Elesclomol

Base Information

• Chemical Name: Elesclomol
• CAS No.: 488832-69-5
• Molecular Formula: C19H20N4O2S2
• Molecular Weight: 400.525
• NSC Number: 174939
• UNII: 6UK191M53P
• DSSTox Substance ID: DTXSID2042642
• Nikkaji Number: J3.403.368D
• Wikipedia: Elesclomol
• Wikidata: Q5359460
• NCI Thesaurus Code: C75291
• Metabolomics Workbench ID: 149553
• ChEMBL ID: CHEMBL1972860
• Mol file: 488832-69-5.mol

Synonyms:elesclomol;STA 4783;STA-4783;STA4783

Chemical Property of Elesclomol

Chemical Property:

• Refractive Index: 1.667
• PKA: 7.99±0.70(Predicted)
• PSA: 128.86000
• Density: 1.313 g/cm³
• LogP: 2.83570
• Solubility.: insoluble in H2O; ≥20.15 mg/mL in DMSO; ≥5.68 mg/mL in EtOH with gentle warming and ultrasonic
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 400.10276824
• Heavy Atom Count: 27
• Complexity: 510

Purity/Quality:

99% ^*data from raw suppliers

Elesclomol ≥98% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C(=S)C1=CC=CC=C1)NC(=O)CC(=O)NN(C)C(=S)C2=CC=CC=C2
• Recent ClinicalTrials: STA-4783/Paclitaxel or Paclitaxel Alone in Melanoma
• Recent EU Clinical Trials: A Randomized, Double-Blind, Phase III Trial of STA-4783 in Combination with Paclitaxel versus Paclitaxel Alone for Treatment of Chemotherapy-Na?ve Subjects with Stage IV Metastatic Melanoma

Technology Process of Elesclomol

There total 12 articles about Elesclomol 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: 82.0%

malonic acid (141-82-2) + N-methylbenzothiohydrazide (21048-05-5) → elesclomol (488832-69-5)

Guidance literature:

With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; at 17 - 25 ℃; for 2h; Product distribution / selectivity; Cooling with water-ice;

Reference yield: 70.0%

N-methylbenzothiohydrazide (21048-05-5) + malonoyl dichloride (1663-67-8) → elesclomol (488832-69-5)

Guidance literature:

With triethylamine; In ethyl acetate;

DOI:10.1016/j.jinorgbio.2013.10.005

Reference yield:

C19H20N4O4 → elesclomol (488832-69-5)

Guidance literature:

C₁₉H₂₀N₄O₄; With perchloric acid; In water; at 0 - 20 ℃;

With sodium sulfide; In water; acetone; at 20 ℃; for 0.5h;

With hydrogenchloride; In water;

DOI:10.1016/j.bmcl.2013.07.032

upstream raw materials:

N-methylbenzothiohydrazide

malonoyl dichloride

malonic acid

N-thiobenzoylpiperidine

Downstream raw materials:

Cu(II)-elesclomol

Ni(II)-elesclomol

2-(hydroxyimino)-N'1,N'3-dimethyl-N'1,N'3-di(phenylcarbonothioyl)malonohydrazide

C₂₂H₂₅N₅O₂S₂

Refernces

• 1、 Xia, Zhiqiang,Jiang, Jun,Sun, Lijun,Tatsuta, Noriaki,Koya, Keizo,Zhang, Junyi,Bohnert, Gary,Chen, Shoujun. "Facile and convenient synthesis of N ′1, N ′3-dialkyl- N ′1, N ′3-bis(arylcarbonothioyl)malonohydrazides via propylphosphonic anhydride coupling". . p. 3394 - 3398. Retrieved 2015/01/09.
• 2、 Chen, Shoujun,Sun, Lijun,Koya, Keizo,Tatsuta, Noriaki,Xia, Zhiqiang,Korbut, Timothy,Du, Zhenjian,Wu, Jim,Liang, Guiqing,Jiang, Jun,Ono, Mitsunori,Zhou, Dan,Sonderfan, Andrew. "Syntheses and antitumor activities of N′1, N′3-dialkyl-N′1,N′3-di- (alkylcarbonothioyl) malonohydrazide: The discovery of elesclomol". . p. 5070 - 5076. Retrieved 2013/09/12.