MINISTRY OF EDUCATION AND TRAINING
HANOI NATIONAL UNIVERSITY OF EDUCATION

LE VAN CO RESEARCH SYNTHESIS, STRUCTURE AND PROPERTIES
OF SOME QUINOLINE DERIVATIVES
ON THE BASIS OF EUGENOL FROM OCIMUM SANCTUM L. OIL
SPECIALITY : ORGANIC CHEMISTRY
Classification : 62.44.01.14
This thesis will be dotted to the Council to perform thesis at the:
Departments of Organic Chemistry – Faculties of Chemistry – Hanoi National
University of Education at the time hour October , 2014.

This Thesis can be found at the Library of Hanoi National University of Education
or Central Library for Science & Technology

3
INTRODUCTION
1. Reasons for selecting topic
Chemistry of heterocyclic compounds is a strong growth sector and has
created many compounds in practical applications. In that field, quinoline
heterocyclic plays an important role. Many compounds containing a quinoline
skeleton is used in various industries such as cosmetics, food, catalysts, dyes and
especially in the pharmaceutical industry. For example, quinine, cinchonine,
chloroquine, pamaquine are used as anti-malarial drugs. Several other
derivatives of quinoline were applied to cure cancer as camptothecin, antibacterial,
antifungal, anti-tuberculosis as bedaquiline
Notably, the diarylquinoline currently classified in one of ten new-generation
antibiotic alternative for antibiotic resistant bacteria have been.
Not only that, the kind of quinoline compounds also have many applications
in chemical analysis: Ferron, snazoxs, brombenzthiazo used as an indicator of
some metals analysis by photometric method. Many ligand complexes with
quinoline compounds are more substituents have very good optical properties of

H NMR,
13
C NMR,
2
D NMR and MS spectrum coordination. Some
compounds was studied further UV-Vis, fluorescence emission spectra and single-
crystal XRD. The spectrums were analyzed in detail, the spectral data and the
system were arranged to draw comment.
● Tested antibacterial activity, antifungal substance with some Gram (+) and
Gram (-), yeasts, molds under successive dilution method. Tested cytotoxicity of
compounds for four cancer cell lines differ. Tested the activity of antioxidant
compounds. In particular, tested the activity against malaria for 7-carboxymethoxy-
6-hydroxy-3-sulfoquinoline (Q).
4. New contributions of the thesis
4.1. Synthesis
– Completing a new method to synthesize quinoline ring from quinone-axi from
eugenol in basil oil led to new quinoline compound is 7-carboxymethoxy-6-
hydroxy-3-sulfoquinoline (Q); Use the single-crystal diffraction method to confirm
the structure of Q; Using dynamic
1
H NMR methods to propose the mechanism for
quinoline cyclization reaction not seen in the references.
– Detect an abnormal nucleophilic reaction of N-metylquinolinium compounds: the
replacement of the carboxymethoxy group (OCH
2
COOH) by ankylamino group (RNH).
Through extensive research this reaction, has proposed an unusual reaction
mechanism.

5

The dissertation consists of 148 typed pages, printed on A4 paper with 26
diagrams, 59 photographs and 45 tables are distributed as follows: Introduction: 03
pages, 25 pages Overview, page 16 Experiments, Results and Discussion page 87,
page 02 Conclusion, references 14 pages. There is also 126 pages of appendix.
CONTENTS OF THE THESIS
Chapter 1. OVERVIEW
Have literature review of domestic and foreign research on the synthesis of
homocyclic and heterocyclic compounds from with eugenol, the main constituent
of Ocimum sanctum L. Oil and preliminary studies on the compounds containing a
quinoline ring. Especially noticed a ring-closed reduction reaction of quinone-aci
derivative creates a quinoline compound (detected by organic synthesis group -
Hanoi National University of Education ) is a new reaction should continued to refine
in order to open up a new direction research of polysubstituted quinoline
derivatives.

6
Chapter 2. EXPERIMENTAL
2.1. SYNTHESIS Q AND SOME DERIVATIVES FROM Q

Scheme 1. Diagram synthetic Q and some derivatives from Q
Results synthesis derivatives of Q
Table 1. Structure and data synthesis of derivatives from Q

Order
Notation
R
1
/R
2


H/OMe
65,2
x
x
x
-
-
x
3
HzQ
H/H
H/NHNH
2

62,3
x
x
x
-
-
x
4
QAc
H/H
COMe/OH
55,1
x
x
x
-

x
x
-
-
x
8
EsQBr
H/Br
H/OMe
65,1
x
x
x
-
x
x
9
HzQBr
H/Br
H/NHNH
2

71,9
x
x
x
-
-
x
10

QNHAc
H/NHCOMe
H/OH
50,0
x
x
x
-
x
x
13
MeQBr
Me/Br
H/OH
66,8
x
x
x
-
x
x
14
MeQNO
2

Me/NO
2

H/OH
-

Order
Notation
Y
Yield
(%)
Spectrums measurement and analysis
IR
1
H
13
C
QC
BC
NOESY
MS
1
R1
PhNH
70,0
x
x
-
-
-
-
-
2
R2
2,4-
(NO

-
x
-
x
5
R5
4-MePh
74,2
x
x
x
-
-
-
-
6
R6
Naphtyl
73,2
x
x
x
x
x
x
-
7
R7
Xyclohexyl
50,0

1
H
13
C
QC
BC
MS
1
S1a
Me
72
0,74
x
x
x
x
x
-
2
S1b
Me
-
0,70
x
x
x
-
x
-
3

-
-
6
S3b
Pr
-
0,65
x
x
x
-
-
-
7
S4a
PhCH
2

74
0,55
x
x
x
x
x
x
8
S4b
PhCH
2

x
x
x
x
-
11
S6a
(*)
64
0,18
x
x
x
-
x
-
12
S6b
CH
2
CH
2
NH
2
.HCl
-
0,08
x
x
x

14
14
14
4
6
2
(*)
: Internal salt);
(
**)
: Thin-layer chromatography in solvent MeOH/CHCl
3
(1:1)) 8
2.4. THE REACTION OF MeQNO
2
WITH ANKYLAMINE
Table 4. Structure and data synthesis of T1-T8 compounds

Order
Notation
R
Yield
(%)
R
f
*
Spectrums measurement and analysis

3
T2
Me
70,3
0,6
x
x
x
-
x
x
4
T3
Et
50,2
0,62
x
x
x
-
x
x
5
T4
Pr
70,4
0,65
x
x
x

x
5
T7
CH
2
CH
2
NH
2
.HCl
58,2
0,3
x
x
x
-
x
x
9
T8
Xiclo-C
6
H
11

-
0,7
x
x
x

Yield
(%)
R
f
*

Spectrums measurement and analysis
IR
1
H
13
C
QC
BC
MS
1
V1
H
Ph
64,0
0,84
x
x
x
-
-
x
2
V2
H

-
x
x
5
V5
H
4-ClPh
71,6
0,80
x
x
x
x
x
x
6
V6
H
4-NO
2
Ph
60,4
0,77
x
x
x
-
-
x
7

2,4-(OH)
2
Ph
50,0
0,81
x
x
x
-
-
-
10
V10
Me
Me
71,3
0,80
x
x
x
x
x
x
11
V11
Me
Et
66,7
0,79
x

-

10
13
13
2
5
9
(R
f
*
: Thin-layer chromatography in solvent MeOH/CHCl
3
(1:1)) 9
Chapter 3. RESULTS and DISCUSSION
3.1. Q: 7-CARRBOXYMETHOXY-6-HYDROXY-3-SULFOQUINOLINE
3.1.1. Complete the synthesis method of Q
By changing the molar ratio of the reactants, temperature, time of reaction
stages and acidulating agent in stage 2, we have found conditions for synthesis
reaction Q with high and stability yield. Compound Q was checked by IR, NMR
and MS spectroscopy, the results consistent with those previously published.
Result analyzed single-crystal diffraction (Figure 1) also shows that Q has
structured in accordance with the expected formula.

Figure 1. structure of Q determined by single-crystal XRD method
3.1.2. Study mechanisms reaction synthesis Q from A0
Through monitoring reaction progress by

3.3.2. NMR and MS spectrum of R1-R7

11
Based on the chemical shift, constant spin-spin interaction and combined
with 2D NMR spectral analysis, we have determined exactly the signal of the
proton resonances of the imines R1-R7,
1
H NMR spectral data are listed in table 6.
Table 6. Signals on the
1
H NMR spectrum of R1-R7,  (ppm), J (Hz)

Y
H2
H4
H8
H7a
H5a
H12
H16
H13
H15
H14
Others
R1

8,79
s;1H
9,15
s;1H

7,47
s;1H
5,04
s;2H
9,93
s;1H
-
8,09
d;1H
J = 10
8,89
d;1H
J=2,5
8,28
dd;1H
J1=2,5
J2=9,5
-
NH: 1,97
R3

8,90
s;1H
9,50
s;1H
7,30
s;1H
4,9
s;2H
9,8

t;1H

H12a: 2,46
R5

8,87
s;1H
9,34
s;1H
7,25
s;1H
4,94
s;2H
9,72
d;1H
J=9,5
7,74 d;2H
J = 8,5
7,35 d;2H
J = 8
-
OH: 15,82
H14a: 2,36
R7

8,64
d;1H
J = 2
8,52
d;1H

+
in quinoline core will make it easy for nucleophilic substitution
reaction with Br to form 5-ankylamino derivatives (5-RNH-Q). But Br atom had
not been replaced so that the OCH
2
COOH group was replaced by RNH groups
forming 7-ankylamino derivatives S1-S8.

In the reaction on the left side above Scheme, OR groups linked to aromatic
was replaced by amine creating NHR group. It is an unprecedented nucleophilic
substitution reaction on the quinoline heterocyclic in particular and on general
aromatic compounds.
In the literature review mentioned, the nucleophile substitution on the 7
th

position of quinoline ring is difficult. Although there are also a number of studies
have been done a number of nucleophilic reactions with halogenated in 7
th
position
of quinoline ring, but have not found substitute reaction -OR group (ether) linked to
the quinoline ring particular and general aromatic. The fact that the alkyl aryl ether
RO-Ar is inert with nucleophilic agents such as Cl
-
, OH
-
, amine, Because in -O-
Ar, the effect of -p conjugated, R-O group sustainable linked with aromatic should
be so difficult to replace.
When cleavage linked RO-Ar with HI, the OR group is not replaced (not
leave), the group OAr is leaving group as HO-Ar. We have the following scheme

C=N bond of quinoline ring at 1540-1610 cm
-1
; in the 3000-3500 cm-1, absorption
peaks on IR spectra of MeQBr blended to form absorption band, but on the
spectrum of S1-S8, there is a clear separation of the two amino fluctuated with
medium intensity. Some absorption peaks on the IR spectra of the series S1-S8 are
listed in Table 3.24 of the thesis.
3.4.3. NMR spectrum of S1-S8

14
Based on the chemical shift, constant spin-spin interaction and combined
with 2D NMR spectral analysis, we have determined exactly the signal of the
proton resonances of S1-S8 compounds,
1
H NMR spectral data are listed in table 7.
Table 7. Signals on the
1
H NMR spectrum of S1-S8,  (ppm), J (Hz)

H1
H2

H4

H8
H11
H12
H13
H11’
(**)

S1b
4,37
s;3H
9,09
s;1H
8,75
s;1H
6,71
s;1H
3,01
d;3H
J = 5
-
-
-
-
-
NH: 7.86
S2a
4,23
s;3H
8,35
d;1H
J = 1
8,26
d;1H
J = 1
6,46
s;1H
2,83

-
-
NH: 7,71
S3a
4,22
s;3H
8,33
s;1H
8,25
s;1H
6,4
s;1H
2,74
t;2H
J = 7,5
1,56
m;2H
J = 7,5
0,90
t;3H
J = 7,5
Bị
che
lấp
1,70
m;2H
J = 7,5
0,96
t;3H
J = 7,5

s;1H
6,53
s;1H
4,63
d;2H
J = 6
H12/H16/H13’/H17’
(**)
: 7,43 t; 4H; J = 7,5
H13/H14/H15: 7,35 t, 3H; J = 7,5
H14’/H16’
(**)
: 7,39 t; 2H; J = 7,5;
H5’
(**)
: 7,26 t; 1H; J = 7,5
NH: 7,79
S4b
4,23
s;3H
9,05
d;1H
J = 1
8,75
s;1H
6,81
s;1H
4,70
d;2H
J = 6

J = 1
8,75
s;1H
6,88
s;1H
3,52
q;2H
J = 5,5
3,71
t;2H
J = 5,5
-
-
-
-
NH: 7,50
S6a

4,27
s;3H
8,46
d;1H
J = 2
8,36
s;1H
6,59
s;1H
3,71
q;2H
J = 6

-
-
NH: 7,85
NH
3
+
: 8,19
S7a
(*)

3,94
s;3H
8,34
s, 1H
8,25
s, 1H
5,90
s, 1H
2,58
d;2H
J = 7
1,35
s;2H
1,63
s;2H
H14:
3,11
s; 2H
-
-

H12’
(**)

H13’
(**)

Others
H12a/H13a/ H15a/ H16a: 1,47 m;4H

(*)
measured in D
2
O);
(**)
H11’ – H17’ the amino protons in salt.
Table 7 shows,
1
H NMR spectrum of the S1a-S7a compounds are similar and
different from the spectrum of MeQBr the signal losing at  = 5.21 ppm of 2 proton
H7a, the resonance signals of H2, H4, H8 shift in the downfield than the spectrum
of MeQBr because of the effect +C of RNH group (replaced OCH
2
COOH group).
Also, in the 7-7.9 ppm appears a triplet with 1H of intensity attributed to NH proton
(RCH
2
NH group).
For S1a-S4a compounds, beside of the resonance signal of 7-ankylamino
molecule (denoted Q-NHR), there appears signals of amino RNH
3

between C6 and C8 (j and i example in Figure 4) that confirmed the amino group R-
NH replaced OCH
2
COOH group in 7
th
position.

16

Figure 4. Part of HMBC spectrum of S6b
Combined results analysis HSQC, HMBC spectrum, the signals on the
13
C
NMR spectrum of S1-S8 has been attributed as in table 8.
Table 8. The chemical shift on the spectrum
13
C NMR of S1-S8

S1a
S1b
S2a
S2b
S3a
S3b
S4a
S4b
S5a
S5b
S6a


141,5
-
141,6
130,6
141,5
C3
135,1
136,3
135,0
136,2
135,0
136,2
135,1
136,5
135,1
136,3
135,7
136,7
134,2
136,2
C4
128,0
136,4
128,1
136,5
128,2
136,5

136,6
128,0

145,8
-
146,1
156,1
145,7
C7
152,6
148,5
151,4
147,5
151,5
147,7
151,3
147,4
151,8
147,9
151,3
147,5

146,5
C8
86,2
90,2
86,26
90,3
86,4
90,4
87,2
91,1
86,5

121,6
125,6
121,8
125,1
121,5
C11
29,1
29,7
36,7
37,3
43,6
44,1
45,6
45,7
44,7
45,2
72,5
45,1
42,4
50,99
C12
-
-
13,7
13,2
21,4
20,8
127,2
128,5
59,1

25,1
C13
-
-
-
-
11,5
11,4
128,5
127,6
-
-
-
-
25,2
24,5
C15
-
-
-
-
-
-
-
-
-
-

Ci
-

C12’
(**)

-

12,6
-
20,4

134,0
-
-
-
-
-
-
- 17

S1a
S1b
S2a
S2b
S3a
S3b
S4a
S4b
S5a

-
-
-
-
-
-
-
-
-
-
-
C14’
(**)

-
-
-
-
-
-
128,5
-
-
-
-
-
-
-
C16’
(**)

-

(*)
measured in D
2
O;
(**)
C11’ – C17’: carbon atoms in the amino salt.
The difference spectrum of S1b-S8b compounds compared to
13
C NMR
spectrum of S1a-S8a are: losing signals of the carbon atoms in the ankylamino ion
(RNH
3
+
); signals of C6 of the S1a-S8a series appear in the 156-158 ppm proved
C6 linked with O
-
group, remaining S1b-S8b series, those signals appear at 145,5 –
146,1 ppm proved the C6 linked with OH group.
For S6 and S7, two amino functions amine is used, on the 13C NMR
spectrum of S6a and S6b have 11 signals corresponding to 11 carbon atoms; S7a
has 13 signals. However, in the spectrum of S7a and S6a the signals of C6
resonance at 156,1 ppm (similar to S1a-S5a), while spectrum of S6b has signal of
C6 at 146,1 ppm (similar to S1b-S5b and S8b). Thus it can be stated, S7a and S6a
form internal salt between the OH group at position 6
th
and 2
nd
NH

+
]
S5b
C
12
H
13
BrN
2
O
5
S
376/378
399/95, 401/100: [M+Na
+
]; 377/28, 379/32: [M+H
+
]
375/92, 377/100: [M-H
+
]
3.4.5. UV-Vis spectrum and fluorescence spectroscopy of a number of S series
The UV-Vis spectrum of MeQBr different from the spectrum of the S1-S3
and S5, it has 4 separate peaks so popular and separated from the spectra of other

18
compounds, while in the spectrum of the remaining compounds, 2 absorption peaks
in the visible range mixed together but still filling enough to realize two distinct
spectral peak tips, in addition have some shoulder spectral. The value λ
max

253/ 0.8539

*
245
286/ 0.6673
*
305
414/ 0,5406

*
385
430/ 0.5510
*
450
S2b
254/ 1.0464
*
240/
284/ 0.7541

*
305/
415/ 0,6965

*
370/
430/ 0.7077

*
440/

values, fluorescence intensity I and width of absorption peaks of a
number of a number of S series are listed in Table 11
Table 11. Fluorescence maxima of research compounds
Compounds
λ
max
(nm)
I (au)
Compounds
λ
max
(nm)
I (au)
width (nm)
MeQBr
644; 685
878; 1033
S4a
543
43872
78,1
S1a
594; 674
6574; 3014
S1b
514
30880
91,4
S2a
600; 674

S1b-S6b are similar too, but also different from MeQBr and S4a. That MeQBr is
not the type of hemixianine and S4a has addition benzene core. Coloring matters
Xianin used in biotechnology CY2, Cy3, Cy3B, Cy3.5 and Cy5 have λ
max
of
fluorescence respectively 506; 570; 572; 594 and 670 nm. The S4a, S1b, S2b and
S5b compounds have λ
max
of fluorescence similar to the foregoing, there are strong
fluorescence intensities and spectral widths so small would certainly be useful for
the purpose of using them in the classification area.
3.5. SPECTRA PROPERTIES AND STRUCTURE OF T1-T8
3.5.1. Infrared spectra of T1-T8
IR spectrum of T1-T8 compounds are similarities: not appear absorption
peak so characteristic vibrations of C=O bond in 1700 -1750 cm
-1
, and in 3000-
3500 cm
-1
appear two amino absorption peak of the average intensity (Table 3.33
of the thesis).
3.5.2. NMR spectrum of T1-T8
1
H NMR spectrum of the T1-T8 compounds are similarities, they differ only
in part amine (RNH) and different from the spectrum of MeQNO
2
: appears only
true signals with the expected structural formula, this means lost the signal at  =
5,1 ppm with equal intensity 2H (H7a) of precursor MeQNO
2

8,48
d;1H
J =1,5
6,76
s;1H
-
-
-
-
-
-
NH
4
+
:
7,10 s
T1b
4,34
s;3H
9,03
s;1H
8,42
s;1H
7,07
s;1H
-
-
-
-
-

3,46
q; 2H
J = 7,5
1,26
t; 3H
J = 7,5
-
-
-
-
NH: 7,75
T4
4,32
s; 3H
8,85
d; 1H
J = 1
8,42
s;1H
6,69
s;1H
3,40
t; 2H
J = 7,5
1,70
m; 2H
J = 7,5
-
-
-

s;1H
3,51
t; 2H
J = 6
3,70
t; 2H
J = 6
-
-
-
-
NH: 7,65
T8
4,33
s;3H
8,86
s;1H
8,40
s;1H
6,75
s;1H
3,77
m;1H
H12e, H16e: 1,96 m; 2H
H12a/H13a/H15a/H16a:1,46m;4H
H13e/H15e: 1,75 m; 2H
H14e: 1,64 d;1H; H14a:1,22 m; 1H
NH: 7,30
On the
13

44,3
44,62
44,56
44,62
44,56
44,64
44,60
C2
136,0
139,9
138,67
138,11
138,16
138,00
138,59
138,18
C3
134,1
136,8
136,59
136,56
136,52
137,56
136,67
136,56
C4
125,4
129,7
128,97
128,44

148,38
C8
90,6
94,5
90,24
89,92
90,02
90,65
90,63
90,11
C9
133,4
135,2
135,59
135,38
135,40
134,94
135,37
135,31
C10
121,4
116,9
117,59
117,87
117,86
118,28
117,66
117,73
C11
-

-
25,03
C15
-
-
-
-
-
-
C14
-
-
-
-
-
127,33
-
24,32

21

T1a
T1b
T2
T3
T4
T5
T6
T8
Ci

299
298/100: [M-H
+
]; 299/11:
13
C; 300/5,7:
34
S;
282/10: [M-H
+
-O]
-
T2
NHCH
3
C
11
H
11
N
3
O
6
S
313
312/100: [M-H
+
]; 313/13:
13
C; 314/6:

S;
325/10: [M-H
+
-CH
3
]
-3.5. QNHNH
2
HYDRAZINE and V1-V13 HYDRAZONES
3.5.1. MeQNHNH
2
: 7-hydrazinyl-6-hydroxy-1-methylquinolinium-3-sunfonate
When heating a mixture of MeQBr and hydrazine excess in 3 hours, we
obtained a yellow solid brown, dark gradually when exposed in air. On Thin-layer
chromatography of the products have 2 different spots close together. We denote
this product is Qhh.
IR and NMR spectrum of Qhh proved OCH
2
COOH group linked to the
aromatic group that has been replaced by NHNH
2
group. Simultaneously Br atom
in position 5 is replaced by H atom as scheme 4.

Scheme 4. Replacement reaction mechanism OCH
2
COOH group lead to NHNH

H NMR spectrum of the
hydrazones as in Table 15.

Table 15. Signals on the
1
H NMR spectrum of V1-V13 Structure
H1
H2

H4

H5
H8
Hi;
H11
H12
H16
H13
H15
H14
Others
V1

4,48
s;1H
9,13
d;1H

s;1H
8,54
s;1H
7,60
s;1H
7,64
d;1H
J = 7,5
-
7,37
t;1H
J = 7,5
7,25
d;1H
J = 7,5
NH: 11,20
OH6: 11,89
H13a: 2,38
V3

4,47
s;1H
9,13
s;1H
8,91
s;1H
7,55
s;1H
7,69
s;1H

6,86 d
J = 8,5
-
NH: 11,04
OH6: 11,85
OH14: 9,90
V5

4,49
s;1H
9,14
d;1H
J = 1
8,93
s;1H
7,57
s;1H
7,75
s;1H
8,55
s;1H
7,85 d;2H
J = 8,5
7,53 d
J = 8,5
-
NH: 11,26
OH6: 11,89
V6


s;1H
8,46
s;1H
7,67 d;2H
J = 9
6,88 d
J = 6
-
NH: 11,03
OH6: 11,85
H14a: 3,01
V8

4,46
s;1H
9,08
s;1H
8,85
s;1H
7,51
s;1H
7,70
s;1H
8,45
s;1H
7,43
d;1H
J = 2
7,18
dd;1H

s;1H
6,37
s;1H
-
NH: 11,04
OH6: 11,85
OH12:11,1
OH14:11,8
V10

4,39
s;1H
9,12
s;1H
8,90
s;1H
7,53
s;1H
7,47
s;1H
2,12
s;3H
-
-
-
-
-
NH: 9,1
Hk:2,06 s;3H
V11

J = 1
8,96
s;1H
7,60
s;1H
7,74
s;1H
-
7,98 dd;2H
J1 = 8,5
J2 = 2
7,48 m;3H
NH: 9,42
OH6: 12,0
Hk:2,46 s;3H
V13

4,44
s;1H
9,10
s;1H
8,89
s;1H
7,59
s;1H
7,53
s;1H
-
7,70 d;2H
J = 8,5

V11
V12
V13
C1
44,1
44,1
44,1
44,1
44,2
44,3
43,9
43,9
43,9
44,0
44,1
44,1
44,0
C2
141,3
141,3
141,3
141,0
141,4
141,8
140,8
141,0
140,8
141,1
141,2
141,6

24
C5
109,3
109,3
109,3
109,0
109,3
109,7
108,9
109,0
108,1
109,0
109,1
109,3
108,8
C6
147,0
147,0
147,0
146,9
147,1
147,5
147,2
147,0
147,0
146,9
146,9
147,1
147,1
C7

136,6
136,8
136,5
137,8
136,7
136,8
136,8
136,6
136,7
136,4
136,7
C10
124,6
124,2
124,6
124,4
124,7
125,0
124,4
124,4
124,4
124,3
124,3
124,7
124,6
C11
134,4
134,3
135,6
125,4

-
-
C14
127,2
124,6
117,2
159,4
134,2
147,1
147,0
149,0
158,3
-
-
129,4
150,5
C13
128,9
138,1
157,7
115,8
128,9
127,8

148,1
102,4
-
9,44
129,4
113,3

-
C14a
C13a:
55,6
-
Ck:
17,0
Ck:
15,7
Ck:
13,4
Ck:
13,0
c. MS spectrum of V1-V13 hydrazones
We have record mass spectrometry of some hydrazones, spectral analysis of
the compounds received the molecular weight equal to molecular weight calculated
by the expected formula (Table 17).
Table 17. Results of the MS spectral analysis of hydrazones

Formula / M
Main peaks, m:z / intensity (%)
V1
C
17
H
15
N
3
O
4

+
];372/31: [M+H
+
]; 357/18: [M+Na
+
–CH
3
];
370/100: [M-H
+
]; 371/23:
13
C; 356/25: [M+H
+
–CH
3
]
V4
C
17
H
15
N
3
O
5
S
373
396/100: [M+Na
+

V6
C
17
H
14
N
4
O
6
S
402
401/100: [M-H
+
]; 402/21:
13
C; 385/36: [M-H
+
–O]
V7
C
19
H
20
N
4
O
4
S
400
401/100: [M+H

13
C; 805/8: [2M-H
+
];
V10
C
13
H
15
N
3
O
4
S
309
332/100: [M+Na
+
]; 310/47: [M+H
+
]; 333/16:
13
C
308/100: [M-H
+
]; 309/16:
13
C; 252/7: [M+Na
+
–SO
3

– Of the 04 sample testing cell toxicity, QNO
2
has cytotoxic activity against four
cancer cell lines at weak; HzQBr has cytotoxic activity against cell carcinoma.
– We only test activity against malaria for 7-carboxymethoxy-6-hydroxy-3-
sulfoquinoline (Q). The results show that Q has activity against the malaria
parasite but not strong.