(2S,4R)-N-((S)-3-(4-((4-((1r,3r)-3-(3-chloro-4-cyanophenoxy)-2,2,4,4-tetramethylcyclobutylcarbamoyl)phenyl)ethynyl)-1,4'-bipiperidin-1'-yl)-1-(4-(4-methylthiazol-5-yl)phenyl)-3-oxopropyl)-1-((S)-2-(1-cyanocyclopropanecarboxamido)-3,3-dimethylbutanoyl)-4-hydroxypyrrolidine-2-carboxamide

ID: ALA4751950

PubChem CID: 162652844

Max Phase: Preclinical

Molecular Formula: C63H74ClN9O7S

Molecular Weight: 1136.86

Molecule Type: Unknown

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  Cc1ncsc1-c1ccc([C@H](CC(=O)N2CCC(N3CCC(C#Cc4ccc(C(=O)N[C@H]5C(C)(C)[C@H](Oc6ccc(C#N)c(Cl)c6)C5(C)C)cc4)CC3)CC2)NC(=O)[C@@H]2C[C@@H](O)CN2C(=O)[C@@H](NC(=O)C2(C#N)CC2)C(C)(C)C)cc1

Standard InChI:  InChI=1S/C63H74ClN9O7S/c1-38-52(81-37-67-38)42-17-15-41(16-18-42)49(68-55(77)50-31-46(74)35-73(50)56(78)53(60(2,3)4)69-59(79)63(36-66)25-26-63)33-51(75)72-29-23-45(24-30-72)71-27-21-40(22-28-71)10-9-39-11-13-43(14-12-39)54(76)70-57-61(5,6)58(62(57,7)8)80-47-20-19-44(34-65)48(64)32-47/h11-20,32,37,40,45-46,49-50,53,57-58,74H,21-31,33,35H2,1-8H3,(H,68,77)(H,69,79)(H,70,76)/t46-,49+,50+,53-,57-,58-/m1/s1

Standard InChI Key:  YLIIPOUNLYQGIU-NMPLUEPVSA-N

Molfile:  

 
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M  END

Alternative Forms

  1. Parent:

    ALA4751950

    ---

Associated Targets(Human)

AR Tclin VHL/Androgen receptor (497 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: UnknownTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Biocomponents

Calculated Properties

Molecular Weight: 1136.86Molecular Weight (Monoisotopic): 1135.5120AlogP: #Rotatable Bonds:
Polar Surface Area: Molecular Species: HBA: HBD:
#RO5 Violations: HBA (Lipinski): HBD (Lipinski): #RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: CX LogP: CX LogD:
Aromatic Rings: Heavy Atoms: QED Weighted: Np Likeness Score:

References

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2. Han X, Wang C, Qin C, Xiang W, Fernandez-Salas E, Yang CY, Wang M, Zhao L, Xu T, Chinnaswamy K, Delproposto J, Stuckey J, Wang S..  (2019)  Discovery of ARD-69 as a Highly Potent Proteolysis Targeting Chimera (PROTAC) Degrader of Androgen Receptor (AR) for the Treatment of Prostate Cancer.,  62  (2): [PMID:30629437] [10.1021/acs.jmedchem.8b01631]
3. Tilley, W D WD, Marcelli, M M, Wilson, J D JD and McPhaul, M J MJ.  1989-01  Characterization and expression of a cDNA encoding the human androgen receptor.  [PMID:2911578]
4. Hamann, L G LG and 8 more authors.  1998-02-12  Synthesis and biological activity of a novel series of nonsteroidal, peripherally selective androgen receptor antagonists derived from 1,2-dihydropyridono[5,6-g]quinolines.  [PMID:9484511]
5. Wang, L G LG, Liu, X M XM, Kreis, W W and Budman, D R DR.  1998-05-01  Androgen antagonistic effect of estramustine phosphate (EMP) metabolites on wild-type and mutated androgen receptor.  [PMID:10076535]
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21. Hasui, Tomoaki and 18 more authors.  2011-12-22  Identification of benzoxazin-3-one derivatives as novel, potent, and selective nonsteroidal mineralocorticoid receptor antagonists.  [PMID:22074142]
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23. Guo, Chuangxing C and 11 more authors.  2012-01-15  Discovery of 3-aryloxy-lactam analogs as potent androgen receptor full antagonists for treating castration resistant prostate cancer.  [PMID:22197140]
24. Yamamoto, Satoshi S and 10 more authors.  2012-04-01  Design, synthesis, and biological evaluation of 4-arylmethyl-1-phenylpyrazole and 4-aryloxy-1-phenylpyrazole derivatives as novel androgen receptor antagonists.  [PMID:22391033]
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26. Yamamoto, Satoshi S and 9 more authors.  2013-01-01  Design, synthesis, and biological evaluation of 3-aryl-3-hydroxy-1-phenylpyrrolidine derivatives as novel androgen receptor antagonists.  [PMID:23199477]
27. Liedtke, Andy J AJ and 7 more authors.  2013-03-28  Development of potent and selective indomethacin analogues for the inhibition of AKR1C3 (Type 5 17β-hydroxysteroid dehydrogenase/prostaglandin F synthase) in castrate-resistant prostate cancer.  [PMID:23432095]
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30. Akita, Kazumasa K and 5 more authors.  2013-11-15  A novel selective androgen receptor modulator, NEP28, is efficacious in muscle and brain without serious side effects on prostate.  [PMID:24177288]
31. Richardson, Timothy I TI and 18 more authors.  2011-02-10  Novel 3-aryl indoles as progesterone receptor antagonists for uterine fibroids.  [PMID:24900294]
32. Li, Huifang H and 8 more authors.  2014-08-14  Discovery of small-molecule inhibitors selectively targeting the DNA-binding domain of the human androgen receptor.  [PMID:25062331]
33. Ullrich, Thomas T and 21 more authors.  2014-09-11  3-alkoxy-pyrrolo[1,2-b]pyrazolines as selective androgen receptor modulators with ideal physicochemical properties for transdermal administration.  [PMID:25121964]
34. Gege, Christian C, Schlüter, Thomas T and Hoffmann, Thomas T.  2014-11-15  Identification of the first inverse agonist of retinoid-related orphan receptor (ROR) with dual selectivity for RORβ and RORγt.  [PMID:25305688]
35. Sundén, Henrik H and 6 more authors.  2015-02-12  Synthesis and biological evaluation of second-generation tropanol-based androgen receptor modulators.  [PMID:25646649]
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38. Shibata, Norihito N and 11 more authors.  2018-01-25  Development of Protein Degradation Inducers of Androgen Receptor by Conjugation of Androgen Receptor Ligands and Inhibitor of Apoptosis Protein Ligands.  [PMID:28594553]
39. Unwalla, Ray R and 18 more authors.  2017-07-27  Structure-Based Approach To Identify 5-[4-Hydroxyphenyl]pyrrole-2-carbonitrile Derivatives as Potent and Tissue Selective Androgen Receptor Modulators.  [PMID:28696695]
40. Nishiyama, Yuko Y and 6 more authors.  2018-07-12  Novel Nonsteroidal Progesterone Receptor (PR) Antagonists with a Phenanthridinone Skeleton.  [PMID:30034593]
41. Rew, Yosup Y and 19 more authors.  2018-09-13  Discovery of a Potent and Selective Steroidal Glucocorticoid Receptor Antagonist (ORIC-101).  [PMID:30091920]
42. Dalal, Kush K and 11 more authors.  2018-09-05  Small molecule-induced degradation of the full length and V7 truncated variant forms of human androgen receptor.  [PMID:30193215]
43. Hwang, Dong-Jin DJ and 7 more authors.  2019-01-24  New Generation of Selective Androgen Receptor Degraders: Our Initial Design, Synthesis, and Biological Evaluation of New Compounds with Enzalutamide-Resistant Prostate Cancer Activity.  [PMID:30525603]
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