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ID: ALA3606024
PubChem CID: 56650290
Max Phase: Preclinical
Molecular Formula: C20H24Cl2FN3O2
Molecular Weight: 428.34
Molecule Type: Small molecule
Associated Items:
Canonical SMILES: NC(=O)c1cc(F)cc2c1C(=O)N(C1CCN(C3CCC(Cl)(Cl)CC3)CC1)C2
Standard InChI: InChI=1S/C20H24Cl2FN3O2/c21-20(22)5-1-14(2-6-20)25-7-3-15(4-8-25)26-11-12-9-13(23)10-16(18(24)27)17(12)19(26)28/h9-10,14-15H,1-8,11H2,(H2,24,27)
Standard InChI Key: CXTSPYBVOJLLFL-UHFFFAOYSA-N
Molfile:
RDKit 2D 28 31 0 0 0 0 0 0 0 0999 V2000 2.6024 -2.6977 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.6003 -1.4977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6387 -0.8963 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2990 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.7000 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 -1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2990 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4133 -1.7530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8032 -3.1233 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5536 -4.4230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0444 -4.5346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6946 -5.8864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8489 -7.1253 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.3532 -7.0124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7031 -5.6606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4994 -8.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9950 -8.5931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6430 -9.9460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7954 -11.1835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9937 -11.2475 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -5.0942 -12.1574 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -4.2998 -11.0683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6518 -9.7155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3114 -2.9665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4916 -3.8582 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 2 0 5 6 1 0 6 7 1 0 6 8 2 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 12 1 0 15 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 1 0 25 18 1 0 11 26 1 0 26 27 2 0 26 28 1 0 28 4 1 0 28 9 2 0 M END
Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Natural Product: No | Oral: No | Chemical Probe: No | Parenteral: No |
Molecule Type: Small molecule | Topical: No | First In Class: No | Black Box: No |
Chirality: No | Availability: No | Prodrug: No |
Molecular Weight: 428.34 | Molecular Weight (Monoisotopic): 427.1230 | AlogP: 3.46 | #Rotatable Bonds: 3 |
Polar Surface Area: 66.64 | Molecular Species: NEUTRAL | HBA: 3 | HBD: 1 |
#RO5 Violations: ┄ | HBA (Lipinski): 5 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): ┄ |
CX Acidic pKa: 12.66 | CX Basic pKa: 8.41 | CX LogP: 2.20 | CX LogD: 1.15 |
Aromatic Rings: 1 | Heavy Atoms: 28 | QED Weighted: 0.75 | Np Likeness Score: -0.59 |
1. Papeo G, Posteri H, Borghi D, Busel AA, Caprera F, Casale E, Ciomei M, Cirla A, Corti E, D'Anello M, Fasolini M, Forte B, Galvani A, Isacchi A, Khvat A, Krasavin MY, Lupi R, Orsini P, Perego R, Pesenti E, Pezzetta D, Rainoldi S, Riccardi-Sirtori F, Scolaro A, Sola F, Zuccotto F, Felder ER, Donati D, Montagnoli A.. (2015) Discovery of 2-[1-(4,4-Difluorocyclohexyl)piperidin-4-yl]-6-fluoro-3-oxo-2,3-dihydro-1H-isoindole-4-carboxamide (NMS-P118): A Potent, Orally Available, and Highly Selective PARP-1 Inhibitor for Cancer Therapy., 58 (17): [PMID:26222319] [10.1021/acs.jmedchem.5b00680] |
2. (2014) 3-oxo-2,3-dihydro-1H-isoindole-4-carboxamides as PARP inhibitors, |
3. Ferraris, Dana D and 6 more authors. 2003-08-04 Design and synthesis of poly(ADP-ribose)polymerase-1 (PARP-1) inhibitors. Part 3: In vitro evaluation of 1,3,4,5-tetrahydro-benzo[c][1,6]- and [c][1,7]-naphthyridin-6-ones. [PMID:12852955] |
4. Penning, Thomas D TD and 22 more authors. 2008-07-15 Discovery and SAR of 2-(1-propylpiperidin-4-yl)-1H-benzimidazole-4-carboxamide: A potent inhibitor of poly(ADP-ribose) polymerase (PARP) for the treatment of cancer. [PMID:18541433] |
5. Zhu, Gui-Dong GD and 16 more authors. 2008-07-15 Synthesis and SAR of novel, potent and orally bioavailable benzimidazole inhibitors of poly(ADP-ribose) polymerase (PARP) with a quaternary methylene-amino substituent. [PMID:18586490] |
6. Menear, Keith A KA and 19 more authors. 2008-10-23 4-[3-(4-cyclopropanecarbonylpiperazine-1-carbonyl)-4-fluorobenzyl]-2H-phthalazin-1-one: a novel bioavailable inhibitor of poly(ADP-ribose) polymerase-1. [PMID:18800822] |
7. Penning, Thomas D TD and 16 more authors. 2009-01-22 Discovery of the Poly(ADP-ribose) polymerase (PARP) inhibitor 2-[(R)-2-methylpyrrolidin-2-yl]-1H-benzimidazole-4-carboxamide (ABT-888) for the treatment of cancer. [PMID:19143569] |
8. Tong, Yunsong Y and 19 more authors. 2009-11-12 Synthesis and evaluation of a new generation of orally efficacious benzimidazole-based poly(ADP-ribose) polymerase-1 (PARP-1) inhibitors as anticancer agents. [PMID:19888760] |
9. Penning, Thomas D TD and 22 more authors. 2010-04-22 Optimization of phenyl-substituted benzimidazole carboxamide poly(ADP-ribose) polymerase inhibitors: identification of (S)-2-(2-fluoro-4-(pyrrolidin-2-yl)phenyl)-1H-benzimidazole-4-carboxamide (A-966492), a highly potent and efficacious inhibitor. [PMID:20337371] |
10. Dunn, Derek D, Husten, Jean J, Ator, Mark A MA and Chatterjee, Sankar S. 2012-01-01 Novel poly(ADP-ribose) polymerase-1 inhibitors. [PMID:22153339] |
11. Cincinelli, Raffaella R and 12 more authors. 2014-02-01 7-Azaindole-1-carboxamides as a new class of PARP-1 inhibitors. [PMID:24398383] |
12. Zhou, Dong and 7 more authors. 2014-03-01 Synthesis, [¹⁸F] radiolabeling, and evaluation of poly (ADP-ribose) polymerase-1 (PARP-1) inhibitors for in vivo imaging of PARP-1 using positron emission tomography. [PMID:24503274] |
13. Maciag, Anna E AE and 11 more authors. 2014-03-27 Nitric oxide (NO) releasing poly ADP-ribose polymerase 1 (PARP-1) inhibitors targeted to glutathione S-transferase P1-overexpressing cancer cells. [PMID:24521039] |
14. Nathubhai, Amit A, Wood, Pauline J PJ, Lloyd, Matthew D MD, Thompson, Andrew S AS and Threadgill, Michael D MD. 2013-12-12 Design and Discovery of 2-Arylquinazolin-4-ones as Potent and Selective Inhibitors of Tankyrases. [PMID:24900625] |
15. Jones, Philip P, Wilcoxen, Keith K, Rowley, Michael M and Toniatti, Carlo C. 2015-04-23 Niraparib: A Poly(ADP-ribose) Polymerase (PARP) Inhibitor for the Treatment of Tumors with Defective Homologous Recombination. [PMID:25761096] |
16. Papeo, Gianluca G and 28 more authors. 2015-09-10 Discovery of 2-[1-(4,4-Difluorocyclohexyl)piperidin-4-yl]-6-fluoro-3-oxo-2,3-dihydro-1H-isoindole-4-carboxamide (NMS-P118): A Potent, Orally Available, and Highly Selective PARP-1 Inhibitor for Cancer Therapy. [PMID:26222319] |
17. Wang, Bing B and 5 more authors. 2016-01-14 Discovery and Characterization of (8S,9R)-5-Fluoro-8-(4-fluorophenyl)-9-(1-methyl-1H-1,2,4-triazol-5-yl)-2,7,8,9-tetrahydro-3H-pyrido[4,3,2-de]phthalazin-3-one (BMN 673, Talazoparib), a Novel, Highly Potent, and Orally Efficacious Poly(ADP-ribose) Polymerase-1/2 Inhibitor, as an Anticancer Agent. [PMID:26652717] |
18. Thorsell, Ann-Gerd and 8 more authors. 2017-02-23 Structural Basis for Potency and Promiscuity in Poly(ADP-ribose) Polymerase (PARP) and Tankyrase Inhibitors. [PMID:28001384] |
19. Chadha, Navriti N and Silakari, Om O. 2017-06-01 Identification of low micromolar dual inhibitors for aldose reductase (ALR2) and poly (ADP-ribose) polymerase (PARP-1) using structure based design approach. [PMID:28438542] |
20. Yuan, Zigao Z and 9 more authors. 2017-08-01 Olaparib hydroxamic acid derivatives as dual PARP and HDAC inhibitors for cancer therapy. [PMID:28601509] |
21. Chen, Wenhua W and 21 more authors. 2017-09-29 Discovery, mechanism and metabolism studies of 2,3-difluorophenyl-linker-containing PARP1 inhibitors with enhanced in vivo efficacy for cancer therapy. [PMID:28692916] |
22. Ferri, Martina M and 6 more authors. 2017-12-15 Targeting Wnt-driven cancers: Discovery of novel tankyrase inhibitors. [PMID:29107427] |
23. Reilly, Sean W and 6 more authors. 2018-06-28 Examination of Diazaspiro Cores as Piperazine Bioisosteres in the Olaparib Framework Shows Reduced DNA Damage and Cytotoxicity. [PMID:29856625] |
24. Jain, Priyancy G PG and Patel, Bhumika D BD. 2019-03-01 Medicinal chemistry approaches of poly ADP-Ribose polymerase 1 (PARP1) inhibitors as anticancer agents - A recent update. [PMID:30684797] |
25. Velagapudi, Uday Kiran UK and 9 more authors. 2019-06-13 Design and Synthesis of Poly(ADP-ribose) Polymerase Inhibitors: Impact of Adenosine Pocket-Binding Motif Appendage to the 3-Oxo-2,3-dihydrobenzofuran-7-carboxamide on Potency and Selectivity. [PMID:31042381] |
26. Boraei, Ahmed T A; Singh, Pankaj K; Sechi, Mario and Satta, Sandro. 2019-11-15 Discovery of novel functionalized 1,2,4-triazoles as PARP-1 inhibitors in breast cancer: Design, synthesis and antitumor activity evaluation. [PMID:31442685] |
27. Cao, Chaoguo and 7 more authors. 2020-10-08 Discovery of SK-575 as a Highly Potent and Efficacious Proteolysis-Targeting Chimera Degrader of PARP1 for Treating Cancers. [PMID:32924477] |
28. Karche, Navnath P and 54 more authors. 2020-12-15 Discovery of isoquinolinone and naphthyridinone-based inhibitors of poly(ADP-ribose) polymerase-1 (PARP1) as anticancer agents: Structure activity relationship and preclinical characterization. [PMID:33120078] |
29. Wang, Hexiang and 33 more authors. 2020-12-24 Discovery of Pamiparib (BGB-290), a Potent and Selective Poly (ADP-ribose) Polymerase (PARP) Inhibitor in Clinical Development. [PMID:33264017] |
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