91772-95-1Relevant academic research and scientific papers
Diamine and Triamine Analogs and Derivatives as Inhibitors of Deoxyhypusine Synthase: Synthesis and Biological Activity
Lee, Young Bok,Park, Myung Hee,Folk, J. E.
, p. 3053 - 3061 (1995)
Deoxyhypusine synthase catalyzes the initial step in the posttranslational formation of the amino acid hypusine ε-(4-amino-2-hydroxybutyl)lysine> in eukaryotic initiation factor 5A (eIF-5A). eIF-5A and its hypusine modification are believed to be essential for cell growth.A number of compounds related to diamines and triamines were synthesized and tested as inhinitors of this enzyme.The findings indicate that the long chain triamines 2a and 2b and their guanyl derivatives 3a, 3b, 4a, and 4b exert inhibition by binding to enzyme through only a portion of their structures at any one time.The inhibition exhibited by N-ethyl-1,7-diaminoheptane 20 and its guanyl derivative 21 supports this notion and is evidence for participation of the secondary amino group in binding to enzyme.There is preliminary evidence that amidino and isothiuronium groups may also serve as basic centers for binding to enzyme.Few of the compounds tested here were comparable in inhibitory potency to 1-guanidino-7-aminoheptane (GC7) the most effective known inhibitor of deoxhypusine synthase, and none proved nearly as efficient as GC7 in inhibiting the enzyme in Chinese hamster ovary cells.Hence, unlike the antiproliferative effect of GC7, for which there is evidence of cause by interference with deoxhypusine synthase catalysis (Park, M.H.; Wolff, E.C.; Lee, Y.B.; Folk, J.E.J.Biol.Chem. 269, 1994, 27827-27832), the effective growth arrest exerted by several of the newly synthesized compounds cannot be attributed to inhibition of hypusine synthesis.
S-DERIVATIVES OF THIOUREA. XX. REACTION OF THIOUREA WITH TERMINAL DIBROMOALKANES
Tkachenko, S. E.,Sal'nikov, D. I.,Lys, Ya. I.,Fedoseev, V. M.,Zhurilin, V. S.
, p. 878 - 884 (2007/10/02)
The kinetics of the reaction of thiourea with terminal dibromoalkanes Br(CH2)nBr, where n= 1-5, were investigated by radiochromatography.It was established that the reaction of thiourea with 1,4-dibromobutane and 1,5-dibromopentane leads to the formation of only products from substitution of one or two bromine atoms by thiourea.In the case of 1,2-dibromoethane and 1,3-dibromopropane 2-amino-2-thiazoline and 2-amino-5,6-dihydro-4H-1,3-thiazine were found in addition to the analogous substitution products.The rate constants of the individual stages of the processes were determined.A series of S-bromoalkylisothioureas Br(CH2)nSC+.(NH2)2Br-, where n= 2-5, were synthesized.It was shown that the rate of their reaction with thiourea is higher than for terminal dibromoalkanes and (for n= 3-5) alkyl halides Br(CH2)nH.It was found that the reactivity varies irregularly with increases in the length of the polymethylene chain for bromoalkylisothioureas, and this evidently results from the superimposition of several effects from the substituent.
