64830-86-0Relevant articles and documents
Synthesis and biological evaluation of 3-amino-1,2,4-triazole derivatives as potential anticancer compounds
Benhida, Rachid,Demange, Luc,Dufies, Maeva,Grytsai, Oleksandr,Hagege, Anais,Martial, Sonia,Pagès, Gilles,Penco-Campillo, Manon,Ronco, Cyril,Valiashko, Oksana
, (2020/10/02)
Two series of compounds carrying 3-amino-1,2,4-triazole scaffold were synthesized and evaluated for their anticancer activity against a panel of cancer cell lines using XTT assay. The 1,2,4-triazole synthesis was revisited for the first series of pyridyl derivatives. The biological results revealed the efficiency of the 3-amino-1,2,4-triazole core that could not be replaced and a clear beneficial effect of a 3-bromophenylamino moiety in position 3 of the triazole for both series (compounds 2.6 and 4.6) on several cell lines tested. Moreover, our results point out an antiangiogenic activity of these compounds. Overall, the 5-aryl-3-phenylamino-1,2,4-triazole structure has promising dual anticancer activity.
S-Benzylisothiourea derivatives as small-molecule inhibitors of indoleamine-2,3-dioxygenase
Matsuno, Kenji,Takai, Kazushige,Isaka, Yoshinobu,Unno, Yuka,Sato, Masayuki,Takikawa, Osamu,Asai, Akira
supporting information; experimental part, p. 5126 - 5129 (2010/10/19)
S-Benzylisothiourea 3a was discovered by its ability to inhibit indoleamine-2,3-dioxygenase (IDO) in our screening program. Subsequent optimization of the initial hit 3a lead to the identification of sub-μM inhibitors 3r and 10h, both of which suppressed kynurenine production in A431 cells. Synthesis and structure-activity relationship of S-benzylisothiourea analogues as small-molecule inhibitors of IDO are described.
HISTAMINE H3 RECEPTOR LIGANDS
-
Page 14, (2010/02/05)
Compounds of formula (I) (and pharmaceutically acceptable salts thereof) are histamine H3 receptor ligands. A in the formula represents (CH2)m, m being from 1 to 3; B is (CH2)n, n being from 1 to 3; x is from 0 to 2; Ris C1 to C10 hydrocarbyl, in which up to 2 carbon atoms may be replaced by O, S or N; and up to 2 hydrogen atoms may be replaced by halogen; Ris H or C1 to C15 hydrocarbyl, in which up to 3 carbon atoms may be replaced by O, S or N, and up to 3 hydrogen atoms may be replaced by halogen; Ris absent when -Y-Z-R2 is attached to W, or is H or C1 to C7 hydrocarbyl when -Y-Z-Ris not attached to W; W is nitrogen; X is -CH2-, -O- or -NR-, Rbeing H or C1 to C3 alkyl; Y replaces a hydrogen atom on any of A, B, W and X, and is C2 to C10 alkylene, in which one non-terminal carbon atom may be replaced by O; and Z is (II), (III), (IV), (V), (VI), or (VII) wherein R, Rand Rare independently H or C1 to C15 hydrocarbyl, in which up to 3 carbon atoms may be replaced by O or N, and up to 3 hydrogen atoms may be replaced by halogen, and Q is H or methyl, or Q is linked to Ror Rto form a five-membered ring or Q is linked to Rto form a six-membered ring
Design, synthesis, and structure-activity relationships of novel non- imidazole histamine H3 receptor antagonists
Linney, Ian D.,Buck, Ildiko M.,Harper, Elaine A.,Kalindjian, S. Barret,Pether, Michael J.,Shankley, Nigel P.,Watt, Gillian F.,Wright, Paul T.
, p. 2362 - 2370 (2007/10/03)
Novel, potent, and selective non-imidazole histamine H3 receptor antagonists have been prepared based on the low-affinity ligand dimaprit (pK(I) 7.32 ± 0.12, pK(B) 5.93 ± 0.17). Detailed structure-activity studies have revealed that N-(4-chlorobenzyl)-N-(6-pyrrolidin-1-ylhexyl)guanidine (pK(I) 8.38 ± 0.21, pK(B) 8.39 ± 0.13), 30, and N-(4-chlorobenzyl)-N-(7- pyrrolidin-1-ylheptyl)guanidine (pK(I) 8.78 ± 0.12, pK(B) 8.38 ± 0.10), 31, exhibit high affinity for the histamine H3 receptor. Antagonists 30 and 31 demonstrate significant selectivity over the other histamine, H1 and H2, receptor subtypes and a 100-fold selectivity in the σ1 binding assay. Compounds 30 and 31 are the most potent, selective non-imidazole histamine H3 receptor antagonists reported in the literature to date.
Flavin receptors. Effect of the acidity of melamine derivatives bearing a 2-arylguanidinium ion on 6-azaflavin binding in chloroform
Moriya,Kajiki,Watanabe,Kondo,Yano
, p. 2539 - 2542 (2007/10/03)
The pK(a)'s of melamine derivatives beating a 2-arylguanidinium ion and their binding constants for 6-aza-10dodecylisoalloxazine (6-azaflavin) were nicely correlated with the Hammett o of the substituents. However, the rates of the oxidations of N-benzyl-
Substituted N-phenylisothioureas: Potent inhibitors of human nitric oxide synthase with neuronal isoform selectivity
Shearer, Barry G.,Lee, Shuliang,Oplinger, Jeffrey A.,Frick, Lloyd W.,Garvey, Edward P.,Furfine, Eric S.
, p. 1901 - 1905 (2007/10/03)
S-Ethyl N-phenylisothiourea (4) has been found to be a potent inhibitor of both the human constitutive and inducible isoforms of nitric oxide synthase. A series of substituted N-phenylisothiourea analogues was synthesized to investigate the structure-activity relationship of this class of inhibitor. Each analogue was evaluated for human isoform selectivity. One analogue, S-ethyl N-[4-(trifluoromethyl)phenyl]isothiourea (39), exhibited 115-fold and 29-fold selectivity for the neuronal isoform versus the inducible and endothelial derived constitutive isoforms, respectively. Studies have shown the substituted N-phenylisothiourea 39 binds competitively with L,-arginine.
A Versatile Synthesis of Novel N,N,N''-Trisubstituted Guanidines
Rasmussen, C. R.,Villani, F. J.,Reynolds, B. E.,Plampin, J. N.,Hood, A. R.,et al.
, p. 460 - 466 (2007/10/02)
N,N,N''-Trisubstituted guanidines (most of them N''-aryl-N-azacycloalkanecarboximidamides) are prepared in generally good yields by S-methylation of monosubstituted thioureas with methyl iodide in methanol or acetone and reaction of the resultant methyl c
Zur Kinetik der Oxydation 3-substituierter 1-Aminoguanidine durch Cerium(IV) in perchlorsaurer Loesung. 1. Teil
Kramer, C.-R.,Schelenz, Th.,Stein, J.
, p. 849 - 864 (2007/10/02)
By known manners synthesized 1-amino-3-aryl-guanidines are oxidatively cyclized to corresponding 3,6-diarylamino-1,2,4,5-tetrazines in perchloric acid solution.The kinetics of this passing with second order model reaction was studied on a selected series of 17 1-amino-3-aryl-guanidine hydronitrates at 4 temperatures in 4 differently concentrated perchloric acid solutions of constant ionic strength by photometric concentration determination of oxidant cerium(IV).From experimental data rate constants, activation parameters and catalytic constants are evaluated by conventional methods, tabulated and discussed with regard to their substituent dependence.
