Synthesis of a C3 Hydroxyproline-modified Carbapenem

被引:0
作者
Valiullina, Z. R. [1 ]
Galeeva, A. M. [1 ]
Miftakhov, M. S. [1 ]
机构
[1] Russian Acad Sci, Ufa Inst Chem, Ufa Fed Res Ctr, Ufa 450054, Russia
关键词
beta-lactam antibiotics; carbapenems; trans-4-l-hydroxyproline; carbapenemenol phosphate; 2-ethoxythiolanone;
D O I
10.1134/S1070428022110173
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Methyl (4R)-4-hydroxy-1-(sulfanylacetyl)-l-prolinate was synthesized starting from trans-4-l-hydroxyprolinate methyl ester hydrochloride and then reacted with the known carbapenem enol phosphate to obtain the corresponding carbapenem and then to chemically more stable methyl ester.
引用
收藏
页码:1664 / 1667
页数:4
相关论文
共 10 条
  • [1] Preparations of two pivotal intermediates for the synthesis of 1-beta-methyl carbapenem antibiotics
    Berks, AH
    [J]. TETRAHEDRON, 1996, 52 (02) : 331 - 375
  • [2] Davidovich Yu.A., 1986, B ACAD SCI USSR CH+, V9, P2139
  • [3] Carbapenems: Past, Present, and Future
    Papp-Wallace, Krisztina M.
    Endimiani, Andrea
    Taracila, Magdalena A.
    Bonomo, Robert A.
    [J]. ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2011, 55 (11) : 4943 - 4960
  • [4] Synthesis of Carbapenems Containing Peptidoglycan Mimetics and Inhibition of the Cross-Linking Activity of a Transpeptidase of l,d Specificity
    Saidjalolov, Saidbakhrom
    Edoo, Zainab
    Fonvielle, Matthieu
    Mayer, Louis
    Iannazzo, Laura
    Arthur, Michel
    Etheve-Quelquejeu, Melanie
    Braud, Emmanuelle
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (10) : 3542 - 3551
  • [5] Design, Synthesis, Structure-Function Relationship, Bioconversion, and Pharmacokinetic Evaluation of Ertapenem Prodrugs
    Singh, Sheo B.
    Rindgen, Diane
    Bradley, Prudence
    Suzuki, Takao
    Wang, Nengxue
    Wu, Hao
    Zhang, Basheng
    Wang, Li
    Ji, Chongmin
    Yu, Hongshi
    Soll, Richard M.
    Olsen, David B.
    Meinke, Peter T.
    Nicoll-Griffith, Deborah A.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (20) : 8421 - 8444
  • [6] Tebipenem pivoxil hydrobromide-No PICC, no problem!
    Sodhi, Varun
    Kronsberg, Kelli A.
    Clark, Mickayla
    Cho, Jonathan C.
    [J]. PHARMACOTHERAPY, 2021, 41 (09): : 748 - 761
  • [7] Novel prodrugs of meropenem with two lipophilic promoieties: synthesis and pharmacokinetics
    Tanaka, Shunkichi
    Matsui, Hiroshi
    Kasai, Masayasu
    Kunishiro, Kazuyoshi
    Kakeya, Nobuharu
    Shirahase, Hiroaki
    [J]. JOURNAL OF ANTIBIOTICS, 2011, 64 (03) : 233 - 242
  • [8] Inhibition of Mycobacterium tuberculosis L,D-Transpeptidase 5 by Carbapenems: MD and QM/MM Mechanistic Studies
    Tolufashe, Gideon F.
    Halder, Amit K.
    Ibeji, Collins U.
    Lawal, Monsurat M.
    Ntombela, Thandokuhle
    Govender, Thavendran
    Maguire, Glenn E. M.
    Lamichhane, Gyanu
    Kruger, Hendrik G.
    Honarparvar, Bahareh
    [J]. CHEMISTRYSELECT, 2018, 3 (48): : 13603 - 13612
  • [9] Synthesis and In Vitro Antibacterial Activity of New C-3-Modified Carbapenems
    Valiullina, Z. R.
    Galeeva, A. M.
    Gimalova, F. A.
    Selezneva, N. K.
    Khasanova, L. S.
    Mavzyutov, A. R.
    Miftakhov, M. S.
    [J]. RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2019, 45 (05) : 398 - 404
  • [10] Novel synthetic route of a pivotal intermediate for the synthesis of 1β-methyl carbapenem antibiotics
    YuO, Yuan
    Zhou, Wu-Chun
    Zhang, Ji
    Zhang, Mei
    Xu, Da-Yong
    Tang, Yun
    Li, Bo-Gang
    Yu, Xiao-Qi
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2006, 10 (04) : 829 - 832