40571-15-1Relevant articles and documents
Design and synthesis of bioactive adamantanaminoalcohols and adamantanamines
Zoidis, Grigoris,Kolocouris, Nicolas,Kelly, John M.,Prathalingam, S. Radhika,Naesens, Lieve,De Clercq, Erik
scheme or table, p. 5022 - 5030 (2010/12/24)
Adamantanamines 16, 18, 21, 24, 27, 28, 30, 32, 35, 36, 37, 40, 46 and 48 were synthesized and tested for anti-influenza A virus and trypanocidal activity. The stereoelectronic requirements for optimal antiviral and trypanocidal potency were investigated.
Design, synthesis, and trypanocidal activity of new aminoadamantane derivatives
Papanastasiou, Ioannis,Tsotinis, Andrew,Kolocouris, Nicolas,Prathalingam, S. Radhika,Kelly, John M.
, p. 1496 - 1500 (2008/12/20)
To develop functionalized adamantanes for treating African trypanosomiasis, we report on the synthesis of new 1-alkyl-2-aminoadamantanes 1a-i, 1-alkyltricyclo[3.3.1.13,7]decan-2-guanylhydrazones 2a-g, and their congeneric thiosemicarbazones 3a,
trans-2,2′-Bi(1-phenyladamantylidene): The most twisted biadamantylidene
Okazaki, Takao,Ogawa, Kohei,Kitagawa, Toshikazu,Takeuchi, Ken'ichi
, p. 5981 - 5986 (2007/10/03)
The Grignard coupling of 2,2-dibromo-1-phenyladamantane gave trans-2,2′-bi(1-phenyladamantylidene) (1-Ph). Single-crystal X-ray analysis indicated that 1-Ph has a 23.2° twisted double bond, which is much more distorted than that of parent 2,2′-biadamantylidene (1-H) and that of the ethyl-substituted derivative (1-Et). A cyclic voltammogram showed a reversible electron oxidation wave at 0.87 V vs Fc/Fc+, which is 0.19 V lower than 1-H, indicating a significant increase in the HOMO energy level due to the distortion. The reaction of 1-Ph with 0.9 equiv of bromine gave an intramolecular Friedel-Crafts alkylation product, while bromination of 1-H and 1-Me has been reported to give a bridged bromonium ion and a rearranged product, 2-(1-methyl-2-adamantylidene)-4-bromotricyclo [5,3,1,03.9]undec-4-ene, respectively.