+ Resolve Article
+ Follow Us
Follow on FacebookFollow on Facebook
Follow on TwitterFollow on Twitter

+ Translate
+ Subscribe to Site Feed
GeoScience Most Shared ContentMost Shared Content

Divergent Synthesis of Three Classes of Antifungal Amphiphilic Kanamycin Derivatives

, : Divergent Synthesis of Three Classes of Antifungal Amphiphilic Kanamycin Derivatives. Journal of Organic Chemistry 81(22): 10651-10663

NlmCategory="UNASSIGNED">A concise and novel method for site-selective alkylation of 1,3,6',3″-tetraazidokanamycin has been developed that leads to the divergent synthesis of three classes of kanamycin A derivatives. These new amphiphilic kanamycin derivatives bearing alkyl chains length of 4, 6, 7, 8, 9, 10, 12, 14, and 16 have been tested for their antibacterial and antifungal activities. The antibacterial effect of the synthesized kanamycin derivatives declines or disappears as compared to the original kanamycin A. Several compounds, especially those with octyl chain at O-4″ and/or O-6″ positions on the ring III of kanamycin A, show very strong activity as antifungal agents. In addition, these compounds display no toxicity toward mammalian cells. Finally, computational calculation has revealed possible factors that are responsible for the observed regioselectivity. The simplicity in chemical synthesis and the fungal specific property make the lead compounds ideal candidates for the development of novel antifungal agents.


PMID: 27715046

DOI: 10.1021/acs.joc.6b01189

Other references

Bazhan, N.M.; Shevchenko, A.Y.; Karkaeva, N.R.; Yakovleva, T.V.; Makarova, E.N., 2004: Agouti yellow mutation increases adrenal response to ACTH in mice. Objective: Agouti protein (AP) and agouti-related protein with a similar sequence and action are endogenous antagonists of melanocortin receptors, implicated in the control of the hypothalamo-pituitary-adrenal (HPA) axis. Dominant mutation of the...

Woywodt, A.; Streiber, F.; Schroeder, M.; D.G.oot, K.; Haller, H.; Haubitz, M., 2002: Circulating endothelial cells are a novel marker of endothelial damage in ANCA-associated small-vessel vasculitis. Lupus 11(9): 590

Carroll, J.; Brind, S.; Swann, K., 2000: Adenophostin A-induced downregulation of inositol 1,4,5-trisphosphate receptors during meiotic maturation inhibits the generation of sperm and Sr2+-induced Ca2+ transients in mature mouse oocytes. Journal of Reproduction & Fertility Abstract Series (25): 15, July

Schvester, D., 1970: Recent advances in knowledge of the insect pests of Pinus pinaster in the Mediterranean region of France. Reviews the causes of the decline of P. pinaster in the south of France, with particular reference to the primary cause, Matsucoccus feytaudi, its population dynamics, natural enemies and problems of control. The Station de Recherches Forestieres,...

Suess, W.M.; Stump, N.; Chai, H.; Kalisker, A., 1986: Mnemonic effects of asthma medication in children. Asthmatic children receiving theophylline or steroid-theophylline combination therapy and normal nonasthmatics were given tests of visual retention and paired-associate learning. The performance of children receiving combination therapy was signif...

Dudka, I.O.; Kolomiyets, I.V., 1997: Peronosporales in plant communities of reserve Medobory. The distribution of the Peronosporales in three main types of plant communities in the reserve mchltMedoborymchgt (Ternopil region, Ukraine) is considered. It is established that 29 species of Peronosporales are observed in the different plant com...

Hauser-Kronberger, C.; Hacker, G.W.; Muss, W.; Saria, A.; Albegger, K., 1993: Autonomic and peptidergic innervation of human nasal mucosa. The localization and distribution of vasoactive intestinal polypeptide (VIP), peptide histidine methionine (PHM), the novel peptide helospectin, neuropeptide tyrosine (NPY) and its C-flanking peptide (C-PON), substance P and calcitonin gene-relate...

Ferroussier, O.; Dlodlo, R.A.; Capo-Chichi, D.; Boillot, F.; Gninafon, M.; Trébucq, A.; Fujiwara, P.I., 2014: Results of rapid and successful integration of HIV diagnosis and care into tuberculosis services in Benin. Benin, where 20 of 54 tuberculosis (TB) clinics caring for 80% of all TB patients began providing integrated human immunodeficiency virus (HIV) care in 2005. To describe the characteristics and TB treatment outcomes of the first cohorts of TB-HIV...

Ruan, V.; Czer, L.S.C.; Awad, M.; Kittleson, M.; Patel, J.; Arabia, F.; Esmailian, F.; Ramzy, D.; Chung, J.; De Robertis, M.; Trento, A.; Kobashigawa, J.A., 2017: Use of Anti-Thymocyte Globulin for Induction Therapy in Cardiac Transplantation: A Review. The most common causes of death after heart transplantation (HTx) include acute rejection and multi-organ failure in the early period and malignancy and cardiac allograft vasculopathy (CAV) in the late period. Polyclonal antibody preparations such...

Foertsch, J.H.; Fischer, A.J., 1949: Pneumococcic meningitis; presentation of a case with operation and recovery. Archives of Otolaryngology 49(6): 637-642