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Schistosomiasis
Organic Compounds to Combat Neglected Tropical Diseases 221
those that presented higher negative reduction potentials were not active as
molluscicides. The observed trends suggest that bio-reduction might play a role in
the molluscicidal activity of this compounds.
In 2011, Zhang and co-workers developed the synthesis of analogues of ginkgolic
acids, a group of 6-alkylsalicylic acids with molluscicidal activity extracted from
the leaves of Ginko biloba [52]. The synthesis of the desired analogues (94) was
accomplished as depicted in Scheme 13. The Wittig reaction between the
intermediate (91) and alkyl aldehydes like (92) afforded olefins (93) in moderate
yields as a mixture of E and Z geometric isomers. In order to investigate the
relevance of the geometry of the double bond on the biocidal activity, they used
conventional column chromatography to separate these isomers. The mixture of
the compounds E- and Z-(93) was then saponified to afford the target compounds
E-(94) and Z-(94) with excellent yields. The molluscicidal assay revealed that the
compound E-(94) presented higher activity than Z-(94). In general, it has been
observed that the molluscicidal activity decreases with the shortening of the alkyl
chain attached to the double bond. The most active compounds presented a C
20
H
41
aliphatic chain as the substituent and presented LD
50
= 22.4 ppm, i.e.
approximately two times more active than its Z analog (Scheme 13).
OEt
C
20
H
41
O
OAc
O
C
20
H
41
OOAc
OEt
PHPh
3
+
Br
-
O
HO
HO
C
20
H
41
O
HO
HO
C
20
H
41
separation
IC
50
= 22.4 ppm
Et
3
N, DMSO
125
o
C, 26h
46 %
NaOH, EtOH
reflux, 5h
94 %
NaOH, EtOH
reflux, 5h
88 %
IC
50
= 47.2 ppm
91
92
93
E-94
Z-94
Scheme 13: Synthesis of analogues of ginkgolic acids and their molluscicidal activities.
It has recently been demonstrated that miltefosine, an alkyllysophospholipid, has
substantial molluscicidal activity [53]. Scanning electron microscopy of B.
alexandrina snails exposed to this compound showed severe damage to the
tentacles with erosion and exfoliation at the apical part. Therefore, it is clear that
phosphorous-containing compounds are important candidates as molluscicidal
drugs.
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222 Organic Compounds to Combat Neglected Tropical Diseases de Oliveira and Neves-Filho
N
N
NR
R NHNH
2
N
N
NR
RN
NH
P
Ph
Ph
Ph
Ph
P
Ph
Ph
O
+
N
N
NR
RN
P
Ph
Ph OH
P
O
EtO OEt
H
N
N
NR
RN
NH
P
S
Cl
P
Cl
S
Cl
Cl
A: P(Ph)
3
Br
2
N
N
NR
RN
H
P
Ph
Ph
Ph
P(OCH
2
CH
2
Cl)
3
N
N
NR
RN
H
POCH
2
CH
2
Cl
N
N
NR
RN
H
P
Ph
Ph
Ph
O
O
P
O
Cl-
R
P
N
N
N
R
N
N
Ph
Ph
Ph
NH
P
H
O
N
N
NR
RN
B:
D:
C:
F:
R = 4-BrC
6
H
4
a = room temperature
b = reflux
D, b
E:
A, a
A, b
B, b
B, a
C, b
E, b
F, b
97
96
98
99
100
101
102
103
95
Scheme 14: Synthesis and evaluated biocidal activity of phosphorous derivatives against B.
alexandrina snails.
Ali and co-workers synthesized a series of phosphorous-containing heterocyclic
and evaluated biocidal activity against B. alexandrina snails [54] (Scheme 14).
The 5,6-bis (4-bromophenyl)-3-hydrazino-1,2,4-triazine (95) was used as
molecular scaffold for the installation of the phosphorus moieties. Derivatization
of (95) was achieved through reaction with phosphorous-containing reagents (96-
103) under different conditions, i.e. stirring at room temperature or reflux. They
observed that temperature plays an important role in the direction of most of the
reaction, since reactions employing the same components resulted in different
products when different temperatures were used. For example, reaction of (95)
Schistosomiasis
Organic Compounds to Combat Neglected Tropical Diseases 223
with the reagent A at room temperature (condition a) produced the heterocyclic
compound (96) in 23% yield, while the same protocol at reflux (condition b)
resulted in the acyclic adduct (97) in 88% yield. The reaction between (95) and
the reagent B behaved similarly to the previous example, but in this case the
cyclic product was formed under refluxing conditions. Other reactions involving
(95) and other phosphorous eletrophiles like C-F afforded the products (100),
(101), (102) and (103), respectively. The synthesized compounds were evaluated
as molluscicidal agents against B. alexandrina. The heterocyclic compounds
exhibited a significant biocidal profile while the acyclic products were less active.
Compound (97) was not toxic in any of the tested concentrations (25-100 ppm).
The authors postulated that this lack of activity might be due to the absent of a N-
P bond in the framework of (97).
In 2007, Abdelrazek and co-workers tested a library of compounds against B.
alexandrine. The most active compounds are depicted in Scheme 15 [55]. After
treatment of (104) with triethyl orthoformate in refluxing acetic anhydride, the
formimidate (105) was synthesized (Scheme 15). Compound (106) was prepared
by Knoevenagel condensation of indole-3-carbaldehyde with malononitrile using
sodium ethoxide as the catalyst. This compound (106) reacted with cyclohexan-
1,3-dione (107) to produce the chromene derivative (108).
N
H
CN
NC
O
O
O
HN
CN
NH
2
O
O
O
CN
N
O
O
O
O
CN
NH
2
O
CH(OEt)
3
Ac
2
O
LC
50/24 h
= 12.0 M
106
107
108
LC
50/24 h
= 11.7 M
105
104
Scheme 15: Synthesis and molluscicidal activity of chromene derivative against B. alexandrine snails.
In 2006, Vasconcellos and co-workers synthesized a diversity of Baylis-Hillman
adducts and tested their molluscicidal activity against B. glabrata (Say) snails
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224 Organic Compounds to Combat Neglected Tropical Diseases de Oliveira and Neves-Filho
[56]. The general synthesis of BH-adducts is shown in Scheme 16; the best results
were achieved for compounds (110a,b) and (111) with LC
50
ranging between 32.3
and 70.6 µM (Scheme 16).
O
Ar
NC
DABCO
O
H
3
CO
2
C
DABCO
Ar
OH
CN
OH
CO
2
CH
3
O
O
O
2
N
+
DMSO/r.t.
+
DMSO/r.t.
Ar =
(32.3 M)
Ar =
(36.3 M)
(70.6 M)
110a,b
111
Scheme 16: Synthesis of Baylis-Hillman adducts and their molluscicidal activity against B.
glabrata (Say) snails.
3. THE STRUCTURAL DIVERSITY OF BIOACTIVE COMPOUNDS
WITH MOLLUSCICIDAL ACTIVITY
Triterpenoid saponins have been considered since the 1970s as a promise of
molluscicides. This review showed that terpenes are still very strong potential
molluscicidal compounds. Diterpenes (34, 35) presented a molluscicidal activity
approximately 30 nM (Fig. 23). Other natural products have displayed activity in
concentrations less than < 1 µM, such as glycoalkaloid ( 29) and triterpenoid (43).
Ten structures, (7, 12, 14b, 36, 41, 48, 68, 85, 89 and 90), presented molluscicidal
activities in concentrations between 1 µM and 5 µM. It is noteworthy to highlight
in this group that cyanolide A (48) inspired first total syntheses. It is also possible
to observe the presence of promising compounds in the class of naphthoquinones
and triterpenoid saponins. Five compounds (14a, 32, 39a, 47, 84) presented
susbtantial activity in concentrations ranging from 5 to 10 µM (Fig. 23).
Table 2 shows the main scaffolds that had less that 4 µM molluscicidal activity
against the Biomphalaria snail genus. Glycosides are present in 50% of the
structures, and the majority of the scaffolds are natural products.
Schistosomiasis
Organic Compounds to Combat Neglected Tropical Diseases 225
34, 35
29, 43
7, 14b, 41, 48, 89
36, 68, 85, 90
12
nM
< 1M
< 5M
<
3M
< 2M
<
10M
14a, 32, 39a, 47, 84
Figure 23: Most active molluscicidal compounds.
Table 2: Bioactive scaffolds against the Biomphalaria snail genus
Lead Compound Class Target Snail LC
(µM)
Scaffolds
Diterpene (34, 35)
Biomphalaria glabrata
0.03
R
R
1
O
OR
2
OR
3
O
Glycoalkaloid (29)
Biomphalaria glabrata
0.11
Dimeric Glycoside (48)
Biomphalaria glabrata
1.2
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226 Organic Compounds to Combat Neglected Tropical Diseases de Oliveira and Neves-Filho
Table 2: contd….
Phloroglucinol (14)
Biomphalaria
peregrine
1.8
Naphthoquinone (89)
Biomphalaria glabrata
1.8
Triterpenoid saponin
(12)
Biomphalaria glabrata
3.7
4. FINAL REMARKS
An obstacle to the use molluscicidal compounds from plant- or marine-origin is
the large-scale attainment of substances from natural sources. Therefore, the
development new non-toxic and molluscicidal compounds is advisable. Another
problem is that the natural compounds are usually very complex, and the synthetic
strategies to get them can also be very expensive for large-scale production, as it
is possible to see in the total synthesis of cyanolide A. The fact that both
extraction from natural sources and production of a synthetic compound are
expensive means that the pharmaceutical industry will be hesitant to invest in
either solution in the near future, particularly as the disease affects mainly people
living in poor places. There are still many scientific and economical obstacles to
be faced before starting programs of development of more selective molluscicidal
compounds. For instance, the lack of information about the molecular targets and
killing mode of action of these compounds in the affected organisms might
hamper a possible rational design of new molecules.
The dilemma between the use of natural products and synthetic compounds has
not yet been settled, and it still remains a challenge to find a substance at the same
time effective and eco-friendly to combat the snails and consequently to achieve
efficient schistosomiasis control.
Schistosomiasis
Organic Compounds to Combat Neglected Tropical Diseases 227
ACKNOWLEDGEMENTS
The authors are grateful to FACEPE-PRONEM (1232.1.06/10) for financial
support. We thank to CAPES for providing access to database through of the
periodicals portal (www.periodicos.capes.gov.br).
CONFLICT OF INTEREST
The authors confirm that this chapter contents have no conflict of interest.
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