DEVELOPMENT OF NOVEL IMAGING FLUORESCENT AGENTS
625
3H, Me), 1.57–1.53 (m, 2H, H-14). 13C NMR
(DMSO-d6): δ 174.0 (CO-17) ,162.5 (CONindom),
161.0 (CO-11), 160.4 (COcoum-2), 154.5 (Carom-5'),
153.8 (Ccoum-10a), 148.6 (Ccoum-4), 147.5 (Carom-4''),
134.4–116.1 (Ccoum + Carom), 105.1 (Cindom-3'), 59.4
(OMe), 42.5 (C-13), 41.8 (C-15), 34.8 (C-18), 24.8
(C-14), 14.0 (CH3). Anal. calculated for C17H16N2O3:
C, 68.91; H, 5.44; N, 9,45; Found: C, 68.02; H, 5.19;
N, 9.08.
N-(3-(2-((2,3-dimethylphenyl)amino)benzamido)-
propyl)-3-oxo-3H-benzo[f]chromene-3-carboxamide
(VIII). White crystals; yield: (0.46 g) 66%; mp: 215–
218°C; TLC system: hexane : ethyl acetate (8 : 2); Rf :
0.63. FT-IR (KBr, cm−1): ν 3348, 3317, 3209 (NH),
3047, 2931 (CH), 1723, 1697 (C=O), 1604, 1565
1
(C=C), 1513 (NH bending), 1172 (C–O). H NMR
(DMSO-d6, δ, ppm): δ 10.45 (br s, 1H , NHmefemanic),
8.95 (br s, 1H, NH-16), 8.90 (s, 1H, Hcoum-4), 8.61 (br
'
s, 1H, NH-12), 8.19 (d, 1H, 1H,
), 8.02 (d, 1H,
A
3arom
N-(3-(2-(3-benzoylphenyl)propanamido)propyl)-3-
H-5), 7.98 (d, 1H, H-8), 7.92–7.09 (10H, Hcoum
+
oxo-3H-benzo[f]chromene-3-carboxamide
(XI).
Harom), 3.77–3.75 (t, 2H, H-13), 3.69–3.66 (t, 2H, H- Brown powder; yield: (0.39 g) 52%; mp: 182–186°C;
TLC system: hexane : ethyl acetate (7 : 3); Rf : 0.63.
H-13). 13C NMR (DMSO-d6): δ 170.8 (CO-17), 161.3 FT-IR (KBr, cm−1): ν 3324, 3310 (NH), 3055, 2931
15), 2.48 (s, 3H, Me), 2.42 (s, 3H, Me), 2.08 (m, 2H,
(CH), 1734, 1713, 1673 (C=O), 1612, 1566 (C=C),
1542 (NH bending), 1226 (C–O). 1H NMR (DMSO-
d6, δ, ppm): δ 8.87 (br s, 1H, NH-16), 8.84 (s, 1H,
Hcoum-4), 8.51 (br s, 1H, NH-12), 7.97 (d, 1H, H-5),
7.75 (d, 1H, H-8), 7.73 (s, 1H, Harom-2A), 7.72–7.29
(12H, Hcoum + Harom), 4.23 (q, 1H, CH), 3.77–3.72 (t,
2H, H-13), 3.69–3.60 (t, 2H, Hz, H-15), 2.75–2.59
(m, 2H, H-13), 1.31 (d, 3H, Me). 13C NMR (DMSO-
d6): δ 193.6 (COPh), 176.8 (CO-17), 161.3 (CO-11),
160.3 (COcoum-2), 153.9 (Ccoum-10a), 147.9 (Ccoum-4),
135.3–116.1 (Ccoum + Carom), 59.2 (C-18), 43.2 (C-13),
41.1 (C-15), 27.9 (C-14), 16.8 (CH3). Anal. calculated
for C33H28N2O5: C, 74.42; H, 5.30; N, 5,26; Found: C,
73.67; H, 5.06; N, 5.01.
(CO-11), 160.3 (COcoum-2), 153.9 (Ccoum-10a), 147.9
(C-2A), 141.5 (Ccoum-4), 141.2 (C-1B), 134.2–116.1
(Ccoum + Carom), 43.2 (C-13), 41.1 (C-15), 27.5 (C-14),
20.7 (Me-2B), 16.8 (Me-3B). Anal. calculated for
C32H29N3O4: C, 73.97; H, 5.63; N, 8,09; Found: C,
72.88; H, 5.41; N, 7.81.
N-(3-(2-(2-fluoro-[1,1'-biphenyl]-4-yl)propana-
mido)propyl)-3-oxo-3H-benzo[f]chromene-3-carbox-
amide (IX). White crystals; yield: (0.35 g) 48%; mp:
223–226°C; TLC system: hexane : ethyl acetate (8 : 2);
Rf : 0.51. FT-IR (KBr, cm−1): ν 3332, 3277 (NH),
3047, 2981 (CH), 1724, 1662 (C=O), 1612, 1566
(C=C), 1527 (NH bending), 1241 (C-O), 911 (C-F).
1H NMR (DMSO-d6, δ, ppm): δ 8.97 (br s, 1H, NH-
16), 8.90 (s, 1H, Hcoum-4), 8.74 (br s, 1H, NH-12),
7.99 (d, 1H, H-5), 7.76 (d, 1H, H-8), 7.76–7.21 (12H,
Hcoum + Harom), 4.30 (q, 1H, H-18), 3.77–3.75 (t, 2H,
H-13), 3.70–3.67 (t, 2H, H-15), 2.33–2.29 (m, 2H,
H-13), 1.40 (d, 3H,Me). 13C NMR (DMSO-d6): δ
174.9 (CO-17), 161.4 (CO-11), 160.3 (COcoum-2),
159.8 (Carom-3'), 153.9 (Ccoum-10a), 148.0 (Ccoum-4),
134.9–115.0 (Ccoum + Carom), 44.1 (C-18), 43.3 (C-13),
41.1 (C-15), 27.7 (C-14), 18.2 (CH3). Anal. calculated
for C31H27FN2O4: C,72.93; H, 5.33; N, 5,49; Found:
C, 71.89; H, 5.08; N, 5.27.
N-(3-(3-(4,5-diphenyloxazol-2-yl)propanamido)-
propyl)-3-oxo-3H-benzo[f]chromene-3-carboxamide
(XII). White powder; yield: (0.36 g) 42%; mp: 226–
229°C; TLC system: hexane : ethyl acetate (7 : 3); Rf :
0.45. FT-IR (KBr, cm−1): ν 3327, 3304 (NH), 3047,
2984 (CH), 1721, 1696 (C=O), 1636 (C=N), 1612,
1
1566 (C=C), 1527 (NH bending), 1211 (C–O). H
NMR (DMSO-d6, δ, ppm): δ 8.96 (br s, 1H, NH-16),
8.89 (s., 1H, Hcoum-4), 8.32 (br s, 1H, NH-12), 7.99
(d, 1H, H-5), 7.88 (d, 1H, H-8), 7.76–7.22 (14H,
Hcoum + Harom), 3.77–3.75 (t, 2H, H-13), 3.69–3.65
(t, 2H, H-15), 2.45–2.42 (t, 2H, 19), 2.29–2.22 (t,
2H, 18), 1.45–1.24 (m, 2H, H-13). 13C NMR
(DMSO-d6): δ 172.0 (CO-17), 161.5 (CO-11), 160.4
(COcoum-2), 155.5(Coxaz-2' + C10a), 148.4 (Coxaz-5'),
N-(3-(2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-
1H-indol-3-yl)acetamido)propyl)-3-oxo-3H-benzo[f]-
chromene-3-carboxamide (X). White powder; yield:
(0.48 g) 62%; mp: 192–194°C; TLC system: hexane :
ethyl acetate (7 : 3); Rf : 0.55; FT-IR (KBr, cm−1): ν
3325, 3278 (NH), 3024, 2954 (CH), 1732, 1689, 1655
(C=O), 1604, 1566 (C=C), 1535 (NH bending), 1231
146.8 (Ccoum-4), 137.6 (C-4'), 135.1–111.2 (Ccoum
+
Carom), 43.2 (C-13), 41.5 (C-15), 37.1 (C-18), 29.5 (C-
19), 26.0 (C-14). Anal. calculated for C35H29N3O5: C,
73.54; H, 5.11; N, 7,35; Found: C, 72.12; H, 4.83; N,
7.09.
1
(C–O), 680 (C–Cl); H NMR (DMSO-d6, δ, ppm):
δ 8.87 (s, 1H, Hcoum-4), 8.83 (br s, 1H, NH-16), 8.72
(br s, 1H, NH-12), 7.97 (d, 1H, H-5), 7.90 (d, 1H, H-8),
7.75 (t, 1H, Hcoum-6), 7.73 (d, 2H, Harom-2 + Harom-6),
7.72 (d, 2H, Harom-3 + Harom-5), 7.70 (t, 1H, Hcoum-7),
7.49 (d, 1H, Hcoum-9), 7.44 (d, 1H, Hindom-7), 7.42 (s,
1H, Hindom-4), 7.40 (d, 1H, Hcoum-10), 7.37 (d, 1H, Hin-
dom-6), 4.57 (s, 3H, OMe), 4.42 (s, 2H, H-18), 3.55–
Acetylcholinesterase inhibition assay [14]: A stock
concentration solution (0.01 M) concentration of each
sample has been prepared and then different concen-
trations (10–2, 10–3, 10–5, 10–7, 10–9 and 10–11 M) of
each sample were prepared by dilution with dimethyl
sulfoxide (DMSO) as solvent. Anti-AChE activity was
measured in human serum as follows: (50 μL) of
3.53 (t, 2H, H-13), 3.42–3.40 (t, 2H, H-15), 3.38 (s, DTNB solution (0.001 M) was added to (2.25 mL) of
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY Vol. 46 No. 4 2020