3-(4-methoxy-3-oxo-1H-isoindol-2-yl)piperidine-2,6-dione - CAS 1416990-15-2

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Molecular Formula
Molecular Weight


    • Specification
      • Synonyms
        2,6-Piperidinedione, 3-(1,3-dihydro-7-methoxy-1-oxo-2H-isoindol-2-yl)-
    • Properties
      • Boiling Point
        581.5±50.0 °C at 760 mmHg
        1.376±0.06 g/cm3
        InChI Key
        Canonical SMILES
    • Reference Reading
      • 1. Synthesis and asymmetric hydrogenation of (3E)-1-benzyl-3-[(2-oxopyridin-1(2H)-yl)methylidene]piperidine-2,6-dione
        Alexander A Bisset, Akira Shiibashi, Jasmine L Desmond, Allan Dishington, Teyrnon Jones, Guy J Clarkson, Takao Ikariya, Martin Wills Chem Commun (Camb). 2012 Dec 21;48(98):11978-80.doi: 10.1039/c2cc36807b.
        The synthesis of (3E)-1-benzyl-3-[(2-oxopyridin-1(2H)-yl)methylidene]piperidine-2,6-dione 5 from N-benzylglutarimide was achieved in three steps. The asymmetric hydrogenation of 4 gave either the product of partial reduction (10) or full reduction (13), depending on the catalyst which was employed, in high ee in each case. Attempts at asymmetric transfer hydrogenation (ATH) of resulted in formation of a racemic product.
        2. A First-in-Human Study of Novel Cereblon Modulator Avadomide (CC-122) in Advanced Malignancies
        Drew W Rasco, Kyriakos P Papadopoulos, Michael Pourdehnad, Anita K Gandhi, Patrick R Hagner, Yan Li, Xin Wei, Rajesh Chopra, Kristen Hege, Jorge DiMartino, Kent Shih Clinical TrialClin Cancer Res. 2019 Jan 1;25(1):90-98.doi: 10.1158/1078-0432.CCR-18-1203.Epub 2018 Sep 10.
        Purpose:Avadomide is a novel, small-molecule therapeutic agent that modulates cereblon E3 ligase activity and exhibits potent antitumor and immunomodulatory activities. This first-in-human phase I study (NCT01421524) evaluated the safety and clinical activity of avadomide in patients with advanced solid tumors, non-Hodgkin lymphoma (NHL), and multiple myeloma.Patients and methods:Thirty-four patients were treated with avadomide in 7 dose-escalation cohorts using a 3 + 3 design (0.5-3.5 mg, 28-day continuous dosing cycles). The primary objectives were to determine the dose-limiting toxicity (DLT), nontolerated dose (NTD), maximum tolerated dose (MTD), recommended phase II dose, and pharmacokinetics of avadomide. The secondary objective was to determine preliminary avadomide efficacy. Exploratory objectives included evaluation of pharmacodynamic effects of avadomide. Results:DLTs were reported in 2 patients, and grade ≥3 treatment-emergent adverse events (TEAEs) occurred in 14 patients (41%). The most common TEAEs (≥15%) were fatigue, neutropenia, and diarrhea. The NTD and MTD were 3.5 and 3.0 mg, respectively. Of 5 patients with NHL, 1 achieved a complete response, and 2 had partial responses. Although no objective responses were observed in patients with solid tumors, 5 of 6 patients with brain cancer experienced nonprogression of ≥6 months. A dose-dependent relationship between Aiolos degradation in peripheral B and T cells occurred within 5 hours of the first dose of avadomide administered, starting at 0.5 mg.Conclusions:Avadomide monotherapy demonstrated acceptable safety and favorable pharmacokinetics in patients with solid tumors, NHL, and multiple myeloma. In addition, 3 objective responses were observed in NHL.
        3. Crystallographic and molecular modeling studies on 3-ethyl-3-(4-pyridyl)piperidine-2,6-dione and its butyl analogue, inhibitors of mammalian aromatase. Comparison with natural substrates: prediction of enantioselectivity for N-alkyl derivatives
        C A Laughton, R McKenna, S Neidle, M Jarman, R McCague, M G Rowlands Comparative StudyJ Med Chem. 1990 Sep;33(9):2673-9.doi: 10.1021/jm00171a052.
        Inhibitors of the cytochrome P450 enzyme aromatase, which is involved in the biosynthesis of estrogens from androgens, are of proven utility in the treatment of hormone-dependent breast cancer. The determination of the crystal structure of one such inhibitor, 3-ethyl-3-(4-pyridyl)piperidine-2,6-dione (2) and its 3-butyl analogue (3) is described. In the absence of three-dimensional structural information for the enzyme, conformational analysis and comparison with natural substrates has been performed in order to define possible "active" conformations. The enhanced inhibitory activity of 3 may be linked to hydrophobic interactions between the side chain and that portion of the enzyme that normally interacts with the B and C rings of a steroid substrate. Information gained from this study and previous studies by other workers has been combined in order to produce a hypothesis to explain the pattern of activity of N(1)-alkyl derivatives of 2. The successful application of this hypothesis to the prediction of the relative aromatase inhibitory activities of the two enantiomers of the N-octyl derivative (4) is described.
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