Da Silva AD. Heterocyclic Pyridinylimines and Pyridinylhydrazones: Synthesis
Letters in Drug Design & Discovery, 2016, Vol. 13, No. 1 113
of compounds is promising for the development of a new
class of agents with important biological properties and fur-
ther studies using acetylation the phenolic hydroxyl group
may lead to less toxic compounds and possibly more active.
[15]
Ahamad, T.; Alshehri, S.M. Synthesis and characterization of
monomeric and polymeric pyridinylimine-based Ni(II) complexes
and their catalytic activities in ethylene oligomerization. Polym.
Int., 2012, 61(11), 1640-1647.
Zai, S.; Gao, H.; Huang, Z.; Hu, H.; Wu, H.; Wu, Q. Substituent
Effects of Pyridine-amine Nickel Catalyst Precursors on Ethylene
Polymerization. ACS Catal., 2012, 2(3), 433-440.
Braymer, J.J.; Choi, J.-S.; DeToma, A.S.; Wang, C.; Nam, K.;
Kampf, J.W.; Ramamoorthy, A.; Lim, M. H. Development of Bi-
functional Stilbene Derivatives for Targeting and Modulating
Metal-Amyloid-β Species. Inorg. Chem., 2011, 50(21), 10724-
[
[
16]
17]
CONFLICT OF INTEREST
The authors confirm that this article content has no con-
flict of interest.
1
0734.
[
18]
Jursic, B.S.; Douelle, F.; Bowdy, K.; Stevens, E.D. A new facile
method for preparation of heterocyclic α-iminonitriles and α-
oxoacetic acid from heterocyclic aldehydes, p-aminophenol, and
sodium cyanide.Tetrahedron Lett., 2002, 43(30), 5361-5365.
Paula, D.T.S.; Carvalho, G.S.G.; Almeida, A.C.; Lourenço, M.; Da
Silva, A.D.; Coimbra, E.S. Synthesis, Cytotoxicity and An-
tileishmanial Activity of Aza-stilbene derivatives. Mediterr. J.
Chem., 2013, 2(3), 493-502.
ACKNOWLEDGEMENTS
The authors gratefully acknowledge FAPEMIG, CNPq,
CAPES and PROPESQ/UFJF for financial support.
[19]
REFERENCES
[
[
[
20]
21]
22]
Calil, N.O.; Carvalho, G.S.G.; Franco, D.C.Z.; Da Silva, A.D.;
Raposo, N.R.B., Antioxidant Activity of Resveratrol Analogs. Lett.
Drug Des. Discov., 2012, 9(1), 8-11.
Walker, G.N.; Klett, M.A. Synthesis of Varied Heterocyclic and
Substituted Aryl Alkyl Secondary Amines, Related Schiff Bases,
and Amides. J. Med. Chem., 1966, 9(4), 624-630.
Wong, W.-Y.; Wong, W.-T. Synthesis, structural characterization
and solvatochromic studies of a series of Schiff base-containing
triosmium alkylidyne carbonyl clusters. J. Organomet. Chem.,
[
1]
Da Silva, C.M.; Da Silva, D.L.; Modolo, L.V.; Alves, R.B.; De
Resende, M. A.; Martins, C. V. B.; De Fátima, Â. Schiff bases: A
short review of their antimicrobial activities. J. Adv. Res., 2011,
2
(1), 1-8.
[2]
[3]
[4]
[5]
Lu, J.; Li, C.; Chai, Y.-F.; Yang, D.-Y.; Sun, C.-R. The antioxidant
effect of imine resveratrol analogues. Bioorg. Med. Chem. Lett.,
2
012, 22(17), 5744-5747.
Dos Santos, J.A.; Lima, R.M.; Pereira, T.V.; Do Carmo, A.M.R.;
Raposo, N.R.B.; Da Silva, A.D. Antioxidant Activity of Thio-
Schiff bases. Lett. Drug Des. Discov., 2013, 10(7), 557-560.
Shakeel, A.S.; Kalyane, N.V.; Karjgi, S.R.; Ahmed, M.L. Synthesis
and antibacterial activity of new Schiff’s bases. Int. J. Pharm., Life
Sciences, 2010, 1(5), 246-249.
1
999, 584(1), 48-57.
[
23]
Frolova, N. A.; Vatsadze, S. Z.; Stash, A. I.; Rakhimov, R. D.; Zyk,
N. V. Oxidation of 3-(3-or 4-pyridyl)-1,5-diphenylformazans in
tetrazolium trichloro metallates: Structural and electrochemical in-
vestigation. Chem. Heterocycl. Compd., 2006, 42(11), 1444-1456.
Grammaticakis, P. The ultraviolet and visible absorption of pyri-
dine derivatives. II. α-, β-, and γ-Pyridinecarboxaldehydes and their
nitrogen derivatives. Bull. Soc. Chim. Fr. 1956, 109, 19.
Hearn, M.J.; Cynamon, M.H.; Chen, M.F.; Coppins, R.; Davis, J.;
Joo-On Kang, H.; Noble, A.; Tu-Sekine, B.; Terrot, M.S.; Trom-
bino, D.; Thai, M.; Webster, E.R.; Wilson, R. Preparation and anti-
tubercular activities in vitro and in vivo of novel Schiff bases of
isoniazid. Eur. J. Org. Chem., 2009, 44(10), 4169-4178.
[
[
24]
25]
Pursche, D.; Triller, M.U.; Reddig, N.; Rompel, A.; Krebs, B.
Synthesis and Characterization of [Mn
3
(ppi)
2
(μ-OAc)
4
(H
2
O)
2 2
]
[
[
6]
7]
Hodnett, E.M.; Dunn, W.J. Structure-antitumor activity correlation
of some Schiff bases. J. Med. Chem., 1970, 13(4), 768-770.
Kumar, S.; Niranjan, M.S.; Chaluvaraju, K.C.; Jamakhandi, C.M.;
Kadadevar, D. Synthesis and Antimicrobial Study of Some Schiff
Bases of Sulfonamides. J. Curr. Pharm. Res., 2010, 1(1), 39-42.
Da Silva, C.M.; Da Silva, D.L.; Martins, C.V.B.; De Resende, M.
A.; Dias, E.S.; Magalhães, T.F.F.; P. Rodrigues, L.; Sabino, A.A.;
Alves, R.B.; De Fátima, A. Synthesis of Aryl Aldimines and their
Activity Against Fungi of Clinical Interest. Chem Biol Drug Des.,
MeOH — Unusual Structural Properties of a Trinuclear Oxygen-
Rich Manganese Complex. Z. Anorg. Allg. Chem., 2003, 629(1),
2
4-28.
[
[
26]
27]
Troisi, L.; Ronzini, L.; Granito, C.; Vitis, L.D.; Pindinelli, E.
Stereoselective
synthesis
and
functionalization
of
4-
[
8]
heterosubstituted β-lactams. Tetrahedron., 2006, 62(7), 1564-1574.
Sebli, C.P.; Howson, S.E.; Clarkson, G.J.; Scott, P., fac-Specific
syntheses of homochiral [Fe(NN[prime or minute]) ] + complexes
3
2
(
NN[prime or minute] = pyridine keto-hydrazone); origins of the
2
011, 78(5), 810-815.
stereoselectivity. Dalton Trans., 2010, 39(18), 4447-4454.
Yumnam, S.; Rajkumari, L. Thermodynamics of the Complexation
of N-(Pyridin-2-ylmethylene) Isonicotinohydrazide with Lighter
Lanthanides. J. Chem. Eng. Data., 2008, 54(1), 28-34.
Mossman, T. Rapid colorimetric assay for cellular growth and sur-
vival: application to proliferation and cytotoxicity assays. J. Immu-
nol. Meth., 1983, 65(1-2), 55-58.
Sreejayan, N.; Rao, M.N., Free radical scavenging activity of cur-
cuminoids. Arzneim., 1996, 46(2), 169-172.
[
9]
Kouznetsov, V.V.; Vargas Méndez, L.Y.; Sortino, M.; Vásquez,
Y.; Gupta, M.P.; Freile, M.; Enriz, R.D.; Zacchino, S.A. Antifungal
and cytotoxic activities of some N-substituted aniline derivatives
bearing a hetaryl fragment. Bioorg. Med. Chem., 2008, 16(2), 794-
[
28]
[29]
8
09.
[
10]
11]
Firsova, Y.N.; Lozinskaya, N.A.; Sosonyuk, S.E.; Proskurnina, M.
V.; Zefirov, N.S., Stable synthetic equivalents of N-unsubstituted
imines: Part 1. Synthesis.Ref. J. Chem., 2012, 2(1), 74-104.
[
30]
[
Jovanović, B.Ž.; Mišić-Vuković, M.; Marinković, A.D.; Vajs, V.
13
[31]
Koleva, I.I.; van Beek, T.A.; Linssen, J.P.H.; Groot, A.; Evstatieva,
L. N. Screening of Plant Extracts for Antioxidant Activity: a Com-
parative Study on Three Testing Methods. Phytochem. Anal., 2002,
Effect of substituents on the C chemical shifts of the azomethine
carbon atom of N-(phenyl substituted)pyridine-3- and -2-aldimines.
J. Mol. Struct., 2002, 642(1-3), 113-118.
1
3(1), 8-17.
[
12]
Stefankiewicz, A.R.; Wałęsa-Chorab, M.; Szcześniak, H.B.; Patro-
niak, V.; Kubicki, M.; Hnatejko, Z.; Harrowfield, J., Grid-corner
analogues: Synthesis, characterization and spectroscopic properties
of meridional complexes of tridentate NNO Schiff-base ligands.
Polyhedron., 2010, 29(1), 178-187.
[
[
[
32]
33]
34]
WHO (World Health Organization). Leishmaniasis. Available at
http://www.who.int/leishmaniasis/en/. Accessed on July 2014.
Croft, S.L.; Olliaro, P. Leishmaniasis chemotherapy-challenges and
opportunities. Clin. Microbiol. Infec., 2011, 17(10), 1478-1483.
Dorlo, T.P.C.; Balasegaram, M.; Beijnen, J.H.; de Vries, P.J. Milte-
fosine: a review of its pharmacology and therapeutic efficacy in the
treatment of leishmaniasis. J. Antimicrob. Chemother., 2012,
[
[
13]
14]
Braymer, J.J.; Merrill, N.M.; Lim, M.H. Characterization of
pyridinylimine and pyridinylmethylamine derivatives and their cor-
responding metal complexes. Inorg. Chim. Acta., 2012, 380, 261-
6
7(11), 2576-2597.
2
68.
Seth, D.K.; Bhattacharya, S. Copper(I) complexes of N-
aryl)pyridine-2-aldimines: Spectral, electrochemical and catalytic
properties. Polyhedron, 2011, 30(15), 2438-2443.
[
35]
Coimbra, E.S.; De Almeida, M.V.; Junior, C.O.R.; Taveira, A.F.;
da Costa, C.F.; de Almeida, A.C.; Reis, E.F.C.; Da Silva, A.D.
Synthesis and Antileishmanial Activity of Lipidic Amino Alcohols.
Chem. Biol. Drug Des., 2010, 75(2), 233-235.
(