13624-01-6Relevant articles and documents
Synthesis and biological evaluation of novel 2,3-disubstituted quinoxaline derivatives as antileishmanial and antitrypanosomal agents
Cogo, Juliana,Kaplum, Vanessa,Sangi, Diego Pereira,Ueda-Nakamura, Tania,Correa, Arlene Goncalves,Nakamura, Celso Vataru
, p. 107 - 123 (2015/03/18)
Quinoxalines belong to the N-containing heterocyclic compounds that stand out as having promising biological activity due to their privileged scaffold. In this work, we report the synthesis, antileishmanial, and antitrypanosomal properties of 46 new 2,3-disubstituted quinoxaline and 40 previously reported derivatives. Among all of the compounds screened for in vitro activity against epimastigotes and trypomastigotes of Trypanosoma cruzi and promastigotes of Leishmania amazonensis as well as mammalian toxicity on LLCMK2 cells and J774 macrophages, analogues from series 5, 6, 7, 9, 12, and 13 displayed high activity at micromolar IC50 and EC50 concentrations. Sixteen quinoxaline derivatives were selected and evaluated on T. cruzi and/or L. amazonensis amastigotes. The most active compounds were 6a-b and 7d-e, on all evolutive forms of L. amazonensis and T. cruzi evaluated with IC50 values 0.1-0.8 1/4M on promastigotes and epimastigotes 1.4-8.6 on amastigotes. Compounds 5k, 12b and 13a were the most selective (SI Combining double low line 19.5-38.4) on amastigotes of T. cruzi. In general their activity was directly related to the methylsulfoxyl, methylsulfonyl, and amine groups as well as the presence of chorine or bromine in the molecules. The current results indicate that these quinoxaline derivatives are novel and promising agents for further development towards a treatment for Chagasg disease and leishmaniasis.
An efficient synthesis of N-substituted 3-nitrothiophen-2-amines
Kumar, Sundaravel Vivek,Muthusubramanian, Shanmugam,Menéndez, J. Carlos,Perumal, Subbu
supporting information, p. 1707 - 1712 (2016/04/10)
A novel protocol for the synthesis of 3-nitro-N-aryl/alkylthiophen-2-amines in good yields from the reaction of α-nitroketene N,S-aryl/alkylaminoacetals and 1,4-dithiane-2,5-diol in the presence of K2CO3 in refluxing ethanol is descr
Synthesis and biological evaluation of novel 2,3-disubstituted quinoxaline derivatives as antileishmanial and antitrypanosomal agents
Cogo, Juliana,Kaplum, Vanessa,Sangi, Diego Pereira,Ueda-Nakamura, Tnia,Corra, Arlene Gonalves,Nakamura, Celso Vataru
, p. 107 - 123 (2015/01/08)
Quinoxalines belong to the N-containing heterocyclic compounds that stand out as having promising biological activity due to their privileged scaffold. In this work, we report the synthesis, antileishmanial, and antitrypanosomal properties of 46 new 2,3-disubstituted quinoxaline and 40 previously reported derivatives. Among all of the compounds screened for in vitro activity against epimastigotes and trypomastigotes of Trypanosoma cruzi and promastigotes of Leishmania amazonensis as well as mammalian toxicity on LLCMK2 cells and J774 macrophages, analogues from series 5, 6, 7, 9, 12, and 13 displayed high activity at micromolar IC50 and EC50 concentrations. Sixteen quinoxaline derivatives were selected and evaluated on T. cruzi and/or L. amazonensis amastigotes. The most active compounds were 6a-b and 7d-e, on all evolutive forms of L. amazonensis and T. cruzi evaluated with IC50 values 0.1-0.8 μM on promastigotes and epimastigotes 1.4-8.6 on amastigotes. Compounds 5k, 12b and 13a were the most selective (SI = 19.5-38.4) on amastigotes of T. cruzi. In general their activity was directly related to the methylsulfoxyl, methylsulfonyl, and amine groups as well as the presence of chorine or bromine in the molecules. The current results indicate that these quinoxaline derivatives are novel and promising agents for further development towards a treatment for Chagasg € disease and leishmaniasis.
Microwave-Assisted synthesis of nitroketene N, S-arylaminoacetals
Sangi, Diego P.,Corre?a, Arlene G.
experimental part, p. 795 - 799 (2010/09/05)
In this paper we report the use of microwaves as heat source to promote the synthesis of a series of nitroketene N, S-acetals with good to excellent isolated yields. These compounds are very useful intermediates for synthesizing nitrogen-containing hetero
Inhibitors for human glutaminyl cyclase by structure based design and bioisosteric replacement
Buchholz, Mirko,Hamann, Antje,Aust, Susanne,Brandt, Wolfgang,B?hme, Livia,Hoffmann, Torsten,Schilling, Stephan,Demuth, Hans-Ulrich,Heiser, Ulrich
experimental part, p. 7069 - 7080 (2010/05/02)
The inhibition of human glutaminyl cyclase (hQC) has come into focus as a new potential approach for the treatment of Alzheimer's disease. The hallmark of this principle is the prevention of the formation of Aβ 3,11(pE)-40,42, as these Aβ-speci
Novel [2-(4-piperidinyl)ethyl](thio)ureas: Synthesis and antiacetylcholinesterase activity
Vidaluc,Calmel,Bigg,Carilla,Stenger,Chopin,Briley
, p. 689 - 695 (2007/10/02)
A series of 1-ar(o)yl-3-[2-(1-benzyl-4-piperidinyl)ethyl](thio)urea derivatives was synthesized and evaluated for antiacetylcholinesterase activity. Most aroyl(thio)urea derivatives showed potent inhibitory activity in the sub-micromolar range. A comparable potency was obtained with the aryl(thio)urea analogues by replacing the phenyl with a 2-pyridyl group. The substituted guanidine variations proved to be almost inactive whereas the nitroethylene analogues appeared to be quite efficient. These results were interpreted in terms of the preferential cis-trans conformation of the aroyl(thio)urea and 2-pyridyl(thio)urea moieties involving the existence of hydrogen bonding. In vivo experiments showed that compound 7m had maximal antiamnestic activity at 0.03 mg/kg with a therapeutic ratio greater than 1000, while cholinergic side effects were only seen at doses 100-fold the maximally effective antiamnestic dose. Compound 7m represents a potentially interesting antidementia agent.
