Synthesis and bioactivity of novel 2-(1,2-benzisothiazol-3-yloxy)-N-(1-aryl-3-cyanopyrazol-5-yl) acetamides

Article abstract of DOI:10.24820/ARK.5550190.P011.091

Nine novel types of 2-(1,2-benzisothiazol-3-yloxy)-N-(1-aryl-3-cyanopyrazol-5-yl)-acetamides were synthesized, and their inhibition effects on selected bacteria (heterotrophic bacteria) and algae (marine chlorella) were evaluated. Results showed that 2-(1,2-benzisothiazol-3-yloxy)-N-(3-cyano-1-(2,4-dimethylphenyl)pyrazol-5-yl) acetamide achieved the highest yield of 81% with good bioactivity against heterotrophic bacteria and marine chlorella.

Full text of DOI:10.24820/ARK.5550190.P011.091

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Arkivoc 2019, part vi, 0-0
Synthesis and bioactivity of
novel 2-(1,2-benzisothiazol-3-yloxy)-N-(1-aryl-3-cyanopyrazol-5-yl) acetamides
Peng Yu*, Xi Li, Xiao Zhang, and Yanhua Xu
College of Environmental Science and Engineering, Nanjing Tech University, Nanjing
Email: yspong@163.com
Received 10-17-2019
Accepted 12-16-2019
Published on line 01-24-2020
Abstract
Nine novel types of 2-(1,2-benzisothiazol-3-yloxy)-N-(1-aryl-3-cyanopyrazol-5-yl)-acetamides were
synthesized, and their inhibition effects on selected bacteria (heterotrophic bacteria) and algae (marine
chlorella) were evaluated. Results showed that 2-(1,2-benzisothiazol-3-yloxy)-N-(3-cyano-1-(2,4-
dimethylphenyl)pyrazol-5-yl) acetamide achieved the highest yield of 81% with good bioactivity against
heterotrophic bacteria and marine chlorella.
Keywords: N-Aryl pyrazole, isothiazolinone, synthesis, bioactivity
DOI: https://doi.org/10.24820/ark.5550190.p011.09
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Introduction
Over the past years, N-arylpyrazole-containing heterocyclic scaffolds have been widely studied in many fields
1-5
because of its diverse biological activities, such as antimicrobial, insecticide, and herbicidal. Meanwhile,
isothiazolone has attracted considerable interest because of its antimicrobial activity against bacteria and
6,7
fungi. Derivatives of isothiazolone also exhibit excellent performance as antibacterial and antifungal agents
and enzyme inhibitors. Multifunctional water treatment agents are currently a hot research topic.14-15 To
8-13
give the target compound excellent biological activity and a broad spectrum of activity, we introduced an N-
16-18
arylpyrazole structure, following the principle of sub-structure group splicing.
Results and Discussion
Synthesis. In connection with our research on the synthesis of novel 2-(1,2-benzisothiazol-3-yloxy)-N-(3-
cyano-1-(substituted-phenyl)pyrazol-5-yl) acetamides aimed at achieving multi-functional antifouling agents,
we describe the synthesis, one crystal structure, and potential antimicrobial activity of these compounds.
Results showed them to exhibit a broad spectrum of activity against heterotrophic bacteria and chlorella. The
synthesis route is shown in Scheme 1: 2-(1,2-benzisothiazol-3-yloxy)-N-(3-cyano-1-(substituted-
phenyl)pyrazole-5-yl) acetamides (8a–8i) were prepared by the reaction of 3-cyano-5-amino-1-(substituted-
phenyl)pyrazole chloroacetamides (5) and 1,2-benzisothiazol-3-one sodium salt (7).
Scheme 1.
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Table 1. Synthesis of compounds 8a-8i
Compound
R
H
Time (h)
Yield (%)
72
Melting Point (℃)
8a
5
5
5
5
5
5
5
5
5
159–161
158–160
178–179
186–188
188–190
199–201
142–144
196–198
182–184
8b
2-methoxy
4-methoxy
4-methyl
4-chloro
4-bromine
2,4-dimethyl
2,6-dichloro
2,4,6-trichloro
70
68
69
59
54
81
72
62
8c
8d
8e
8f
8g
8h
8i
Compound 8g was subjected to single crystal X-ray crystallography, and intensity data were measured
using an Enraf-Nonius CAD4 four-circle diffractometer. Under the condition of 293(2)K, the MoKα ray
(
λ=0.71073 Å) monochromated with a graphite monochromator was irradiated in ω/2θ scanning modes and
XSCANS. Diffraction data were collected between 2.2°<θ<25.4°, and 3656 diffraction points were collected and
reduced, including 3063 independent diffraction points, 1534 strong points (I>2σ), and R(int)=0.056 after
absorption correction, orthogonal crystal system, space group Pbca, refinement result R=0.0789, wR=0.1341
(
w=1/[σ2(Fo 2) +(0.1000P)2 + 0.0000P], P = (Fo2 + 8fc 2) / 3 ), S = 1.008. The highest peak of residual electron
density is 0.166 e/Å3, and the lowest valley is -0.218 e/Å3. SHELXS-97 program was used to identify the rough
structure by a direct method, and the data were refined by the SHEXLX-97 full matrix least squares method
(
Fig. 2), with all non-hydrogen atoms anisotropically corrected. All hydrogen atoms underwent theoretical
19,20
hydrogenation.
Figure 1. ORTEP diagram of 8g. thermal ellipsoids are shown at the 30% probability level.
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Figure 2. Crystal packing of 8g.
Table 2. Crystal data and structure refinement of compound 8g
Empirical formula
CCDC number
Formula weight (g/mol)
Crystal size (mm)
Crystal system
Space group
C
21
H
17
N
5
O S
2
980925
403.46
0.30×0.20×0.10
Orthorhombic
Pbca
a (Å)
b (Å)
c (Å)
V (Å3)
7.1230 (14)
18.236(4)
30.579(6)
3972.1 (14)
8
Z
Crystal density
λ(MoKa) (Å)
1.349
0.71073
F(000)
1680
Theta range for data collection
h, k and l ranges
Reflections measured
Independent reflections
Observed reflection (I > 2σ(I))
Rint
2.2°to 25.4°
0≤h≤8, 0≤k≤21, 0≤l≤36
3656
3603
1534
0.056
Final R* indices (I > 2σ(I))
Goodness-of-fit
R=0.079, wR = 0.165
1.008
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Table 3. Selected Bond Distances (Å) and Bond Angles (°) of 8g
Bond
S-C1
S-N1
O1-C7
O1-C8
N1-C7
C1-C2
C1-C6
N2-C9
Dist.
Bond
C2-C3
N4-N3
N4-C10
N4-C14
C3-C4
N5-C13
C4-C5
C10-C11
C11-C12
C6-C7
C12-N3
Angle
Dist.
Bond
Dist.
1.646(5)
1.671(3)
1.343(4)
1.448(4)
1.287(5)
1.398(6)
1.445(5)
1.368(4)
1.388(4)
1.364(5)
1.212(4)
(°)
1.376(7)
1.361(4)
1.371(5)
1.441(5)
1.418(7)
1.148(5)
1.411(5)
1.365(5)
1.370(5)
1.419(5)
1.334(5)
(°)
C12-C13
C14-C15
C14-C19
C15-C16
C16-C17
C17-C18
C17-C20
C18-C19
C19-C21
C8-C9
1.436(6)
1.355(5)
1.390(5)
1.391(5)
1.385(5)
1.373(6)
1.512(6)
1.395(5)
1.493(5)
1.498(5)
N2-C10
C5-C6
O2-C9
Angle
Angle
(°)
C1-S-N1
C7-O1-C8
C7-N1-S
C2-C1-C6
C2-C1-S
C6-C1-S
C9-N2-C10
C3-C2-C1
N3-N4-C10
N3-N4-C14
C10-N4-C14
C2-C3-C4
C5-C4-C3
C6-C5-C4
C5-C6-C7
93.9(2)
C5-C6-C1
C7-C6-C1
N1-C7-O1
N1-C7-C6
O1-C7-C6
O1-C8-C9
O2-C9-N2
O2-C9-C8
N2-C9-C8
C11-C10-N4
C11-C10-N2
N4-C10-N2
C10-C11-C12
N3-C12-C11
N3-C12-C13
124.3(4)
105.5(4)
122.3(4)
118.0(4)
119.6(4)
110.1(3)
123.6(3)
120.1(4)
116.2(3)
107.0(3)
132.8(4)
120.2(3)
104.5(4)
114.0(4)
118.4(4)
C11-C12-C13
N5-C13-C12
C12-N3-N4
127.6(4)
176.1(5)
103.0(3)
122.2(4)
117.6(4)
120.3(4)
120.6(4)
119.4(4)
118.4(4)
121.4(4)
120.2(5)
123.5(4)
115.8(4)
124.3(4)
119.9(4)
114.8(3)
110.6(3)
115.8(5)
132.3(5)
111.9(3)
122.8(3)
120.9(6)
111.5(3)
121.5(3)
127.1(3)
121.9(5)
118.8(5)
118.1(5)
130.1(4)
C15-C14-C19
C15-C14-N4
C19-C14-N4
C14-C15-C16
C17-C16-C15
C18-C17-C16
C18-C17-C20
C16-C17-C20
C17-C18-C19
C14-C19-C18
C14-C19-C21
C18-C19-C21
Table 4. Intramolecular and intermolecular hydrogen bonds of 8g
D–H…A
d(D–H)
d(H…A)
d(D…A)
∠
DHA
N2-H2A··O1
C11-H11A· ·O2
C21-H21C··N5 i
0.86
0.93
0.96
2.18
2.45
2.59
2.604 (3)
2.869 (5)
3.535 (5)
110
107
168
Symmetry codes: (i) x−1/2, −y+1/2, −z.
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Figs. 1 and 2 correspond to compound 8g, Tables 2 and 3 provide detailed information on the parameters of
the compound and the major bond lengths and bond angles. Table 4 shows the hydrogen bonds in the crystal
structure. The C-C bonds have lengths of 1.355(5)–1.512(6) Å, which are typical C-C bond lengths and consistent
with the literature. Due to the conjugation effect of the pyrazole ring, the C14–N4 bond is long (1.441(5) Å),
which is between a standard C–N single bond (1.471 Å) and a C=N double bond (1.273 Å). The range of the bond
angles between the atoms on the benzene ring is between 115.8(5)° and 124.3(4)°, but the average value is 120°,
indicating that the benzene ring is a stable coplanar six-membered ring. The intermolecular hydrogen bonds N-
H··O and C-H··O form a twisted five-membered ring and a six-membered ring, respectively, and the
intermolecular hydrogen bond C-H·· N causes the molecule to form a multi-layered structure.
Crystallographic data for the structure reported in this paper have been deposited n the Cambridge data
center with deposition number CCDC 980925.
Biological assay: Batch antimicrobial experiments were conducted in six parallel samples, and the average
results are listed in Table 6. Heterotrophic bacteria and marine chlorella were selected as typical targets for their
normal existence in bodies of water, and are important parameters reflecting water quality. The results showed
that the target compounds exert good inhibition against the tested organisms.
Table 6. Comparison of the bioactivity of synthesized compounds 8 against heterotrophic bacteria and marine
chlorella
Inhibition rate of heterotrophic bacteria (%)
Compound
Inhibition rate of Marine Chlorella (%)
1
00ppm
91.3
94.3
94.5
100
50ppm
85.3
86.9
90.2
98.2
88.4
85.2
90.2
81.6
95.3
42.8
25ppm
62.1
75.5
81.2
80.7
58.9
67.8
68.5
64.3
81.9
22.5
8a
60.29
65.81
65.305
67.955
68.48
72.5
71.02
73.99
74.01
53.5
8b
8c
8d
8e
98.9
95.2
97.7
96.2
100
8f
8g
8h
8i
BIT-20
80.1
Conclusions
This study demonstrated the synthesis and antimicrobial activities of 2-(benzisothiazol-3-yloxy)-N-(3-cyano-1-
aryl-5-yl) acetamides. Bioactivity testing showed that the compounds exert satisfactory inhibition effects against
heterotrophic bacteria and marine chlorella, with rates more than 58.9% and 60.29% for heterotrophic bacteria
and marine chlorella at a dosage of 25 ppm, respectively. The highest yield obtained was 81%, indicating that
compounds with an aryl-pyrazole and a benzisothiazolone spliced together have high biological activities and low
toxicities and represent a new direction for further structural optimization and biological studies on such
synthetic acetamides.
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Experimental Section
General. All chemicals used in this study were commericallly available. Melting points were recorded on a X-4
binocular spectra melting apparatus. IR spectra in KBr were recorded on a PerkinElmer PE-683 IR spectrometer.
1
The H NMR spectra were determined using TMS as an internal reference with a Avance Bruker-500 instrument
operating at 500 MHz or an Avance Bruker-300 instrument operating at 400 MHz. Elemental analyses were
performed by an Elementer Vario EL III elementary analysis instrument. Compounds were synthesized in
21
accordance the method described in our previous work.
Benzisothiazolinone sodium salt. A mixture of benzisothiazol-3(8H)-one (6) (0.01 mol) and NaH (0.011 mol) in
MeOH (40 mL) was stirred and heated at refluxed for 2 h. The remaining MeOH was evaporated under negative
pressure. The crude product was washed with MeOH and dried to obtain benzisothiazolin-3-one sodium salt (7)
as a white solid, mp >300 ℃.
3-Cyano-5-amino-1-(substituted-phenyl)pyrazoles. Ethyl 2,3-dicyanopropanoate (0.01 mol), NaOAc (0.03 mol),
and EtOH (50 mL) were mixed in a 150 mL round-bottomed flask. Then, the mixture was added to a substituted
aniline diazonium salt within 20 min and stirred at 5 ℃ for 8 h, after which, the mixture was extracted with
CH
2
Cl (3 x 30 mL). Ammonia was then added to the combined organic extracts to adjust the pH to 9–10. After
2
addition, the mixture was stirred at rt for 3 h. The organic phase was washed and then concentrated. After
cooling, the crude product precipitated, was filtered off, washed with EtOH, dried, and then recrystallized from
toluene to afford the 3-cyano-5-amino-1-(substituted-phenyl)pyrazole (4).
3
-Cyano-5-amino-1-(substituted-phenyl)pyrazole chloroacetamide. Chloroacetyl chloride (0.015 mol) was
added dropwise to a CH Cl solution of 3-cyano-5-amino-1-(substituted-phenyl)pyrazole (0.01 mol in 30 mL) at
–5 ℃, and the mixture obtained was stirred at rt for 8 h with Et N (0.015 mol) as an acid acceptor. After the
reaction, the remaining CH Cl was evaporated under reduced pressure to obtain crude 3-cyano-5-amino-1-
substituted-phenyl)pyrazole chloroacetamide (5).
2
2
0
3
2
2
(
Synthesis of 2-(1,2-benzisothiazol-3-yloxy)-N-(3-cyano-1-(substituted-phenyl)pyrazol-5-yl) acetamides (2). With
KI as a catalyst, a benzisothiazolone sodium salt (7) (0.006 mol) was reacted with a solution of 3-cyano-5-amino-
1
-(substituted-phenyl)pyrazole chloroacetamide in DMF (40 mL), at 100 ℃ for 4 h. The solutioin was
concentrated and poured into H O, and a solid was precipitated, filtered off, washed, and dried. The product (8a-
i) was purified by column chromatography.
2
1
2
5
2
6
2
5
-(1,2-Benzisothiazol-3-yloxy)-N-(3-cyano-1-phenylpyrazol-5-yl) acetamide (8a). H NMR (CDCl
.15 (s, 2H, CH ), 7.15 (s, 1H, C–H), 7.08～7.88 (m, 9H, Ar–H), 8.60 (s, 1H, N–H); IR (KBr) v: 3177(N–H), 3058(C–H),
246(C≡N), 1724(C=O), 1596(C=N), 1546(C=C), 1262(C–N), 645(C–S) cm . Anal. Calcd. (%) for C19
0.79; H, 3.49; N, 18.66. Found (%): C, 61.01; H, 3.35; N, 18.68.
-(1,2-Benzisothiazol-3-yloxy)-N-(3-cyano-1-(2-methoxyphenyl)pyrazol-5-yl) acetamide (8b). H NMR (CDCl
00 MHz) δ: 3.84(s, 3H, CH
3
, 500 MHz) δ:
2
-
1
H
13
N
5
O S: C,
2
1
3
,
3
O), 5.17 (s, 2H, CH ), 7.14 (s, 1H, C–H), 6.78～7.87 (m, 8H, Ar–H), 8.31 (s, 1H, N–H); IR
2
-
1
(
KBr) v: 3295(N–H), 3170(C–H), 2241(C≡N), 1713(C=O), 1596(C=N), 1557(C=C), 1321(C–N), 647(C–S) cm . Anal.
Calcd. (%) for C20 S: C, 59.25; H, 3.73; N, 17.27. Found (%): C, 59.28; H, 3.61; N, 17.29.
-(1,2-Benzisothiazol-3-yloxy)-N-(3-cyano-1-(4-methoxyphenyl) pyrazol-5-yl) acetamide (8c). H NMR (CDCl
00 MHz) δ: 3.85(s, 3H, CH O), 5.14 (s, 2H, CH ), 6.99 (s, 1H, C–H), 7.01～7.82 (m, 8H, Ar–H), 8.34 (s, 1H, N–
H
15
N
O
5 3
1
2
5
3
,
3
2
H); IR (KBr) v: 3383(N–H), 3167(C–H), 2241(C≡N), 1717(C=O), 1597(C=N), 1557(C=C), 1323(C–N), 1225(C–F),
-
1
6
2
47(C–S) cm . Anal. Calcd. (%) for C20
H
15
N
5
O
3
S: C, 59.25; H, 3.73; N, 17.27. Found (%): C, 59.20; H, 3.62; N, 17.35.
1
-(1,2-Benzisothiazol-3-yloxy)-N-(3-cyano-1-(4-methylphenyl)pyrazol-5-yl) acetamide (8d). H NMR (CDCl
3
, 500
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MHz) δ: 2.39 (s, 3H, CH
3
), 5.15 (s, 2H, CH
2
), 7.18 (s, 1H, C–H), 6.86～7.88 (m, 8H, Ar–H), 8.51 (s, 1H, N–H); IR
-
1
(
KBr) v: 3401(N–H), 3171(C–H), 2241(C≡N), 1725(C=O), 1589(C=N), 1556(C=C), 1324(C–N), 646(C–S) cm .
Anal. Calcd. (%) for C20
H
15
N
5
O
2
S: C, 61.68; H, 3.88; N, 17.98. Found (%): C, 61.59; H, 3.77; N, 17.83.
1
2-(1,2-Benzisothiazol-3-yloxy)-N-(3-cyano-1-(4-chlorophenyl) pyrazol-5-yl) acetamide (8e). H NMR (CDCl
3
, 500
MHz) δ: 5.16 (s, 2H, CH
078(C–H), 2242(C≡N), 1712(C=O), 1589(C=N), 1557(C=C), 1334(C–N), 1120(C–F), 647(C–S) cm . Anal. Calcd. (%)
S: C, 55.68; H, 2.95; N, 17.09. Found (%): C, 55.75; H, 2.90; N, 17.14.
-(1,2-Benzisothiazol-3-yloxy)-N-(3-cyano-1-(4-bromophenyl)pyrazol-5-yl)acetamide (8f). H NMR (CDCl3, 500
2
), 7.18 (s, 1H, C–H), 6.99～7.84 (m, 8H, Ar–H), 8.58 (s, 1H, N–H); IR (KBr) v: 3386(N–H),
-
1
3
for C19
2
H
12ClN
O
5 2
1
MHz) δ: 5.15 (s, 2H, CH2), 7.19 (s, 1H, C–H), 6.98～7.85 (m, 8H, Ar–H), 8.60 (s, 1H, N–H); IR (KBr) v: 3259(N–
H), 3057(C–H), 2374(C≡N), 1674(C=O), 1597(C=N), 1539 (C=C), 1290(C–N), 1066 (C–Br), 650(C–S) cm-1. Anal.
Calcd. (%) for C19H12BrN5O2S: C, 50.23; H, 2.66; N, 15.42. Found (%): C, 50.34; H, 2.53; N, 15.38.
1
2-(1,2-Benzisothiazol-3-oxy)-N-(3-cyano-1-(2,4-dimethylphenyl)pyrazole-5-yl) acetamide (8g). H NMR (CDCl
3
,
5
00 MHz) δ: 2.02 (s, 6H, CH
3
), 5.11 (s, 2H, CH ), 7.12 (s, 1H, C–H), 6.74～7.85 (m, 7H, Ar–H), 8.46 (s, 1H, N–H);
2
-
1
IR (KBr) v: 3386(N–H), 3169(C–H), 2243(C≡N), 1716(C=O), 1595(C=N), 1558(C=C), 1323(C–N), 648(C–S) cm . Anal.
Calcd. (%) for C H N O S: C, 62.52; H, 4.25; N, 17.36. Found (%): C, 62.42; H, 4.18; N, 17.43.
21 17 5 2
1
2
5
-(1,2-Benzisothiazol-3-yloxy)-N-(3-cyano-1-(2,6-dichlorophenyl)pyrazol-5-yl) acetamide (8h). H NMR (CDCl
00 MHz) δ: 5.16 (s, 2H, CH ), 7.22 (s, 1H, C–H), 7.11～7.86 (m, 7H, Ar–H), 8.77 (s, 1H, N–H); IR (KBr) v:
202(N–H), 3056(C–H), 2242(C≡N), 1689(C=O), 1596(C=N), 1560(C=C), 1259 (C–N), 1146(C–Cl), 649(C–S) cm .
3
,
2
-
1
3
Anal. Calcd. (%) for C19
H
11
C
l2
N
5
O
2
S: C, 51.36; H, 2.50; N, 15.76. Found (%): C, 51.30; H, 2.54; N, 15.82.
1
2
-(1,2-Benzisothiazol-3-yloxy)-N-(3-cyano-1-(2,4,6-dichlorophenyl)pyrazol-5-yl) acetamide (8i). H NMR (CDCl
3
,
5
00 MHz) δ: 5.18 (s, 2H, CH
246(N–H), 3078(C–H), 2247(C≡N), 1718(C=O), 1654(C=N), 1556(C=C), 1388(C–N), 1168(C–Cl), 651(C–S) cm .
S: C, 47.67; H, 2.11; N, 14.63. Found (%): C, 47.72; H, 2.18; N, 14.58.
2
), 7.25 (s, 1H, C–H), 7.11～7.86 (m, 6H, Ar–H), 8.75(s, 1H, N–H); IR (KBr) v:
-
1
3
Anal. Calcd. (%) for C19
H
10Cl
3
N
O
5 2
Acknowledgements
This work was funded by the National Key R&D Program of China (Grant No. 2017YFB0602500), Natural Science
Foundation of China (21607074), and Natural Science Research Program of Jiangsu (Grant No. 16KJA610002).
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