: Thymectacin
• CAS No.: 232925-18-7
• Molecular Formula: C₂₁H₂₅BrN₃O₉P
• Molecular Weight: 574.322
• UNII: 2ZRZ4TSW3F
• DSSTox Substance ID: DTXSID00177862
• Nikkaji Number: J1.483.744B,J3.616.614B
• Wikipedia: Thymectacin
• Wikidata: Q7799611
• NCI Thesaurus Code: C1882
• Metabolomics Workbench ID: 149399
• Mol file: 232925-18-7.mol

Synonyms:thymectacin

Chemical Property of Thymectacin

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 168.25000
• Density: 1.597g/cm³
• LogP: 2.70860
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 11
• Exact Mass: 573.05118
• Heavy Atom Count: 35
• Complexity: 909

Purity/Quality:

95% ^*data from raw suppliers

NB-1011 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)OC)NP(=O)(OCC1C(CC(O1)N2C=C(C(=O)NC2=O)C=CBr)O)OC3=CC=CC=C3
• Isomeric SMILES: C[C@@H](C(=O)OC)NP(=O)(OC[C@@H]1[C@H](C[C@@H](O1)N2C=C(C(=O)NC2=O)/C=C/Br)O)OC3=CC=CC=C3
• Recent ClinicalTrials: NB1011 in Treating Patients With Metastatic or Recurrent Colorectal Cancer

Technology Process of Thymectacin

There total 3 articles about Thymectacin 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: 69.0%

phenyl methoxyalaninyl phosphorochloridate (142629-80-9) + (E)-5-(2-bromovinyl)-2'-deoxyuridine (69304-47-8) → (E)-5-(2-bromovinyl)-2'-deoxy-5'-uridyl phenyl L-methoxyalaninylphosphoramidate (232925-18-7)

Guidance literature:

With 1-methyl-1H-imidazole; In tetrahydrofuran; at -80 ℃;

DOI:10.1016/j.bmc.2005.02.041

Reference yield: 53.0%

L-alanine methyl ester hydrochloride (2491-20-5) + O-phenyl phosphorodichloridate (770-12-7) + (E)-5-(2-Bromovinyl)-2'-deoxy-L-uridine → (E)-5-(2-bromovinyl)-2'-deoxy-5'-uridyl phenyl L-methoxyalaninylphosphoramidate (232925-18-7)

Guidance literature:

L-alanine methyl ester hydrochloride; O-phenyl phosphorodichloridate; With 1-methyl-1H-imidazole; In dichloromethane; at -10 - 0 ℃;

(E)-5-(2-Bromovinyl)-2'-deoxy-L-uridine; In dichloromethane; at -5 ℃;

DOI:10.1021/op025562c

Reference yield:

O-phenyl phosphorodichloridate (770-12-7) → (E)-5-(2-bromovinyl)-2'-deoxy-5'-uridyl phenyl L-methoxyalaninylphosphoramidate (232925-18-7)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / CH₂Cl₂ / -80 - 20 °C

2: 69 percent / N-methylimidazole / tetrahydrofuran / -80 °C

With 1-methyl-1H-imidazole; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmc.2005.02.041

upstream raw materials:

phenyl methoxyalaninyl phosphorochloridate

(E)-5-(2-bromovinyl)-2'-deoxyuridine

O-phenyl phosphorodichloridate

L-alanine methyl ester hydrochloride

Refernces

Anti-cancer ProTides: Tuning the activity of BVDU phosphoramidates related to thymectacin

10.1016/j.bmc.2005.02.041

The research focuses on the development and optimization of anti-cancer ProTides, specifically phosphoramidates related to thymectacin, aimed at enhancing their in vitro potency against colon and prostate cancer cell lines. The study involved the synthesis of twelve analogues of the lead anti-cancer agent thymectacin, with the goal of tuning its ester and amino acid regions to improve potency. The synthesis was achieved through a one-step reaction using phosphorochloridate chemistry, and the resulting compounds were fully characterized, revealing the presence of two phosphate diastereoisomers. The anti-cancer effects of these compounds were evaluated against breast (MDA MB231), colon (HT115), and prostate (PC-3) cancer cell lines using the MTT assay, which measures cell viability by converting a tetrazolium salt into a formazan precipitate. The实验结果 showed significant enhancements in potency with certain structural modifications, particularly the replacement of the methyl ester with a benzyl ester, which resulted in a 175-fold increase in potency against colon cancer cells. The compounds were further analyzed using NMR spectroscopy to confirm their structures and to distinguish between the diastereoisomers.

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