Name: ARD-2585
Brand: BOC Sciences
Rating: 5 (1 reviews)

Size

Price

Stock

Quantity

$--

In stock

Solubility

Soluble in DMSO

Storage

Store at -20°C

IUPACName

N-[(1r,4r)-4-(3-chloro-4-cyano-N-methylanilino)cyclohexyl]-4-[4-[1-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl]azetidin-3-yl]piperazin-1-yl]benzamide

Synonyms

Benzamide, N-[trans-4-[(3-chloro-4-cyanophenyl)methylamino]cyclohexyl]-4-[4-[1-[2-(2,6-dioxo-3-piperidinyl)-2,3-dihydro-1,3-dioxo-1H-isoindol-5-yl]-3-azetidinyl]-1-piperazinyl]-; N-((1r,4r)-4-((3-chloro-4-cyanophenyl)(methyl)amino)cyclohexyl)-4-(4-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)azetidin-3-yl)piperazin-1-yl)benzamide; N-[trans-4-[(3-Chloro-4-cyanophenyl)methylamino]cyclohexyl]-4-[4-[1-[2-(2,6-dioxo-3-piperidinyl)-2,3-dihydro-1,3-dioxo-1H-isoindol-5-yl]-3-azetidinyl]-1-piperazinyl]benzamide; ARD 2585; ARD2585

Boiling Point

1032.7±65.0°C at 760 Torr

Density

1.46±0.1 g/cm3

InChI Key

LUCHABJUYSYJAT-RVWRWSNSNA-N

InChI

InChI=1S/C41H43ClN8O5/c1-46(30-9-4-26(22-43)35(42)21-30)28-10-5-27(6-11-28)44-38(52)25-2-7-29(8-3-25)47-16-18-48(19-17-47)32-23-49(24-32)31-12-13-33-34(20-31)41(55)50(40(33)54)36-14-15-37(51)45-39(36)53/h2-4,7-9,12-13,20-21,27-28,32,36H,5-6,10-11,14-19,23-24H2,1H3,(H,44,52)(H,45,51,53)/t27-,28-,36?

Canonical SMILES

N#CC1=CC=C(C=C1Cl)N(C)C2CCC(NC(=O)C3=CC=C(C=C3)N4CCN(CC4)C5CN(C6=CC=C7C(=O)N(C(=O)C7=C6)C8C(=O)NC(=O)CC8)C5)CC2

1. Discovery of ARD-2585 as an Exceptionally Potent and Orally Active PROTAC Degrader of Androgen Receptor for the Treatment of Advanced Prostate Cancer

Hoda Metwally,Bukeyan Miao,Weiguo Xiang,Aleksas Matvekas,Miao He,Bo Wen,Lu Wang,Yu Wang,Paul D Kirchhoff,Duxin Sun,Shaomeng Wang,Xin Han,Lijie Zhao,Chong Qin,Donna McEachern J Med Chem . 2021 Sep 23;64(18):13487-13509. doi: 10.1021/acs.jmedchem.1c00900.

We report herein the discovery of exceptionally potent and orally bioavailable PROTAC AR degraders with ARD-2585 being the most promising compound. ARD-2585 achieves DC50values of ≤0.1 nM in the VCaP cell line with AR gene amplification and in the LNCaP cell line carrying an AR mutation. It potently inhibits cell growth with IC50values of 1.5 and 16.2 nM in the VCaP and LNCaP cell lines, respectively, and achieves excellent pharmacokinetics and 51% of oral bioavailability in mice. It is more efficacious than enzalutamide in inhibition of VCaP tumor growth and does not cause any sign of toxicity in mice. ARD-2585 is a promising AR degrader for extensive investigations for the treatment of advanced prostate cancer.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C₁V₁ = C₂V₂