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Dengue Fever
Organic Compounds to Combat Neglected Tropical Diseases 51
OH
N
H
OH
OH
HO
OH
N
OH
OH
HO
(CH
2
)
2
CH
3
OH
N
OH
OH
HO
(CH
2
)
5
HO
OH
N
OH
OH
HO
(CH
2
)
5
HO
OH
N
OH
OH
HO
(CH
2
)
6
O
F
F
CM-10-18
deoxynorijimycin
Scheme 20: The structural evolution of iminosugar analogues from deoxynorijimycin .
The N-terminal domain of the flavivirus NS5 protein contains an S-
adenosylmethionine (SAM)-dependent RNA methyltransferase that is involved in
the final steps of the capping process; in particular, it is responsible for catalysing
the nucleophilic mechanism of methylation of the N-7 of the guanosine cap and
the 2-O’ of the ribose subunit, yielding S-adenosylhomocysteine (SAH) as a by-
product (Scheme 21) [59].
Because this process is essential for viral replication, it represents a valid target
for anti-viral drug discovery and some active inhibitors of DV methyltransferase
(DVMTase) have been described. Despite the need for a complete mechanistic
elucidation, a potentially promising inhibitor is a good starting point for the
further design of lead compounds for this target. Ribavarin -5-triphospate, a GTP
analogue [60], sinefungin (SIN), a SAM analogue [61, 62], and aurintricarboxylic
acid (ATA), are able to inhibit DV 2-O’-MTase. SIN is also able to inhibit N7-
MTase [63], as can some SAH analogues that can bind both N7 and 2-O’-MTases.
Ribavirin is a synthetic broad spectrum anti-viral used to treat RNA infections
[64]. The classical synthesis process involves acid catalyzed coupling of cyano-
1,2,4-triazole, or trimethylsylil derivatives of the triazole, with the respective
ribofuranose (Scheme 22) [65]. A common metabolite of this anti-viral is 5′-
triphosphate (RBT) [66]. RBT can be obtained synthetically [60] by an ‘one-pot-
two-step’ procedure using POCl
3
and trimethylphosphate, in the presence of the
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52 Organic Compounds to Combat Neglected Tropical Diseases Rezende et al.
strong base proton sponge [67], forming an dichloridate intermediate, which is
converted to RBT by the addition of pirophosphate solution (Scheme 22).
Scheme 21: The capping process mediated by nucleophilic attack at SAM.
N
N
N
CN
H
O
AcO
AcO
OAc
OAc
N
N
N
CN
Si
O
AcO
AcO
OAc
Br
O
O
N
HO
OH
N
N
NH
2
O
P
Cl
Cl
O
O
HO
N
HO
OH
N
N
NH
2
O
RBT
O
O
OH
HO
N
N
N
O
P
O
O
O-
P
O
O
-O
P
OOH
-O
H
2
N
+
1
. H+, acid catalyzed fusion
2
. NH
4
OH
1
. POCl
3
,(CH
3
O)
3
PO
+
Ribavirin
Ribavirin
Proton Sponge
pyrophosphate
Scheme 22: Ribavarin and the synthesis of RBT.
SIN is a nucleoside obtained from the fermentation broth of Streptomyces
griseolus [62, 68] and also by total synthesis [69, 70]. One of the stereocontrolled
NH
N
N
7
O
NH
2
N
O
OH
H
H
H
H
OH
O
P
O-
O
O
P
O
OO-
P
O-O
O
O
2'
H
Base
O
POOH
N
N
N
N
H
2
N
O
OH
OH
S
Me
NH
2
HO
2
C
N
N
N
N
NH
2
O
HO
HO
S
Me
NH
2
CO
2
H
NH
N
N
7
O
NH
2
N
O
OH
H
H
H
H
OH
O
P
O-
O
O
P
O
OO-
P
O-O
O
O
2'
Base
O
POOH
N
N
N
N
NH
2
O
OH
HO
S
H
2
N
HO
2
C
SAM
S
A
M
SAH
Methyltransferase
catalysis
+
5'
5'
Dengue Fever
Organic Compounds to Combat Neglected Tropical Diseases 53
synthetic approaches involves a Curtius rearrangement towards amino
functionality incorporation and an asymmetric hydrogenation (Approach A in
Scheme 23) [70]. Another strategy (Approach B in Scheme 23) involves 2 nitro-
aldol condensation for chain elongation and further amino functionality
introduction [69].
N
N
N
N
NH
2
O
OH
HO
S
NH
2
HO
2
C
Me
O
OH
HO
OMe
HO
O
O
O
OMe
HO
2
C
O
OH
HO
H
2
N
H
EtO
2
C
NH
2
H
N
N
N
N
NH
2
O
O
O
N
N
N
N
NH
2
O
2
N
O
O
O
OMe
N
H
Cbz
R
SAM
O
O
O
N
N
N
N
NH
2
OH
CO
2
Bn
OHC
NH
2
H
O
N
N
NO
2
RO
BnO
2
C
NH
2
H
O
O
N
N
NH
2
(+)-Sinefungin
Oxidation and
Nitro-Aldol condensation
Swern oxidation/Horner-Emmons
olefination
Curtius rearrangement
Nitro-Aldol condensation
A
pp
r
oach
A
reduction
Approach B
Scheme 23: Sinefungin (SIN) synthesis and structural analogy to SAM.
SAH and its analogues are selective competitive inhibitors of MTases based on
the structure of SAM with substitution on the adenine moiety to occupy a cavity
located above the SAM-binding pocket (Scheme 24) [71]. Interestingly, the
modified SAH showed a high selectivity for virus MTase. This is a serious
limitation of this therapeutic approach, because this class of enzyme is involved in
different kinds of biological activities in humans; these compounds, however,
feature a promising structure to be explored in the search for anti-virals.
There are several other examples of DENV inhibitors with different mechanisms
of action, which were discovered in the biological screening of older drugs (Fig.
1). Teicoplanin, an glycopeptide antibiotic, and the adamantine derivative LCTA-
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54 Organic Compounds to Combat Neglected Tropical Diseases Rezende et al.
Figure 1: Known drugs with alternative anti-viral activity.
949 inhibited DENV entry in vitro with a low cytotoxicity [72]. Narasin [73] is a
natural polyether antibiotic used in prevention of coccidiosis in chicken [74],
which has shown a tendency to disrupt DENV protein synthesis [75]. Lovastatin,
a marketed hypocholesteremic agent, showed an ability to reduce DENV infection
by interfering with the transport of secretory proteins from the ER to the Golgi
apparatus, affecting the virus assembly [76]. The movement of essential proteins
is also affected by Ivermectin [77], a semisynthetic anti-helmintic which inhibits
importins , proteins involved in the nuclear import of viral proteins [78].
Ivermectin also inhibits viral replication as a consequence of the inhibition of NS3
helicase [79].
O
NH
HO
HO
O
HO
O
HN
OH
HO
O
HO
O
O
H
N
HO
N
H
O
HO
O
OH
OH
N
H
Cl
O
OO
H
N
O
Cl
O
HO
H
N
O
OH
NH
2
H
H
H
O
O
O
N
H
HO
OH
OH
O
O
NH
HO
HO
O
HO
O
N
H
OH
NH
OH
O
O
HN
HO
NH
O
OH
O
OH
HO
NH
Cl
O
O
O
HN
O
Cl
O
OH
HN
O
OH
NH
H
H
H
O
O
O
N
H
HO
HO
HO
O
Boc
O
O
OOH
O
O
O
O
O
HH
OH
OH
OH
H
O
O
O
OHO
H
H
O
O
H
O
O
O
H
O
HO
O
O
O
H
O
O
OH
H
OH
teicoplanin
narasin
lovastatin
ivermectin
LCTA-949
Dengue Fever
Organic Compounds to Combat Neglected Tropical Diseases 55
Scheme 24: SAH and the synthesis of its analogues.
As we have seen, several natural products are available for anti-viral studies,
especially for studies on DV. Within the secondary metabolites, flavonoids are
widely described in the literature as DENV inhibitors. Although mechanistic
evaluation is required for some of these products, they represent good potential
starting material for the development of innovative anti-virals. Quercetin [80],
Glabranine, and 7-O-Glabranine [81] showed potential DENV inhibition with low
cytotoxicity in the in vitro models used. Other flavonoids were identified as
DENV NS5 polymerase inhibitors, such as Chartaceone D [82], isolated from the
bark of Cryptocarya chartacea, and podocarpusflavone A, extracted from
Dacrydium balansae, both of which had low in vitro cytotoxicity (Fig. 2).
O
OH
O
O
O
O
O
O
O
OH
OH
OH
OOH
HO
OHO
OH O
OH
O
O
OH
O
OOH
OH
HO
OH
O
O
O
HO
Glabranine
7-O'-Methyl-Glabranine
quercetin
Chartaceone D
podocarpusflavone A
Figure 2: Known anti-viral flavonoids.
O
HO
N
HO
OH
N
N
N
H
N
R
1
O
I
N
HO
OH
N
N
N
H
N
R
1
NIS H
2
O, dioxane
O
S
N
HO
OH
N
N
N
H
N
R
1
HO
O
NH
2
O
S
N
AcO
OAc
N
N
N
Cl
MeO
O
NHFmoc
LiOH
O
S
N
HO
OH
N
N
N
H
N
HO
O
NH
2
Cl
PPh
3
, DMF
l-homocysteine
1) p-chloro-aniline
SAH, R1= H
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56 Organic Compounds to Combat Neglected Tropical Diseases Rezende et al.
CONCLUSIONS
Although the ongoing efforts in the search for DENV inhibitors have resulted in a
panel of diverse potential therapeutics, none of these have been effective in the
clinical trials. This situation, reinforced by the fact that there is no vaccine against
DENV, demonstrates that the only way to decrease the disease incidence at the
present time is to control the vector. Despite the short duration of the symptoms of
this disease, which could lead to questions in terms of our investment in drug
development projects, the lethality of the hemorrhagic form of the disease and the
serotype evolution of the virus could enhance the severity of DENV as a health
issue, especially in developing and tropical countries. The refore, the development of
more rational approaches towards drug design, together with a deeper knowledge of
the biochemistry of DENV, could increase the chances of success in developing
effective DENV inhibitors. In this context, all the findings described in the literature
will allow the development of a library of hits and lead compounds useful for
classical or modern medicinal chemistry -driven drug discovery.
ACKNOWLEDGEMENTS
We acknowledge Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
(CAPES), Conselho Nacional de Desenvolvimento Científico e Tecnológico
(CNPq) and Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
for the financial support to the authors.
CONFLICT OF INTEREST
The authors confirm that this chapter contents have no conflict of interest.
REFERENCES
[1] Organization, W. W. H., Dengue: Guidelines for Diagnosis, Treatment, Prevention and
Control. 2009; p 157.
[2] Ray, D.; Shi, P.-Y., Recent Advances in Flavivirus Antiviral Drug Discovery and Vaccine
Development. Recent Patents on Anti-Infective Drug Discovery 2006, 1 (1), 45-55; Ghosh,
D.; Basu, A., Present perspectives on flaviviral chemotherapy. Drug Discovery Today
2008, 13 (13-14), 619-624.
[3] Lescar, J.; Luo, D.; Xu, T.; Sampath, A.; Lim, S. P.; Canard, B.; Vasudevan, S. G.,
Towards the design of antiviral inhibitors against flaviviruses: The case for the
Dengue Fever
Organic Compounds to Combat Neglected Tropical Diseases 57
multifunctional NS3 protein from Dengue virus as a target. Antiviral Research 2008, 80 (2),
94-101.
[4] Stevens, A. J.; Gahan, M. E.; Mahalingam, S.; Keller, P. A., The Medicinal Chemistry of
Dengue Fever. Journal of Medicinal Chemistry 2009, 52 (24), 7911-792 6; Noble, C. G.;
Chen, Y.-L.; Dong, H.; Gu, F.; Lim, S. P.; Schul, W.; Wang, Q.-Y.; Shi, P.-Y., Strategies
for development of dengue virus inhi bi t o rs. Ant iviral Research 2010, 85 (3), 450-462.
[5] Perera, R.; Khaliq, M.; Kuhn, R. J., Closing the door on flaviviruses: Entry as a target for
antiviral drug design. Antiviral Research 2008, 80 (1), 11-22.
[6] Yang, C. C.; Hsieh, Y. C.; Lee, S. J.; Wu, S. H.; Liao, C. L.; Tsao, C. H.; Chao, Y. S.;
Chern, J. H.; Wu, C. P.; Yueh, A., Novel dengue virus-specific NS2B/NS3 protease
inhibitor, BP2109, discovered by a high-throughput screening assay. Antimicrob Agents
Chemother 2011, 55 (1), 229-38.
[7] Frimayanti, N.; Chee, C. F.; Zain, S. M.; Rahman, N. A., Design of New Competitive
Dengue Ns2b/Ns3 Protease Inhibitors-A Computational Approach. International Journal of
Molecular Sciences 2011, 12 (2), 1089-1100.
[8] Chee, C. F.; Ab dullah, I.; Buckle, M. J. C.; Abd Rahman, N., An efficient synthesis of (+/-
)-panduratin A and (+/-)-isopanduratin A, inhibitors of dengue-2 viral activ ity. Tetrahedron
Letters 2010, 51 (3), 495-498; Kiat, T. S.; Pippen, R.; Yusof, R.; Ibrahim, H.; Norzulaani,
K.; Rahman, N. A., Inhibitory activity of cyclohexenyl chalco ne derivatives and flav onoids
of fingerroot, Boesenbergia rotunda (L.), towards dengue-2 virus NS3 protease. Bioorganic
& Medicinal Chemistry Letters 2006, 16 (12), 3337-3340.
[9] Steuer, C.; Gege, C.; Fischl, W.; Heinonen, K. H.; Bartenschlager, R.; Klein, C. D.,
Synthesis and biological evaluation of alpha-ketoamides as inhibitors of the Dengue virus
protease with antiviral activity in cell-culture. Bioorganic & Medicinal Chemistry 2011, 19
(13), 4067-4074.
[10] Nitsche, C.; Steuer, C.; Klein, C. D., Arylcyanoacrylamides as inhibitors of the Dengue and
West Nile virus proteases. Bioorganic & Medicinal Chemistry 2011, 19 (24), 7318-7337.
[11] Arav apalli, S.; Lai, H.; Teramoto, T.; Alliston, K. R.; Lushington, G. H.; Ferguson, E. L.;
Padmanabhan, R.; Groutas, W. C., Inhibitors of Dengue virus and West Nile virus
proteases based on the aminobenzamide scaffold. Bioorganic & Medicinal Chemistry
2012, 20 (13), 4140-4148.
[12] Tomlinson, S. M.; Malmstrom, R. D.; Russo, A.; Mueller, N.; Pang, Y.-P.; Watowich, S. J.,
Structure-based discovery of dengue virus protease inhibitors. Antiviral Research 2009, 82
(3), 110-114.
[13] Tomlinson, S. M.; Watowich, S. J., Anthracene-based inhibitors of dengue virus NS2B-
NS3 protease. Antiviral Research 2011, 89 (2), 127-135.
[14] Gao, Y.; Cui, T.; Lam, Y., Synthesis and disulfide bond conn ectivity-activity studies of a
kalata B1-inspired cyclopeptide against dengue NS2B-NS3 protease. Bioorganic &
Medicinal Chemistry 2010, 18 (3), 1331-1336.
[15] Chanprapaph, S.; Saparpakorn, P.; Sangma, C.; Niyomrattanakit, P.; Hannongbua, S.;
Angsuthanasombat, C.; Katzenmeier, G., Competitive inhibition of the dengue virus NS3
serine protease by synthetic peptides representing polyprotein cleavage sites. Biochemical
and Biophysical Research Communications 2005, 330 (4), 1237-1246.
[16] Schueller, A.; Yin, Z.; Ch ia, C. S. B.; Doan, D. N. P.; Kim, H.-K.; Shang, L.; Loh, T. P.;
Hill, J.; Vasudevan, S. G., Tripeptide inhibitors of dengue and West Nile virus NS2B-NS3
protease. Antiviral Research 2011, 92 (1), 96-101.
Данная книга находится в списке для перевода на русский язык сайта https://meduniver.com/
58 Organic Compounds to Combat Neglected Tropical Diseases Rezende et al.
[17] Nitsche, C.; Behnam, M. A. M.; Steuer, C.; Klein, C. D., Retro peptide-hybrids as selective
inhibitors of the Dengue virus NS2B-NS3 prot ease. A nt ivi r al Research 2012, 94 (1), 72-79.
[18] Barros, T. G.; Pinheiro, S.; Williamson, J. S.; Tanuri, A.; Gomes, M., Jr.; Pereira, H. S.;
Brindeiro, R. M.; Neto, J. B. A.; Antunes, O. A. C.; Muri, E. M. F., Pseudo-peptides
derived from isomannide : inhibitors of serine proteases. Amino Acids 2010, 38 (3), 701-
709.
[19] Mendgen, T.; Steuer, C.; Klein, C. D., Privileged Scaffolds or Promiscuous Binders: A
Comparative Study on Rhodanines and Related Heterocycles in Medicinal Chemistry.
Journal of Medicinal Chemistry 2012, 55 (2), 743-753.
[20] Tiew, K.-C.; Dou, D.; Teramoto, T.; Lai, H.; Alliston, K. R.; Lushington, G. H.;
Padmanabhan, R.; Groutas, W. C., Inhibition of Dengue virus and West Nile virus
proteases by click chemistry -derived benz d isothiazol-3(2H)-one derivatives. Bioorganic
& Medicinal Chemistry 2012, 20 (3), 1213-1221.
[21] Chan, D. C.; Kim, P. S., HIV entry and its inhibition. Cell 1998, 93 (5), 681-684.
[22] Modis, Y.; Ogata, S.; Clements, D.; Harrison, S. C., A ligand-binding pocket in the dengue
virus envelope glycoprotein. Proceedings of the National Academy of Sciences of the
United States of America 2003, 100 (12), 6986-6991.
[23] Wang, Q.-Y.; Patel, S. J.; Vangrevelinghe, E.; Xu, H. Y.; Rao, R.; Jaber, D.; Schul, W.; Gu,
F.; Heudi, O.; Ma, N. L.; Poh, M. K.; Phong, W. Y.; Keller, T. H.; Jacoby, E.; Vasudevan,
S. G., A Small-Molecule Dengue Virus Entry Inhibitor. Antimicrobial Agents and
Chemotherapy 2009, 53 (5), 1823-1831.
[24] Zhou, Z.; Khaliq, M.; Suk, J.-E.; Patkar, C.; Li, L.; Kuhn, R. J.; Post, C. B., Antiviral
Compounds Discovered by Virtual Screening of Small-Molecule Libraries against Dengue
Virus E Protein. Acs Chemical Biology 2008, 3 (12), 765-775.
[25] Li, Z.; Khaliq, M.; Zhou, Z.; Post, C. B.; Kuhn, R. J.; Cushman, M., Design, synthesis, and
biological evaluation of antiviral agents targe ting flavivirus envelope proteins. Journal of
Medicinal Chemistry 2008, 51 (15), 4660-4671.
[26] Mayhoub, A. S.; Khaliq, M.; Kuhn, R. J.; Cushman, M., Design, Synthesis, and Biological
Evaluation of Thiazoles Targeting Flavivirus Envelope Proteins. Journal of Medicinal
Chemistry 2011, 54 (6), 1704-1714.
[27] Mayhoub, A. S.; Khaliq, M.; Botting, C.; Li, Z.; Kuhn, R. J.; Cushman, M., An
investigation of phenylthiazole antiflaviviral agents. Bioorganic & Medicinal Chemistry
2011, 19 (12), 3845-3854.
[28] Lee, E.; Pavy, M.; Young, N.; Freeman, C.; Lobigs, M., Antiviral effect of the heparan
sulfate mimetic, PI-88, against dengue and encephalitic flaviviruses. Antiviral Research
2006, 69 (1), 31-38.
[29] Perez Recalde, M.; Carlucci, M. J.; Noseda, M. D.; Matulewicz, M. C., Chemical
modifications of algal mannans and xylomannans: Effects on antiviral activity.
Phytochemistry 2012, 73, 57-64.
[30] Qiu, H.; Tang, W.; Tong, X.; Ding, K.; Zuo, J., Structure elucidation and sulfated
derivatives preparation of two alpha-D-glucans from Gastrodia elata Bl. and their anti-
dengue virus bioactivities. Carbohydrate Research 2007, 342 (15), 2230-2236.
[31] Ono, L.; Wollinger, W.; Rocco, I. M.; Coimbra, T. L. M.; Gorin, P. A. J.; Sierakowski, M.
R., In vitro and in vivo antiviral properties of sulfated galactomannans against yellow fever
virus (BeH111 strain) and dengue 1 virus (Hawaii strain). Antiviral Research 2003, 60 (3),
201-208.
Dengue Fever
Organic Compounds to Combat Neglected Tropical Diseases 59
[32] Alen, M. M. F.; De Burghgraeve, T.; Kaptein, S. J. F.; Balzarini, J.; Neyts, J.; Schols, D.,
Broad Antiviral Activity of Carbohydrate-Binding Agents against the Four Serotypes of
Dengue Virus in Monocyte-Derived Dendritic Cells. Plos One 2011, 6 (6).
[33] Rees, C. R.; Costin, J. M.; Fink, R. C.; McMichael, M.; Fontaine, K. A.; Isern, S.; Michael,
S. F., In vitro inhibition of dengue virus entry by p-sulfoxy-cinnamic acid and structurally
related combinatorial chemistries. Antiviral Research 2008, 80 (2), 135-142.
[34] Qi, R.-f.; Zhang, L.; Chi, C.-w., Biological characteristics of dengue virus and potential
targets for drug design. Acta Biochimica Et Biophysica Sinica 2008, 40 (2), 91-101;
Sampath, A.; Padmanabhan, R., Molecular targets for flavivirus drug discovery. Antiviral
Research 2009, 81 (1), 6-15.
[35] Yin, Z.; Chen, Y.-L.; Schul, W.; Wang, Q.-Y.; Gu, F.; Duraiswamy, J.; Kondreddi, R. R.;
Niyomrattanakit, P.; Lakshminarayana, S. B.; Goh, A.; Xu, H. Y.; Liu, W.; Liu, B.; Lim, J.
Y. H.; Ng, C. Y.; Qing, M.; Lim, C. C.; Yip, A.; Wang, G.; Chan, W. L.; Tan, H. P.; Lin,
K.; Zhang, B.; Zou, G.; Bernard, K. A.; Garrett, C.; Beltz, K.; Dong, M.; Weaver, M.; He,
H.; Pichota, A.; Dartois, V.; Keller, T. H.; Shi, P.-Y., An adenosine nucleoside inhibitor of
dengue virus. Proceedings of the National Academy of Sciences of the United States of
America 2009, 106 (48), 20435-20439; Chen, Y.-L.; Yin, Z.; Duraiswamy, J.; Schul, W.;
Lim, C. C.; Liu, B.; Xu, H. Y.; Qing, M.; Yip, A.; Wang, G.; Chan, W. L.; Tan, H. P.; Lo,
M.; Liung, S.; Kondreddi, R. R.; Rao, R.; Gu, H.; He, H.; Keller, T. H.; Shi, P.-Y.,
Inhibition of Dengue Virus RNA Synthesis by an Adenosine Nucleoside. Antimicrobial
Agents and Chemotherapy 2010, 54 (7), 2932-2939.
[36] Chen, Y.-L.; Yin, Z.; Lakshminarayana, S. B.; Qing, M.; Schul, W.; Duraiswamy, J.;
Kondreddi, R. R.; Goh, A.; Xu, H. Y. ; Yip, A.; Liu, B.; Weaver, M.; Dartois, V.; Keller, T.
H.; Shi, P.-Y., Inhibition of Dengue Virus by an Ester Prodrug of an Adenosine Analog.
Antimicrobial Agents and Chemotherapy 2010, 54 (8), 3255- 3 261.
[37] D’hooghe, M.; Mollet, K.; De Vreese, R.; Jonckers, T. H. M.; Dams, G.; De Kimpe, N.,
Design, Synthesis, and Antiviral Evaluation of Purine -β-lactam and Purine-aminopropanol
Hybrids. Journal of Medicinal Chemistry 2012, 55 (11), 5637-5641.
[38] Bourjot, M.; Leyssen, P.; Eydoux, C.; Guillemot, J.-C.; Canard, B.; Rasoanaivo, P.;
Gueritte, F.; Litaudon, M., Flacourtosides A-F, Phenolic Glycosides Isolated from
Flacourtia ramontchi. Journal of Natural Products 2012, 75 (4), 752-758.
[39] Nair, V.; Chi, G.; Shu, Q.; Julander, J.; Smee, D. F., A heterocyclic molecule with
significant activity against dengue virus. Bioorganic & Medicinal Chemistry Letters 2009,
19 (5), 1425-1427.
[40] Diamond, M. S.; Zachariah, M.; Harris, E., Mycophenolic acid inhibits dengue virus
infection by preventing replication of viral RNA. Virology 2002, 304 (2), 211-221;
Takhampunya, R.; Ubol, S.; Houng, H. S.; Cameron, C. E.; Padmanabhan, R., Inhibition of
dengue virus replication by mycophenolic acid and ribavirin. Journal of General Virology
2006, 87, 1947-1952.
[41] Canonica, L.; Santanie.E; Scolasti.C; Kroszczy.W; Ranzi, B. M.; Rindone, B.,
BIOSYNTHESIS OF MYCOPHENOLIC ACID. Journal of the Chemical Society-Perkin
Transactions 1 1972, (21), 2639-&.
[42] Arns, W.; Cibrik, D. M.; Walker, R. G.; Mourad, G.; Budde, K.; Mueller, E. A.; Vincenti,
F., Therapeutic drug monitoring of mycophenolic acid in solid organ transplant patients
treated with mycophenolate mofetil: Review of the literature. Transplantation 2006, 82 (8),
1004-1012.
Данная книга находится в списке для перевода на русский язык сайта https://meduniver.com/
60 Organic Compounds to Combat Neglected Tropical Diseases Rezende et al.
[43] Markland, W.; McQuaid, T. J.; Jain, J.; Kwong, A. D., Broad-spectrum antiviral activity of
the IMP dehydrogenase inhibitor VX-497: a comparison with ribavirin and demonstration
of antiviral additivity with alpha interferon. Antimicrobial Agents and Chemotherapy 2000,
44 (4), 859-866.
[44] Nair, V., IMPDH Inhibitors: Discovery of Antivir al Agents against Emerging Diseases. In
Antiviral Drug Discovery for Emerging Diseases and Bioterrorism Threats, John Wiley &
Sons, Inc.: 2005; pp 178-202.
[45] Lim, P.-Y.; Keating, J. A.; Hoover, S.; Striker, R.; Bernard, K. A., A Thiopurine Drug
Inhibits West Nile Virus Production in Cell Culture, but Not in Mice. Plos One 2011, 6
(10).
[46] Wang, Q.-Y.; Bushell, S.; Qing, M.; Xu, H. Y.; Bonavia, A.; Nunes, S.; Zhou, J.; Poh, M.
K.; de Sessions, P. F.; Niyomrattanakit, P.; Dong, H.; Hoffmaster, K.; Goh, A.; Nilar, S.;
Schul, W.; Jones, S.; Kramer, L.; Compton, T.; Shi, P.-Y., Inhibition of Dengue Virus
through Suppression of Host Pyrimidine Biosynthesis. Journal of Virology 2011, 85 (13),
6548-6556.
[47] Wang, Q.-Y.; Kondreddi, R. R.; Xie, X.; Rao, R.; Nilar, S.; Xu, H. Y.; Qing, M.; Chang,
D.; Dong, H.; Yokokawa, F.; Lakshminarayana, S. B.; Goh, A.; Schul, W.; Kramer, L.;
Keller, T. H.; Shi, P.-Y., A Translation Inhibitor That Suppresses Dengue Virus In Vitro
and In Vivo. Antimicrobial Agents and Chemotherapy 2011, 55 (9), 4072-4080.
[48] Chao, B.; Tong, X.-K.; Tang, W.; Li, D.-W.; He, P.-L.; Garcia, J.-M.; Zeng, L.-M.; Gao,
A.-H.; Yang, L.; Li, J.; Nan, F.-J.; Jacobs, M.; Altmeyer, R.; Zuo, J.-P.; Hu, Y.-H.,
Discovery and Optimization of 2,4-Diaminoquinazoline Derivatives as a New Class of
Potent Dengue Virus Inhibitors. J o ur nal of Medicinal Chemistry 2012, 55 (7), 3135-3143.
[49] Sebastian Barradas, J.; Ines Errea, M.; D'Accorso, N. B.; Sepulveda, C. S.; Talarico, L. B.;
Damonte, E. B., Synthesis and antiviral activity of azoles obtained from carbohydrates.
Carbohydrate Research 2008, 343 (14), 2468-2474.
[50] Sayce, A. C.; Miller, J. L.; Zitzmann, N., Targeting a host process as an antiviral approach
against dengue virus. Trends in Microbiology 2010, 18 (7), 323-330.
[51] Hohenschutz, L. D.; Bell, E. A.; Jewess, P. J.; Leworthy, D. P.; Pryce, R. J.; Arnold, E.;
Clardy, J., Castanospermine, a 1,6,7,8-Tetrahydroxyoctahydroindolizine Alkaloid, from
Seeds of Castanospermum-Australe. Phytochemistry 1981, 20 (4), 811-814.
[52] Jensen, T.; Mikkelsen, M.; Lauritsen, A.; Andresen, T. L.; Gotfredsen, C. H.; Madsen, R.,
A Concise Synthesis of Castanospermine by the Use of a Transannular Cyclization. The
Journal of Organic Chemistry 2009, 74 (22), 8886-8889; Bowen, E. G.; Wardrop, D. J.,
Diastereoselective Nitrenium Ion-Mediated Cyclofunctionalization: Total Synthesis of (+)-
Castanospermine. Organic Letters 2010, 12 (22), 5330-5333.
[53] Whitby, K.; Pierson, T. C.; Geiss, B.; Lane, K.; Engle, M.; Zhou, Y.; Doms, R. W.;
Diamond, M. S., Castanospermine, a potent inhibitor of dengue virus infection in vitro and
in vivo. Journal of Virology 2005, 79 (14), 8698-8706.
[54] Asano, N.; Oseki, K.; Tomioka, E.; Kizu, H.; Matsui, K., N-containing sugars fromMorus
alba and their glycosidase inhibitory activities. Carbohydrate Research 1994, 259 (2), 24 3-
255; Evans, S. V.; Fellows, L. E.; Shing, T. K. M.; Fleet, G. W. J., Glycosidase inhibition
by plant alkaloids which are structural analogues of monosaccharides. Phytochemistry
1985, 24 (9), 1953-1955.
[55] Chang, J.; Wang, L.; Ma, D.; Qu, X.; Guo, H.; Xu, X.; Mason, P. M.; Bourne, N.; Moriarty,
R.; Gu, B.; Guo, J.-T.; Block, T. M., Novel Imino Sugar Derivatives Demonstrate Potent
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