scholarly journals Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

Author(s):  
Tobias G. Kapp ◽  
Maximilian Fottner ◽  
Horst Kessler
Keyword(s):  

Author(s):  
Si-Qing Wang ◽  
Wei-Yi Qi ◽  
Xue-Song Yin ◽  
Bing-Feng Shi

7-Deoxycylindrospermopsin is a member of cylindrospermopsin marine alkaloid containing a cyclic guanidine group. Herein, we present a concise formal total synthesis of (±)-7-deoxycylindrospermopsin in 14 steps from commercailly available 4-methoxypyridine....



2015 ◽  
Vol 72 (10) ◽  
pp. 2605-2620 ◽  
Author(s):  
Bich Ngoc Tran ◽  
Quang Tri Bui ◽  
Young Sil Jeon ◽  
Ho Seok Park ◽  
Ji-Heung Kim


1968 ◽  
Vol 2 (2) ◽  
pp. 98-99
Author(s):  
M. I. Plekhan ◽  
P. A. Babich
Keyword(s):  


Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 3000 ◽  
Author(s):  
Anna Spivak ◽  
Rezeda Khalitova ◽  
Darya Nedopekina ◽  
Lilya Dzhemileva ◽  
Milyausha Yunusbaeva ◽  
...  

Triterpene acids, namely, 20,29-dihydrobetulinic acid (BA), ursolic acid (UA) and oleanolic acid (OA) were converted into C-28-amino-functionalized triterpenoids 4–7, 8a, 15, 18 and 20. These compounds served as precursors for the synthesis of novel guanidine-functionalized triterpene acid derivatives 9b–12b, 15c, 18c and 20c. The influence of the guanidine group on the antitumor properties of triterpenoids was investigated. The cytotoxicity was tested on five human tumor cell lines (Jurkat, K562, U937, HEK, and Hela), and compared with the tests on normal human fibroblasts. The antitumor activities of the most tested guanidine derivatives was lower, than that of corresponding amines, but triterpenoids with the guanidine group were less toxic towards human fibroblasts. The introduction of the tris(hydroxymethyl)aminomethane moiety into the molecules of triterpene acids markedly enhanced the cytotoxic activity of the resulting conjugates 15, 15c, 18b,c and 20b,c irrespective of the triterpene skeleton type. The dihydrobetulinic acid amine 15, its guanidinium derivative 15c and guanidinium derivatives of ursolic and oleanolic acids 18c and 20c were selected for extended biological investigations in Jurkat cells, which demonstrated that the antitumor activity of these compounds is mediated by induction of cell cycle arrest at the S-phase and apoptosis.



1991 ◽  
Vol 176 (1) ◽  
pp. 301-308 ◽  
Author(s):  
Gopalan Soman ◽  
Abebe Haregewoin ◽  
Richard C. Hom ◽  
Robert W. Finberg




2007 ◽  
Vol 35 (2) ◽  
pp. 401-404 ◽  
Author(s):  
M.A. Grillo ◽  
V. Battaglia ◽  
S. Colombatto ◽  
C.A. Rossi ◽  
A.R. Simonian ◽  
...  

The charge of the agmatine analogues AO-Agm [N-(3-aminooxypropyl)guanidine], GAPA [N-(3-aminopropoxy)guanidine] and NGPG [N-(3-guanidinopropoxy)guanidine] is deficient as compared with that of agmatine and they are thus able to inhibit agmatine transport in liver mitochondria. The presence of the guanidine group is essential for an optimal effect, since AO-Agm and NGPG display competitive inhibition, whereas that of GAPA is non-competitive. NGPG is the most effective inhibitor (Ki=0.86 mM). The sequence in the inhibitory efficacy is not directly dependent on the degree of protonation of the molecules; in fact NGPG has almost the same charge as GAPA. When the importance of the guanidine group for agmatine uptake is taken into account, this observation suggests that the agmatine transporter is a single-binding, centre-gated pore rather than a channel.



1993 ◽  
Vol 152 (1-2) ◽  
pp. 57-60 ◽  
Author(s):  
Sylvain Lehmann ◽  
Catherine Quirosa-Guillou ◽  
Ute Becherer ◽  
Claude Thal ◽  
Jean-Pierre Zanetta


1995 ◽  
Vol 5 (18) ◽  
pp. 2065-2070 ◽  
Author(s):  
Sebastian Knieps ◽  
Martin C. Michel ◽  
Stefan Dove ◽  
Armin Buschauer


2011 ◽  
Vol 11 (12) ◽  
pp. 10387-10395 ◽  
Author(s):  
Ya-Lei Dong ◽  
Hai-Juan Zhang ◽  
Na Yan ◽  
Lei Zhou ◽  
Zhen-Yang Zhang ◽  
...  


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