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S1
Supplementary material
Stereoselective synthesis of natural product inspired carbohydrate
fused pyrano[3,2-c]quinolones as antiproliferative agents
Priti Kumari,
a Chintam Narayana,
a Shraddha Dubey,
b Ashish Gupta
b and Ram Sagar
a,c
aDepartment of Chemistry, School of Natural Sciences, Shiv Nadar University (SNU), NH91, Tehsil-Dadri, Gautam
Buddha Nagar, Uttar Pradesh, 201314, India. bDepartment of Life Sciences, School of Natural Sciences, Shiv Nadar University (SNU), NH91, Tehsil-Dadri,
Gautam Buddha Nagar, Uttar Pradesh, 201314, India. cDepartment of Chemistry, Institute of Science, Banaras Hindu University, Varanasi, Uttar Pradesh, 221005, India.
*E-mail (Corresponding author): [email protected]; [email protected],
S. No. Contents Page No.
1 Synthesis of Compound 1a and 1b S2
2 Synthesis and NMR data of 4-hydroxyquinolones1-11 S2-S6
3 Copies of 1H NMR and
13C NMR of pyrano[3,2-c]quinolones12-33a/b S7-S28
4 NOE, 1H-
1H COSY and
1H-
13C HSQC spectra of compound 12 S29-S30
5 Copies of 1H &
13C NMR of 34 and N-methyl pyrano[3,2-c]quinolones 35 S31-S32
6 Cell viability data for all compounds against MCF-7 and HepG2 cell lines S33-S34
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2018
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S2
General experimental procedures
Synthesis of 2-C-formyl galactal 1a and 2-C-formyl glucal 1b: In a 100 ml round bottom flask
30 ml anhydrous DMF was added followed by dropwise addition of POCl3(0.6 mL, 21.6 mmol)
at 0 °C and resulting mixture was stirred for 30 min under Argon atmosphere. A solution
(dissolved in anhydrous DMF) of 3,4,6-tri-O-benzyl-D-galactal (2.99 g, 7.20 mmol) was added
to this dropwise within 30 min. The resulting reaction mixture was stirred at 0 °C to room
temperature for 5 h which shows disappearance of starting material (TLC). Reaction mixture was
quenched by slow addition of (within 30 min) of chilled NaHCO3 (30 mL) solution at 0 °C.
Mixture was extracted with ethyl acetate (3 × 30mL).and combined organic layer washed with
brine solution (3 × 30mL).then dried over anhydrous Na2SO4. The combined organic layer was
evaporated under vaccume to get crude residue which was purified though flash column
chromatography and pure 2-C-formyl galactal 1a was isolated in 94 % isolated yield (3.0 g).
Similarly using 3,4,6-tri-O-benzyl-D-galucal and adopting above protocol 2-C-formyl glucal 1b
was obtained in 54 % (1.7g) isolated yield.1
Synthesis of 4-hydroxyquinolones 1-11: In an oven dried 25 ml round bottom flask Aniline (1
mL, 1.024 gm 10.99 mmol) and Meldrum’s Acid (1.583 gm,10.99 mmol ) were taken and heated
at 80 °C for 2 h. After consumption of starting material (TLC), added ethylacetate and aquous
solution of sodium bicarbonate. Resulting suspension partitioned in separating funnel and
aqueous layer washed with ethyl acetate (3 × 50 mL). The aqueous layer acidified with conc.HCl
until pH 1-2 then extracted with dichloromethane (3 × 35 mL). The combined organic layer dried
over anhydrous Na2SO4 filtered and evaporated on rotary evaporator to get solid residue which
was forwarded next step without further purification. The solid residue (1.9 g) and Eaton’s
reagent (9.5 g, 5 equiv/w) was heated at 80 °C for 1 h or till disappearance of starting material
(TLC). The reaction mixture cooled down and added ice cold water and keep stirring for 30 min
then solid precipitate appeared which was filtered using Buchner funnel under vaccum till
dryness to get almost pure 4-hydroxyquinolone 1 in 80 % yield (1.41gm).2 Similar reaction
protocol was followed for preparation of various other 4-hydroxyquinolone (2-11 and 34) using
corresponding anilines (Table S1).
References
1. N.G. Ramesh, K.K. Balasubramanian, Tetrahedron Lett. 1991, 32 , 3875-3878.
2. (a) S-J. Park, J-C Lee, K-I.Lee. Bull. Korean Chem. Soc. 2007, 28, 1203-1205, (b) K. Arya,
M. Agarwal, Bioorg. Med. Chem. Lett. 2007, 17, 86-93.
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S3
Table S1. Synthesis of 4-hydroxyquinolone 1-11.
NH2
R1
R2
R3
R4
NH
O
OH
1-11
R1
R2
R3
R4
+i) 85 oC, 1-2 h, then
ii) Eaton's reagent,
65 oC, 1-2 h
O
O
O
O
Entry R
1 R
2 R
3 R
4 Product Time (h) Yield (%)
1 H H H H 1 1 80
2 H H H F 2 2 70
3 H H OPh H 3 2 69
4 H H H NO2 4 1 53
5 H H H OCF3 5 2 81
6a H H- CF3 H 6 1 55
7 H H H CHMe2 7 2 70
8a H H Cl H 8 1 60
9a H H Br H 9 2 65
10 H H H CF3 10 1 58
11 H Cl CF3 H 11 2 51 aTwo regioisomers were formed in these cases, they were purified and isolated yields of desired isomer is given.
4-hydroxyquinolin-2(1H)-one (1).1H NMR (400 MHz, DMSO-d6): δ 11.31 (brs, 1H, OH),
11.20 (s, 1H, NH), 7.76 (dd, J = 1.2 Hz, J = 8.0 Hz, 1H, H-5),7.47-7.45 (t, J = 7.2Hz, 1H, H-6),
7.25 (d, J = 8.0 Hz, 1H, H-8), 7.14 (t, J = 7.2Hz, 1H, H-7), 5.72 (s,1H, H-3) 13
C NMR (100
MHz, DMSO-d6), δ: 163.9, 162.8, 139.6, 131.3, 123.1, 121.4, 115.5, 115.4, 98.6 (C-3).
HRMS(ESI), calcd, m/z C9H7NO2, [M+H]+
162.0549; Found: 162.0573.
NH
O
OH
2F
8-Flouro-4-hydroxyquinolin-2(1H)-one (2).1H NMR (400 MHz, DMSO-d6): δ 11.53 (brs, 1H,
OH), 11.21 (s, 1H, NH), 7.61 (d, J = 8.0 Hz, 1H, H-5), 7.41(ddd, J = 11.2 Hz, J = 8.0 Hz and J =
1.2 Hz, 1H, H-7), 7.13 (td, J = 4.8 Hz, J = 8.0 Hz,1H, H-6), 5.79 (s, 1H, H-3), 13
C NMR (100
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S4
MHz, DMSO-d6): δ 163.5, 162.4, 121.3, 121.2, 118.9, 117.8, 116.5, 116.3, 99.6 (C-3).
HRMS(ESI), calcd, m/z C9H6FNO2[M+H]+ 180.0455;Found: 180.0479.
NH
O
OH
3
PhO
7-phenoxy-4-hydroxyquinolin-2(1H)-one(3) 1H NMR (400 MHz, DMSO-d6): 11.44 (s, 1H,
OH), 11.16 (s, 1H, NH), 7.78 (d, J = 9.2 Hz, 1H, H-5), 7.47-6.80 (m, 7H, ArH), 5.67 (s, 1H, H-
3), 13
C NMR (100 MHz, DMSO-d6): δ 164.1, 163.0, 159.9, 141.2, 130.7, 130.1, 125.2, 117.3,
112.6, 103.1, HRMS(ESI), calcd, m/z C15H11NO3, [M+H]+ 254.0817; Found: 254.0849
NH
O
OH
4NO2
8-Nitro-4-hydroxyquinolin-2(1H)-one (4). (400 MHz, DMSO-d6): δ 12.07(s, 1H, OH), 10.60(s,
1H, NH), 8.45(dd, J =8.4 Hz and J =1.2 Hz, 1H, H-5), 8.26 (dd, J =8.0 Hz and J =1.2 Hz, 1H,
H-7), 7.37 (t, J = 8.0 Hz, 1H, H-6), 5.88 (s, 1H, H-3), 13
C NMR (100 MHz, DMSO-d6): δ 162.6,
133.9, 131.2, 128.8, 121.2, 118.4, 98.9 (C-3), HRMS(ESI), calcd, m/z C9H6N2O4, [M+H]+
207.0400;Found: 207.0432.
NH
O
OH
5CF3O
8-triflouromethoxy-4-hydroxy-2H-benzopyran-2-one (5). 1H NMR (400 MHz, DMSO-d6): δ
11.62 (brs, 1H, OH), 11.37 (brs, 1H, NH), 7.81 (dd, J = 8.0 Hz and J =1.6 Hz, 1H, H-5), 7.57
(dd, J = 8.0 Hz and J =1.6 Hz, 1H, H-7), 7.21 (t, J = 8.0 Hz, 1H, H-6), 5.81 (s, 1H, H-3); 13
C
NMR (100 MHz, DMSO-d6): δ 163.7, 162.2, 134.7, 132.6, 123.6, 122.4, 121.3, 117.8, 99.6 (C-
3), HRMS(ESI), calcd, m/z C10H6F3NO3, [M+H]+ 246.0373; Found: 246.0411.
NH
O
OH
6
F3C
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S5
7-triflouromethyl-4-hydroxyquinolin-2(1H)-one (6). 1H NMR (400 MHz, DMSO-d6): δ 11.61
(brs, 1H, OH), 11.48 (brs, 1H, NH), 7.98 (d, J = 8.4 Hz, 1H, H-5), 7.62 – 7.58(m, 1H), 7.45 (d, J
= 8.4 Hz, 1H, H-6), 5.86 (s, 1H, H-3), 13
C NMR (100 MHz, DMSO-d6): δ 163.7, 162.8, 162.0,
141.8, 139.4, 130.4, 124.7, 121.2, 112.4, 100.6 (C-3), HRMS(ESI), calcd, m/z C10H6F3NO2,
[M+H]+ 230.0423; Found: 230.0458.
NH
O
OH
7
Me2HC
8-isopropyl-4-hydroxyquinolin-2(1H)-one (7). 1H NMR (400 MHz, DMSO-d6): δ 10.69 (brs,1H
NH), 7.72 (dd, J = 8.0 Hz and J = 1.2 Hz, 1H, H-5), 7.50 (dd, J = 7.9 Hz and J = 1.4 Hz,1H, H-
7), 7.18 (t, J = 15.8 Hz,1H, H-6), 5.86 (s, 1H, H-3), 3.60 (septate, J = 6.8 Hz, 1H, CH of
CHMe2), 1.19 (d, J = 6.8 Hz, 6H, CHMe2), 13
C NMR (100 MHz, DMSO-d6): δ 168.9,168.8,
141.2, 139.2, 132.8, 126.7, 125.7,120.7, 102.3 (C-3), 30.7 (CH), 28.2 (Me2), HRMS(ESI), calcd,
m/z C12H13NO2, [M+H]+ 204.1019; Found: 204.1016.
NH
O
OH
8
Cl
7-chloro-4-hydroxyquinolin-2(1H)-one (8). 1H NMR(400 MHz, DMSO-d6): δ 11.51 (brs, 1H,
OH), 11.36 (brs, 1H, NH), 7.76 (d, J= 8.8 Hz, 1H, H-5), 7.41 (d, J = 8.0 Hz, 1H, H-6), 7.18-7.15
(m, 1H), 5.80 (s, 1H, H-3), 13
C NMR (100 MHz, DMSO-d6): δ 163.9, 162.9, 142.2, 135.7,
131.3, 130.3, 125.1, 121.7, 115.4, 112.5, 100.2 (C-3), HRMS(ESI), calcd, m/z C9H6ClNO2,
[M+H]+ 196.0159; Found: 196.0170.
NH
O
OH
9
Br
7-bromo-4-hydroxyquinolin-2(1H)-one (9).1H NMR (400 MHz, DMSO-d6): δ 11.51 (brs, 1H,
OH), 11.28 (brs, 1H, NH), 7.70 (d, J= 8.8 Hz, 1H, H-5), 7.43 (d, J = 8.0 Hz, 1H, H-6), 7.18-7.15
(m, 1H), 5.80 (s, 1H, H-3), 13
C NMR (100 MHz, DMSO-d6): δ 163.8, 162.7, 142.3, 131.5,
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S6
128.6, 125.1, 117.7, 114.6, 100.3 (C-3), HRMS(ESI), calcd, m/z C9H6BrNO2, [M+K]+ 277.9219;
Found: 277.0997.
NH
O
OH
10
CF3
8-triflouromethyl-4-hydroxyquinolin-2(1H)-one (10).1H NMR (400 MHz, DMSO-d6): δ 11.81
(brs,1H, OH), 9.94 (brs, 1H, NH), 8.13 (d, J = 8.0 Hz, 1H, H-5), 7.90 (d, J = 8.0 Hz, 1H, H-7),
7.33 (t, J = 7.9 Hz, 1H, H-6), 5.88 (s, 1H, H-3),.13
C NMR (400 MHz, DMSO-d6): δ 169.9,
168.9, 163.5, 162.5, 141.2, 134.4, 131.5, 129.1, 128.3, 123.0, 121.3, 120.4, 100.1 (C-3),
HRMS(ESI), calcd, m/z C10H6F3NO2, [M+H]+ 230.0423; Found: 230.0458.
NH
O
OH
Cl
F3C
11 6-chloro-7-triflouromethyl-4-hydroxyquinolin-2(1H)-one (11).
1H NMR (400 MHz, DMSO-
d6): δ 11.55 (s, 1H, OH), 7.93 (s, 1H, H-8), 7.71 (s, 1H, H-5), 5.86 (s, 1H, H-3); 13
C NMR (100
MHz, DMSO-d6): δ 168.2, 167.3, 165.7, 142.7, 130.5, 129.2, 128.8, 126.6, 123.9, 120.3,106.2
(C-3), HRMS(ESI), calcd, m/z C10H5ClF3NO2, [M+H]+ 264.0034; Found: 264.0037.
4-hydroxy-1-methylquinolin-2(1H)-one (34).
1H NMR (400 MHz, DMSO-d6): δ 11.34 (s, 1H,
OH), 7.89 (dd, J = 1.2 Hz, 1H, H-8), 7.61 (ddd, J = 1.2 Hz, J = 7.2 Hz, 1H, H-6), 7.46 (d, J =
8.4 Hz, 1H, H-5), 7.24 (td, J = 0.8 Hz, J = 8.0 Hz, 1H, H-7), 5.88 (s, 1H, H-3), 3.53(s, 3H, N-
CH3); 13
C NMR (100 MHz, DMSO- d6): δ 162.9, 161.4, 140.4, 131.7, 123.5, 121.6, 116.5, 114.9,
98.4, 28.8 (CH3); HRMS(ESI), calcd, m/z C10H9NO2, [M+H]+ 176.07; Found: 176.0805.
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S7
1
12
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S8
13
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S9
14
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S10
15
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S11
16
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S12
17
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S13
18
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S14
19
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S15
20
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S16
21
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S17
22
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S18
23a/b
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S19
24a/b
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S20
25a/b
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S21
26a/b
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S22
27a/b
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S23
28a/b
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S24
29a/b
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S25
30a/b
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S26
31a/b
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S27
32a/b
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S28
33a/b
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S29
NOE of 12
1H-
1H COSY of 12
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S30
1H-
13C HSQC of 12
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S31
34
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S32
35
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Results for Cell Viability testing of Compounds 12-22 and 23a/b-33a/b at 25 µM
concentration in MCF-7 Cell line
Compound 19
Compound 30a/b Compound 33a/b
Compound 24a/b
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S34
RESUL TS FOR C EL L VIABI LI TY T ES TING O F COMPOUNDS 12-2 2, 23a/b-33a/ b AT 25 µM CONC. IN MCF-7 CE LL LIN E
MAfdasfkdas ,vdmsv
RESUL TS FOR C EL L VIABI LI TY T ES TING O F COMPOUNDS 12-2 2, 23a/b-33a/ b AT 25 µM CONC. IN MCF-7 CE LL LIN E
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UntreatedDoxorubicin 1µM 5µM 10µM 20µM
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Untreated Doxorubicin 1µM 5µM 10µM 20µM
Results for Cell Viability testing of Compounds 12-22 and 23a/b-33a/b at 25 µM
concentration in HepG2 Cell line
Compound 15 Compound 30a/b
Compound 33a/b