On the importance of the pore inner cavity for the ionophoric activity of 1,3-alternate calix[4]arene/steroid conjugates

被引:7
|
作者
Izzo, Irene
Maulucci, Nakia
Martone, Cristina
Casapullo, Agostino
Fanfoni, Lidia
Tecilla, Paolo
De Riccardis, Francesco
机构
[1] Univ Salerno, Dept Chem, I-84081 Baronissi, Salerno, Italy
[2] Univ Salerno, Dept Pharmaceut Sci, I-84084 Salerno, Italy
[3] Univ Trieste, Dept Chem Sci, I-34127 Trieste, Italy
关键词
ionophores; amphiphiles; steroids; calix[4]arenes;
D O I
10.1016/j.tet.2006.04.028
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,3-Alternate calix[4]arenes, decorated with four nonpolar 'all-trans' tetracyclic nuclei and cation-stabilizing beta-methoxyethoxy appendages, were synthesized from commercially available starting materials and through straightforward functional groups transformations/couplings. Their Na+-transport activities, when compared with those exerted by the known conformationally-rigidified 1,3-alternate calix[4]-arene AB/cis cholic acid conjugates, suggest that the cation conductance is related to the morphology of the pendant steroids. (c) 2006 Published by Elsevier Ltd.
引用
收藏
页码:5385 / 5391
页数:7
相关论文
共 50 条
  • [41] ON THE ORIGIN OF HIGH IONOPHORICITY OF 1,3-ALTERNATE CALIX[4]ARENES - PI-DONOR PARTICIPATION IN COMPLEXATION OF CATIONS AND EVIDENCE FOR METAL-TUNNELING THROUGH THE CALIX[4]ARENE CAVITY
    IKEDA, A
    SHINKAI, S
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) : 3102 - 3110
  • [42] Three-Dimensional Tetranuclear Cd(II) Coordination Network Based on a 1,3-Alternate Calix[4]arene Derivative
    Lee, Eunji
    Ju, Huiyeong
    Moon, Suk-Hee
    Kang, Youngjin
    Park, Ki-Min
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2015, 36 (08): : 2124 - 2127
  • [43] Photochemically size-controllable dendrimers including a 1,3-alternate calix[4]arene as a core and azobenzene moieties as branches
    Nagasaki, T
    Noguchi, A
    Matsumoto, T
    Tamagaki, S
    Ogino, K
    ANALES DE QUIMICA-INTERNATIONAL EDITION, 1997, 93 (05): : 341 - 346
  • [44] Synthesis, complexation and photophysics of 1,3-alternate calix[4]arene-crowns-6 bearing fluorophoric units on the bridge
    Casnati, A
    Giunta, F
    Sansone, F
    Ungaro, R
    Montalti, M
    Prodi, L
    Zaccheroni, N
    SUPRAMOLECULAR CHEMISTRY, 2001, 13 (03) : 419 - 434
  • [45] Guest-Induced 2-D Metallopolycapsular Networks Based on a 1,3-Alternate Calix[4] arene Derivative
    Lee, Eunji
    Ju, Huiyeong
    Kang, Youngjin
    Lee, Shim Sung
    Park, Ki-Min
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (16) : 6052 - 6056
  • [46] Anion recognition by diureido-calix[4]arenes in the 1,3-alternate conformation
    Curinova, Petra
    Stibor, Ivan
    Budka, Jan
    Sykora, Jan
    Lang, Kamil
    Lhotak, Pavel
    NEW JOURNAL OF CHEMISTRY, 2009, 33 (03) : 612 - 619
  • [47] CATION-BINDING PROPERTIES OF A NOVEL 1,3-ALTERNATE CALIX[4]BISCROWN - FORMATION OF 1/1-COMPLEX AND 1/2-COMPLEX AND UNIQUE CATION TUNNELING ACROSS A CALIX[4]ARENE CAVITY
    KOH, KN
    ARAKI, K
    SHINKAI, S
    ASFARI, Z
    VICENS, J
    TETRAHEDRON LETTERS, 1995, 36 (34) : 6095 - 6098
  • [48] STRUCTURES OF POTASSIUM ENCAPSULATED WITHIN THE 1,3-ALTERNATE CONFORMATION OF CALIX[4]ARENES
    BEER, PD
    DREW, MGB
    GALE, PA
    LEESON, PB
    OGDEN, MI
    JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1994, (23): : 3479 - 3485
  • [49] TETRA-O-ALKYLATED CALIX[4]ARENES IN THE 1,3-ALTERNATE CONFORMATION
    VERBOOM, W
    DATTA, S
    ASFARI, Z
    HARKEMA, S
    REINHOUDT, DN
    JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (20): : 5394 - 5398
  • [50] Selective metal detection in an unsymmetrical 1,3-alternate calix[4]biscrown chemosensor
    Bok, JH
    Kim, HJ
    Lee, JW
    Kim, SK
    Choi, JK
    Vicens, J
    Kim, JS
    TETRAHEDRON LETTERS, 2006, 47 (08) : 1237 - 1240