Synthesis of stereoisomeric 4-(2-methylindolin-1-yl)and 4-(2-methylindol-1-yl) derivatives of glutamic acid

被引：4
|
作者：
Krasnov, VP [1 ]
Vigorov, AY [1 ]
Nizova, IA [1 ]
Grishakov, AN [1 ]
Evstigneeva, NG [1 ]
Kodess, MI [1 ]
机构：
[1] Russian Acad Sci, Ural Branch, IYa Postovsky Inst Organ Synth, Ekaterinburg 620219, Russia
来源：
RUSSIAN CHEMICAL BULLETIN | 2004年 / 53卷 / 06期
基金：
俄罗斯基础研究基金会;
关键词：
glutamic acid; 2-methylindoline; 2-methylindole; nucleophilic substitution; stereoisomers;
D O I：
10.1023/B:RUCB.0000042295.70355.47
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The reaction of dimethyl (2S,4RS)-N-phthaloyl-4-bromoglutamate with 2-methylindoline afforded diastereomeric 4-(2 -methylindolin-1-yl)-(S)-glutamic acid derivatives, whose oxidation gave rise to 4-(2-methylindol-1-yl)-(S)-glutamic acid derivatives.
引用
收藏
页码：1327 / 1330
页数：4
相关论文
共 50 条
  • [41] 4-(4-Hydroxymethyl-1H-1,2,3-triazol-1-yl)benzoic acid
    Ishak, Dayang Hazwani Abang
    Tajuddin, Hairul Anuar
    Abdullah, Zanariah
    Abd Halim, Siti Nadiah
    Tiekink, Edward R. T.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O1658 - U431
  • [42] Prop-2-en-1-yl 4-(4,5-diphenyl-1H-imidazol-2-yl)benzoate
    Mohamed, Shaaban K.
    Akkurt, Mehmet
    Marzouk, Adel A.
    Abdelhamid, Antar A.
    Santoyo-Gonzalez, Francisco
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O1105 - +
  • [43] 1-[4-(1H-benzoimidazol-2-yl)-phenyl]-3-[4-(1H-benzoimidazol-2-yl)-phenyl]-urea derivatives as small molecule heparanase inhibitors
    Pan, WT
    Miao, HQ
    Xu, YJ
    Navarro, EC
    Tonra, JR
    Corcoran, E
    Lahiji, A
    Kussie, P
    Kiselyov, AS
    Wong, WC
    Liu, H
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (02) : 409 - 412
  • [44] Dithiophosphonation of 4-(1H-pyrrol-1-yl)phenol and 4-(1H-imidazol-1-yl)phenol
    I. S. Nizamov
    E. N. Nikitin
    E. S. Batyeva
    I. D. Nizamov
    M. P. Shulaeva
    O. K. Pozdeev
    R. A. Cherkasov
    Russian Journal of Organic Chemistry, 2015, 51 : 1272 - 1276
  • [45] Dithiophosphonation of 4-(1H-pyrrol-1-yl)phenol and 4-(1H-imidazol-1-yl)phenol
    Nizamov, I. S.
    Nikitin, E. N.
    Batyeva, E. S.
    Nizamov, I. D.
    Shulaeva, M. P.
    Pozdeev, O. K.
    Cherkasov, R. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 51 (09) : 1272 - 1276
  • [46] 4-[(E)-2-(Pyridin-2-yl)ethenyl]pyridineterephthalic acid (2/1)
    Castro-Montes, Paola
    Guerrero-Alvarez, Jorge A.
    Hopfl, Herbert
    Campos-Gaxiola, Jose J.
    Cruz-Enriquez, Adriana
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O3383 - +
  • [47] 4-{[4-(Hydroxymethyl)piperidin-1-yl]methyl}phenol
    Simoes, M. C. R.
    Landre, I. M. R.
    Moreira, M. S.
    Viegas, C., Jr.
    Doriguetto, A. C.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O2275 - +
  • [48] 4-(pyrrol-1-yl)-1,2,4-triazole
    Hellyer, Ryan M.
    Joule, John A.
    Larsen, David S.
    Brooker, Sally
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2007, 63 : O358 - O360
  • [49] Design, synthesis and antimycobacterial evaluation of 1-(4-(2-substitutedthiazol-4-yl)phenethyl)-4-(3-(4-substitutedpiperazin-1-yl)alkyl)piperazine hybrid analogues
    Nagesh, Hunsur Nagendra
    Suresh, Amaroju
    Sairam, Sirigina Devesh Sathya Sri
    Sriram, Dharmarajan
    Yogeeswari, Perumal
    Sekhar, Kondapalli Venkata Gowri Chandra
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 84 : 605 - 613
  • [50] (S)-(-)-4-[4-[2-(isochroman-1-yl)ethyl]-piperazin-1-yl]benzenesulfonamide, a selective dopamine D-4 antagonist
    TenBrink, RE
    Bergh, CL
    Duncan, JN
    Harris, DW
    Huff, RM
    Lahti, RA
    Lawson, CF
    Lutzke, BS
    Martin, IJ
    Rees, SA
    Schlachter, SK
    Sih, JC
    Smith, MW
    JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (13) : 2435 - 2437
12345