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(R)-1-(2-(2,5-dichlorobenzamido)acetamido)-3-methylbutylboronic acid

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(R)-1-(2-(2,5-dichlorobenzamido)acetamido)-3-methylbutylboronic acid Basic information

Product Name:
(R)-1-(2-(2,5-dichlorobenzamido)acetamido)-3-methylbutylboronic acid
Synonyms:
  • MLN2238
  • IxazoMib
  • (R)-1-(2-(2,5-dichlorobenzamido)acetamido)-3-methylbutylboronic acid
  • IXAZOMIB;MLN 2238;MLN-2238
  • CS-1976
  • 1-(2-(2,5-dichlorobenzamido)acetamido)- 3-methylbutylboronic acid
  • B-[(1R)-1-[[2-[(2,5-dichlorobenzoyl)amino]acetyl]amino]-3-methylbutyl]boronic acid
  • ixazomib(MLN2238)
CAS:
1072833-77-2
MF:
C14H19BCl2N2O4
MW:
361.03
EINECS:
810-246-8
Product Categories:
  • Inhibitors
  • Inhibitor
  • apis
Mol File:
1072833-77-2.mol
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(R)-1-(2-(2,5-dichlorobenzamido)acetamido)-3-methylbutylboronic acid Chemical Properties

Melting point:
>142°C (subl.)
Density 
1.306
storage temp. 
-20°C Freezer
solubility 
DMSO (Sparingly), Methanol (Slightly)
pka
9.67±0.43(Predicted)
form 
Solid
color 
White to Pale Yellow
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(R)-1-(2-(2,5-dichlorobenzamido)acetamido)-3-methylbutylboronic acid Usage And Synthesis

Uses

Ixazomib is a proteasome inhibitor that acts by preventing cell growth in solid tumours. It is an anticancer agent that is used to treat patients with multiple myeloma and is potentially neurotoxic.

Definition

ChEBI: A glycine derivative that is the amide obtained by formal condensation of the carboxy group of N-(2,5-dichlorobenzoyl)glycine with the amino group of [(1R)-1-amino-3-methylbutyl]boronic acid. The active metabolite of ixa omib citrate, it is used in combination therapy for treatment of multiple myeloma.

Synthesis

1201903-02-7

11113-50-1

1072833-77-2

The diol borate ester (5 g) of MLN9708 intermediate was mixed with concentrated hydrochloric acid (5 mL), boric acid (1.9 g) and diisopropyl ether (100 mL) at room temperature. After the reaction mixture was stirred for 5 hours, the solid product was collected by filtration and washed with diisopropyl ether (25 mL). Subsequently, the resulting solid was dried under vacuum conditions to give the final (R)-(1-(2-(2,5-dichlorobenzamido)acetamido)-3-methylbutyl)boronic acid (Txazomib) in 86.5% yield.

in vivo

Ixazomib (MLN2238) shows antitumor activity in the CWR22 xenograft model. The antitumor effects of Ixazomib (MLN2238) dosed at 14 mg/kg i.v. or 7 mg/kg i.v. are compared with Bortezomib dosed at 0.8 mg/kg i.v. or 0.4 mg/kg i.v. on a twice weekly regimen. The high dose for both Ixazomib (MLN2238) and Bortezomib (HY-10227) shows similar antitumor activity in this model (T/C=0.36 and 0.44, respectively). However, Ixazomib (MLN2238) (7 mg/kg) shows greater efficacy at a 0.5 MTD dose compared with a 0.5 MTD dose of Bortezomib (0.4 mg/kg; T/C=0.49 compared with T/C=0.79, respectively) Ixazomib (MLN2238) shows time-dependent reversible proteasome inhibition; however, the proteasome dissociation half-life (t1/2) for Ixazomib (MLN2238) is determined to be 18 minutes[1].

target

chymotrypsin-like proteolytic (β5) site of the 20S proteasome

References

[1] Patent: WO2018/158697, 2018, A1. Location in patent: Page/Page column 25

(R)-1-(2-(2,5-dichlorobenzamido)acetamido)-3-methylbutylboronic acidSupplier

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