AT9283

Base Information

• Chemical Name: AT9283
• CAS No.: 896466-04-9
• Molecular Formula: C₁₉H₂₃N₇O₂
• Molecular Weight: 381.437
• Hs Code.: 2934999090
• Mol file: 896466-04-9.mol

Synonyms:Urea, N-cyclopropyl-N'-[3-[6-(4-morpholinylmethyl)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]-;

Chemical Property of AT9283

Chemical Property:

• Refractive Index: 1.714
• PKA: 10.58±0.10(Predicted)
• PSA: 110.96000
• Density: 1.45 g/cm³
• LogP: 2.47090
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: insoluble in H2O; ≥19.05 mg/mL in DMSO; ≥47.6 mg/mL in EtOH with ultrasonic

Purity/Quality:

98%,99%, ^*data from raw suppliers

AT-9283 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: AT-9283 is a broad spectrum kinase inhibitor that potently inhibits Aurora A, Aurora B, JAK2, JAK3, and c-ABL (IC50s = 3, 3, 1.2, 1.1, and 4 nM, respectively). It also potently (IC50 = <1 μM) inhibits many other kinases, including serine/threonine kinases as well as receptor and non-receptor tyrosine kinases. As Aurora kinases have roles in mitosis, inhibitors of these kinases, including AT-9283, have potential in cancer therapy. Consistent with this, AT-9283 is effective in preventing proliferation of cancer cells both in vitro and in vivo and this effect may be enhanced by combination therapy with other chemotherapeutics.[Cayman Chemical]

Technology Process of AT9283

There total 5 articles about AT9283 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: 56.8%

8-(morpholinomethyl)-2H-benzo[4,5]imidazo[1,2-c]pyrazol[3,4-e]pyrimidine-5(4H)-ketone (896466-73-2) + C16H16N6O2 (896466-74-3) + Cyclopropylamine (765-30-0) → AT9283 (896466-04-9)

Guidance literature:

In 1-methyl-pyrrolidin-2-one; at 95 - 105 ℃; for 16 - 24h; Product distribution / selectivity;

Reference yield: 37.0%

3-(5-(morpholinylmethyl)-1H-benzo[d]imidazol-2-yl)-1H-pyrazole-4-amine (825619-30-5) + 1,1'-carbonyldiimidazole (530-62-1) + Cyclopropylamine (765-30-0) → AT9283 (896466-04-9)

Guidance literature:

3-(5-(morpholinylmethyl)-1H-benzo[d]imidazol-2-yl)-1H-pyrazole-4-amine; 1,1'-carbonyldiimidazole; In tetrahydrofuran; for 16h; Reflux;

Cyclopropylamine; In N,N-dimethyl-formamide; at 100 ℃; for 16h;

DOI:10.1021/jm800984v

Reference yield:

8-(morpholinomethyl)-2H-benzo[4,5]imidazo[1,2-c]pyrazol[3,4-e]pyrimidine-5(4H)-ketone (896466-73-2) + Cyclopropylamine (765-30-0) → AT9283 (896466-04-9)

Guidance literature:

In 1-methyl-pyrrolidin-2-one; at 100 ℃; for 9h; Product distribution / selectivity;

upstream raw materials:

8-(morpholinomethyl)-2H-benzo[4,5]imidazo[1,2-c]pyrazol[3,4-e]pyrimidine-5(4H)-ketone

Cyclopropylamine

C₁₆H₁₆N₆O₂

3-(5-(morpholinylmethyl)-1H-benzo[d]imidazol-2-yl)-1H-pyrazole-4-amine

Refernces

• 1、 Howard, Steven,Berdini, Valerio,Boulstridge, John A.,Carr, Maria G.,Cross, David M.,Curry, Jayne,Devine, Lindsay A.,Early, Theresa R.,Fazal, Lynsey,Gill, Adrian L.,Heathcote, Michelle,Maman, Sarita,Matthews, Julia E.,McMenamin, Rachel L.,Navarro, Eva F.,O'Brien, Michael A.,O'Reilly, Marc,Rees, David C.,Reule, Matthias,Tisi, Dominic,Williams, Glyn,Vinkovi?, Mladen,Wyatt, Paul G.. "Fragment-based discovery of the pyrazol-4-yl urea (AT9283), a multitargeted kinase inhibitor with potent aurora kinase activity". experimental part. p. 379 - 388. Retrieved 2009/09/29.
• 2、 -. "PHARMACEUTICAL COMPOUNDS". Page/Page column 233. . Retrieved 2010/11/28.