Synthesis of new chiral arylsulfonamides based on carane amino alcohols

被引:0
|
作者
Grebyonkina, O. N. [1 ]
Banina, O. A. [1 ]
Rumyantsev, R. V. [2 ]
Baidamshina, D. R. [3 ]
Kolesnikova, A. I. [3 ]
Lezina, O. M. [1 ]
Rubtsova, S. A. [1 ]
机构
[1] Russian Acad Sci, Inst Chem, Ural Branch, Fed Res Ctr,Komi Sci Ctr, 48 Ul Pervomayskaya, Syktyvkar 167000, Russia
[2] Russian Acad Sci, GA Razuvaev Inst Organometall Chem, 49 Ul Tropinina, Nizhnii Novgorod 603950, Russia
[3] Kazan Fed Univ, Inst Fundamental Med & Biol, 18 Ul Kremlevskaya, Kazan 420008, Russia
关键词
monoterpenoids; (+)-3-carene; streptocide; sulfonamide; X-ray diffraction analysis; antimicrobial activity; ANTITUMOR-ACTIVITY; OLEANOLIC ACID;
D O I
10.1007/s11172-024-4345-0
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
New optically active arylsulfonamides, including carane-containing streptocide analogs, were synthesized by the reaction of carane amino alcohols with tosyl- and N-acetylsulfanilyl chlorides. Sulfonamide, which was prepared based on (-)-4 beta-amino-3 alpha-hydroxy-cis-carane, was studied by X-ray diffraction. The synthesized sulfonamides and the starting amino alcohols were evaluated for antimicrobial activity.
引用
收藏
页码:2238 / 2247
页数:10
相关论文
共 50 条
  • [1] Stereoselective synthesis of carane-based chiral β- and γ-amino acid derivatives via conjugate addition
    Szakonyi, Zsolt
    Csor, Arpad
    Haukka, Matti
    Fueloep, Ferenc
    TETRAHEDRON, 2015, 71 (29) : 4846 - 4852
  • [2] Simple and efficient synthesis of chiral amino alcohols with an amino acid-based skeleton
    Paulina Juszczyk
    Regina Kasprzykowska
    Aleksandra S. Kołodziejczyk
    Letters in Peptide Science, 2003, 10 (2): : 79 - 82
  • [3] Simple and efficient synthesis of chiral amino alcohols with an amino acid-based skeleton
    Juszczyk, P
    Kasprzykowska, R
    Kolodziejczyk, AS
    LETTERS IN PEPTIDE SCIENCE, 2003, 10 (02): : 79 - 82
  • [4] Cyclotriveratrylenes:: Synthesis of a new C3-symmetric chiral amino alcohols
    Thomas, RM
    Iyengar, DS
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1998, 37 (07): : 625 - 627
  • [5] Synthesis and application of a new isothiocyanate as a chiral derivatizing agent for the indirect resolution of chiral amino alcohols and amines
    Kleidernigg, OP
    Posch, K
    Lindner, W
    JOURNAL OF CHROMATOGRAPHY A, 1996, 729 (1-2) : 33 - 42
  • [6] Carane amino alcohols as organocatalysts in asymmetric aldol reaction of isatin with acetone
    Banina, O. A.
    Sudarikov, D. V.
    Nigmatov, A. G.
    Frolova, L. L.
    Slepukhin, P. A.
    Zlotin, S. G.
    Kutchin, A. V.
    RUSSIAN CHEMICAL BULLETIN, 2017, 66 (02) : 293 - 296
  • [7] Carane amino alcohols as organocatalysts in asymmetric aldol reaction of isatin with acetone
    O. A. Banina
    D. V. Sudarikov
    A. G. Nigmatov
    L. L. Frolova
    P. A. Slepukhin
    S. G. Zlotin
    A. V. Kutchin
    Russian Chemical Bulletin, 2017, 66 : 293 - 296
  • [8] Convenient Methods for the Synthesis of Chiral Amino Alcohols and Amines
    Periasamy, Mariappan
    Gurubrahamam, Ramani
    Sanjeevakumar, Nalluri
    Dalai, Manasi
    Alakonda, Laxhmaiah
    Reddy, Polimera Obula
    Suresh, Sundaram
    Satishkumar, Sakilam
    Padmaja, Meduri
    Reddy, Meda Narsi
    Suresh, Surisetti
    Anwar, Shaik
    Muthukumaragopal, G. P.
    Vairaprakash, Pothiappan
    Seenivasaperumal, Muthu
    CHIMIA, 2013, 67 (1-2) : 23 - 29
  • [9] Straightforward synthesis of chiral sulfonate-based ionic liquids from amino alcohols for chiral recognition
    Feuge, Niklas
    Wilhelm, Rene
    CHIRALITY, 2023, 35 (12) : 993 - 1011
  • [10] Synthesis of atropisomeric 1-phenylpyrrole-derived amino alcohols: New chiral ligands
    Faigl, Ferenc
    Matravoelgyi, Bela
    Szoellosy, Aron
    Czugler, Matyas
    Tarkanyi, Gabor
    Vekey, Karoly
    Kubinyi, Miklos
    CHIRALITY, 2012, 24 (07) : 532 - 542