283166-82-5Relevant academic research and scientific papers
Quinolones: Novel probes in antifilarial chemotherapy
Srivastava, Sanjay K.,Chauhan, Prem M. S.,Bhaduri, Amiya P.,Fatima, Nigar,Chatterjee, Ranjit K.
, p. 2275 - 2279 (2000)
Quinolones have been discovered in our laboratory was a new class of antifilarial agents. This has led to the design, synthesis, and antifilarial evaluation of a number of N-substituted quinol-4(1H)-one-3-carboxamide derivatives 4-6. The macrofilaricidal activity of the target compounds was initially evaluated in vivo against Acanthoeilonema viteae by oral administration of 200 mg/kg x 5 days. Among all the synthesized compounds, 13 displayed activity, with the most potent compound (4a) exhibiting 100% macrofilaricidal and 90% microfilaricidal activities. Compound 4e elicited significant macrofilaricidal (80%) response while compound 5c showed 100% sterilization of female worms. Finally, the two most potent macrofilaricidal compounds, namely 4a and 4e, have been screened for their potency against DNA topoisomerase II, and it has been observed that both have the capability to interfere with this enzyme at 10 μmol/mL concentration. The structure- activity relationship (SAR) associated with position-3 and aryl ring substituents is discussed.
Synthesis, cytotoxicity and mechanistic evaluation of 4-oxoquinoline-3- carboxamide derivatives: Finding new potential anticancer drugs
Forezi, Luana Da S. M.,Tolentino, Nathalia M. C.,De Souza, Alessandra M. T.,Castro, Helena C.,Montenegro, Raquel C.,Dantas, Rafael F.,Oliveira, Maria E. I. M.,Silva Jr., Floriano P.,Barreto, Leilane H.,Burbano, Rommel M. R.,Abrahim-Vieira, Barbara,De Oliveira, Riethe,Ferreira, Vitor F.,Cunha, Anna C.,Boechat, Fernanda Da C. S.,De Souza, Maria Cecilia B. V.
, p. 6651 - 6670 (2014/06/10)
As part of a continuing search for new potential anticancer candidates, we describe the synthesis, cytotoxicity and mechanistic evaluation of a series of 4-oxoquinoline-3-carboxamide derivatives as novel anticancer agents. The inhibitory activity of compounds 10-18 was determined against three cancer cell lines using the MTT colorimetric assay. The screening revealed that derivatives 16b and 17b exhibited significant cytotoxic activity against the gastric cancer cell line but was not active against a normal cell line, in contrast to doxorubicin, a standard chemotherapeutic drug in clinical use. Interestingly, no hemolytical activity was observed when the toxicity of 16b and 17b was tested against blood cells. The in silico and in vitro mechanistic evaluation indicated the potential of 16b as a lead for the development of novel anticancer agents against gastric cancer cells.
Design, synthesis, and biological evaluation of new 1,8-naphthyridin-4(1H)- on-3-carboxamide and quinolin-4(1H)-on-3-carboxamide derivatives as CB 2 selective agonists
Manera, Clementina,Benetti, Veronica,Castelli, M. Paola,Cavallini, Tiziana,Lazzarotti, Sara,Pibiri, Fabio,Saccomanni, Giuseppe,Tuccinardi, Tiziano,Vannacci, Alfredo,Martinelli, Adriano,Ferrarini, Pier Luigi
, p. 5947 - 5957 (2007/10/03)
On the basis of docking studies carried out using the recently published cannabinoid receptor models, new 1,8-naphthyridin-4(1H)-on-3-carboxamide and quinolin-4(1H)-on-3-carboxamide derivatives were designed, synthesized, and tested for their affinities toward the cannabinoid CB1 and CB 2 receptors. Compound 10, which presented p-fluorobenzyl and carboxycycloheptylamide substituents bound in the 1 and 3 positions of the 1,8-naphthyiridine-4-one nucleus, showed a high CB2 affinity with a Ki of 1.0 nM. The substitution of the naphthyridine-4-one nucleus with the quinoline-4-one system determined a general increase in CB2 affinity. In particular, the N-cyclohexyl-7-chloro-1-(2-morpholin-4-ylethyl) quinolin-4(1H)-on-3-carboxamide (40) possessed a remarkable affinity, with Ki of 3.3 nM, which was also accompanied by a high selectivity for the CB2 receptor (Ki(CB1/Ki(CB 2) ratio greater than 303). Moreover, the [35S]GTPγ binding assay and functional studies on human basophils indicated that the 1,8-naphthyridin-4(1H)-on-3-carboxamide derivatives behaved as CB1 and CB2 receptor agonists.
