Hesperadin

Base Information

• Chemical Name: Hesperadin
• CAS No.: 422513-13-1
• Molecular Formula: C29H32N4O3S
• Molecular Weight: 516.664
• Mol file: 422513-13-1.mol

Synonyms:N-[(3Z)-2-oxo-3-[phenyl-[4-(piperidin-1-ylmethyl)anilino]methylidene]-1H-indol-5-yl]ethanesulfonamide;UNII-PTR491OS14;Hesperadin;

Chemical Property of Hesperadin

Chemical Property:

• Melting Point: 228 °C
• PKA: 9.14±0.20(Predicted)
• PSA: 102.41000
• Density: 1.326
• LogP: 6.61640
• Storage Temp.: Refrigerator
• Solubility.: DMSO, Methanol

Purity/Quality:

98% min ^*data from raw suppliers

Hesperadin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Hesperadin is a multi-kinase inhibitor. It inhibits human Aurora kinase B (IC50 = 250 nM) and its T. brucei homolog Aurora kinase-1 (IC50 = 40 nM) in in vitro kinase assays. Hesperadin (1 μM) inhibits AMPK, LCK, MKK1, MAPKAP-K1, CHK1, and PHK in a panel of 25 kinases. It also inhibits MEKK2 in ATPase and transphosphorylation assays with IC50s of 60 and 34 nM, respectively. Hesperadin (50-100 nM) induces polyploidy and defects in cytokinesis and spindle assembly as well as inhibits proliferation of HeLa cells and overrides mitotic arrest induced by paclitaxel or monastrol . Hesperadin also induces toxicity in HepG2 cells with a toxic concentration (TC50) value of less than 0.2 μM. It inhibits replication of clinical isolates of influenza A and B viruses with EC50s ranging from 0.22 to 2.21 μM in a plaque formation assay. Hesperadin inhibits the growth of T. brucei, L. major promastigotes and amastigotes, and P. falciparum with EC50 values ranging from 0.01 to 2.37 μM, but has less activity against T. cruzi (EC50 = 39 μM).
• Uses: Hesperadin phosphorylates human mitotic protein complexes that control physiological changes within the cell to allow for proper and successful chromosome segregation. It also targets aurora kinases i n cancer treatment, affecting the chromosomes’regulation during mitosis. Hesperadin phosphorylates human mitotic protein complexes that control physiological changes within the cell to allow for proper and successful chromosome segregation. It also targets aurora kinases in cancer treatment, affecting the chromosomes’ regulation during mitosis.

Technology Process of Hesperadin

There total 12 articles about Hesperadin 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: 83.0%

(Z)-5-amino-3-{phenyl[(4-(piperidin-1-ylmethyl)phenyl)-amino]methylidene}-1,3-dihydro-2H-indolin-2-one + Ethanesulfonyl chloride (594-44-5) → hesperadin (422513-13-1)

Guidance literature:

In pyridine; dichloromethane; water; at 0 - 20 ℃; for 0.75h; Inert atmosphere;

DOI:10.1021/acs.joc.1c01269

Reference yield:

4-nitrobenzyl chloride (100-14-1) → hesperadin (422513-13-1)

Guidance literature:

Multi-step reaction with 7 steps

1: tetrahydrofuran

2: triethylamine / dichloromethane / 16 h / 5 - 20 °C

3: pyridin-1-ium-1-yl[pyridin-1-ium-1-yl(sulfido)phosphinothioyl]sulfanyl-sulfido-thioxo-phosphane / pyridine / 0.67 h / 70 - 110 °C

4: hydrogenchloride / water; methanol / pH 2 - 3

5: N,N-dimethyl-formamide / 12 h / 20 °C

6: hydrogen / dichloromethane; methanol / 4 h / 3040.2 Torr / Autoclave

7: water; dichloromethane; pyridine / 0.75 h / 0 - 20 °C / Inert atmosphere

With hydrogenchloride; pyridin-1-ium-1-yl[pyridin-1-ium-1-yl(sulfido)phosphinothioyl]sulfanyl-sulfido-thioxo-phosphane; hydrogen; triethylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; 5: |Eschenmoser Sulfide Contraction;

DOI:10.1021/acs.joc.1c01269

Reference yield:

piperidine (110-89-4) → hesperadin (422513-13-1)

Guidance literature:

Multi-step reaction with 7 steps

1: tetrahydrofuran

2: triethylamine / dichloromethane / 16 h / 5 - 20 °C

3: pyridin-1-ium-1-yl[pyridin-1-ium-1-yl(sulfido)phosphinothioyl]sulfanyl-sulfido-thioxo-phosphane / pyridine / 0.67 h / 70 - 110 °C

4: hydrogenchloride / water; methanol / pH 2 - 3

5: N,N-dimethyl-formamide / 12 h / 20 °C

6: hydrogen / dichloromethane; methanol / 4 h / 3040.2 Torr / Autoclave

7: water; dichloromethane; pyridine / 0.75 h / 0 - 20 °C / Inert atmosphere

With hydrogenchloride; pyridin-1-ium-1-yl[pyridin-1-ium-1-yl(sulfido)phosphinothioyl]sulfanyl-sulfido-thioxo-phosphane; hydrogen; triethylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; 5: |Eschenmoser Sulfide Contraction;

DOI:10.1021/acs.joc.1c01269

upstream raw materials:

(Z)-5-nitro-3-{phenyl[(4-(piperidin-1-ylmethyl)phenyl)-amino]methylidene}-1,3-dihydro-2H-indolin-2-one

Ethanesulfonyl chloride

5-nitrooxindole

4-nitrobenzyl chloride

Refernces

• 1、 -. "Use of Lck inhibitors for treatment of immunologic diseases". . . Retrieved 2008/06/13.