134477-39-7Relevant articles and documents
Efficient synthesis of iminoctadine, a potent antifungal agent and polyamine oxidase inhibitor (PAO)
Raffi, Francesco,Corelli, Federico,Botta, Maurizio
, p. 3013 - 3016 (2007)
Iminoctadine (1,17-diguanidino-9-azaheptadecane), isolated from a mixture of polyamines and guanidines known as guazatine that is used in agriculture as a fungicide, showed interesting activity as human antifungal agent and PAO inhibitor. In this paper, w
Concurrent Formation of N-H Imines and Carbonyl Compounds by Ruthenium-Catalyzed C-C Bond Cleavage of β-Hydroxy Azides
Lee, Jeong Min,Bae, Dae Young,Park, Jin Yong,Jo, Hwi Yul,Lee, Eunsung,Rhee, Young Ho,Park, Jaiwook
supporting information, p. 4608 - 4613 (2020/06/05)
A commercial cyclopentadienylrutenium dicarbonyl dimer ([CpRu(CO)2]2) efficiently catalyzes the formation of N-H imines and carbonyl compounds simultaneously from β-hydroxy azides via C-C bond cleavage under visible light. Density functional theory calculations for the cleavage reaction support the mechanism involving chelation of alkoxy azide species and liberation of nitrogen as the driving force. The synthetic utility of the reaction was demonstrated by a new amine synthesis promoted by chemoselective allylation of imine and synthesis of isoquinoline.
A gram-scale synthesis of a macrocyclic amidinourea with strong antifungal activity through a Fukuyama tri-protected polyamine intermediate
Borgini, Matteo,Orofino, Francesco,Truglio, Giuseppina I.,Balestri, Lorenzo,Botta, Maurizio
, p. 168 - 177 (2019/07/09)
Systemic fungal infections are, nowadays, of crucial importance and, thus, in the last decade, we explored the great potential of natural and synthetic guanylated compounds, a great amount of work that led to the development of new non-azole antifungal co
Synthesis of linear and cyclic guazatine derivatives endowed with antibacterial activity
Maccari, Giorgio,Sanfilippo, Stefania,De Luca, Filomena,Deodato, Davide,Casian, Alexandru,Dasso Lang, Maria Chiara,Zamperini, Claudio,Dreassi, Elena,Rossolini, Gian Maria,Docquier, Jean-Denis,Botta, Maurizio
, p. 5525 - 5529 (2015/01/08)
Antibiotic resistance has reached alarming levels in many clinically-relevant human pathogens, and there is an increasing clinical need for new antibiotics active on drug-resistant Gram-negative pathogens who rapidly evolve towards pandrug resistance phenotypes. Here, we report on two related classes of guanidinic compounds endowed with antibacterial activity. The two best compounds (9a and 13d) exhibited the most potent antibacterial activity with MIC values ranging 0.12-8 μg/ml with most tested pathogens, including both Gram-positive and Gram-negative bacteria. Interestingly, MIC values were not affected (1-8 μg/ml) when measured using recent clinical isolates with various antibiotic resistance determinants. The results reported herein identify guazatine derivatives as an interesting starting point for the optimization of a potentially novel class of antibacterial agents.
Kinase-mediated trapping of bi-functional conjugates of paclitaxel or vinblastine with thymidine in cancer cells
Aspland, Simon E.,Ballatore, Carlo,Castillo, Rosario,Desharnais, Joel,Eustaquio, Trisha,Goelet, Philip,Guo, Zijian,Li, Qing,Nelson, David,Sun, Chengzao,Castellino, Angelo J.,Newman, Michael J.
, p. 5194 - 5198 (2008/02/02)
In the present work, we explore the possibility of introducing selectivity to existing chemotherapeutics via the design of non-pro-drug, bi-functional molecules comprising a microtubule-binding agent and a substrate for a disease-associated kinase. The design, synthesis, and in vitro biological evaluation of paclitaxel-thymidine and vinblastine-thymidine bi-functional conjugates are reported here. This work provides the first account of 'kinase-mediated trapping' of cancer therapeutics.
Toward Efficient Zn(II)-Based Artificial Nucleases
Boseggia, Elisa,Gatos, Maddalena,Lucatello, Lorena,Mancin, Fabrizio,Moro, Stefano,Palumbo, Manlio,Sissi, Claudia,Tecilla, Paolo,Tonellato, Umberto,Zagotto, Giuseppe
, p. 4543 - 4549 (2007/10/03)
A series of cis-cis-triaminocyclohexane Zn(II) complex-anthraquinone intercalator conjugates, designed in such a way to allow their easy synthesis and modification, have been investigated as hydrolytic cleaving agents for plasmid DNA. The ligand structure
Synthesis and Binding Properties of 2-Amino-5-phosphono-3-pentenoic Acid Photoaffinity Ligands as Probes for the Glutamate Recognition Site of the NMDA Receptor
Heckendorn, Roland,Allgeier, Hans,Baud, Jaqueline,Gunzenhauser, Wilfried,Angst, Christof
, p. 3721 - 3726 (2007/10/02)
Four ω-benzoylated (E)-2,10-diamino-4-(phosphonomethyl)dec-3-enoic acids have been synthesized and tested in vitro for binding to the glutamate recognition site of the NMDA (N-methyl-D-aspartate) receptor.The ω-4-azidosalicylamide derivative 24 was iodinated to give the photoaffinity ligand 25 (CGP 55802 A) which showed an IC50 value of 34 nM in the in vitro 3H>CGP 39653 binding assay.This compound and its radioactive 125I-form are the first photoaffinity ligands for the NMDA receptor with high affinity to the glutamate recognition site.
