Dendrodoine

Base Information

• Chemical Name: Dendrodoine
• CAS No.: 75351-10-9
• Molecular Formula: C₁₃H₁₂N₄OS
• Molecular Weight: 272.33
• NSC Number: 606400
• DSSTox Substance ID: DTXSID00226329
• Wikidata: Q83105709
• Metabolomics Workbench ID: 168451
• Mol file: 75351-10-9.mol

Synonyms:dendrodoine;dendrodoine A

Chemical Property of Dendrodoine

Chemical Property:

• Vapor Pressure: 6.16E-10mmHg at 25°C
• Boiling Point: 495°C at 760 mmHg
• Flash Point: 253.1°C
• PSA: 90.12000
• Density: 1.404g/cm³
• LogP: 2.31640
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 272.07318219
• Heavy Atom Count: 19
• Complexity: 352

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C1=NSC(=N1)C(=O)C2=CNC3=CC=CC=C32

Technology Process of Dendrodoine

There total 3 articles about Dendrodoine 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:

5-(N,N-dimethylamino)-1,3,4-oxathiadiazol-2-one (90545-89-4) + 1H-indol-3-yl(oxo)acetonitrile (19194-62-8) → 5-<(3-N-dimethyl-amino)-1,2,4-thiadiazolyl>-3-indanyl methanone (75351-10-9)

Guidance literature:

In N,N-dimethyl-formamide; at 145 - 150 ℃;

DOI:10.1016/S0040-4020(01)91096-8

Reference yield:

indole (120-72-9) → 5-<(3-N-dimethyl-amino)-1,2,4-thiadiazolyl>-3-indanyl methanone (75351-10-9)

Guidance literature:

Multi-step reaction with 3 steps

1: diethyl ether / 1 h / 0 °C

2: 53 percent / acetonitrile; toluene / 6 h / 110 °C

3: 20 mg / dimethylformamide / 145 - 150 °C

In diethyl ether; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0040-4020(01)91096-8

Reference yield:

Indole-3-carbonyl chloride (59496-25-2) → 5-<(3-N-dimethyl-amino)-1,2,4-thiadiazolyl>-3-indanyl methanone (75351-10-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / acetonitrile; toluene / 6 h / 110 °C

2: 20 mg / dimethylformamide / 145 - 150 °C

In N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0040-4020(01)91096-8

upstream raw materials:

5-(N,N-dimethylamino)-1,3,4-oxathiadiazol-2-one

1H-indol-3-yl(oxo)acetonitrile

indole

Indole-3-carbonyl chloride

Refernces

Synthesis of [2,4-bis(arylamino)thiazol-5-yl](1-methyl-1h-benzimidazol-2- yl)methanones

10.1002/jhet.162

The research focuses on the synthesis and characterization of novel analogs of the cytotoxic marine alkaloid dendrodoine. The purpose of this study is to develop new compounds with potential anticancer activity by replacing the 3-amino-1,2,4-thiadiazole unit in dendrodoine with a 2-aminothiazole unit, thereby expanding the scope for substituent manipulation and functionalization. The [4+1] heterocyclization reaction was employed to synthesize the novel 1-methyl-1H-benzimidazole derivatives. The synthesized compounds were characterized by elemental analysis, IR, NMR, and mass spectral data. The study concludes that the synthesized 2,4-bis(arylamino)thiazol-5-ylmethanones exhibit promising anticancer activity at submicromolar concentrations, indicating their potential as new therapeutic agents.

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