Synthesis and biological study of medicinally important Mannich bases derived from 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a pentahydroxy naphthacene carboxamide

Article abstract of DOI:10.1016/j.bmcl.2006.11.001

The paper describes synthesis and antibacterial study of biologically active Mannich bases of carboxamide derivative employing Mannich reaction of 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a pentahydroxy naphthacene carboxamide with various sulfonamides/secondary amines .They were analysed by elemental analysis and characterized by UV, IR and ¹H NMR spectroscopic studies. The Mannich bases were screened for antibacterial activity against various gram-negative bacteria at various concentrations and were analysed statistically. The result has shown that the compounds are quite active against pathogens under study and were non-toxic. All the synthesized compounds were found to be low lethal as ascertained by LD₅₀ test.

Full text of DOI:10.1016/j.bmcl.2006.11.001

Bioorganic & Medicinal Chemistry Letters 17 (2007) 645–648
Synthesis and biological study of medicinally important Mannich
bases derived from 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-
octahydro-3,6,10,12,12a pentahydroxy
naphthacene carboxamide
*
Sheela Joshi, Anju Das Manikpuri and Prapti Tiwari
School of Chemical Sciences, Devi Ahilya University, Takshshila Campus, Khandwa Road, Indore, India
Received 7 September 2006; revised 29 October 2006; accepted 1 November 2006
Available online 6 November 2006
Abstract—The paper describes synthesis and antibacterial study of biologically active Mannich bases of carboxamide derivative
employing Mannich reaction of 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a pentahydroxy naphthacene car-
boxamide with various sulfonamides/secondary amines .They were analysed by elemental analysis and characterized by UV, IR
1
and H NMR spectroscopic studies. The Mannich bases were screened for antibacterial activity against various gram-negative bac-
teria at various concentrations and were analysed statistically. The result has shown that the compounds are quite active against
pathogens under study and were non-toxic. All the synthesized compounds were found to be low lethal as ascertained by LD50 test.
Ó 2006 Elsevier Ltd. All rights reserved.
The carboxamide derivatives represented as 4-(dimeth-
ylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a
pentahydroxy naphthacene carboxamide are antibiot-
ics which form a group of natural products having
notable antibacterial activity towards a broad range
of pathogenic micro-organisms and are characterized
by very low toxicity to the mammalian hosts of
these pathogens. These properties together with the
fact that the compounds are well absorbed and fully
active, when administered orally, have made tetracy-
cline one of the most useful families of chemothera-
peutic agents.
za, urinary tract infections, chronic bronchitis, etc. It
has also been used for cancer detection and bone
studies.
1
–4
Sulfa drugs are building blocks of several types of Man-
5
–10
nich bases.
pharmacological properties: antibacterial, anticancer,
The sulfonamide nucleus has well-known
1
1
12
1
3
14
15
antiinflammatory, carbonic inhibitory,
6
and insecticidal. In view of the above and in continua-
tion of our earlier study, we report antibacterial activity
of 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-
analgesic
1
1
7
3,6,10,12,12a pentahydroxy naphthacene carboxamide
Mannich bases and their comparative study with
sulfonamides.
There range of activity includes an inhibitory or a
destructive effect on rickettsiae, large virus of the
lymphogranuloma-pesittacosis group gram +ve and
gram Àve cocci and bacilli. They are used for Rocky
Mountain spotted fever, typhus, Q-fever, viral pneumo-
nia and for some other viral and bacterial infections,
such as, conjunctivitis, trachoma brucellosis and for
the treatment of infections such as hemophilus influen-
Various drugs obtained from Mannich reaction have
proved to be more effective and less toxic than their par-
1
8
ent compounds. The versatile utility of the Mannich
1
bases in polymers, dispersants in lubricating oil
9
20
2
1
and in pharmaceutical chemistry prompted us to pre-
pare a series of amino methyl derivatives and evaluate
their biological significance and toxicity. Statistics are
used for final comparison.
Keywords: 4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,
12,12a pentahydroxy naphthacene carboxamide; sulfonamides; Man-
nich bases; Antibacterial activity; Toxicity and statistical analysis.
In continuation of our earlier investigations, we report
the synthesis of Mannich bases of 4-(dimethylamino)-
1,4,4a, 5,5a, and 6,11,12a-octahydro-3,6,10,12,12a pen-
*
Corresponding author. Tel.: +091 731 247 8204; fax: +091 731
372; e-mail addresses: spjoshi11@rediffmail.com; anjudas792000@
yahoo.co.in
0
2
2
tahydroxy naphthacene carboxamide.
0
960-894X/$ - see front matter Ó 2006 Elsevier Ltd. All rights reserved.
doi:10.1016/j.bmcl.2006.11.001

646
S. Joshi et al. / Bioorg. Med. Chem. Lett. 17 (2007) 645–648
Mannich bases of 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-
octahydro-3,6,10,12,12a pentahydroxy naphthacene
carboxamide were achieved in two steps, in the initial
step we get Mannich bases from primary amines, that
is, sulfonamides and finally Mannich bases from second-
ary amines are synthesized. Scheme 1 summarizes the
procedures used to prepare the Mannich bases (4a–4f)
from the carboxamide derivative. These newly synthe-
sized compounds were characterized by elemental anal-
In case of P. multocida the minimum zone of inhibition
was recorded for Mannich base 4a, while the maximum
was noted for 4c.The concentration 40 mg/ml was found
to be significantly superior to all the concentrations. The
2
4
results were statistically analysed.
Further, Table 2 reveals that Mannich bases are statisti-
cally superior to their corresponding sulfonamides in
exhibiting antibacterial activity. None of the sulfona-
mides had shown any activity at these concentrations.
From the statistical data it is revealed that in case of
S. enteritidis, Mannich bases 4a and 4c are significantly
superior to sulfadiazene and sulfanilamide in inhibiting
the growth of this pathogen. The rest sulfonamide fails
to show any activity against S. enteritidis.
1
23
ysis, UV, IR, H NMR spectral studies.
The antimicrobial screening was performed using paper
disc method on pathogenic strains of Salmonella enteri-
tidis and Pasturella multocida. The Mannich bases were
studied for their antibacterial property at concentrations
À1
of 20–40 mgml using methanol as solvent. The solvent
did not exhibit any activity at the concentrations used.
On comparing the antibacterial activity of Mannich bases
to their corresponding sulfonamides against P. multocida,
it indicates that 4c, 4d, 4e and 4f have shown zone of inhi-
bition, thus proving superiority over sulfonamides.
Table 1 reflects that Mannich bases 4a and 4b are statisti-
cally at par but these are significantly superior to com-
pounds 4c, 4e and 4f against S. enteritidis.The highest
zone of inhibition was recorded in concentration 40 mg/
ml followed by the concentration 30 and 20 mg/ml.
The results were statistically evaluated by analysis of
variance. The null hypothesis was tested using F test.
0
OH
O
OH
H
O
(
i)0 C(1/2 hour)
O
HO
O
OH
H
O
O
S
O
H
(ii) reflux
HN
H
OH
O
S
+H2N
NH R
OH
NH2
+
H
O
HN
NH
R
OH
CH3
O
OH
CH3
CH3
CH3
H
N
OH
O
CH3
H
N
CH3
OH
4(a-f)
1
2
3(a-f)
N
(
3a-4a); R = Sulphadiazene
N
O
CH3
N
(
3b-4b); R = Sulphamethoxazol3
(
3c-4c); R = Sulphanilamide
3d-4d); R = Sulphaguanidine
3e-4e); R = Sulphadoxine
NH2
NH.NH2
(
N
N
(
H3C
O
O
CH3
(
3f-4f); R = Sulphacetamide
COCH3
Scheme 1. Synthesis of Mannich bases (4a–4f).
Table 1. Antibacterial screening of Mannich bases ( Zone of inhibition in mm)
Compound Salmonella enteritidis (concn in lg/ml)
Pasturella multocida (concn in lg/ml)
2
0
30
40
Av
20
30
40
Av
4
4
4
4
4
4
a
b
c
d
e
f
20.00
21.06
14.68
13.20
15.00
—
20.86
21.22
15.02
13.86
15.20
—
21.20
22.06
16.00
14.20
15.46
—
20.68
21.44
15.23
13.75
15.22
—
20.40
21.26
28.36
24.08
22.15
26.20
23.12
20.80
22.00
28.60
24.26
23.30
27.26
23.76
21.86
23.20
29.08
25.20
24.40
28.30
24.58
21.02
22.15
28.68
24.51
23.28
27.25
Av of concn
19.00
19.17
19.95
S.Ed.
CD at 5%
S.Ed.
CD at 5%
Compound
Concn
Inter-action
0.093
0.008
0.024
0.201
0017
0.051
0.083
0.039
0.118
0.176
0.079
0.250
Note: S.Ed., standard error of difference; CD, critical difference.

S. Joshi et al. / Bioorg. Med. Chem. Lett. 17 (2007) 645–648
647
Table 2. Comparative study of antibacterial activity of Mannich bases and their parent sulfonamides (Zone of inhibition in mm)
Compound
Salmonella enteritidis (concn in lg/ml)
Pasturella multocida (concn in lg/ml)
2
0
30
40
Av
20
30
40
Av
4
a
4
a
20.00
10.00
14.68
15.00
15.00
10.00
13.20
10.00
15.00
—
20.86
15.00
15.02
15.00
15.20
12.00
13.86
15.00
15.20
—
21.20
20.00
15.50
18.00
15.46
16.00
14.20
18.00
15.46
—
20.68
15.00
16.00
16.00
15.22
12.66
13.75
14.33
15.22
—
20.40
28.00
21.26
24.00
28.36
22.00
24.08
20.00
22.15
22.00
26.20
20.46
20.80
30.00
22.00
26.00
28.60
25.00
24.26
25.00
23.30
24.00
27.26
21.22
21.86
39.00
23.20
28.00
29.08
28.00
25.20
25.00
24.40
25.00
28.30
22.15
21.02
29.33
22.15
26.00
28.68
25.00
24.51
23.33
23.28
23.66
27.27
21.27
b
b
4
c
4
c
d
d
4
e
4
f
e
f
—
—
—
—
—
—
—
—
S.Ed.
CD at 5%
S.Ed.
CD at 5%
Mannich base and sulfonamides
Concentration
Interaction
0.329
0.054
0.154
0.706
0.111
0.331
0.220
0.027
0.096
0.456
0.056
0.200
Note: S.Ed, standard error of difference; CD, critical difference.
If the values of the calculated F are higher than the
table value of F at 5% level, the character under
study is said to be significantly influenced by the
treatment. The significant or non-significant difference
due to each of the treatments was judged under each
character using standard error of difference (S.Ed)
and critical difference (CD) values. The S.Ed between
two treatments was calculated using error mean sum
of squares (EMS). The CD were computed by multi-
plying the S.Ed value with the t-table (at 5%) value
for the error degree of freedom in order to judge
the minimum difference in the means to qualify the
treatment effects.
Acknowledgment
The authors wish to express gratitude, Director, CDRI,
Lucknow, for recording elemental analysis and NMR
spectra of the compounds.
References and notes
1. Goodmann, L. S.; Gilman, A. G. The Pharmacological
Basis of Therapeutics, 9th ed.; McGraw Hill Co: New
York, 1998.
. Lacthman, L.; The Theory and Practice of Industrial
Pharmacy, 3rd ed., 1987
2
3
. Backett, A. H.; Stenlake, S.; Stables, J. B., Practical
Pharmaceutical Chemistry, Part 1, 3rd ed., 1986.
4. National Formulary, 13th ed., 1970.
. Sriram, D.; Yogeeswari, P.; Reddy, S. P. Bioorg. Med.
Chem. Lett. 2006, 15–16, 2113.
The Mannich bases were also screened for their toxicity
by preliminary LD50 test. The test was performed on
white mice weighing 25 g. Doses were given orally as
well as intraperitoneally and mice were kept under
observation for 72 h for each trial. The Mannich bases
showed no adverse toxic effect even at an oral dose of
5
2
5
6. Yogeeswari, P.; Sriram, D.; Kavya, R.; Tiwari, S. BioMed.
Pharmacother. 2005, 59, 501.
7
8
9
. Malinka, W.; Swiatek, P.; Filipek, B.; Sapa, J.; Jezierska,
A.; Koll, A. Farmaco 2005, 60, 961.
. Negm, N. A.; Morsy, S. M.; Said, M. M. Bioorg. Med.
Chem. 2005, 1, 13, 5921.
. Gokce, M.; Bakir, G.; Kupeli, M. F.; Sahin, E.; Yesilada,
E. Arzneimittelforschung 2005, 55, 318.
1
600 mg/kg of the body weight of mice. However, when
dose was administered intraperitoneally, they proved to
be lethal at the dose level of 1000 mg/kg of the body
weight of mice.
In Conclusion the 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-
pentahydroxy
1
0. Gul, H. I.; Calis, U.; Vepsalainem, J. Arzneimittelfors-
chung 2004, 54, 359.
octahydro-3,6,10,12,12a
naphthacene
carboxamide (Mannich bases) appeared to be better
and more potent antibacterial agents than the sulfon-
amides themselves. We, therefore, conclude that the
Mannich bases could be used as constructive drug in
preference to sulfonamides. Our findings will prove
useful to those chemists, pharmacists and medicinal
chemists who are interested in the synthesis of poten-
tial Mannich bases as drugs with minimum side effects
and also having comparatively low cost. Understand-
ing of Mannich reaction, use of Mannich base for
large-scale production of chemicals and synthesis of
new exotic materials are some of the intellectual chal-
lenges for the future generation of chemists.
11. Mandloi, D.; Joshi, S.; Khadikar, P. V.; Khosla, N.
Bioorg. Med. Chem. Lett. 2005, 17, 15, 405.
12. Sondhi, S. M.; Johar, M.; Singhal, N.; Dastidar, S. G.;
Shukla, R.; Raghubir, R. Monatshefte Fur Chem. 2000, 13,
5
11.
1
1
3. Sondhi, S. M.; Johar, M.; Singhal, N. Polymer 1998, 29, 771.
4. Supuran, C. T.; Scozzafava, A.; Jurca, B. C.; Ilies, M. A.
Eur. J. Med. Chem. 1998, 33, 83.
1
5. Sahina, M. F.; Badikoglub, Gokce M.; Kupeli, E.;
Yesilada, E. Arch. pharm. (Weinheim) 2004, 337, 445.
6. Joshi, S.; Khosla, N.; Tiwari, P. Bioorg. Med. Chem. 2004,
12, 571.
1
17. Joshi, S.; Matkar, S.; Khosla, N.; Bhandari, V. J. Indian
ChemSoc. 1997, 74, 56.

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1
1
2
2
8. Tramontiny, M.; Angioliny, L.; Ghedini, N. Polymer
998, 29, 771.
9. Goto, M.; Minoe, T. Jpn. Kokai Tokkyo Koho 1995, JP06,
85.
0. Mitsch, A.; Wibner, P.; Sattler, I.; Schlitzer, M. Arch.
Pharm. Pharm. Med. Chem. 2001, 334, 40.
1. General procedure for the preparation of Mannich base of
(KBr) 3445 mas (NH) in sec amide, 3350 mNH of SO
2
NH,
1
3050 m (@C–H) of aromatic ring, 2945 mas C–H in CH ,
2
2735 m >CH N<, 1810 m (C@O), 1345, m S@O, 1110, m
2
as
1
(C–H) in disubstituted benzene, 850 out of plane C–H in
disubstituted aromatic ring, H NMR 2.49 (d, 2H, J = 7.5,
1
CH
CONH); 11.20 (s, 1H, SO NH); 1.60 (s, 1H, C Me ); 2.62
2
); 5.60 (s, 1H, NH); 6.50–7.90 (m, ArH); 7.10 (s, 1H,
2
6
2
4
-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a
(s, 1H, Nme
1H, C ); 3.20 (s, 1H, C
Compound (4d)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-
octahydro-3,6,10,12,12a pentahydroxy naphthacene car-
2
); 2.10 (s, 1H, C4a); 2.40 (s, 1H, C5a); 2.30 (s,
).
pentahydroxy naphthacene carboxamide-4-(dimethylami-
no)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a penta-
hydroxy naphthacene carboxamide (0.01 mol) was
dissolved in 20 ml methanol. This was followed by equimo-
lar addition of sulfonamide (0.01 mol) in small installments
with constant stirring at efficient ice cooling. The reaction
mixture was cooled well. Then 2.5 ml of formaldehyde
solution (37%) was added slowly with continuous stirring.
The mixture waskept as such for half anhour afteradjusting
the pH of reacting mixture to 3.5–4 with hydrochloric acid.
After half an hour, the resulting reacting mixture was placed
on a water bath for refluxing. The reflux time varied with
different sulfonamides used. The mixture was then kept at
5
4
boxamido methylsulfaguanidine,
30 34 6
C H N O10S, mp
À185 to 186 °C, C(%)—53.60 (53.73), H(%)—5.02 (5.07),
N(%)—12.50 (12.53), UV 218 (S@O), 255 (Ar Ring),
264(sulfonamide moiety), 366 (diketone-moiety), IR (KBr)
3446 mas (NH) in sec amide, 3335 mNH of SO
(@C–H) of aromatic ring, 2900 mas C–H in CH
>CH N<, 1810 m (C@O), 1340, m S@O, 1120, m(C–H) in
2
NH, 3045 m
2
, 2730 m
2
as
disubstituted benzene, 830 out of plane C–H in disubsti-
1
2
tuted aromatic ring, H NMR 2.60 (d, 2H, J = 7.5, CH );
5.90 (s, 1H, NH); 6.50–7.80 (m, ArH); 7.20 (s, 1H,
CONH); 11.10 (s, 1H, SO NH); 1.70 (s, 1H, C Me ); 2.70
0
°C for 4 days, when the desired product formed. The
2
6
2
Mannich base formed was recrystallized with dry distilled
methanol/ethanol/DMF.
2. Physical and spectral characteristics of compound (4a–4f):
(s, 1H, Nme
1H, C ); 3.10 (s, 1H, C
2
); 2.20 (s, 1H, C4a); 2.30 (s, 1H, C5a); 2.40 (s,
).
5
4
2
Compound (4e)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-
octahydro-3,6,10,12,12a pentahydroxy naphthacene car-
boxamido methyl sulfadoxine, C35
to 238 °C, C(%)—54.60 (54.83), H(%)—4.96 (4.96),
N(%)—10.96 (10.96), UV 220 (S@O), 252 (Ar Ring), 260
(sulfonamide moiety), 364 (diketone-moiety), IR (KBr)
Compound
2a-octahydro-3,6,10,12,12a pentahydroxy naphthacene
carboxamido methyl sulfadiazine, C33 10S, mp
59–160 °C, C(%)—56.02 (55.09), H(%)—4.68 (4.81),
N(%)—11.60 (11.89), UV 220 (S@O), 252 (Ar Ring), 260
sulfonamide moiety), 363 (diketone-moiety), IR (KBr)
441mas (NH) in sec amide, 3327 mNH of SO NH, 3055 m
(4a)-4-(dimethylamino)-1,4,4a,5,5a,6,11,
1
H
38
6
N O
12S, mp À236
H
34
6
N O
1
(
3
2
3440 mas (NH) in sec amide, 3350 mNH of SO NH, 3060m
(@C–H) of aromatic ring, 2930 mas C–H in CH , 2730 m
2
2
(
@C–H) of aromatic ring, 2941 mas C–H in CH , 2731 m
>CH N<, 1805 m (C@O), 1330, m S@O, 1115, m (C–H) in
2
2
as
>
CH
disubstituted benzene, 838 out of plane C–H in disubsti-
2
N<, 1838 m (C@O), 1330, mas S@O, 1149, m (C–H) in
disubstituted benzene, 825 out of plane C–H in disubsti-
1
tuted aromatic ring, H NMR 2.80 (d, 2H, J = 7.5, CH
5.80 (s, 1H, NH); 6.60–7.10 (m, ArH); 7.10 (s, 1H,
CONH); 11.20 (s, 1H, SO NH); 1.80 (s, 1H, C Me ); 2.60
(s, 1H, Nme ); 2.10 (s, 1H, C4a); 2.30 (s, 1H, C5a); 2.40 (s,
1H, C ); 3.00 (s, 1H, C ).
2
);
1
tuted aromatic ring, H NMR 2.90 (d, 2H, J = 7.5, CH );
2
5
.60 (s, 1H, NH); 6.50–7.90 (m, ArH); 7.20 (s, 1H,
CONH); 11.70 (s, 1H, SO NH); 1.80 (s, 1H, C Me ); 2.67
s, 1H, Nme ); 2.20 (s, 1H, C4a); 2.40 (s, 1H, C5a); 2.30 (s,
H, C ); 3.09 (s, 1H, C ).
2
6
2
2
6
2
2
(
1
2
5
4
Compound (4f)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-
octahydro-3,6,10,12,12a pentahydroxy naphthacene car-
boxamido methyl sulfacetamide, C31
to 219 °C, C(%)—55.42 (55.52), H(%)—5.01 (5.07),
N(%)—8.30 (8.32), UV 220 (S@O), 252 (Ar Ring), 260
(sulfonamide moiety), 366 (diketone-moiety), IR (KBr)
5
4
Compound (4b)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-
octahydro-3,6,10,12,12a pentahydroxy naphthacene car-
boxamido methylsulfamethoxazole, C33
34
H N
4
O
11S, mp À218
H
35
5
N O
11S, mp
À148 to 150 °C, C(%)—55.80 (55.85), H(%)—4.90 (4.93),
N(%)—9.80 (9.87), UV 222 (S@O), 254 (Ar Ring),
262(sulfonamide moiety), 366 (diketone-moiety), IR
2
3442 mas (NH) in sec amide, 3355 mNH of SO NH, 3050 m
(
3
2
KBr) 3440 mas (NH) in sec amide, 3320 mNH of SO NH,
(@C–H) of aromatic ring, 2940 mas C–H in CH , 2740 m
2
2
040 m (@C–H) of aromatic ring, 2920 mas C–H in CH2,
730 m >CH N<, 1820 m (C@O), 1340, mas S@O, 1120, m
>CH N<, 1820 m (C@O), 1335, m S@O, 1112, m (C–H) in
2
as
2
disubstituted benzene, 830 out of plane C–H in disubsti-
1
(
C–H) in disubstituted benzene, 850 out of plane C–H in
tuted aromatic ring, H NMR 2.90 (d, 2H, J = 7.5, CH
5.90 (s, 1H, NH); 6.70–7.20 (m, ArH); 7.30 (s, 1H,
CONH); 11.60 (s, 1H, SO NH); 1.80 (s, 1H, C Me ); 2.70
(s, 1H, Nme ); 2.10 (s, 1H, C4a); 2.40 (s, 1H, C5a); 2.60 (s,
1H, C ); 3.00 (s, 1H, C ).
2
);
1
disubstituted aromatic ring, H NMR 2.80 (d, 2H, J = 7.5,
CH ); 5.80 (s, 1H, NH); 6.60–7.10 (m, ArH); 7.20 (s, 1H,
CONH); 11.80 (s, 1H, SO NH); 1.70 (s, 1H, C Me ); 2.60
s, 1H, Nme ); 2.20 (s, 1H, C4a); 2.50 (s, 1H, C5a); 2.30 (s,
H, C ); 3.10 (s, 1H, C ).
2
2
6
2
2
6
2
2
(
1
2
5
4
23. Shriner, R. L.; Hermann, C. K. F.; Morill, T. C.;
Curtin, D. Y.; Fuson, R. C. The systematic identifi-
cation of organic compounds, 7th ed.; John Wiley and
Sons: London, 1998.
24. Taylor, W. B. Biometrics 1957, 13, 1.
25. Turner, R. A. Screening Methods in Pharmacology;
Academic: New York, 1965, Vol. 1, p. 27.
5
4
Compound (4c)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-
octahydro-3,6,10,12,12a pentahydroxy naphthacene car-
boxamido methyl sulfanilamide, C H N O S, mp À169
2
9
32
4
10
to 170 °C, C(%)—55.40(55.41), H(%)—5.08 (5.09),
N(%)—8.90 (8.91), UV 220 (S@O), 252 (Ar Ring),
2
61(sulfonamide moiety), 363 (diketone-moiety), IR