Synthesis of two isotopically labeled versions of NEDD8-activating enzyme (NAE) inhibitor

被引:5
|
作者
Li, Yuexian [1 ]
Plesescu, Mihaela [1 ]
Prakash, Shimoga R. [1 ]
机构
[1] Millennium Pharmaceut Inc, Dept Drug Metab & Phannacokinet, Isotope Chem Grp, Cambridge, MA 02139 USA
关键词
NAE inhibitor; MLN4924; (14)C-6-chloro-7-deazapurine D(8)-(S)-1-aminoindan;
D O I
10.1016/j.tetlet.2011.02.033
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of two isotopically labeled versions of an investigational NAE inhibitor (MLN4924) is reported. (14)C-MLN4924 was synthesized from (14)C-thiourea in eight steps. D(8)-MLN4924 was prepared from D(9)-3-phenylpropanoic acid in seven steps. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1807 / 1810
页数:4
相关论文
共 50 条
  • [41] Targeting the protein ubiquitination machinery in melanoma by the NEDD8-activating enzyme inhibitor pevonedistat (MLN4924)
    Kit Man Wong
    Lindsey N. Micel
    Heather M. Selby
    Aik Choon Tan
    Todd M. Pitts
    Stacey M. Bagby
    Anna Spreafico
    Peter J. Klauck
    Stephen J. Blakemore
    Peter F. Smith
    Alice McDonald
    Allison Berger
    John J. Tentler
    S. Gail Eckhardt
    Investigational New Drugs, 2017, 35 : 11 - 25
  • [42] Initial testing of the investigational NEDD8-activating enzyme inhibitor MLN4924 by the pediatric preclinical testing program
    Smith, Malcolm A.
    Maris, John M.
    Gorlick, Richard
    Kolb, E. Anders
    Lock, Richard
    Carol, Hernan
    Keir, Stephen T.
    Reynolds, C. Patrick
    Kang, Min H.
    Morton, Christopher L.
    Wu, Jianrong
    Smith, Peter G.
    Yu, Jie
    Houghton, Peter J.
    PEDIATRIC BLOOD & CANCER, 2012, 59 (02) : 246 - 253
  • [43] SYNERGISTIC COMBINATION OF MLN4924, AN INVESTIGATIONAL SMALL MOLECULE INHIBITOR OF NEDD8-ACTIVATING ENZYME (NAE), WITH AZACITIDINE, A HYPOMETHYLATING AGENT, IN PRE-CLINICAL AML CANCER MODELS
    Traore, T.
    Milhollen, M.
    Grossman, S.
    Thomas, M.
    Narayanan, U.
    Garnsey, J.
    HAEMATOLOGICA, 2012, 97 : 435 - 435
  • [44] Inhibition of NEDD8-activating enzyme: a novel approach for the treatment of acute myeloid leukemia
    Swords, Ronan T.
    Kelly, Kevin R.
    Smith, Peter G.
    Garnsey, James J.
    Mahalingam, Devalingam
    Medina, Ernest
    Oberheu, Kelli
    Padmanabhan, Swaminathan
    O'Dwyer, Michael
    Nawrocki, Steffan T.
    Giles, Francis J.
    Carew, Jennifer S.
    BLOOD, 2010, 115 (18) : 3796 - 3800
  • [45] Quantifiable analysis of cellular pathway inhibition of a Nedd8-activating enzyme inhibitor, MLN4924, using AlphaScreen
    Yan, Zhong-Hua
    Burkhardt, Anne
    Loke, Huay-Keng
    Chen, Jesse
    Xu, Qing
    Brauer, Pam
    Ma, Jingya
    Lin, Yafang
    Garcia, Khris
    Dick, Lawrence R.
    Bembenek, Michael E.
    ANALYTICAL BIOCHEMISTRY, 2013, 439 (02) : 109 - 115
  • [46] Nedd8-Activating Enzyme Is a Druggable Host Dependency Factor of Human and Mouse Cytomegalovirus
    Flores-Martinez, Yulia Alejandra
    Le-Trilling, Vu Thuy Khanh
    Trilling, Mirko
    VIRUSES-BASEL, 2021, 13 (08):
  • [47] A Phase I Trial of Nedd8-Activating Enzyme (NAE) Inhibitor, Pevonedistat (PEVO) in Combination with Ibrutinib in Patients with Relapsed/Refractory (R/R) Non- Hodgkin Lymphoma (NHL)
    Torka, Pallawi
    Kambhampati, Swetha
    Muir, Alexandra
    Orand, Kirsten
    Smith, Lynne
    Herrera, Alex F.
    Lewis, Lionel
    Hernandez-Ilizaliturri, Francisco J.
    Chen, Lu
    Danilov, Alexey V.
    BLOOD, 2021, 138
  • [48] Therapeutic Effects of a NEDD8-Activating Enzyme Inhibitor, Pevonedistat, on Sclerodermatous Graft-versus-Host Disease in Mice
    Pai, Chien-Chun Steven
    Khuat, Lam T.
    Chen, Mingyi
    Murphy, William J.
    Abedi, Mehrdad
    BIOLOGY OF BLOOD AND MARROW TRANSPLANTATION, 2017, 23 (01) : 30 - 37
  • [49] MLN4924, a First-in-Class NEDD8-Activating Enzyme Inhibitor, Attenuates IFN-β Production
    Song, Hui
    Huai, Wanwan
    Yu, Zhongxia
    Wang, Wenwen
    Zhao, Jing
    Zhang, Lining
    Zhao, Wei
    JOURNAL OF IMMUNOLOGY, 2016, 196 (07): : 3117 - 3123
  • [50] Immunomodulatory effects of pevonedistat, a NEDD8-activating enzyme inhibitor, in chronic lymphocytic leukemia-derived T cells
    Scott Best
    Vi Lam
    Tingting Liu
    Nur Bruss
    Adam Kittai
    Olga V. Danilova
    Susan Murray
    Allison Berger
    Nathan D. Pennock
    Evan F. Lind
    Alexey V. Danilov
    Leukemia, 2021, 35 : 156 - 168